Journal articles: 'Alkaloidy'

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Han, Sunkyu, Sangbin Jeon, and Joonoh Park. "Syntheses of Dimeric Securinega Alkaloids." Synlett 28, no. 18 (August 22, 2017): 2353–59. http://dx.doi.org/10.1055/s-0036-1590864.

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The isolation of flueggenines A and B by Yue and co-workers in 2006 has triggered a burst of isolation reports of dimeric and oligomeric securinega alkaloid natural products. The compelling molecular structures of these compounds with various modes of connection between monomeric securinega units have posed intriguing challenges to the synthetic organic community. Herein, we have categorized high-order securinega alkaloids based on their biosynthetic mode of dimerization or oligomerization. We then have compiled all reported syntheses of dimeric securinega alkaloids based on our classification.1 Introduction2 Categorization of High-Order Securinega Alkaloid Natural Products3 Syntheses of Type I Dimeric Securinega Alkaloids4 Syntheses of Type II Dimeric Securinega Alkaloids5 Synthesis of Type III Dimeric Securinega Alkaloid6 Conclusion

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Muszyński, Jan. "Alkaloidy europejskich gatunków Lycopodium [Alkaloide der europäischen Lycopodium-Arten.]." Acta Societatis Botanicorum Poloniae 11, no. 3 (2017): 277–86. http://dx.doi.org/10.5586/asbp.1934.016.

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Muszyński, J. "Alkaloidy i glikozydy flawonowe widłaków [Alkaloide und Flavonglukoside der Lycopodien]." Acta Societatis Botanicorum Poloniae 24, no. 2 (2017): 237–44. http://dx.doi.org/10.5586/asbp.1955.014.

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Navrátilová, Zdeňka, and Jiří Patočka. "Veratrum alkaloids: biology, chemistry, pharmacology and toxicology." Kontakt 13, no. 3 (September 29, 2011): 345–55. http://dx.doi.org/10.32725/kont.2011.040.

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Mróz, Michalina, Katarzyna Pastusiak, and Paweł Bogdański. "Potencjalne możliwości wykorzystania berberyny w przeciwdziałaniu insulinooporności i w cukrzycy typu 2." Postępy Higieny i Medycyny Doświadczalnej 75, no. 1 (January 1, 2021): 790–801. http://dx.doi.org/10.2478/ahem-2021-0038.

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Abstrakt Insulinooporność to stan zmniejszonej wrażliwości tkanek docelowych na działanie insuliny, mimo jej prawidłowego lub podwyższonego stężenia w surowicy krwi. Jest ważnym czynnikiem w patogenezie zespołu metabolicznego, w tym stanu przedcukrzycowego i cukrzycy typu 2, a także chorób sercowo-naczyniowych oraz zespołu policystycznych jajników. Wzrasta zainteresowanie wykorzystaniem środków pochodzenia roślinnego w leczeniu pacjentów z chorobami metabolicznymi. Jednymi z nich są rośliny z rodziny berberysowatych zawierające alkaloidy izochinolinowe, takie jak berberyna. Sugeruje się, iż berberyna może wpływać na zmniejszenie insulinooporności, gospodarkę węglowodanową oraz metabolizm lipidów. Naukowcy wykazali, że ten roślinny alkaloid może tłumić różnicowanie adipocytów i wspomagać redukcję masy ciała. Inne właściwości berberyny obejmują działanie hipotensyjne oraz ochronne wobec śródbłonka naczyniowego. W artykule skoncentrowano się przede wszystkim na przedstawieniu potencjalnych możliwości wykorzystania berberyny w przeciwdziałaniu insulinooporności w cukrzycy typu 2.

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Věžník, František, Eva Táborská, Hana Bochořáková, František Tureček, Vladimír Hanuš, and Jiří Slavík. "Alkaloids of Papaver nudicaule SUBSP. xanthopetalum (TRAUTV.) FEDDE and P. nudicaule SUBSP. album (REGEL) FEDDE from the section Scapiflora REICHB." Collection of Czechoslovak Chemical Communications 52, no. 6 (1987): 1634–40. http://dx.doi.org/10.1135/cccc19871634.

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The alkaloidal composition in the two title taxa differs only quantitatively. Both contain amurine as the main alkaloid. P. nudicaule ssp. xanthopetalum contains muramine, protopine and alkaloid PN1 (probably identical with (±)-nudaurine (Ia)) as dominant alkaloids; further were isolated amurensine, epialpinine, cryptopine, mecambridine and alpinigenine. Allocryptopine, papaverrubines A, B, D and G, palmatine and coptisine were detected chromatographically. The quaternary alkaloid fraction afforded cis-N-methylstylopinium hydroxide (as the iodide II) which was isolated for the first time from P. nudicaule. In P. nudicaule ssp. album the alkaloid PN1, epialpinine, amurensine and muramine represented the dominant alkaloids, accompanied with mecambridine, protopine, cryptopine, allocryptopine and alpinigenine. Among the quaternary alkaloids N-methylstylopinium hydroxide was found.

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El-Shazly, A., A. M. Ateya, L. Witte, and M. Wink. "Quinolizidine Alkaloid Profiles of Retama raetam, R. sphaerocarpa and R. monosperma." Zeitschrift für Naturforschung C 51, no. 5-6 (June 1, 1996): 301–8. http://dx.doi.org/10.1515/znc-1996-5-607.

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Abstract About 28 quinolizidine alkaloids and the dipiperidine alkaloids am modendrine, dehydroammodendrine and N -formylammodendrine were identified in the alkaloidal extracts of Retama raetam, Retama sphaerocarpa and Retama monosperma by capillary GLC and GLCMS. Alkaloid profiles of the three Retama species with a Mediterranean distribution are more similar than alkaloid patterns of different organs of the same plant. Whereas sparteine and retamine are the major components of stems, lupanine, retam ine, N-methylcytisine and cytisine dominate in flowers and pods, and cytisine in seeds indicating a high degree of organ specificity of alkaloid storage.

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El-Shazly, Assem. "Pyrrolizidine Alkaloid Profiles of Some Senecio Species from Egypt." Zeitschrift für Naturforschung C 57, no. 5-6 (June 1, 2002): 429–33. http://dx.doi.org/10.1515/znc-2002-5-604.

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Alkaloid profiles of two Egyptian Senecio species (Senecio aegyptius var. discoideus and S. desfontainei) in addition to a cultivated species (S. cineraria) were studied using capillary GLC and GLC-mass spectrometry with respect to pyrrolizidine alkaloids (PAs). Four alkaloids were identified in S. aegyptius var. discoideus, 8 in S. desfontainei and 13 in S. cineraria. Some of these alkaloids have not been reported from these plants. The alkaloidal pattern of different plant organs (flowers, leaves, stem, root) were also investigated. Senecionine has been found to be a one of the major alkaloid in all studied species, it was isolated and its structure was elucidated by 1H- and 13C-NMR.

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Kłys, Małgorzata, Sebastian Rojek, Martyna Maciów-Głąb, and Karol Kula. "Alkaloidy opium w toksykologicznej praktyce medyczno-sądowej Zakładu Medycyny Sądowej UJ CM." Archives of Forensic Medicine and Criminology 4 (2013): 301–6. http://dx.doi.org/10.5114/amsik.2013.46305.

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10

Slavík, Jiří, and Leonora Slavíková. "Alkaloids of Meconopsis cambrica (L.) VIG. and M. robusta HOOK. f. et THOMS." Collection of Czechoslovak Chemical Communications 61, no. 12 (1996): 1815–22. http://dx.doi.org/10.1135/cccc19961815.

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Additional alkaloids (+)-roemerine (3b), (+)-corytuberine (3d), (-)-N-methylmecambridinium and alkaloid MC 2 (the last two as iodides) were isolated as minor alkaloidal components from Meconopsis cambrica (L.) VIG. (Papaveraceae) besides of the dominant known alkaloids (-)-mecambrine (1), (-)-mecambridine (2), (-)-flavinantine (4) and (+)-magnoflorine (5), and a small amount of (+)-mecambroline (3a). Minute quantities of protopine, allocryptopine, roemeroline, papaverrubine D and C, berberine, coptisine, corysamine and palmatine were identified by thin layer chromatography (TLC). From M. robusta HOOK. f. et THOMS., protopine, (-)-amurensinine (6) and two incompletely characterized alkaloids MRO 1 and MRO 2 were isolated, and allocryptopine, cryptopine, rhoeadine, 6-methoxy-2-methyl-1,2,3,4-tetrahydro-β-carboline, alkaloid MR 1, coptisine, corysamine, magnoflorine, corytuberine and N-methylamurensininium salt were detected on TLC.

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11

Wink, M., and L. Witte. "Quinolizidine Alkaloids as Nitrogen Source for Lupin Seedlings and Cell Cultures." Zeitschrift für Naturforschung C 40, no. 11-12 (October 1, 1985): 767–75. http://dx.doi.org/10.1515/znc-1985-11-1204.

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Abstract The alkaloid patterns during germination and seedling development of Lupinus polyphyllus, L. angustifolius, L. albus, L. pubescens, Cytisus scoparius, Baptisia australis, Spartium junceum and Laburnum anagyroides were studied by capillary glc and EI-MS and CI-MS. The alkaloid contents were relatively high in the seeds and decreased by 20-100% during germination and the early developmental stages. The plants with fully developed leaves were able to synthesize new alkaloids. The decrease of alkaloid concentrations during germination was interpreted in terms of alkaloid turnover and use of the alkaloidal nitrogen for seedling development. The ability of plants to rely on the alkaloidal nitrogen as a nitrogen source could also be shown in lupin cell cultures which could survive and even grow on media which contained sparteine as the sole nitrogen source.

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Sreevidya, Narasimhan, and Shanta Mehrotra. "Spectrophotometric Method for Estimation of Alkaloids Precipitable with Dragendorff's Reagent in Plant Materials." Journal of AOAC INTERNATIONAL 86, no. 6 (November 1, 2003): 1124–27. http://dx.doi.org/10.1093/jaoac/86.6.1124.

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Abstract A rapid, easy, and simple spectrophotometric method was developed for the estimation of total alkaloids precipitated by Dragendorff's reagent (DR) in plant materials. It is based on the formation of yellow bismuth complex in nitric acid medium with thiourea. The yellow-colored complex formed obeys Lambert-Beer's law in the concentration range of 0.06–50 μg/mL with λmax at 435 nm. Using this method, the alkaloidal percentage of certain alkaloids (ajamalicine, papaverine, cinchonine, piperine, berberine) and some plant materials containing alkaloids (Berberis aristata, Solanum nigrum, and Piper longum) were determined. The method was compared with other methods. It can be used for routine analysis of commercial samples by industries dealing with herbal drugs for standardization of plant materials containing alkaloids and for alkaloid-containing pharmaceutical products.

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El-Shazly, Assem, Abdel-Monem M. Ateya, and Michael Wink. "Quinolizidine Alkaloid Profiles of Lupinus varius orientalis, L. albus albus, L. hartwegii, and L. densiflorus." Zeitschrift für Naturforschung C 56, no. 1-2 (February 1, 2001): 21–30. http://dx.doi.org/10.1515/znc-2001-1-204.

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Abstract Alkaloid profiles of two Lupinus species growing naturally in Egypt (L. albus albus [synonym L. term is], L. varius orientalis) in addition to two New World species (L. hartwegii, L. densiflorus) which were cultivated in Egypt were studied by capillary GLC and GLC-mass spectrometry with respect to quinolizidine alkaloids. Altogether 44 quinolizidine, bipiperidyl and proto-indole alkaloids were identified; 29 in L. albus, 13 in L. varius orientalis, 15 in L. hartwegii, 6 in L. densiflorus. Some of these alkaloids were identified for the first time in these plants. The alkaloidal patterns of various plant organs (leaves, flowers, stems, roots, pods and seeds) are documented. Screening for antimicrobial activity of these plant extracts demonstrated substantial activity against Candida albicans, A spergillus flavus and Bacillus subtilis.

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Marsi Mbayo Kitambala, Emery Kalonda Mutombo, Blandine Nkiko Niyibizi, Grégoire Sangwa Kamulete, Glauber Mbayo Kalubandika, Jean Mulamba Muidikija, Evodie Numbi wa Ilunga, et al. "The in vitro antisickling effect of purified alkaloids of Cremaspora triflora (Thonn.) K. Schum. (Rubiaceae) and Macaranga schweinfurthii Pax. (Euphorbiaceae)." World Journal of Advanced Research and Reviews 9, no. 3 (March 30, 2021): 129–37. http://dx.doi.org/10.30574/wjarr.2021.9.3.0074.

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Introduction and objective: Sickle cell disease is an inherited pathology to an abnormality of hemoglobin precisely hemoglobin S for which there is no curative therapy. It mainly affects sub-Saharan African and Caribbean populations. Thus, this study aims to make the phytochemical screening of Cremaspora triflora and Macaranga schweinfurthii as well as to evaluate the antisickling activity of their purified alkaloids. Methodology: Chemical screening was performed using color and precipitation tests as well as the foam index method. The extraction of the alkaloids was carried out with organic solvents in a basic medium while the purification by open column chromatography. The evaluation of the antisickling activity was carried out by Emmel’s test. Results: The chemical screening highlighted alkaloids, steroids, saponins, tannins, and terpenoids in the species studied. Flavonoids and anthocyanins were present in organs of Macaranga schweinfurthii, but absent in Cremaspora triflora. The extraction showed that Macaranga schweinfurthii leaves contained 0.59% alkaloids and 0.73% alkaloids in Cremaspora triflora leaves. The alkaloids purification allowed to obtain an alkaloidal fraction MS1 (1.24 g, 70.05%) from Macaranga schweinfurthii and two fractions [CT2 (0.934 g, 63.97%) and CT3 (0.006 g, 0.41 %)] from Cremaspora triflora which tested positive with Dragendorff and Wagner reagents. The antisickling activity evaluation showed that the SIR varied between 36.00% (0.25 mg/ml) and 90.66% (1 mg/ml) for the alkaloid solutions of Cremaspora triflora (IC50 of 0.51 mg/ml) as well as between 4.00% (0.25 mg/ml) and 33.33% (1 mg/ml) for the alkaloid solutions of Macaranga schweinfurthii (IC50 of 1.40 mg/ml). Conclusion: This study showed that the purified alkaloids of the studied plant species have an inhibitory power on sickling.

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Brodziak, Aneta, Jolanta Król, and Anna Nowaczek. "Naturalne substancje pochodzenia roślinnego negatywnie oddziałujące na zdrowie krów oraz jakość mleka." Zywnosc Nauka Technologia Jakosc/Food Science Technology Quality 110, no. 1 (2017): 33–47. http://dx.doi.org/10.15193/zntj/2017/110/171.

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Celem pracy było omówienie zagrożeń dla zdrowia zwierząt wywołanych przez naturalne substancje szkodliwe, tj. fitotoksyny i mikotoksyny pochodzące z pasz, z uwzględnieniem ich negatywnego wpływu na jakość mleka, a w konsekwencji na zdrowie człowieka. Jako najbardziej szkodliwe związki pochodzące z pasz najczęściej wymieniane są: alkaloidy, glikozydy, saponiny, olejki eteryczne i kwasy organiczne, a także toksyny produkowane przez grzyby pleśniowe. Mniejszą szkodliwością charakteryzują się natomiast: glukozynolany, kumaryny i pochodne furanokumaryny, lektyny, a także fitoestrogeny. Zarówno związki szkodliwe występujące naturalnie w zielonce i w innych paszach objętościowych, jak również mikotoksyny stanowią potencjalne zagrożenie dla zdrowia i życia zwierząt, oddziałując na ich produkcyjność, jak też na jakość surowców, w tym mleka. Największe zagrożenie dla zdrowia zwierząt i ludzi stanowi aflatoksyna B1 z uwagi na jej udowodnione działanie kancerogenne i mutagenne. Jak wskazują raporty z systemu RASFF, rzadko dochodzi jednak do wystąpienia tego typu zagrożeń. Wynika to z selektywnego pobierania paszy przez zwierzęta, zwłaszcza wypasane, jak również z działań podejmowanych przez hodowców w ramach Dobrych Praktyk Rolniczych.

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Nicola, Carla, Mirian Salvador, Adriana Escalona Gower, Sidnei Moura, and Sergio Echeverrigaray. "Chemical Constituents Antioxidant and Anticholinesterasic Activity ofTabernaemontana catharinensis." Scientific World Journal 2013 (2013): 1–10. http://dx.doi.org/10.1155/2013/519858.

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The present work aimed to analyze the alkaloid content of the ethanolic extract ofTabernaemontana catharinensis(Apocynaceae family) and its fractions as well as to evaluate their antioxidant and anticholinesterasic activities. The analyses of the ethanolic extract ofT. catharinensisby mass spectrometry allowed identifying the presence of the alkaloids 16-epi-affinine, coronaridine-hydroxyindolenine, voachalotine, voacristine-hydroxyindolenine, and 12-methoxy-n-methyl-voachalotine, as well as an alkaloid withm/z385.21 whose spectrum suggests a derivative of voacristine or voacangine. The extract and its alkaloid rich fractions showed antioxidant activity, especially those that contain the alkaloidm/z385.21 or 16-epi-affinine with DPPH scavenging activity (IC50) between 37.18 and 74.69 μg/mL. Moreover, the extract and its fractions exhibited anticholinesterasic activity, particularly the fractions characterized by the presence of 12-methoxy-n-methyl-voachalotine, with IC50= 2.1 to 2.5 μg/mL. Fractions with 16-epi-affinine combined good antioxidant (IC50= 65.59 to 74.69 μg/mL) and anticholinesterasic (IC50= 7.7 to 8.3 μg/mL) activities, representing an option for further studies aimed at treating neurodegenerative diseases.

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Bhambhani, Sweta, Kirtikumar R. Kondhare, and Ashok P. Giri. "Diversity in Chemical Structures and Biological Properties of Plant Alkaloids." Molecules 26, no. 11 (June 3, 2021): 3374. http://dx.doi.org/10.3390/molecules26113374.

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Phytochemicals belonging to the group of alkaloids are signature specialized metabolites endowed with countless biological activities. Plants are armored with these naturally produced nitrogenous compounds to combat numerous challenging environmental stress conditions. Traditional and modern healthcare systems have harnessed the potential of these organic compounds for the treatment of many ailments. Various chemical entities (functional groups) attached to the central moiety are responsible for their diverse range of biological properties. The development of the characterization of these plant metabolites and the enzymes involved in their biosynthesis is of an utmost priority to deliver enhanced advantages in terms of biological properties and productivity. Further, the incorporation of whole/partial metabolic pathways in the heterologous system and/or the overexpression of biosynthetic steps in homologous systems have both become alternative and lucrative methods over chemical synthesis in recent times. Moreover, in-depth research on alkaloid biosynthetic pathways has revealed numerous chemical modifications that occur during alkaloidal conversions. These chemical reactions involve glycosylation, acylation, reduction, oxidation, and methylation steps, and they are usually responsible for conferring the biological activities possessed by alkaloids. In this review, we aim to discuss the alkaloidal group of plant specialized metabolites and their brief classification covering major categories. We also emphasize the diversity in the basic structures of plant alkaloids arising through enzymatically catalyzed structural modifications in certain plant species, as well as their emerging diverse biological activities. The role of alkaloids in plant defense and their mechanisms of action are also briefly discussed. Moreover, the commercial utilization of plant alkaloids in the marketplace displaying various applications has been enumerated.

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Breiterová, Kateřina, Miroslav Ločárek, Eliška Kohelová, Markéta Talácková, Daniela Hulcová, Lubomír Opletal, and Lucie Cahlíková. "Daffodils as Potential Crops of Biologically-active Compounds: Assessment of 40 Ornamental Taxa for their Alkaloid Profile and Cholinesterases Inhibition Activity." Natural Product Communications 13, no. 4 (April 2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300410.

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Many varieties of Narcissus (Amaryllidaceae) are planted on a large scale for ornamental purposes and at the same time they represent a rich reservoir of potential small chemical molecules that display several medicinal properties. Of the Amaryllidaceae alkaloids, considerable attention has been given to galanthamine, which possesses acetylcholinesterase inhibitory activity. Recent investigation has shown the pharmaceutical potential of other Amaryllidaceae alkaloids, such as lycorine, haemanthamine, and pancratistatine, primarily as anticancer drugs. In the current study, 40 Narcissus taxa were evaluated for their alkaloid profile by GC-MS. The aim of this work was to find the most suitable Narcissus varieties for a reliable source of galanthamine, lycorine, and haemanthamine for commercial production. Based on their mass spectra, 97 typical Amaryllidaceae alkaloids were detected of which 49 were identified. The highest concentrations of pharmaceutically-interesting Amaryllidaceae alkaloids were identified in the ornamental taxa N. cv Sundisc (galanthamine), N. cv. Jenny (lycorine), and N. cv. Sealing (haemanthamine). All alkaloidal extracts were also screened for their acetylcholinesterase and butyrylcholinesterase inhibitory activities.

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Berkova, Strahil, and Rawia Zayed. "Comparison of Tropane Alkaloid Spectra Between Datura innoxia Grown in Egypt and Bulgaria." Zeitschrift für Naturforschung C 59, no. 3-4 (April 1, 2004): 184–86. http://dx.doi.org/10.1515/znc-2004-3-409.

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The alkaloid spectra of Datura innoxia plants grown in Egypt and Bulgaria were investigated by GC-MS. Thirty-eight alkaloids were detected in the roots, leaves and fruits of the plants. Five new alkaloids for D. innoxia are reported. Alkaloid spectra of Egyptian and Bulgarian plants differ significantly in respect to their alkaloid composition and main alkaloids accumulated in the plant organs.

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Doncheva, Tsvetelina, Gabriela Yordanova, Vassil Vutov, Nadezhda Kostova, and Stefan Philipov. "Comparative Study of Alkaloid Pattern of Four Bulgarian Fumaria Species." Natural Product Communications 11, no. 2 (February 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100220.

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The alkaloid pattern of four Fumaria species ( Fumaria kralikii, Fumaria rostellata, Fumaria schleicherii, Fumaria thuretii) growing in Bulgaria was investigated by GC-MS and twenty isoquinoline alkaloids were determined. Phytochemical investigation of the alkaloid composition on Fumaria thuretii Boiss was made for the first time. The alkaloid profile of the species was compared at two levels, between different species and within two species from different habitats. Two chemotypical groups, based on the types of isoquinoline alkaloids were suggested. To group A belong species F. kralikii, F. rostellata (F. r. 1) and F. thuretii containing more than 50% spirobenzylisoquinoline alkaloids of the crude alkaloid mixtures. To group B belong species F. rostellata (F. r. 2) and F. schleicherii containing more than 40% protopine alkaloids and relatively high percentage phthaldeisoquinoline alkaloids (11–19%). In group A phthaldeisoquinoline alkaloids were not detected.

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AL-Khateeb, Iqbal Hasan. "A New Method for the Isolation and Purification of Trigonelline as Hydrochloride from Trigonella foenum-graecum L." Baghdad Science Journal 16, no. 3 (September 1, 2019): 0550. http://dx.doi.org/10.21123/bsj.2019.16.3.0550.

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Separation of Trigonelline, the major alkaloid in fenugreek seeds, is difficult because the extract of these seeds usually contains Trigonelline, choline, mucilage, and steroidal saponins, in addition to some other substances. This study amis to isolate the quaternary ammonium alkaloid (Trigonelline) and choline from fenugreek seeds (Trigonella-foenum graecum L.) which have similar physiochemical properties by modifying of the classical method. Seeds were defatted and then extracted with methanol. The presence of alkaloids was detected by using Mayer's and Dragendorff's reagents. In this work, trigonilline was isolated with traces of choline by subsequent processes of purification using analytical and preparative TLC techniques. Further identification was done by using HPLC, IR and MP. Pure Trigonelline was isolated from the seeds of Trigonella-foenum graecum excluding other alkaloid like choline. In this study, a new, fast and convenient method for isolation and purification of Trigonelline from fenugreek seeds has been established. Unlike other methods, this one excludes all the non-alkaloidal components from the fenugreek seeds extract.

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Sun, Bo, Yu-Xiao Tian, Fen Zhang, Qing Chen, Yong Zhang, Ya Luo, Xiao-Rong Wang, Fu-Cheng Lin, Jun Yang, and Hao-Ru Tang. "Variations of Alkaloid Accumulation and Gene Transcription in Nicotiana tabacum." Biomolecules 8, no. 4 (October 15, 2018): 114. http://dx.doi.org/10.3390/biom8040114.

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To increase the understanding of alkaloid biosynthesis in Nicotiana tabacum during whole plant growth periods, variations of the contents of alkaloids and the transcription of key biosynthetic genes in fresh leaves were investigated in three varieties at five developmental stages. Six alkaloids were analyzed by gas chromatograph–mass spectrometry (GC–MS) and the most abundant alkaloid was observed during the upper leaves maturing stage in the varieties, among which the alkaloid content of K326 was the highest. Considering the genetic effect, variance analysis indicated that the developmental stage played a predominant role in alkaloid accumulation. Moreover, the levels of biosynthetic gene transcripts in the leaves at the vigorous growing stage might contribute to the contents of alkaloids in the leaves during the maturing stages. To further illuminate the metabolism of alkaloid biosynthesis, a correlation among alkaloids was also documented.

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Dank, Christian, Randy Sanichar, Ken-Loon Choo, Madeline Olsen, and Mark Lautens. "Recent Advances Towards Syntheses of Diterpenoid Alkaloids." Synthesis 51, no. 21 (August 5, 2019): 3915–46. http://dx.doi.org/10.1055/s-0037-1611897.

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The diterpenoid alkaloids serve as a rich source of synthetic targets for organic chemists, due to the intriguing structure of the overlapping ring systems, along with biological activities commonly associated with compounds of this group. Fifteen total syntheses and numerous synthetic studies towards construction of ring fragments have been reported since 2010. This review article gives a brief overview of diterpenoid alkaloids and summarizes the recent synthetic efforts.1 Introduction1.1 Structural Classification and Biosynthetic Origin1.2 Structure Elucidation of the Aconitum Alkaloids2 Total Syntheses2.1 C18-Diterpenoid Alkaloids2.2 C19-Diterpenoid Alkaloids2.3 C20-Diterpenoid Alkaloids3 Strategies To Synthesize Ring Systems3.1 Radical-Based Cyclizations3.2 Ruthenium-Mediated Enyne Cycloisomerization3.3 Reductive Coupling3.4 Diels–Alder Reactions3.5 Oxidative Dearomatization/Diels–Alder Sequence3.6 Transannular Aziridation3.7 Intramolecular [5+2] Cycloaddition3.8 Miscellaneous4 Conclusion

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Chaplin, JF. "Die Züchtung von TabakimHinblick auf verschieden hohe Alkaloidgehalte - Tobacco Breeding in View of Different Levels of Alcaloid Contents." Beiträge zur Tabakforschung International/Contributions to Tobacco Research 14, no. 1 (December 1, 1987): 1–9. http://dx.doi.org/10.2478/cttr-2013-0578.

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AbstractTwo systems of genetic control are involved in the quality and level of total alkaloids in tobacco (Nicotianatabacum L.). A single locus controls the conversion of nicotine to nornicotine and two loci control total alkaloid levels. These levels may be further modified by minor genes or quantitative factors. Breeding lines and cultivars of flue-cured tobacco have been developed with varying levels of total alkaloids (nicotine). Levels of nicotine in tobacco range from near zero in cigar strains up to 4.5 % in Burley varieties. Within the collection of N. tabacumgermplasm and Nicotiana species maintained by the Agricultural Research Service of the U.S. Department of Agriculture, total alkaloid levels range from 0.20 % to 7.87 %. Flue-cured lines of tobacco with varying levels of total alkaloids have been developed and characterized. In general the high alkaloid lines had the highest grade indexes. All of the extremely low alkaloid lines were also lower in grade index indicating that total alkaloids do have some relationship with the grade index. The high total alkaloid lines were lower in yield. However, it is believed that the levels of total alkaloids reported do not result from yield variation. N. rustica generally has considerably higher total alkaloid levels, based on percent dry weight, than N. tabacum. With the stabilizing of a low total alkaloid line of N. tabacum (0.20 %) it was feasible to introgress the gene(s) for alkaloid production from N. rustica into N. tabacum. Indications are that more than one gene is responsible for total alkaloid production in this material. Also preliminary indications are that the genes for total alkaloid production in N. rustica may be the same as those in N. tabacum.

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Lim, Hyeonggeun, Sikwang Seong, and Sunkyu Han. "Syntheses of Post-Iboga Alkaloids." Synthesis 51, no. 14 (February 19, 2019): 2737–58. http://dx.doi.org/10.1055/s-0037-1612061.

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Post-iboga alkaloids are secondary metabolites that are biosynthetically derived from iboga-type alkaloids via rearrangements of the indole and/or isoquinuclidine moieties. Herein, we categorize post-iboga alkaloids into five types based on the biosynthetic mode of transformation of the iboga scaffold. We then describe reported syntheses of post-iboga alkaloids, including our laboratory’s recent contributions, based on our own categorization.1 Introduction1.1 Iboga and Post-Iboga Alkaloids1.2 Classification of Post-Iboga Alkaloids1.2.1 Introduction to Type I Post-Iboga Alkaloids1.2.2 Introduction to Type II Post-Iboga Alkaloids1.2.3 Introduction to Type III Post-Iboga Alkaloids1.2.4 Introduction to Type IV Post-Iboga Alkaloids1.2.5 Introduction to Type V Post-Iboga Alkaloids2 Syntheses of Post-Iboga Alkaloids2.1 Syntheses of Type I Post-Iboga Alkaloids2.1.1 Syntheses of Monomeric Type I Post-Iboga Alkaloids2.1.2 Syntheses of Dimeric Type I Post-Iboga Alkaloids2.2 Syntheses of Type II Post-Iboga Alkaloids2.3 Synthetic Studies Toward Type III Post-Iboga Alkaloids2.4 Syntheses of Type IV Post-Iboga Alkaloids2.5 Synthesis of Type V Post-Iboga Alkaloids3 Conclusion and Outlook

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26

Vieira, Ivo J. C., Walter L. B. Medeiros, Cecilia S. Monnerat, Jucimar J. Souza, Leda Mathias, Raimundo Braz-Filho, Angelo C. Pinto, Priscila M. Sousa, Claudia M. Rezende, and Rosângela De A. Epifanio. "Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures." Anais da Academia Brasileira de Ciências 80, no. 3 (September 2008): 419–26. http://dx.doi.org/10.1590/s0001-37652008000300003.

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The pharmacotherapyfor Alzheimer's disease (AD) includes the use of acetylcholinesterase inhibitors (AChEI). Recent investigations for novel AD therapeutic agents from plants suggested that Tabernaemontana genus is a promising source of novel anticholinesterasic indole alkaloids. In this work two fast screening techniques were combined in order to easily identify novel cholinesterase inhibitors (ChEI). Gas chromatography-mass spectrometry (GC-MS) of the less polar alkaloidic fractions obtained from the acid-base extraction of the stalk of T. laeta revealed thirteen monoindole alkaloids, four of them confirmed by co-injection with previously isolated alkaloids. The others were tentatively identified by mass fragmentation analysis. By gas chromatography with flame ionization detection (GC-FID) and using isatin as internal standard, affinisine and voachalotine were determined as major compounds. These fractions and fourteen previously isolated alkaloids, obtained from root bark of T. laeta and T. hystrix were investigated for acetyl (AChE) and butyrylcholinesterase (BuChE) inhibitory activities by the modified Ellman's method in thin layer chromatography(TLC-ChEI). Results showed selective inhibition of the alkaloids heyneanine and Nb-methylvoachalotine for BuChE, and 19-epi-isovoacristine for AChE, whereas olivacine, affinisine, ibogamine, affinine, conodurine and hystrixnineinhibited both enzymes. In addition to confirming that monoterpenoid indole alkaloids can be novel therapeutic agents for AD, this is the first report of the ChEI activity of olivacine, a pyridocarbazole alkaloid.

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Berkov, Strahil, Luba Evstatieva, and Simeon Popov. "Alkaloids in Bulgarian Pancratium maritimum L." Zeitschrift für Naturforschung C 59, no. 1-2 (February 1, 2004): 65–69. http://dx.doi.org/10.1515/znc-2004-1-214.

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A GC/MS analysis of alkaloids from leaves, bulbs and roots of Pancratium maritimum was performed. From the identified 16 alkaloids, 5 alkaloids were reported for the first time for this plant. Several compounds with pharmacological activity were found. Haemanthamine was main alkaloid in the leaves and bulbs whereas galanthane was found to be main alkaloid in roots.

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28

Jones, Nadiá M., M. Gabriela Bernardo-Gil, and M. Graço Lourenco. "Comparison of Methods for Extraction of Tobacco Alkaloids." Journal of AOAC INTERNATIONAL 84, no. 2 (March 1, 2001): 309–16. http://dx.doi.org/10.1093/jaoac/84.2.309.

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Abstract Ultrasound and microwave techniques were used to extract tobacco alkaloids, and response surface methodology was used to optimize extraction conditions. Ultrasonic technique factors were temperature, 30–85°C; time, 3–45 min; solvent volume, 8–80 mL. Microwave extraction factors were pressure, 15–75 psi; time, 3–40 min; power, 30–90% of the maximum magnetron power of 650 W. Soxhlet and solvent AOAC-modified extraction methods were also applied after some improvements. Nicotine, nornicotine, anabasine, and anatabine were quantified by gas chromatography. A steam distillation International Standards Organization method for total alkaloid evaluation was used as reference. The results obtained by the different methods were compared using a least squares deviation test. The ultrasonic and the proposed modified-AOAC extraction method were the more convenient with regard to practicability and precision. The relative deviations (n = 5) were as follows: For the ultrasonic method in low-level alkaloid tobaccos, 0.7% nicotine and 1.4–14% minor alkaloids; in high-level alkaloid tobaccos, 2.4% nicotine and 4.5–5.1% minor alkaloids. For the modified AOAC method in low-level alkaloid tobaccos, 0.9% nicotine and 2.4–11.6% minor alkaloids; and in high-level alkaloid tobaccos, 1.7% nicotine and 2.0–2.4% minor alkaloids.

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29

Meles, Dewa Ketut, Wurlina Wurlina, and Dewa Putu Anom Adnyana. "Measurement of Alkaloids Achyranthes Aspera Linn Level Using Thin Layer Chromatography Method and High-Performance Liquid Chromatography." KnE Life Sciences 3, no. 6 (December 3, 2017): 378. http://dx.doi.org/10.18502/kls.v3i6.1146.

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One of the plants with the potential to be developed into a raw material for anti-breast cancer drugs is jarong (Achyranthes aspera linn). Allegedly alkaloid of Achryranthes aspera linn leaves showed anticancer activity in vitro in mice myeloma cells is extremely potent. In vivo study showed that the alkaloid Achyranthes aspera linn causes apoptosis and healing in breast cancer cells in mice induced by benzopyrene. Alkaloids of Achyranthes aspera linn leaves as anticancer been listed on Incestual Property Rights (IPR) since October 12, 2012, with number P00201299839. This study aims to prove the existence of alkaloids in the leaves of Achyranthes aspera linn using thin layer chromatography (TLC), determine the level of alkaloids in the leaves alkaloid fraction of Achyranthes aspera using High-Performance Liquid Chromatography (HPLC) and alkaloid fraction dose as an anticancer and dosing for the study. Alkaloid qualitative measurement results with thin layer chromatography showed alkaloid in orange. Alkaloid levels using HPLC has a retention time of 3.482 minutes, a wavelength of 254 nm, there are 13 kinds of chemical substances with the major components amounted to 52.36% alkaloids, the other component is the green substance with a peak area of 13.0624%, while other chemical substances in a very small peak area of between 0.428% until 8.3598%. Alkaloid fraction dose of Achyranthes aspera used in the study as anticancer is controlled the dose of 0 mg/kg, 1 treatment dose of 60 mg/kg, 2 treatment dose of 75 mg/kg and 3 treatment dose of 90 mg/kg. Keywords: Alkaloids, Achyranthes aspera linn, TLC, HPLC.

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30

Đukić, Miloš, Jelena Jovanović, Gordana Stojanović, and Snežana Jovanović. "Chemical composition of the alkaloid extract isolated from Hylotelephium spectabile (Boreau) H. Ohba x telephium (L.) H. Ohba aerial parts." Advanced Technologies 10, no. 2 (2021): 5–8. http://dx.doi.org/10.5937/savteh2102005d.

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There are many motives to study alkaloids within Crassulaceae family, such as chemotaxonomic consideration of alkaloid distribution and evaluation of their biological potential. Data on alkaloids from Sedum telephium (syn. H. telephium) aroused interest for further alkaloid investigation within the genus Hylotelephium H. Ohba. Thus, the aim of this study was to investigate and characterize other plant sources of alkaloids from the same genus. An alkaloid extract (AE-HS) was isolated from fresh aerial parts of a cultivated hybrid H. spectabile x telephium. The chemical composition of AE-HS was determined by GC-MS (gas chromatography - mass spectrometry) method. Eight components were identified, which made up 91.8% of the sample. The most present component of AE-HS was g-crotonolactone (78.6%) followed by 3-methyl-2-butenal (8.6%) and (E)-coniferyl alcohol (2.8%). Nicotine was identified as the only alkaloid in the AE-HS (0.4%). Along with many non-alkaloid compounds, a previous study found six alkaloids in AE of S. telephium (~7%), suggesting differences from our results. Additionally, alkaloid distribution is limited within other genera of the family and belonging to the same genus does not mean a uniform qualitative composition. Further analyzes of AEs of Hylotelephium taxa would certainly shed light on the pattern of alkaloid distribution.

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31

Scott, Peter M., Gary A. Lombaert, Peter Pellaers, Stanley Bacler, and Judy Lappi. "Ergot Alkaloids in Grain Foods Sold in Canada." Journal of AOAC INTERNATIONAL 75, no. 5 (September 1, 1992): 773–79. http://dx.doi.org/10.1093/jaoac/75.5.773.

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Abstract Six pharmacologically active ergot alkaloids (ergonovine [ergometrine], ergosine, ergotamine, ergocornine, α-ergokryptine, and ergocristine) were determined by liquid chromatography with fluorescence detection in over 400 samples of grain foods. The survey was conducted over a 6-year period for rye flour, wheat flour, and bran/bran cereal, and a 5-year period for rye bread/crispbread; triticale flour was analyzed over a total of 3 years. The predominant alkaloids found were ergocristine and ergotamine. Rye flour was the most contaminated food; the incidence of alkaloid-positive samples was 118/128, annual mean concentrations of total alkaloids in positive samples ranged from 70 to 414 ng/g, and 1 sample contained as high as 3972 ng total alkaloids/g. In wheat flour, total alkaloid concentrations were much lower than in rye flour, with annual means in positive samples (68/93) of 15-68 ng/g. Bran/bran cereal had alkaloid concentrations similar to those in wheat flour, with annual means of 12-69 ng total alkaloids/g positive samples (incidence 29/35). Triticale flour was also an important source of ergot alkaloids; incidence was 24/26, and annual mean total alkaloid concentrations in positive samples were 46-283 ng/g. Ergot alkaloids were found in rye bread (46/100) and other heat-processed rye flour products (6/14). Annual mean total alkaloids in positive rye bread/crispbread samples ranged from 4.8 to 100 ng/g; the latter included a sample with 1248 ng total alkaloids/g.

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32

Panaccione, Daniel, James Kotcon, Christopher Schardl, Richard Johnson, and Joseph Morton. "Ergot alkaloids are not essential for endophytic fungus-associated population suppression of the lesion nematode, Pratylenchus scribneri, on perennial ryegrass." Nematology 8, no. 4 (2006): 583–90. http://dx.doi.org/10.1163/156854106778614074.

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AbstractSeveral endophytic fungi of the genus Neotyphodium form symbiotic associations with Lolium spp. grasses and are renowned for production of bioactive alkaloids such as ergot alkaloids. Some of these endophytes make their grass partners less suitable as hosts for endoparasitic nematodes, including Pratylenchus spp. The potential for ergot alkaloids to affect nematode motility was investigated in vitro. Ergovaline, the ergot alkaloid pathway end product of several Neotyphodium spp., was the only ergot alkaloid tested that inhibited motility of Pratylenchus scribneri. The association of ergot alkaloids with nematode population suppression was examined in glasshouse experiments with strains of the perennial ryegrass endophyte Neotyphodium sp. isolate Lp1 (syn. Neotyphodium lolii × Epichloë typhina) that have been genetically modified to lack ergot alkaloids or to have an altered ergot alkaloid profile. Populations of P. scribneri were significantly smaller in pots of perennial ryegrass containing the wild-type, ergot alkaloid-producing endophyte than in pots of endophyte-free perennial ryegrass. Elimination of certain complex ergot alkaloids (ergovaline and lysergic acid amides) in one gene knockout strain, or complete elimination of ergot alkaloids in another, did not affect the ability of the endophyte to suppress populations of nematode. Presence and concentrations of ergot alkaloids in pseudostems were as expected based on presence and genotype of endophyte in each plant, but frequently were undetectable or in low concentration in roots. The data indicate that ergot alkaloids do not contribute significantly to the endophyte-associated suppression of Pratylenchus spp.

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33

Turner, Matthew, Roberto Cruz, Jordan Elwell, John French, Jared Mattos, and Owen McDougal. "Native V. californicum Alkaloid Combinations Induce Differential Inhibition of Sonic Hedgehog Signaling." Molecules 23, no. 9 (September 1, 2018): 2222. http://dx.doi.org/10.3390/molecules23092222.

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Veratrum californicum is a rich source of steroidal alkaloids such as cyclopamine, a known inhibitor of the Hedgehog (Hh) signaling pathway. Here we provide a detailed analysis of the alkaloid composition of V. californicum by plant part through quantitative analysis of cyclopamine, veratramine, muldamine and isorubijervine in the leaf, stem and root/rhizome of the plant. To determine whether additional alkaloids in the extracts contribute to Hh signaling inhibition, the concentrations of these four alkaloids present in extracts were replicated using commercially available standards, followed by comparison of extracts to alkaloid standard mixtures for inhibition of Hh signaling using Shh-Light II cells. Alkaloid combinations enhanced Hh signaling pathway antagonism compared to cyclopamine alone, and significant differences were observed in the Hh pathway inhibition between the stem and root/rhizome extracts and their corresponding alkaloid standard mixtures, indicating that additional alkaloids present in these extracts are capable of inhibiting Hh signaling.

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Nikolic, Milan, and Sinisa Djordjevic. "Alkaloids in the pharmaceutical industry: Structure, isolation and application." Chemical Industry 57, no. 10 (2003): 471–78. http://dx.doi.org/10.2298/hemind0310471n.

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By the end of the 18th and the beginning of the 19th century a new era began in medicine, pharmaceutics and chemistry that was strongly connected with alkaloids and alkaloid drugs. Even before that it was known that certain drugs administered in limited doses were medicines, and toxic if taken in larger doses (opium, coke leaves, belladonna roots, monkshood tubers crocus or hemlock seeds). However, the identification, isolation and structural characterization of the active ingredients of the alkaloid drugs was only possible in the mid 20th century by the use of modern extraction equipment and instrumental methods (NMR, X-ray diffraction and others).In spite of continuing use over a long time, there is still great interest in investigating new drugs, potential raw materials for the pharmaceutical industry, as well as the more detailed investigation and definition of bio-active components and the indication of their activity range, and the partial synthesis of new alkaloid molecules based on natural alkaloids. The scope of these investigations, especially in the field of semi-synthesis is to make better use of the bio-active ingredients of alkaloid drugs, i.e. to improve the pharmacological effect (stronger and prolonged effect of the medicine, decreased toxicity and side effects), or to extend or change the applications. A combined classification of alkaloids was used, based on the chemical structure and origin, i.e. the source of their isolation to study alkaloid structure. For practical reasons, the following classification of alkaloids was used: ergot alkaloids, poppy alkaloids, tropanic alkaloids purine derivative alkaloids, carbon-cyclic alkaloids, and other alkaloids. The second part of this report presents a table of general procedures for alkaloid isolation from plant drugs (extraction by water non-miscible solvents, extraction by water-miscible solvents and extraction by diluted acid solutions). Also, methods for obtaining chelidonine and glaucine as hydrochloride bases and salts were presented in more details. Data from leading world pharmacopoeias (Ph. Eur. Ill/s 2000, DAB 1996, USP 23, JP XIII, BP 1993, Ph. Jug. IV) were used in the study of application of the pure alkaloids in pharmaceutical forms with predetermined doses. A comparative study of these data shows that a great number of preparations are produced worldwide based on alkaloids and alkaloids with modified structure. These medicines have found use in modern therapeutic practice in many countries. Most products are produced on the basis of caffeine, theophylline, ephedrine, atropine, scopolamine, reserpine and pilocarpine.

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35

Santana, Omar, Matías Reina, Ana Luisa Anaya, Fidel Hernández, M. Elena Izquierdo, and Azucena González-Coloma. "3-O-Acetyl-narcissidine, a Bioactive Alkaloid from Hippeastrum puniceum Lam. (Amaryllidaceae)." Zeitschrift für Naturforschung C 63, no. 9-10 (October 1, 2008): 639–43. http://dx.doi.org/10.1515/znc-2008-9-1004.

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In the context of the study on plant defensive compounds we have isolated the main alkaloid from Hippeastrum puniceum (Amaryllidaceae), 3-O-acetyl-narcissidine (1), and its biological activities tested against two divergent insect species and several plant species. 1 was isolated from the bioactive alkaloidal fraction of H. puniceum. Its chemical structure was established by spectroscopic analysis. The biological activity tests showed that 1 is an antifeedant against the polyphagous insect Spodoptera littoralis but not against the olyphage Leptinotarsa decemlineata. Furthermore, the root growth of Amaranthus hypochondriacus, Rottboellia cochinchinensis, Panicum maximum and Solanum lycopersicum was significantly affected by 1. These results suggest a plant protective role for H. puniceum alkaloids.

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36

Cahlíková, Lucie, Radim Kučera, Anna Hošt’álková, Jiří Klimeš, and Lubomír Opletal. "Identification of Pavinane Alkaloids in the Genera Argemone and Eschscholzia by GC-MS." Natural Product Communications 7, no. 10 (October 2012): 1934578X1200701. http://dx.doi.org/10.1177/1934578x1200701008.

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The genera Eschscholtzia and Argemone(Papaveraceae) represent a rich source of pavinane alkaloids, the identification of which in alkaloid extracts is generally problematic without standards. The alkaloid extracts of three Argemone and four Eschscholtzia species were analyzed using GC-MS. The alkaloids were identified based on comparison of their mass spectra with commercial libraries, with reported data in the literature and with spectra of reference compounds. A total of 23 alkaloids of six structural types (pavinane, protopine, benzylisoquinoline, benzophenanthridine, aporphine and protoberberine) were identified. The fragmentation pathway of pavinane alkaloids was used for their identification. O-Methylneocaryachine has been reported for the first time from a natural sources and the alkaloid pattern of Eschscholzia pulchella has been analyzed and described for the first time.

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37

Bäumel, P., W. D. Jeschke, L. Witte, F. C. Czygan, and P. Proksch. "Uptake and Transport of Quinolizidine Alkaloids in Cuscuta reflex a Parasitizing on Lupinus angustifolius." Zeitschrift für Naturforschung C 48, no. 5-6 (June 1, 1993): 436–43. http://dx.doi.org/10.1515/znc-1993-5-607.

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Abstract Cuscuta reflexa, Lupinus angustifolius, Quinolizidine Alkaloids, Parasitism During parasitism on Lupinus angustifolius the phanerogamic parasite Cuscuta reflexa takes up quinolizidine alkaloids from L. angustifolius via haustoria that tap xylem and phloem vessels of the host. The alkaloid pattern of the haustorial region of C. reflexa as revealed by GLC as well as by GLC-M S closely resembles that of infested lupin stems. With increasing distance from the haustoria towards the apex of C. reflexa the complex alkaloid pattern of the host is significantly reduced. Whereas alkaloid esters such as 13-benzoyloxylupanine and 13-cinnamoyloxy-lupanine are prominent peaks in the alkaloid profiles of the host as well as of the haustorial region of the parasite they are not detected in the apex of C. reflexa but are replaced by their respective alcohol com ponent 13-hydroxylupanine. This change of alkaloid profiles is accompanied by a strong decline of alkaloid concentration which drops from ap proximately 11 m g/g dry wt. in the haustorial region of C. reflexa to 0.2 m g/g dry wt. in the apex. Alkaloid analyses of xylem sap and phloem exudate from L. angustifolius suggest that uptake of host plant alkaloids by C. reflexa is mainly via the phloem even though a contribution of xylem sap to the supply of alkaloids to the parasite can not be excluded.

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38

Shukla, S., H. K. Yadav, A. Rastogi, B. K. Mishra, and S. P. Singh. "Alkaloid diversity in relation to breeding for specifi c alkaloids in opium poppy (Papaver somniferum L.)." Czech Journal of Genetics and Plant Breeding 46, No. 4 (December 14, 2010): 164–69. http://dx.doi.org/10.17221/96/2009-cjgpb.

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Papaver somniferum is a chief source of diverse physiologically active alkaloids, required by the pharmaceutical industry. The present study describes the diversity of the alkaloid spectrum of 122 opium poppy accessions of Indian origin by means of a cluster analysis based on Mahalanobis generalised distances. The accessions could be grouped into 11 clusters according to their relationship between the contents of morphine, codeine, thebaine, narcotine and papaverine in raw opium. The diversity of the alkaloid spectrum of 11 clusters reflected the very low correlations between the contents of the individual alkaloids across the 122 entries, found earlier. The clusters represented almost all possible combinations of the high content of an alkaloid with high or low content of another alkaloid. Although on average the morphine content exceeds the sum of the other four alkaloids, in one cluster the narcotine content (15.3%) was even higher than that of morphine (14.6%) and the content of the remaining alkaloids was also extremely high. The variation range among the clusters was for papaverine between 0.14% to 5.3%, while for morphine between 12.4% to 18.0%. The results indicate a large space for the breeding of opium poppy for individual alkaloids or particular combinations of alkaloids, as required by pharmaceutical industries.

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39

Grusie, T., V. Cowan, J. Singh, J. McKinnon, and B. Blakley. "Proportions of predominant Ergot alkaloids (Claviceps purpurea) detected in Western Canadian grains from 2014 to 2016." World Mycotoxin Journal 11, no. 2 (April 25, 2018): 259–64. http://dx.doi.org/10.3920/wmj2017.2241.

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Ergot alkaloids, produced by the fungus Claviceps purpurea, are contaminants of cereal crops. Depending on various factors, the relative composition of individual ergot alkaloids can differ among samples. The objective was to determine if the percentage of individual ergot alkaloids were similar across different cereal grains (barley n=39, rye n=7, triticale n=9, wheat n=94) collected in Western Canada over different years. Ergocristine was the predominant alkaloid accounting for half of the total alkaloids in all grain types. This study documented that barley, rye, triticale and wheat collected across Western Canada had similar percentages of ergocornine (6±1%, P=0.201), ergocristine (48±2%, P=0.939), ergocryptine (17±2%, P=0.302) and ergosine (5±0.5%, P=0.239). There were differences between grain types for ergometrine (P=0.027) and ergotamine (P=0.011), which ranged between 6 to 13% and 11 to 24%, respectively, of the total alkaloid content in different cereals. Both barley and wheat alkaloid percentages were similar between 2015 and 2016; ergocornine (7±1%, P=0.969), ergocristine (47±2%, P=0.680), ergocryptine (18±2%, P=0.572), ergometrine (8±1%, P=0.080), ergosine (15±1%, P=0.119) and ergotamine (P=0.189). The ergocornine percentage was higher in wheat (P=0.017) as compared to barley for 2015/2016 samples. Ergometrine was higher in barley (P=0.002) as compared to wheat for 2015/2016 samples. While two of the alkaloid proportions varied statistically, overall proportions of the six ergot alkaloids were comparable among the four grain types collected across Western Canada. If proportions of ergot alkaloids are similar across a region, then it may be deemed acceptable to recommend a maximum total ergot alkaloid concentration for that region. However, areas that exhibit variation among the ergot alkaloid proportions, individual ergot alkaloid guidelines based on a toxic equivalence factor, may be more appropriate. In contrast, since major differences were not seen between years or grain type, from a producer perspective there may be limited biological/toxicological significance for individual alkaloid guidelines.

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Ayer, William A., Lois M. Browne, A. Warren Elgersma, and Peter P. Singer. "Identification of some L-numbered Lycopodium alkaloids." Canadian Journal of Chemistry 68, no. 8 (August 1, 1990): 1300–1304. http://dx.doi.org/10.1139/v90-200.

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The pioneering research on Lycopodium alkaloids carried out by R. H. F. Manske and L. Marion led to the characterization of a large number of alkaloids. Many of these alkaloids were designated by numbers preceded by an L (e.g., L1, which has since been shown to be dihydrolycopodine). While the identity of many of these alkaloids has now been established, several remain unreported. We have examined samples of alkaloids L15, L16, L17, L18, L22, L24, L25, L26, L28, L29, L31, and L35, obtained from Marion's collection, by GC–MS and GC–IR, and report herein the identity of these alkaloids and alkaloid mixtures. Most of the samples proved to be mixtures of known alkaloids. Acetylannofoline (5), a component of alkaloid L17, and 5,15-oxidolycopodane (9), a component of alkaloids L28 and L31, are identified for the first time as natural products. A complete listing of the L-numbered alkaloids is provided. Keywords: Lycopodium alkaloids, alkaloids, acetylannofoline, oxidolycopodane.

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Sidibe, Mamadou Sadialiou, Olimjon Panjiyev, Rikhsivoy ZIYAEV, Sory Fofana, and Golib Shodiyev. "Alcaloides Des Annonacees : Xyloethiopine, Un Nouvel Alcaloide De Xylopia Aethiopica A.Rich." International Journal for Research in Applied Science and Engineering Technology 10, no. 3 (March 31, 2022): 1635–40. http://dx.doi.org/10.22214/ijraset.2022.41036.

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Abstract: We studied the alkaloid composition of Xylopia aethiopica A. Rich ( Annona-ceae) leaves collected in republic of Guinea and isolated for the first time and identified the 3 benzyltetrahydroisoquinolines alkaloids: armépavine; coclaurine ; Nméthylcoclaurine, and a new alkaloid - xyloethiopine Keywords: Annonaceae; Xylopia aethiopica A. Rich., Alkaloids: benzyltetrahydroisoquinolines: armépavine ; coclaurine ; Nméthylcoclaurine ; xyloethiopine.

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Slavík, Jiří, Ladislav Dolejš, and Leonora Slavíková. "Alkaloids from Corydalis solida (L.) SW. mass spectrometry of quaternary benzylisoquinoline alkaloids." Collection of Czechoslovak Chemical Communications 50, no. 10 (1985): 2299–309. http://dx.doi.org/10.1135/cccc19852299.

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From the strongly polar fraction from the tubers of Corydalis solida (L.) SW., a new quaternary alkaloid, (+)-N-methyllaudanidinium iodide, was isolated after conversion to iodides. Mass spectrometric behaviour of this type of quaternary alkaloids is described. In the tubers (0.37% of alkaloids) the main alkaloid component is (+)- and (±)-tetrahydropalmatine; other dominant alkaloids include protopine, (+)-corydaline, allocryptopine, dehydrocorydaline and jatrorrhizine. (±)-Corybulbine, (+)-corypalmine, (-)-isocorypalmine, (-)-scoulerine, (-)-stylopine, corysamine, palmatine, (+)-N-methyllaudanidinium hydroxide, (-)-cis-N-methylcanadinium hydroxide and cis-N-methylstylopinium hydroxide represent minor alkaloids. The last three mentioned were isolated in the form of iodides. Bulbocapnine, coptisine, berberine and columbamine were detected in trace amounts. The main alkaloid of the aerial parts of the plant (0.35% of alkaloids) is berberine, accompanied by coptisine, (-)- and (±)-canadine, (-)-stylopine, isoboldine, protopine, columbamine and (-)-cis-N-methylcanadinium hydroxide (isolated in the form of iodide) as significant components. Among minor alkaloids allocryptopine, (-)-isocorypalmine, (+)-corypalmine, (±)- and (-)-tetrahydropalmatine, corysamine, dehydrothalictricavine, palmatine and cis-N-methylstylopinium hydroxide (as iodide) were isolated and trace amounts of jatrorrhizine and bulbocapnine were detected.

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Coyle, Christine M., and Daniel G. Panaccione. "An Ergot Alkaloid Biosynthesis Gene and Clustered Hypothetical Genes from Aspergillus fumigatus." Applied and Environmental Microbiology 71, no. 6 (June 2005): 3112–18. http://dx.doi.org/10.1128/aem.71.6.3112-3118.2005.

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ABSTRACT The ergot alkaloids are a family of indole-derived mycotoxins with a variety of significant biological activities. Aspergillus fumigatus, a common airborne fungus and opportunistic human pathogen, and several fungi in the relatively distant taxon Clavicipitaceae (clavicipitaceous fungi) produce different sets of ergot alkaloids. The ergot alkaloids of these divergent fungi share a four-member ergoline ring but differ in the number, type, and position of the side chains. Several genes required for ergot alkaloid production are known in the clavicipitaceous fungi, and these genes are clustered in the genome of the ergot fungus Claviceps purpurea. We investigated whether the ergot alkaloids of A. fumigatus have a common biosynthetic and genetic origin with those of the clavicipitaceous fungi. A homolog of dmaW, the gene controlling the determinant step in the ergot alkaloid pathway of clavicipitaceous fungi, was identified in the A. fumigatus genome. Knockout of dmaW eliminated all known ergot alkaloids from A. fumigatus, and complementation of the mutation restored ergot alkaloid production. Clustered with dmaW in the A. fumigatus genome are sequences corresponding to five genes previously proposed to encode steps in the ergot alkaloid pathway of C. purpurea, as well as additional sequences whose deduced protein products are consistent with their involvement in the ergot alkaloid pathway. The corresponding genes have similarities in their nucleotide sequences, but the orientations and positions within the cluster of several of these genes differ. The data indicate that the ergot alkaloid biosynthetic capabilities in A. fumigatus and the clavicipitaceous fungi had a common origin.

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Pawelka, Karl-Heinz, and Joachim Stöckigt. "Indole Alkaloids from Ochrosia elliptica Plant Cell Suspension Cultures." Zeitschrift für Naturforschung C 41, no. 4 (April 1, 1986): 381–84. http://dx.doi.org/10.1515/znc-1986-0402.

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From cell suspension cultures of Ochrosia elliptica Labill. eight different monoterpenoid indole alkaloids were isolated and comprised three alkaloid classes viz. Corynanthe/Heteroyohimbine (tetrahydroalstonine, cathenamine, pleiocarpamine and two methoxylated heteroyohimbines), Strychnos (norfluorocurarine), Apparicine (apparicine and epchrosine). A ll these compounds except the Strychnos alkaloid are biogenetically closely related to the known alkaloids occurring in Ochrosia plants, although such alkaloids have not previously been detected in O. elliptica. Epchrosine has not before been described as a natural product.

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45

Sarikaya, Buket Bozkurt, Nehir Unver Somer, Gulen Irem Kaya, Mustafa Ali Onur, Jaume Bastida, and Strahil Berkov. "GC-MS Investigation and Acetylcholinesterase Inhibitory Activity of Galanthus rizehensis." Zeitschrift für Naturforschung C 68, no. 3-4 (April 1, 2013): 118–24. http://dx.doi.org/10.1515/znc-2013-3-407.

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GC-MS (gas chromatography-mass spectrometry) analyses of alkaloids in the aerial parts and bulbs of Galanthus rizehensis Stern (Amaryllidaceae), collected during two different vegetation periods, was performed. Twenty three alkaloids were identified in four different alkaloid extracts. Acetylcholinesterase (AChE) inhibitory activities of the alkaloid extracts were tested. Both the highest alkaloid diversity and the most potent inhibitory activity (IC50 12.94 μg/ml) were obtained in extracts from the bulbs of G. rizehensis collected during the fruiting period.

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Táborská, Eva, Milena Mikešová, František Věžník, and Jiří Slavík. "Alkaloids of the two Hypecoum L. species." Collection of Czechoslovak Chemical Communications 52, no. 2 (1987): 508–13. http://dx.doi.org/10.1135/cccc19870508.

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Alkaloids from Hypecoum procumbens L. and H. leptocarpum HOOK. F. et THOMS. were investigated. Protopine was the dominant alkaloid in both species. From H. procumbens chelerythrine and corydine were newly isolated in addition to the earlier detected alkaloids allocryptopine, sanguinarine, coptisine, and isocorydine. From H. leptocarpum allocryptopine, isocorydine and corydine were isolated for the first time, in addition to the earlier described alkaloids protopine, sanguinarine, chelerythrine and coptisine. Cryptopine was detected chromatographically. From the fraction of strongly polar alkaloids of both species magnoflorine, (-)-trans-N-methyl-stylopinium hydroxide, and in small amounts a new secoberbine alkaloid of oxohypecorinine structure, procumbine (I), and two further alkaloids of unsolved structure were isolated in the form of iodides.

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Galek, R., E. Sawicka-Sienkiewicz, D. Zalewski, S. Stawiński, and K. Spychała. "Searching for low alkaloid forms in the Andean lupin (Lupinus mutabilis) collection." Czech Journal of Genetics and Plant Breeding 53, No. 2 (May 16, 2017): 55–62. http://dx.doi.org/10.17221/71/2016-cjgpb.

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The Andean lupin (Lupinus mutabilis Sweet) is the only cultivated species of the genus Lupinus originating from South America. Attempts were made to introduce this species to European soil and climatic conditions. The main disadvantages of the Andean lupin include too long and non-uniform maturation of pods in a plant, dropping flowers and pod buds, and a high alkaloid content (up to 5%). The aim of this study was to identify in post-mutagen treated material genotypes with low alkaloid content in seeds, which would be useful for improving L. mutabilis by breeding. The iodine test was annually performed to test the presence of alkaloids in seeds, using Lugol’s solution (I in KI). Based on the turbidity of the test samples, the investigated plants were divided into four groups, labelled as follows: G – individuals with a high content of alkaloids (very bitter), P – individuals with an intermediate content of alkaloids (bitter), PS – individuals with a low alkaloid content (fairly sweet) and S – individuals with a very low alkaloid level (sweet). For further propagation, mainly individuals from the S and PS groups were selected, and by part from the group P, while all bitter forms (G group) were rejected. Thirty chosen lines were examined for the content and composition of alkaloids by gas chromatography. The alkaloid content did not exceed 0.1% in 13 favourable lines, and even two lines had less than 0.05%. The seeds of the studied material contained 7 to 9 different alkaloids. The prevailing alkaloids in the seeds of the Andean lupin were 4-hydroxylupanine and lupanine. Significant progress has been achieved in reducing the content of alkaloids in subsequent generations of the investigated representatives of Lupinus mutabilis from South America.

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Magpantay, Hilbert D., Ivane N. Malaluan, Joe Anthony H. Manzano, Mark Tristan Quimque, Kirstin Rhys Pueblos, Natalija Moor, Simon Budde, et al. "Antibacterial and COX-2 Inhibitory Tetrahydrobisbenzylisoquinoline Alkaloids from the Philippine Medicinal Plant Phaeanthus ophthalmicus." Plants 10, no. 3 (March 1, 2021): 462. http://dx.doi.org/10.3390/plants10030462.

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Phaeanthus ophthalmicus (Roxb. ex G.Don) J.Sinclair (previously known as P. ebracteolatus (Presl) Merr) is a Philippine medicinal plant occurring as evergreen shrub in the lowland forests of Luzon islands. It is used traditionally by Filipinos to treat bacterial conjunctivitis, ulcer and wound infections. Based on previous investigations where cyclooxygenase-2 (COX-2) functions as immune-linked factor in infectious sensitivities to bacterial pathogens by triggering pro-inflammatory immune-associated reactions, we investigated the antimicrobial and COX inhibitory activities of the extracts and tetrahydrobisbenzylisoquinoline alkaloids of P. ophthalmicus in vitro and in silico to validate its ethnomedicinal uses. Thus, the dichloromethane–methanol (DCM–MeOH) crude extract and alkaloid extracts exhibiting antibacterial activities against drug-resistant bacterial strains such as methicillin-resistance Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus (VRE), Klebsiella pneumoniae + CRE and Pseudomonas aeruginosa + MBL afforded (+)-tetrandrine (1) and (+)-limacusine (2) as the major biologically active tetrahydrobisbenzylisoquinoline alkaloidal constituents after purification. Both tetrahydrobisbenzylisoquinoline alkaloids 1 and 2 showed broad spectrum antibacterial activity with strongest inhibition against the Gram-negative bacteria MβL-Pseudomonas aeruginosa Klebsiella pneumoniae + CRE. Interestingly, the alkaloid limacusine (2) showed selective inhibition against ovine COX-2 in vitro. These results were ascertained by molecular docking and molecular dynamics simulation experiments where alkaloid 2 showed strong affinity in the catalytic sites of Gram-negative bacterial enzymes P. aeruginosa elastase and K. pneumoniae KPC-2 carbapenemase (enzymes involved in infectivity mechanisms), and of ovine COX-2. Overall, our study provides credence on the ethnomedicinal use of the Philippine medicinal plant P. ophthalmicus as traditional plant-based adjuvant to treat bacterial conjunctivitis and other related infections. The antibacterial activities and selective COX-2 inhibition observed for limacusine (2) point to its role as the biologically active constituent of P. ophthalmicus. A limited number of drugs with COX-2 inhibitory properties like celecoxib also confer antibacterial activity. Thus, tetrahydrobisbenzyl alkaloids, especially 2, are promising pharmaceutical inspirations for developing treatments of bacterial/inflammation-related infections.

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Wink, Michael, and Ludger Witte. "Cell-Free Synthesis of the Alkaloids Ammodendrine and Smipine." Zeitschrift für Naturforschung C 42, no. 3 (March 1, 1987): 197–204. http://dx.doi.org/10.1515/znc-1987-0304.

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The bipiperidyl alkaloid ammodendrine was detected in 28 plant species as a minor alkaloid besides quinolizidine alkaloids. Cadaverine serves as a precursor for both quinolizidine alkaloids and for ammodendrine, since labelled cadaverine is incorporated into both rings of ammodendrine. Cell-free extracts of Lupinus arboreus and of Pisum sativum, which contain an active diamine oxidase form ammodendrine from cadaverine and pyruvate. In addition to ammodendrine other alkaloids such as smipine, tetrahydroanabasine and tripiperideine could be detected. Possible reaction schemes are discussed.

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Bracher, Franz, Dirk Hildebrand, and Ludger Ernst. "β-Carboline Alkaloids, V: Total Synthesis of the Antimicrobial Marine Alkaloid Eudistomin T. β-Carbolin-Alkaloide, 5. Mitt.: Totalsynthese des marinen Alkaloides Eudistomin T." Archiv der Pharmazie 327, no. 2 (1994): 121–22. http://dx.doi.org/10.1002/ardp.19943270212.

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Journal articles on the topic 'Alkaloidy'

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