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Journal articles on the topic '–Trihydroxy–12'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Fuchino, Hiroyuki, Hisanori Nakamura, Yuka Toyoshima, et al. "Two New Abietanes from Lycopodium deuterodensum." Australian Journal of Chemistry 51, no. 2 (1998): 175. http://dx.doi.org/10.1071/c97182.

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Two new abietanes, 6,11,14-trihydroxy-12-methoxyabieta-5,8,11,13-tetraene-3,7-dione (lycopod-abietane A) and 6,11,14-trihydroxy-12-methoxy-3α,18-cycloabieta-5,8,11,13-tetraen-7-one (lycopod-abietane B), were isolated from Lycopodium deuterodensum together with lycopodine, α-onocerin, 21-episerratenediol, 21-episerratriol and 16-oxoserratenediol.

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2

Matsuzaki, Keiichi, Kayo Murano, Yurika Endo, and Susumu Kitanaka. "Nortriterpene Saponins from Akebia trifoliata." Natural Product Communications 9, no. 12 (2014): 1934578X1400901. http://dx.doi.org/10.1177/1934578x1400901208.

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Three new nortriterpene saponins, 2α,3β,20α-trihydroxy-30-norolean-12-en-28-oic acid O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (3), 2α,3β,20α-trihydroxy-30-norolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (4), and 2α,3β,23-trihydroxy-30-noroleana-12,19-dien-28-oic acid O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (6), were isolated from the methanol extract of the pericarps of Akebia trifoliata Koidzumi (Lardizabalaceae), t

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3

Hosokawa, Masashi, Ching T. Hou та David Weisleder. "Production of Novel Tetrahydroxyfuranyl Fatty Acids from α-Linolenic Acid by Clavibacter sp. Strain ALA2". Applied and Environmental Microbiology 69, № 7 (2003): 3868–73. http://dx.doi.org/10.1128/aem.69.7.3868-3873.2003.

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ABSTRACT Previously, it was reported that a newly isolated microbial culture, Clavibacter sp. strain ALA2, produced trihydroxy unsaturated fatty acids, diepxoy bicyclic fatty acids, and tetrahydroxyfuranyl fatty acids (THFAs) from linoleic acid (C. T. Hou, J. Am. Oil Chem. Soc. 73:1359-1362, 1996; C. T. Hou and R. J. Forman III, J. Ind. Microbiol. Biotechnol. 24:275-276, 2000; C. T. Hou, H. Gardner, and W. Brown, J. Am. Oil Chem. Soc. 75:1483-1487, 1998; C. T. Hou, H. W. Gardner, and W. Brown, J. Am. Oil Chem. Soc. 78:1167-1169, 2001). In this study, we found that Clavibacter sp. strain ALA2 p

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4

Vera, Janne Rojas, Christopher G. Dacke, Gerald Blunden, and Asmita V. Patel. "Smooth Muscle Relaxant Triterpenoid Glycosides from Rubus idaeus (Raspberry) Leaves." Natural Product Communications 1, no. 9 (2006): 1934578X0600100. http://dx.doi.org/10.1177/1934578x0600100902.

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A methanol extract of Rubus idaeus leaves had a relaxant activity on transmurally stimulated Guinea pig ileum preparations in vitro. The extract, when fractionated by column chromatography, yielded two distinct bands with pharmacological activity. After extensive column and preparative TLC separation, several compounds with smooth muscle relaxant properties were obtained. From band two, three triterpenoid glycosides were characterized, which had significant muscle relaxant activity. From spectroscopic and spectrometric data, these were identified as 3β-(O-β-D-glucopyranosyl)-olean-12-ene-1α, 2

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5

Muema, Felix Wambua, Consolata Nanjala, Millicent Akinyi Oulo, and Phurpa Wangchuk. "Phytochemical Content and Antidiabetic Properties of Most Commonly Used Antidiabetic Medicinal Plants of Kenya." Molecules 28, no. 20 (2023): 7202. http://dx.doi.org/10.3390/molecules28207202.

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Traditional medicinal plants have been used for decades in folk medicines in the treatment and management of several ailments and diseases including diabetes, pain, ulcers, cancers, and wounds, among others. This study focused on the phytochemical and antidiabetic activity of the commonly used antidiabetic medicinal species in Kenya. Phytochemical profiling of these species revealed flavonoids and terpenoids as the major chemical classes reported which have been linked with strong biological activities against the aforementioned diseases, among others. However, out of the selected twenty-two s

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6

Arriaga-Giner, F. J., J. Rullkötter, T. M. Peakman, and E. Wollenweber. "New Triterpenes from the Frond Exudate of the Fern Notholaena rigida." Zeitschrift für Naturforschung C 46, no. 7-8 (1991): 507–12. http://dx.doi.org/10.1515/znc-1991-7-801.

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Abstract Two new triterpenoids, isolated from the frond exudate of the fern Notholaena rigida, have been identified as 3 β, 12 β,25-trihydroxy-(20 R-24 R)-epoxy-dammarane- 12-acetate (1), and 24 R,25-diO-isopropyliden-9(19)-cyclolanostan-3 β-ol (5), based on NMR spectroscopic studies.

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7

Vydrina, Valentina Afanasievna, Marina Petrovna Yakovleva, Aleksey Aleksandrovich Kravchenko, Rasul' Rustemovich Sayakhov, and Gumer Yusupovich Ishmuratov. "HYDROBORATION-OXIDATION OF GLYCIRRETHIC ACID’S DERIVATIVES." chemistry of plant raw material, no. 2 (June 10, 2020): 101–9. http://dx.doi.org/10.14258/jcprm.2020025468.

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The hydroboration-oxidation reaction is widely used in the chemistry of terpenoids both for proving the structure of new compounds isolated from natural raw materials and for the directed synthesis of low molecular weight bioregulators. Moreover, most of the known examples affect mono- and sesquiterpenes, a much smaller number - for di- and triterpenoids: most are represented by hydroboration-oxidation of localized double bonds, examples for conjugated dienes are limited only by hydroboration-oxidation of cis-eudesma-6,11-diene, abietic acid and its methyl ester. We found that the reduct

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8

Nidhi, Srivastava. "New Triterpenoid Glycosides from the Stem Bark of Samanea Saman." International Journal of Basic Sciences and Applied Computing (IJBSAC) 2, no. 11 (2020): 4–7. https://doi.org/10.35940/ijbsac.K0164.0321120.

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From the stem bark of Samanea saman two new triterpenoid glycoside have been isolated and characterized as 3, 22 – dihydroxyolean -12-ene-24-0--D-xylopyranoside 1 and 1, 2, 3-trihydroxy-16-0-acetylolean-12-ene-28-oic-0 [--Darabinopyranosyl (1→3)] --D-arabinopyranoside 2 by spectral and chemical studies.

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9

Hegazy, Mohamed-Elamir F., Ahmed Abdel-Lateff, Amira M. Gamal-Eldeen, et al. "Anti-inflammatory Activity of New Guaiane Acid Derivatives from Achillea Coarctata." Natural Product Communications 3, no. 6 (2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300604.

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Chromatographic investigation of the methylene chloride/methanol extract of aerial parts of Achillea coarctata afforded two new guaiane acid derivatives, 1α,6α,8α-trihydroxy-5α,7βH-guaia-3,10(14),11(13)-trien-12-oic acid (1) and 1α,6α,8α-trihydroxy-5α,7βH-guaia-3,9,11(13)-trien-12-oic acid (2), in addition to three known compounds, ligustolide-A (3), arteludovicinolide-A (4) and austricin (5). Structures were elucidated by spectroscopic analyses including: 1H and 13C NMR, COSY, HMQC, HMBC and NOESY NMR spectroscopy, as well as MS analysis. Proliferation of beneficial macrophages was significan

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10

Wang, Dingyong, Guocheng Li, Yujing Feng, and Suying Xu. "Two new oleanane triterpene glycosides from Gymnema inodorum." Journal of Chemical Research 2008, no. 11 (2008): 655–57. http://dx.doi.org/10.3184/030823408x375115.

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Two new oleanane triterpene glycosides were isolated from the n-BuOH extract of Gymnema inodorum. On the basis of spectroscopic evidences, their structures were elucidated as 2α, 3β-dihydroxy-olean-12-ene-23, 28-dioic acid-3-O-β-D-glucopyrano-side and 2α, 3β, 15β-trihydroxy-olean-12-ene-23, 28-dioic acid-3-O-β-D-gluco-pyranoside.

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11

R., N. Yadava, and Jain Parol. "New biologically active flavonol glycoside from Cassia sophera Linn." Journal of Indian Chemical Society Vol. 84, Jul 2007 (2007): 683–87. https://doi.org/10.5281/zenodo.5824348.

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Natural Products Laboratory, Department of Chemistry, Dr. H. S. Gour University, Sagar-470 003, Madhya Pradesh, India <em>Manuscript received 12 October 2006, accepted 4 May 2007</em> A new biologically active flavonol glycoside 1, m.p. 282-284 <sup>o</sup>c, m.f. C<sub>33</sub>H<sub>40</sub>O<sub>19</sub>, [M]<sup>+</sup> 740 (FABMS), has been isolated from ethanolic extract of the leaves of <em>Cassia sophera</em> Linn. along with a known compound 2, 8-prenyl- 3, 7 ,4' -trihydroxy-5-methoxyflavone. Compound I was characterized as 3, 7 ,4' -trihydroxy-7-mcthoxyflavone-5-<em>0</em

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12

Jahan, Nusrat, Abdul Malik, Nighat Afza, M. Iqbal Choudhary, and S. Shahzad-ul-Hassan. "Triterpenes from Mimusops elengi." Zeitschrift für Naturforschung B 55, no. 12 (2000): 1206–10. http://dx.doi.org/10.1515/znb-2000-1215.

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Two new triterpenes, 3β,19α,23-trihydroxy-urs-12-ene (1) and 3β-(p-hydroxy-c/s-cinnamoyloxy) urs-12-en-28-oic acid (2) have been isolated from the methanolic extract of Mimusops elengi along with 3β-(p-hydroxy-trans-cinnamoyloxy)urs-12-en-28-oic acid (3), which has been obtained for the first time from this species, and ursolic acid (4), respectively. Their structures were established through chemical and spectral studies. Compounds (3) and (4) were found to exhibit potent inhibitory activity against α-glucosidase enzyme.

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13

El Hazzam, Khadija, Jawhar Hafsa, Mansour Sobeh, et al. "An Insight into Saponins from Quinoa (Chenopodium quinoa Willd): A Review." Molecules 25, no. 5 (2020): 1059. http://dx.doi.org/10.3390/molecules25051059.

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Saponins are an important group found in Chenopodium quinoa. They represent an obstacle for the use of quinoa as food for humans and animal feeds because of their bitter taste and toxic effects, which necessitates their elimination. Several saponins elimination methods have been examined to leach the saponins from the quinoa seeds; the wet technique remains the most used at both laboratory and industrial levels. Dry methods (heat treatment, extrusion, roasting, or mechanical abrasion) and genetic methods have also been evaluated. The extraction of quinoa saponins can be carried out by several

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14

Rumampuk, Rymond J., Emma J. Pongoh, Ponis Tarigan, Anthony J. Herlt, and Lewis N. Mander. "A TRITERPENE ESTER SAPONIN FROM THE SEED OF Barringtonia asiatica." Indonesian Journal of Chemistry 3, no. 3 (2010): 149–55. http://dx.doi.org/10.22146/ijc.21880.

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A triterpene ester saponin has been isolated from the seed of Barringtonia asiatica and its structure has been established by extensive application of high-resolution FABMS and two dimensional NMR techniques to be 3-O-{[β-D-galactopyranosyl(1→3)-β-D-glucopyranosyl(1→2)]-β-D-glucuronopyranosyloxy}-22-O-[2-methylbutyroyloxy]-15,16,28-trihydroxy-(3β,15α,16α,22α)-olean-12-ene. Keywords: Barringtonia asiatica, Lecythidaceae, triterpenoid

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15

Pandey, Jitendra, Bang Yeon Hwang, Hyeong-Kyu Lee, and Amrit Poudel. "Pimarane Diterpenoids from Aerial Parts of Lycopus lucidus and Their Antimicrobial Activity." Evidence-Based Complementary and Alternative Medicine 2022 (February 4, 2022): 1–9. http://dx.doi.org/10.1155/2022/5178880.

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The ethyl acetate fraction obtained from aerial parts of L. lucidus was subjected for isolation of new bioactive compounds, which enabled isolation of five new pimarane-type diterpenoids, namely, 3β, 8β, 12β, 18-tetrahydroxy pimar-15-ene (10), 7α, 8β, 12β, 18-tetrahydroxy pimar-15-ene (11), 3β, 8β, 11β, 12α, 18-pentahydroxy pimar-15-ene (12), 12β acetoxy, 8β, 3β, 18-trihydroxy pimar-15-ene (13), and 3β acetoxy, 8β, 12β, 18-trihydroxy pimar-15-ene (14), along with nine known compounds. The structures were elucidated by spectroscopic analysis and comparison with literature data. The isolated new

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16

Tran, Thang Dinh. "CHARACTERIZATION OF CYTOCHALASINS AND STEROIDS FROM THE FRUITING BODIES OF Daldinia concentrica (BOLTON FR. CES. & DE NOT) IN VIETNAM." Vietnam Journal of Science and Technology 56, no. 4A (2018): 83. http://dx.doi.org/10.15625/2525-2518/56/4a/12949.

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ABSTRACT-HCTN_14[11]-cytochalasa-6(12), 13-diene- 1, 21-dione-7, 18, 19- trihydroxy-16,18-dimethyl-10-phenyl-(7S*, 13E, 16S*, 18S*, 19R*) (1), [11]-cytochalasa-6(12),13-dien-1,21-dion-7,18-dihydroxy-16,18-dimethyl-10-phenyl -(7S*, 13E, 16S*, 18R*) (2), ergosterol (3) and ergosterol peroxit (4) were isolated from the methanolic extract of the fruit body of Daldinia concentrica. The structures of these compounds were elucidated using a combination of UV, IR, 1D and 2D NMR techniques (1H-, 13C-NMR, COSY, HSQC and HMBC) and MS analyses.

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17

Wan, Jiang, Xiao-Juan Wang, Nan Guo, et al. "Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi (Rubus chingii Hu) and Their NF-kappa B Inhibitory Effects." Molecules 26, no. 7 (2021): 1911. http://dx.doi.org/10.3390/molecules26071911.

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During a phytochemical investigation of the unripe fruits of Rubus chingii Hu (i.e., Fructus Rubi, a traditional Chinese medicine named “Fu-Pen-Zi”), a number of highly oxygenated terpenoids were isolated and characterized. These included nine ursane-type (1, 2, and 4–10), five oleanane-type (3, 11–14), and six cucurbitane-type (15–20) triterpenoids, together with five ent-kaurane-type diterpenoids (21–25). Among them, (4R,5R,8R,9R,10R,14S,17S,18S,19R,20R)-2,19α,23-trihydroxy-3-oxo-urs-1,12-dien-28-oic acid (rubusacid A, 1), (2R*,4S*,5R*,8R*,9R*,10R*,14S*,17S*, 18S*,19R*,20R*)-2α,19α,24-trihyd

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18

Pongoh, Emma J., Rymond J. Rumampuk, Ponis Tarigan, Anthony J. Herlt, and Lewis N. Mander. "ISOLATION OF AN ANTIFEEDANT TRITERPENOID FROM THE SEED OF Barringtonia asiatica." Indonesian Journal of Chemistry 4, no. 1 (2010): 49–57. http://dx.doi.org/10.22146/ijc.21873.

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An antifeedant triterpenoid saponin has been isolated from the seed of Barringtonia asiatica and its structure elucidated mainly by two dimensional NMR spectroscopy is identified as 3-O-{[β-D-galactopyranosyl(1→3)-β-D-glucopyranosyl (1→2)]-β-D-glucuronopyranosyloxy}-22-O-[2-(E)-methyl-2-butenyloyloxy]-15, 16,28-trihydroxy-(3β,15α,16α,22α)-olean-12-ene. This compound showed antifeedant activity towards Epilachna sp larvae Keywords: Barringtonia asiatica, saponin, antifeedant

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19

Lazanaki, Maria, George Tsikalas, Olga S. Tsiftsoglou, Haralambos Katerinopoulos, Dimitra Hadjipavlou-Litina, and Diamanto Lazari. "Secondary Metabolites and Their Biological Evaluation from the Aerial Parts of Staehelina uniflosculosa Sibth. & Sm. (Asteraceae)." International Journal of Molecular Sciences 25, no. 19 (2024): 10586. http://dx.doi.org/10.3390/ijms251910586.

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Phytochemical investigation of Staehelina uniflosculosa Sibth. & Sm. resulted in the isolation of twenty-two natural products: eleven sesquiterpene lactones, artemorin (1), tamirin (2), tanachin (3), reynosin (4), baynol C (5), desacetyl-β-cyclopyrethrosin (6), 1β-hydroxy-4α-methoxy-5α,7α,6β-eudesm-11(13)-en-6,12-olide (7), 1β,4α,6α-trihydroxyeudesm-11-en-8α,12-olide (8), 1β-hydroxy-arbusculin A (9), methyl-1β,4α,6α-trihydroxy-5α,7αH-eudesm-11(13)-en-12-oate (10) and methyl-1β,6α,8α-trihydroxy-5α,7αH-eudesma-4(15),11(13)-dien-12-oate (11); one lignan, pinoresinol (12); one norisoprenoid, l

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20

KATO, Tadahiro, Yoshihiro YAMAGUCHI, Toshifumi HIRUKAWA, and Naoko HOSHINO. "Structural elucidation of naturally occurring 9, 12, 13-trihydroxy fatty acids by a synthetic study." Agricultural and Biological Chemistry 55, no. 5 (1991): 1349–57. http://dx.doi.org/10.1271/bbb1961.55.1349.

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21

Saleem, Muhammad, Sumaira Hareem, Ajmal Khan, et al. "Dual inhibitors of urease and carbonic anhydrase-II from Iris species." Pure and Applied Chemistry 91, no. 10 (2019): 1695–707. http://dx.doi.org/10.1515/pac-2019-0407.

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Abstract Twenty seven (1–27) known natural organic compounds were isolated for first time from two species of Iris, i.e. loczyi and Iris unguicularis. The structures of these compounds were deduced from the spectral data of NMR, IR, and mass spectrogram. These were evaluated against urease and carbonic anhydrase inhibition studies. For carbonic anhydrase-II inhibition studies, these compounds were evaluated by biochemical mechanism based in vitro bio-assay. Some compounds showed significant inhibition against CA-II enzyme. Compartively, compound (12) showed IC50 value of 17.60 ± 0.08 μM agains

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22

Alam, Tanveer, Ahmed Sulaeman Al Harrasi, Bahar Ahmed, Lubna Najam, and Shah Alam Khan. "Three New Flavonoid Glycosides from the Fruits of Luffa echinata Roxb.- a Hepatoprotective Plant." Dhaka University Journal of Pharmaceutical Sciences 15, no. 2 (2017): 117–25. http://dx.doi.org/10.3329/dujps.v15i2.30924.

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Phytochemical investigation of bioactive polar extracts of Luffa echinata Roxb. fruits led to the isolation and characterization of three new flavone glycosides viz., 3,5,7,3?,4?-pentahydroxyflavone-3-[-O-?-Dglucopyranosyl- 7-O-?-D-glucopyranoside (1),3,5,7-trihydroxy-(7?,8?- dioxo,9?,10?,-dihydro[a]cyclohex ?13?,(14?), ?11?(12)-12?,13?,-dimethyl)-flavone-7-[-O-?-D-galactopyranosyl-(1?2)]-O-?-D-glucopyranoside (2), and 5,7,8,4?- tetrahydroxy flavone-7-[-O-?-D-xylosyl-(1?2)]-O-?-D-glucopyranoside (3). The structures of the newly isolated compounds were elucidated on the basis of spectral data

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23

Liu, Juanjuan, Jingke Zhang, Mengnan Zeng, et al. "Anti-Pulmonary Fibrosis Activities of Triterpenoids from Oenothera biennis." Molecules 27, no. 15 (2022): 4870. http://dx.doi.org/10.3390/molecules27154870.

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Five new triterpenoids, oenotheralanosterols C-G (1–5), with seven known triterpenoidcompounds, namely 2α,3α,19α-trihydroxy-24-norurs4,12-dien-28-oic acid (6), 3β,23-dihydroxy-1-oxo-olean-12-en-28-oic acid (7), remangilone C (8), knoxivalic acid A (9), termichebulolide (10), rosasecotriterpene A (11), androsanortriterpene C (12), were extracted and separated from the dichloromethane part of Oenothera biennis L. The anti-pulmonary fibrosis activities of all the compounds against TGF-β1-induced damage tonormal human lung epithelial (BEAS-2B) cells were investigated in vitro. The results showed t

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24

Benayache, Feryal, Massimiliano D'Ambola, Roberta Cotugno, et al. "A New Triterpene Glucoside from Genista numidica." Natural Product Communications 13, no. 9 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300902.

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A new oleanolic acid triterpene glucoside, 3- O-β-D-glucopyranosyl-3β,21β,28-trihydroxy-olean-12-en-27-oic acid (1), has been isolated together with twelve known compounds from the chloroform and ethyl acetate extracts of Genista numidica Spach (Fabaceae) aerial parts. The structures were elucidated by spectroscopic and spectrometric analyses, mainly 1D-, 2D-NMR and MS data, and comparison with the literature. The antiproliferative activity of isolates was investigated on Jurkat, HeLa, and MCF7 cell lines. The most active triterpene, 3- O-β-D-glucopyranosyl-olean-12-en-3β,27,28,29-tetraol, sho

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25

Calderón, Angela I., Johayra Simithy, Giuliana Quaggio, Alex Espinosa, Jose Luis López-Pérez, and Mahabir P. Gupta. "Triterpenes from Warszewiczia coccinea (Rubiaceae) as Inhibitors of Acetylcholinesterase." Natural Product Communications 4, no. 10 (2009): 1934578X0900401. http://dx.doi.org/10.1177/1934578x0900401002.

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Seventy-six plant extracts from the Panamanian flora have been screened for acetylcholinesterase (AChE) inhibitors by thin-layer chromatography (TLC) bioautography. The most promising extracts with AChE inhibitory and free radical scavenging activities at 100 μg were those of Tabernaemontana panamensis (Markgr., Boiteau & L. Allorge) Leeuwenb., Pentagonia macrophylla Benth., and Warszewiczia coccinea (Vahl) Klotzsch. Bioguided fractionation of W. coccinea stem extract afforded two triterpenes, 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid (1) and 3β,6β-dihydroxy-olean-12-en-28-oic acid (sumar

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26

Argay, G., A. Kálmán, B. Ribár, S. Vladimirov та D. Živanov-Stakić. "Structures of two related bufadienolides: gamabufotalin (3β,11α,14-trihydroxy-5β,14β-bufa-20,22-dienolide) and arenobufagin (3β,11α,14-trihydroxy-12-oxo-5β,14β-bufa-20,22-dienolide)". Acta Crystallographica Section C Crystal Structure Communications 43, № 5 (1987): 922–26. http://dx.doi.org/10.1107/s0108270187093569.

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27

Dawé, Amadou, Benjamin Talom, Gilbert Deccaux Wabo Fotso Kapche, et al. "Termiglaucescin, a new polyhydroxy triterpene glucoside from Terminalia glaucescens with antioxidant and anti-inflammatory potential." Zeitschrift für Naturforschung C 72, no. 5-6 (2017): 203–8. http://dx.doi.org/10.1515/znc-2016-0178.

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Abstract Termiglaucescin (1), a new triterpene glucoside, has been isolated from the ethyl acetate extract of the root bark of Terminalia glaucescens Planch. ex Benth, together with 11 known compounds, β-D-glucopyranosyl 2α,3β,6β-trihydroxy-23-galloylolean-12-en-28-oate (2), arjunglucoside I (3), sericoside (4), arjungenin (5), sericic acid (6), arjunetin (7), chebuloside II (8), 3,3′,4-tri-O-methylelagic acid (9), 3,3′-di-O-methylelagic acid (10), β-sitosterol (11) and stigmasterol (12). Compounds 2, 3, 7, 8 and 9 are reported from the plant for the first time. The structures of the isolated

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28

Reyes, Carolina P., Ignacio A. Jiménez, and Isabel L. Bazzocchi. "Pentacyclic Triterpenoids from Maytenus cuzcoina." Natural Product Communications 12, no. 5 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200508.

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Phytochemical analysis of the root bark extract of Maytenus cuzcoina (Celastraceae) led to the isolation and characterization of sixteen triterpenoids with a 6/6/6/6/6 pentacyclic system, including the new 22α-hydroxy-29-methoxy-3β-tetradecanoate-olean-12-ene, and 3β,24β-epoxy-29-methoxy-2α,3α,6α-trihydroxy- D:A-friedelane that is reported for the first time as a natural product. This is the first instance of the isolation of a tetradecanoate triterpene ester from a Celastraceae species. The structures were elucidated on the basis of spectrometric and spectroscopic methods, including 1D and 2D

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29

Ahmad, Viqar Uddin, Saima Arshad, Sadia Bader, et al. "A New Triterpenoidal Saponin and a Flavone Glycoside from Stachys parviflora." Natural Product Communications 2, no. 9 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200903.

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A new triterpenoidal saponin, stachyssaponin C (1), identified as 3β, 15α, 21β-trihydroxy-olean-12-ene-28-oic acid 3- O-[α-L-rhamnopyranosyl-(1→3)- O-6″- O-acetyl-β-D-glucopyranosyl-(1→2)- O-β-D-glucopyranoside] and a flavone glycoside stachyfloroside A (2), characterized as 5,8-dihydroxy-2-(3′-hydroxy-4′-methoxy)-7 [(6″”- O-acetyl-β-D-allopyranosyl-(1→2)- O-α-D-glucopyranosyl-(1→2)- O-β-D-glucopyranosyl)oxy]-4H-1-benzopyran-4-one, were isolated from the n-butanol extract of Stachys parviflora (Lamiaceae). The structures were elucidated by extensive spectroscopic (especially 2D NMR) experiment

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30

Ayer, William A., Samuel K. Attah-Poku, Lois M. Browne, and Helena Orszanska. "The chemistry of the blue stain fungi. Part 3. Some metabolites of Ceratocystisminor (Hedgcock) Hunt." Canadian Journal of Chemistry 65, no. 4 (1987): 765–69. http://dx.doi.org/10.1139/v87-130.

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The metabolites formed in still cultures by Ceratocystisminor, one of the fungal species associated with the blue stain disease of pine, have been isolated and identified as ceratenolone (5), 6,8-dihydroxy-3-methylisocoumarin (2), 8-hydroxy-6-methoxy-3-methylisocoumarin (8), 3,4-dihydro-6,8-dihydroxy-3-methylisocoumarin (10), 3,4-dihydro-3-methyl-3,6,8-trihydroxy-3-methylisocoumarin (12), 3,4-dihydro-3-methyl-3,4,6,8-tetrahydroxyisocoumarin (13), and succinic acid. Ceratenolone (5), a new type of natural product, forms an intensely blue chelate with ferric ions. This chelate may be responsible

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31

Abdelrahman, Doaa, Michael Benn, Ryan Hellyer, Masood Parvez, and Oliver E. Edwards. "Some oxidation products of lycoctonine revisited." Canadian Journal of Chemistry 84, no. 9 (2006): 1167–73. http://dx.doi.org/10.1139/v06-144.

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The structure of a chromic acid oxidation product of the norditerpenoid alkaloid lycoctonine (1) was established as hydroxylycoctonal (3) by spectrometric analyses and X-ray crystallography of its reduction product, hydroxylycoctonine (5); the structure of lycoxonine, a chromic acid oxidation product of the lactam, lycoctonam (7), was similarly confirmed as N-ethyl-4,7,8-trihydroxy-1α,6β,14α,16β-tetramethoxy-19-oxoaconitane (8). Reduction of lycoxonine with lithium aluminium hydride gave the 1,14-di-O-methyl ether (12) of the bisnorditerpenoid alkaloid delbine (9).Key words: norditerpenoid, bi

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32

Fun, Hoong-Kun, Shea-Lin Ng, Ibrahim Abdul Razak, Nawong Boonnak, and Suchada Chantrapromma. "12-(1,1-Dimethyl-2-propenyl)-5,9,10-trihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one." Acta Crystallographica Section E Structure Reports Online 62, no. 1 (2005): o130—o132. http://dx.doi.org/10.1107/s1600536805040328.

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33

Sandjo, Louis P., Chi G. Fru, Victor Kuete, et al. "Elatumic Acid: A New Ursolic Acid Congener from Omphalocarpum elatum Miers (Sapotaceae)." Zeitschrift für Naturforschung C 69, no. 7-8 (2014): 276–82. http://dx.doi.org/10.5560/znc.2014-0050.

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A new triterpene diastereomer, 1, of the previously reported 3β,6β,19α-trihydroxy-urs-12-en- 28-oic acid-24-carboxylic acid methyl ester was obtained from the stem bark of Omphalocarpum elatum Miers (Sapotaceae) along with α-amyrin acetate (2), spinasterol (3), spinasterol 3-O-β-Dglucopyranoside (4), and tormentic acid (5). The structures of the isolates were established on the basis of NMR and mass spectrometric data and by comparison with those previously reported in the literature. Compound 1 showed weak antibacterial activity against E. aerogenes ATCC13048 and EA3, K. pneumoniae ATCC29916,

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34

Kuroki, S., M. Une, and E. H. Mosbach. "Synthesis of potential cholelitholytic agents: 3 alpha,7 alpha,12 alpha-trihydroxy-7 beta-methyl-5 beta-cholanoic acid, 3 alpha,7 beta,12 alpha-trihydroxy-7 alpha-methyl-5 beta-cholanoic acid, and 3 alpha,12 alpha-dihydroxy-7 xi-methyl-5 beta-cholanoic acid." Journal of Lipid Research 26, no. 10 (1985): 1205–11. http://dx.doi.org/10.1016/s0022-2275(20)34268-1.

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35

Somanathan, R., and S. Krisans. "Synthesis of C-22, C-23-3H-labeled 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestane." Journal of Lipid Research 26, no. 6 (1985): 774–75. http://dx.doi.org/10.1016/s0022-2275(20)34336-4.

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36

Al-Mekhlafi, Nabil Ali, Khozirah Shaari, Faridah Abas та ін. "New Flavan and Alkyl α,β-Lactones from the Stem Bark of Horsfieldia Superba". Natural Product Communications 8, № 4 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800409.

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In the present study phytochemical investigation of the methanol extract of the stem bark of Horsfieldia superba led to the isolation of twenty compounds (1-20), of which three (1-3) were new. However, compounds 2 and 3 were previously reported as synthetic α, β-lactones. The compounds were characterized as (-)-3,4′,7-trihydroxy-3′-methoxyflavan (1), (-)-5,6-dihydro-6-undecyl-2 H-pyran-2-one (2), and (-)-5,6-dihydro-6-tridecyl-2 H-pyran-2-one (3). Seventeen other known compounds were also isolated and identified as (-)-viridiflorol (4), hexacosanoic acid (5), β-sitosterol (6), methyl 2,4-dihyd

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37

Bodede, Olusola, Garland K. More, Roshila Moodley, et al. "New Alk(en)ylhydroxycyclohexanes with Tyrosinase Inhibition Potential from Harpephyllum caffrum Bernh. Gum Exudate." Molecules 27, no. 12 (2022): 3839. http://dx.doi.org/10.3390/molecules27123839.

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This work presents the first report on the phytochemical investigation of Harpephyllum caffrum Bernh. gum exudate. A known cardanol, 3-heptadec-12′-Z-enyl phenol (1) and three new alk(en)ylhydroxycyclohexanes, namely, (1R,3R)-1,3-dihydroxy-3-[heptadec-12′(Z)-enyl]cyclohexane (2) (1S,2S,3S,4S,5R)-1,2,3,4,5-pentahydroxy-5-[octadec-13′(Z)-enyl]cyclohexane (3) and (1R,2S,4R)-1,2,4-trihydroxy-4-[heptadec-12′(Z)-enyl]cyclohexane (4) were isolated from the gum. The structures of the compounds were determined by extensive 1D and 2D NMR spectroscopy and HR-ESI-MS data. The ethanolic extract of the gum

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38

Arita, Makoto, Francesca Bianchini, Julio Aliberti, et al. "Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1." Journal of Experimental Medicine 201, no. 5 (2005): 713–22. http://dx.doi.org/10.1084/jem.20042031.

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The essential fatty acid eicosapentaenoic acid (EPA) present in fish oils displays beneficial effects in a range of human disorders associated with inflammation including cardiovascular disease. Resolvin E1 (RvE1), a new bioactive oxygenated product of EPA, was identified in human plasma and prepared by total organic synthesis. Results of bioaction and physical matching studies indicate that the complete structure of RvE1 is 5S,12R,18R-trihydroxy-6Z,8E,10E,14Z,16E-EPA. At nanomolar levels, RvE1 dramatically reduced dermal inflammation, peritonitis, dendritic cell (DC) migration, and interleuki

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39

Ferth, Roland, Andreas Baumann, Wolfgang Robien, and Brigitte Kopp. "Cardenolide aus Ornithogalum nutans (2 n = 28), 1. Mitteilung / Cardenolides from Ornithogalum nutans (2 n = 28), Part." Zeitschrift für Naturforschung B 47, no. 10 (1992): 1444–58. http://dx.doi.org/10.1515/znb-1992-1017.

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From leaves and bulbs of Ornithogalum nutans L. (2 n = 28), seventeen cardenolides were isolated by column chromatography, DCCC and TLC. The structure elucidation was performed by means of 1H NMR, 13C NMR, HH-Cosy, HC-Cosy and FAB-MS studies and identification of the sugar moieties by GLC after acid hydrolysis of the cardenolides. Sugar compounds were identified as digitoxose, 3-acetyl-digitoxose, 2-deoxy-allose, 6-deoxy-allose, rhamnose, xylose and apiose. Glycosides of 7β,15β, 16 α-trihydroxy-uzarigenin, 8β,16 α-dihy-droxy, 15-oxo-uzarigenin, 3 β, 11β-dihydroxy, 12-oxo, 18-nor-5 α-card-13-en

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40

Dookhun, Veedeeta, and Andrew J. Bennet. "Synthesis and biological evaluation of a bicyclo[4.1.0]heptyl analogue of glucose-1-phosphate." Canadian Journal of Chemistry 82, no. 9 (2004): 1361–64. http://dx.doi.org/10.1139/v04-109.

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The synthesis of a bicyclo[4.1.0]heptyl analogue of glucose-1-phophate, (1R,2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)-bicyclo[4.1.0]heptan-2-yl dihydrogen phosphate (5) is reported. The synthetic route chosen started with methyl α-D-glucopyranoside and was accomplished in 11 steps with an overall yield of 3%. Compound 5 was tested as a potential substrate of UTP:α-D-glucose-1-phosphate uridylyltransferase, the enzyme that converts glucose-1-phosphate into UDP-glucose. However, the conformationally restricted glucose-1-phosphate analogue 5 was found to be a weakly binding inhibitor, ra

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41

ARUN, K. BARUA, GHOSH SAROJ, BASU KALYAN, and PATRA AMARENDRA. "Structure and Stereochemistry of Mollugogenol-G -A Triterpenoid Sapogenin from Mollugo hirta." Journal Of Indian Chemical Society Vol. 66, Jan 1989 (1989): 64–66. https://doi.org/10.5281/zenodo.6132734.

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Department of Chemistry, University College of Science, Calcutta-700 009 <em>Manuscript received 18 April 1988, revised 12 July 1988, accepted 23 September 1988</em> A number of triterpenoid saponins and sapogenins have earlier been reported from this laboratory from <em>Mollugo hita<sup>1,</sup></em> and <em>Mollugo spergula<sup>2</sup>. </em>The present communication reports the isolation of a new triterpenoid sapogenin called mollugogenol-G, the structure of which has been established as 3\(\beta\),16\(\beta\) ,22-trihydroxy-21\(\propto\)-H-hop-5-ens (1a). The&

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42

Chantrapromma, Suchada, Nawong Boonnak, Hoong-Kun Fun, Shazia Anjum, and Atta-ur-Rahman. "5,9,10-Trihydroxy-2,2-dimethyl-12-(3-methylbut-2-enyl)-2H,6H-pyrano[3,2-b]xanthen-6-one methanol solvate." Acta Crystallographica Section E Structure Reports Online 61, no. 7 (2005): o2136—o2138. http://dx.doi.org/10.1107/s1600536805018192.

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43

Liu, Xiuhua, Dongbao Zhao, and Hanqing Wang. "Phenolic compounds from Celastrus angulatus." Journal of Indian Chemical Society Vol.79, Mar 2002 (2002): 259–60. https://doi.org/10.5281/zenodo.5846201.

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Chemistry and Chemical Engineering College of Henan University, Kaifeng-475001, P.R. China <em>E-mail</em> : xiuhual@371.net <em>Fax</em> : 086-378-2852533 Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou-730000, P. R. China <em>Manuscript received 12 January 2001, revised 24 July 2001, accepted 6 August 2001</em> Four phenolic compounds (+)-catechin (1), (-)-epicatechin (2), 2,4,6-trimethoxyphenol-l<em>-Ο</em>-β-D-glucopyranoside (3), 3β,7,3'- trihydroxy- 4'-methoxyflavan-l<em>-Ο</em>-β-D-glucopyranoside (4) together with dulcit

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44

Longue Ekon, Jean Pierre, Achille Nouga Bissoue, Marie Fomani, et al. "Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta." Zeitschrift für Naturforschung B 70, no. 11 (2015): 837–42. http://dx.doi.org/10.1515/znb-2015-0083.

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AbstractTwo new 24-nor-ursane-type triterpenoids, 2α,3β,19α-trihydroxy-24-norurs-4(23),12-dien-28-oic acid (1) and 3β-acetoxy-2α,19α-dihydroxy-24-norurs-4(23),12-dien-28-oic acid (2), along with 15 known compounds were isolated from the methanol extract of the twigs of Mostuea hirsuta. While 2-hydroxymethylbenzamide (13) was isolated for the first time from the natural source, compounds 3–12 are reported here for the first time from the genus Mostuea. Their structures were elucidated by means of spectroscopic analyses including 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometric da

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45

Tsiftsoglou, Olga S., Nikos Krigas, Christos Gounaris, et al. "Isolation of Secondary Metabolites from Achillea grandifolia Friv. (Asteraceae) and Main Compounds’ Effects on a Glioblastoma Cellular Model." Pharmaceutics 15, no. 5 (2023): 1383. http://dx.doi.org/10.3390/pharmaceutics15051383.

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This study aims at the isolation and structural determination of the secondary metabolites of the herbaceous perennial plant Achillea grandifolia Friv. (Asteraceae). The examination of the non-volatile content of the leaves and flowers of A. grandifolia afforded the isolation of sixteen secondary metabolites. On the basis of NMR spectra, the identified compounds included ten sesquiterpene lactones; three guaianolides—rupicolin A (1), rupicolin B (2), and (4S,6aS,9R,9aS,9bS)-4,6a,9-trihydroxy-9-methyl-3,6-dimethylene-3a,4,5,6,6a,9,9a,9b-octahydro-3H-azuleno [4,5-b]furan-2-one (3); two eudesmano

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46

IKEGAWA, Shigeo, Takaaki GOTO, Hiroo WATANABE, and Junichi GOTO. "Stereoisomeric Inversion of (25R)- and (25S)-3.ALPHA.,7.ALPHA.,12.ALPHA.-Trihydroxy-5-.BETA.cholestanoic Acids in Rat Liver Peroxisome." Biological & Pharmaceutical Bulletin 18, no. 7 (1995): 1027–29. http://dx.doi.org/10.1248/bpb.18.1027.

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47

Jo, Yang Hee, Seon Beom Kim, Jong Hoon Ahn, Qing Liu, Bang Yeon Hwang, and Mi Kyeong Lee. "Inhibitory Activity of Benzophenones from Anemarrhena asphodeloides on Pancreatic Lipase." Natural Product Communications 8, no. 4 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800419.

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Pancreatic lipase is a key enzyme for lipid absorption by hydrolysis of total dietary fats. Therefore, inhibition of pancreatic lipase is suggested to be an effective therapy in the regulation of obesity. The EtOAc-soluble fraction of Anemarrhena asphodeloides rhizomes significantly inhibited pancreatic lipase activity as assessed using porcine pancreatic lipase as an in vitro assay system. Further fractionation of the EtOAc-soluble fraction of A. asphodeloides led to the isolation of a new benzophenone glycoside, zimoside A (1), together with the eleven known compounds iriflophenone (2), 2,4′

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48

Stefani, Ricardo, Karin Schorr, Juliana Maria Tureta, Walter Vichnewski, Irmgard Merfort, and Fernando B. Da Costa. "Sesquiterpene Lactones from Dimerostemma Species (Asteraceae) and in vitro Potential Anti-Inflammatory Activities." Zeitschrift für Naturforschung C 61, no. 9-10 (2006): 647–52. http://dx.doi.org/10.1515/znc-2006-9-1006.

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AbstractTwo Brazilian species of Dimerostemma (Asteraceae) were chemically investigated. Two known sesquiterpene lactones (STLs), a germacrolide and an eudesmanolide, were isolated from D. episcopale while D. brasilianum afforded the new germacranolide 1β,5β,10α-trihydroxy- 8α-angeloyloxy-germacra-3,11(13)-dien-6α,12-olide in addition to a known one. Structure identification based on NMR and MS analyses. 1β,10α,4α,5β-Diepoxy-8α-angeloyloxycostunolide isolated from D. brasilianum was studied for its anti-inflammatory activity. This STL completely inhibited DNA binding of the transcription facto

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49

Dauk, Melanie, Patricia Lam, and Mark A. Smith. "The role of diacylglycerol acyltransferase-1 and phospholipid:diacylglycerol acyltransferase-1 and -2 in the incorporation of hydroxy fatty acids into triacylglycerol in Arabidopsis thaliana expressing a castor bean oleate 12-hydroxylase geneThis paper is one of a selection of papers published in a Special Issue from the National Research Council of Canada – Plant Biotechnology Institute." Botany 87, no. 6 (2009): 552–60. http://dx.doi.org/10.1139/b09-011.

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Expression of oleate 12-hydroxylase genes in Arabidopsis results in the accumulation of hydroxy fatty acids in seed triacylglycerol (TAG). The pathways by which these unusual fatty acids become incorporated into TAG are not well understood. We expressed a fatty acid hydroxylase cDNA in Arabidopsis mutant lines to assess the role of three enzymes implicated in TAG assembly in this species. Plants deficient in the expression of phospholipid:diacylglycerol acyltransferase-1 or -2 accumulated hydroxy fatty acids and showed no differences to equivalent transformed wild-type plants. Plants lacking d

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50

Uehara, Ayumi, Kazuhide Shimoda, Yoshinori Murai, and Tsukasa Iwashina. "Flavonoid Aglycones and Glycosides from the Leaves of some Japanese Artemisia Species." Natural Product Communications 13, no. 5 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300510.

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Sixteen Japanese Artemisia taxa were surveyed for flavonoid aglycones and glycosides. The leaves were rinsed with acetone and then extracted with MeOH. Isolated flavonoids were identified by UV, LC-MS, acid hydrolysis, 1H and 13C NMR, and/or HPLC comparisons with authentic samples. Thus, nine flavone aglycones, apigenin (10), luteolin (5), chrysoeriol (11), hispidulin (6), jaseosidin (7), nepetin (15), sudachitin (8), luteolin 7-methyl ether (13) and eupatilin (14), three flavonol aglycones, axillarin (9), quercetin 3-methyl ether (16) and 5,7,4′-trihydroxy-3,6-dimethoxyflavone (12), one flava

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