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Journal articles on the topic 'Trienic compound'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Whitaker, Bruce D., and Theophanes Solomos. "Farnesene and Trienes in Apple Peel Quantified by HPLC." HortScience 31, no. 4 (1996): 640a—640. http://dx.doi.org/10.21273/hortsci.31.4.640a.

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Farnesene and its conjugated triene oxidation products in apple peel are positively correlated with, and thought to be involved in, the storage disorder superficial scald. Levels of these compounds are often estimated by dipping fruit in hexane and measuring the absorbance of the crude extracts at 232 nm (farnesene) and 269 or 281 minus 290 nm (trienes). We have devised a C18 HPLC method with UV detection at 232 and 269 nm that allows the simultaneous quantitation of 80 ng of farnesene and trienes. Using this method we have confirmed the recent report that one conjugated trien-6-ol comprises 9

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2

Jovanović-Šanta, Suzana, Silvana Andrić, Radmila Kovačević, and Vjera Pejanović. "Synthesis and Biological Activity of New 16,17-Secoestrone Derivatives." Collection of Czechoslovak Chemical Communications 65, no. 1 (2000): 77–82. http://dx.doi.org/10.1135/cccc20000077.

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Starting from estrone 3-benzyloxy-17β-hydroxyestra-1,3,5(10)-trien-16-one oxime (3b) was synthesized, which underwent Beckmann fragmentation giving the 3-benzyloxy-17-oxo- 16,17-secoestra-1,3,5(10)-triene-16-nitrile (4b). Sodium borohydride reduction of this compound afforded 3-benzyloxy-17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile (5b). The deprotection of the 3-hydroxy group was achieved by action of hydrogen upon derivatives 4b and 5b in presence of Pd/C as a catalyst, yielding 3-hydroxy-17-oxo-16,17-secoestra- 1,3,5(10)-triene-16-nitrile (4a) and 3,17-dihydroxy-16,17-secoestra-1,

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3

Sakač, Marija N., Dušan A. Miljković, Katarina M. Penov Gaši, et al. "Synthesis, X-ray Crystal Structure and Antiestrogenic Activity of 17-Methyl-16,17-secoestra-1,3,5(10)-triene Derivatives." Collection of Czechoslovak Chemical Communications 70, no. 1 (2005): 63–71. http://dx.doi.org/10.1135/cccc20050063.

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Starting from 3-(benzyloxy)-16-(hydroxyimino)-estra-1,3,5(10)-trien-17-one (1) several 17-methyl-16,17-secoestratriene derivatives were synthesized. In the first step of synthesis, hydroxyimino ketone 1 was transformed into 3-(benzyloxy)-16-(hydroxyimino)-17α-methylestra-1,3,5(10)-trien-17β-ol (2), the Beckmann fragmentation of which gave 3-(benzyloxy)-17-methyl-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (3a). Reduction of 3a with sodium borohydride yielded (17S)-3-(benzyloxy)-17-hydroxy-17-methyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile (4a), whose configuration at the newly formed

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4

Zheng, Xiang, Gai Kuo, Dou De-Qiang, Kang Ting-Guo, Shi Yu-Yuan, and Dong Feng. "New Compounds from Leaves of Smallanthus sonchifolius." Natural Product Communications 4, no. 9 (2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400909.

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A new octadecatrienoic acid and a new benzyl glycoside, along with a known compound, were isolated from the leaves of Smallanthus sonchifolius. The structures of the two new compounds were elucidated as 13(R)-hydroxy-octadeca-(9E,11E,15Z)-trienoic acid (1) and benzyl alcohol 7-O-α-L-arabinopyranosyl(1″→2′)-β-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence. The known compound was identified as 13(R)-hydroxy-octadeca-(9Z,11E,15Z)-trienoic acid (3) by comparison of its spectral data with that reported. Compound 3 was isolated for the first time from the title pl

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5

Sakač, Marija N., Katarina M. Penov Gaši, Mirjana Popsavin, Evgenija A. Djurendić, Silvana Andrić, and Radmila M. Kovačević. "Synthesis and Estrogenic Activity Screening of Some 6,9-Disubstituted Estradiol Derivatives." Collection of Czechoslovak Chemical Communications 70, no. 4 (2005): 479–86. http://dx.doi.org/10.1135/cccc20050479.

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Oxidation of estradiol dipropionate (1) with chromium(VI) oxide-3,5-dimethylpyrazole complex yielded 9α-hydroxy-6-oxoestra-1,3,5(10)-triene-3,17β-diyl dipropionate (2) and 6-oxoestra-1,3,5(10)-triene-3,17β-diyl dipropionate (3). Dehydration of compound 2 with phosphorus(V) oxide or acetic anhydride gave 6-oxoestra-1,3,5(10),9(11)-tetraene-3,17β-diyl dipropionate (5). Reduction of compounds 2 and 5 with sodium borohydride afforded 3,6β,9α-trihydroxyestra-1,3,5(10)-triene-17β-yl propionate (4) and 3,6β-dihydroxyestra-1,3,5(10),9(11)-tetraene-17β-yl propionate (6), respectively. The action of thi

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6

Eschenko, N. D., F. E. Putilina, O. V. Galkina, et al. "Study of osteoprotective and hypolipidemic effects of estrogen 8a a-analogues." Biomeditsinskaya Khimiya 61, no. 6 (2015): 724–30. http://dx.doi.org/10.18097/pbmc20156106724.

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The aim of this work was to study the ability of some estrogen 8a-analogues, that have CH 3 -group in the C-3 position, exhibit osteoprotective and cholesterolemic effects. The properties of these analogues was comparisoned with effects of native estradiol and 17a-ethynylestradiol (EE). We showed that compounds 3 ((d,l)-17b-acethoxy-3-methoxy-8a-estra-1,3,5(10)-triene) and 4 ((d,l)-3-methoxy-8a-estra-1,3,5(10)-triene-17-one) had the same osteoprotective and cholesterolemic effects as EE. The utherotropic effects of compound 3 and EE were the same, while the utherotropic activity of 17-keto der

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7

Jovanovic-Santa, Suzana, Evgenija Djurendic, Dusan Lazar, and Slobodanka Stankovic. "Alternative syntheses of 3-hydroxy-17-bromo-16,17-secoestra-1,3,5(10)-triene-16-nitrile and crystallographic studies of two intermediates." Journal of the Serbian Chemical Society 70, no. 4 (2005): 569–77. http://dx.doi.org/10.2298/jsc0504577j.

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Abstract: Starting from estrone 3-benzyloxy-17-hydroxy-16,17-secoestra-1,3,5(10)-triene- 16-nitrile (1) was synthesized in several synthetic steps. This compound was the key intermediate in the syntheses of other 17-substituted-16,17-secoestrone derivatives. Among them 3-hydroxy-17-bromo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (5) is of special interest, because of its antiestrogenic activity, with no estrogenic properties. For this reason an alternative pathway for the synthesis of this compound was sought. The structures of 3-benzyloxy-17-bromo-16,17-secoestra-1,3,5(10)-triene- 16-nitril

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8

Mosaddik, Ashik, and Peter G. Waterman. "A Sesquiterpene, Clerodane Diterpenes and a Furanone from the Roots of Casearia Multinervosa (Flacourtiaceae/Salicaceae)." Natural Product Communications 1, no. 8 (2006): 1934578X0600100. http://dx.doi.org/10.1177/1934578x0600100801.

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The roots of Casearia multinervosa (Flacourtiaceae/Salicaceae) have yielded the new compounds 10ε-acetoxyhumula-3,7-diene (1), (rel)-(2S,5S,6S,8R,9R,10S)-6-hydroxy-2-(2-methylbutanoyloxy)-clero-3,13(16),14-trien-4,5-dial (2), (rel)-(2R,5R,6R,8S,9S,10R)-6-methoxy-2-(2-methylbutanoyloxy)-clero-3,13(16),14-trien-4,5-dial (3), (rel) (2S,5S,6S,8R,9R,10S, 18R,19S)-18-acetoxy-18,19-epoxy-6-hydroxy-2-(2-methylbutanoyloxy)-19-methoxyclero-3,13(16),14-triene (4), and 3ε-(hexadec-11-enyl)-4ε-hydroxy-5-methylene-2,3-dihydrofuran-2-one (5).

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9

Sakač, Marija N., Katarina M. Penov Gaši, Evgenija A. Djurendić, Silvana Andrić, and Dušan A. Miljković. "Synthesis and Biological Evaluation of 17-[4-(2-Aminoethoxy)phenyl]-16,17-secoestra-1,3,5(10)-triene Derivatives." Collection of Czechoslovak Chemical Communications 72, no. 3 (2007): 403–10. http://dx.doi.org/10.1135/cccc20070403.

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Starting from 3-(benzyloxy)-16-(hydroxyimino)estra-1,3,5(10)-trien-17-one (1), 3-(benzyloxy)- 17-{4-[2-(dimethylamino)ethoxy]phenyl}-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (3a) was synthesized. Reduction of 3a with sodium borohydride yielded secocyano alcohol 4a, as well as the secoamino alcohol 5a when reduction was performed with sodium borohydride in the presence of cobalt(II) salt. Deprotection of the C-3 hydroxy group in compounds 3a-5a by catalytic hydrogenolysis resulted in the corresponding 3-hydroxy derivatives 3b-5b. Compounds 3b-5b were tested on residual estrogenic and

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10

Cambie, RC, PI Higgs, KC Lee, et al. "Directed ortho Metalation Studies on Podocarpic Acid Derivatives: Advantageous Use of a LICKOR Base." Australian Journal of Chemistry 44, no. 10 (1991): 1465. http://dx.doi.org/10.1071/ch9911465.

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Methyl 13-(N,N- diethylcarbamoyl )-12-methoxypodocarpa-8,11,13-trien-19-oate (2), 13-(N,N- diethylcarbamoyl )-12,19-dimethoxypodocarpa-8,11,13-triene (8) and N,N-diethyl-2-methoxy-4,5-dimethylbenzamide (15) were prepared for studies involving lithiation directed ortho to the tertiary amide group, in which the use of a LICKOR base was advantageous. Some dynamic features of the n.m.r. spectra of the amides are discussed. Oxazoline derivatives of both tile monocyclic and diterpenoid compounds were synthesized.

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11

Gomes, Ligia R., John N. Low, Alan B. Turner, Alexander W. Nowicki, Thomas C. Baddeley, and James L. Wardell. "Crystal structures and Hirshfeld surface analyses of a des-A-B-aromatic steroidal compound, and two of its derivatives, having a trans-2,3,4,5-tetrahydro-3a-methyl-7-methoxybenz[e]indane skeleton – structural comparisons with reported tetrahydrobenz[e]indene derivatives." Zeitschrift für Naturforschung B 74, no. 9 (2019): 649–63. http://dx.doi.org/10.1515/znb-2019-0094.

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AbstractThe crystal structures and Hirshfeld surface analyses of the des-A-B-aromatic steroid derivative, (3a,9b)-1,2,3a,4,5,9b-hexahydro-7-methoxy-3a-methyl-3H-benz[e]-inden-3-one (or 5-methoxy-des-A-estra-5,7,9-triene-17-one) 1, its acetohydrazide derivative, 2, and its hydrazone derivative, 3, are reported. All three compounds crystallize in chiral space groups: compounds 1 and 2 in the orthorhombic space group P212121 each with one molecule in the asymmetric unit, and compound 3 in the monoclinic space group P21 with two similar but independent molecules, Mol A and Mol B, in the asymmetric

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12

Perry, NB, JW Blunt, and MHG Munro. "Cytotoxic and Antifungal C14 Amines From a New Zealand Ascidian: Major Lipid Components of Pseudodistoma novaezelandiae." Australian Journal of Chemistry 44, no. 4 (1991): 627. http://dx.doi.org/10.1071/ch9910627.

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The principal cytotoxic and antifungal components of the compound ascidian Pseudodistoma novaezelandiae were the C14 triene amines (3) and (4). These compounds were major lipid components, present at similar levels to fatty acids and sterols. C12 and C14 diene amines (5) and (6) were also present at lower levels.

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13

Tani, Kazuki, Takashi Kamada, Chin-Soon Phan, and Charles S. Vairappan. "A New Bioactive Cembranolide Sarcophytonolide V from Bornean Soft Coral Genus Sarcophyton." Natural Product Communications 14, no. 8 (2019): 1934578X1986837. http://dx.doi.org/10.1177/1934578x19868375.

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A new cembranolide diterpene, sarcophytonolide V (1), along with 6 known compounds, isosarcophytonolide D (2), (4 Z,8 S*,9 R*,12 E,14 E)-9-hydroxy-1-(prop-1-en-2-yl)-8,12-dimethyl-oxabicyclo[9.3.2]-hexadeca-4,12,14-trien-18-one (3), (7 E,11 E)-3,4-epoxy-7,11,15-cembratriene (4), (1 S*,3 S*,4 S*,7 E,11 E)-3,4-epoxy-13-oxo-7,11,15-cembratriene (5), (-)-eunicenone (6), and 2-[( E, E, E)-7′,8′-epoxy-4′,8′,12′-trimethylcyclotetradeca-1′,3′,11′-trienyl]propan-2-ol (7) were isolated from the Bornean soft coral Sarcophyton sp. Their structures were elucidated based on spectroscopic data, such as nucle

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14

Piers, Edward, and Richard W. Friesen. "Annulations leading to diene systems. Total syntheses of the dolastane-type diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol and (±)-amijitrienol." Canadian Journal of Chemistry 70, no. 4 (1992): 1204–20. http://dx.doi.org/10.1139/v92-157.

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Alkylation of the substituted cycloalkanones 14a–d and 30 with (Z)-1-bromo-4-methyl-3-trimethylstannyl-2-pentene (13) produced compounds 15a–d and 33, which were readily converted into the corresponding enol trifluoromethane-sulfonates (triflates) 16a–d and 34. Intramolecular Pd(O)-catalyzed coupling of the vinylstannane and enol triflate functions in 16a–d and 34 provided the dienes 17a–d and 35. The annulation product 35 served as a suitable starting material for the total syntheses of the dolastane diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol (2) and (±)-amijitrienol (3). The

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15

El-Sayed, A. M., AR Gibb, and D. M. Suckling. "Chemistry of the sex pheromone gland of the fall webworm Hyphantria cunea discovered in New Zealand." New Zealand Plant Protection 58 (August 1, 2005): 31–36. http://dx.doi.org/10.30843/nzpp.2005.58.4250.

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The sex pheromone glands of two females of the fall webworm Hyphantria cunea Drury (Lepidoptera Arctiidae) that were discovered in Auckland in March 2003 were extracted in hexane and were subjected to GCMS analysis Four compounds were identified (9Z12Z15Z)octadeca91215trienal (9Z12Z)octadeca912dienal (3Z6Z)9S10Rcisepoxyhenicosa36diene and (13Z6Z)9S10Rcis910epoxyhenicosa136triene The ratio of these four compounds in the gland extracts was 660627901 Except for a trace amount of the trienic epoxide detected in the New Zealand sample the ratio of the three other compounds was very similar to nativ

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16

Venianakis, Themistoklis, Christina Oikonomaki, Michael G. Siskos, Alexandra Primikyri, and Ioannis P. Gerothanassis. "DFT Calculations of 1H NMR Chemical Shifts of Geometric Isomers of Conjugated Linolenic Acids, Hexadecatrienyl Pheromones, and Model Triene-Containing Compounds: Structures in Solution and Revision of NMR Assignments." Molecules 26, no. 11 (2021): 3477. http://dx.doi.org/10.3390/molecules26113477.

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A DFT study of the 1H NMR chemical shifts, δ(1H), of geometric isomers of 18:3 conjugated linolenic acids (CLnAs), hexadecatrienyl pheromones, and model triene-containing compounds is presented, using standard functionals (B3LYP and PBE0) as well as corrections for dispersion interactions (B3LYP-D3, APFD, M06–2X and ωB97XD). The results are compared with literature experimental δ(1H) data in solution. The closely spaced “inside” olefinic protons are significantly more deshielded due to short-range through-space H…H steric interactions and appear close to or even beyond δ-values of aromatic sys

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17

Yunnikova, Lidiya P., Yuliya E. Likhareva, and Svetlana Yu Balandina. "N-TROPYLATION OF ARYLAMINES." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 62, no. 2 (2019): 79–84. http://dx.doi.org/10.6060/ivkkt.20196202.5751.

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An efficient method for introduction of biogenic tropylium cycle into aromatic amines molecules is offered. Introduction is carried out in the presence of imidazole as a strong base. Interaction between tropylium salts (tetrafluoroborate or perchlorate) and aromatic amines with either nitro- or acetyl groups (meta-nitroaniline, para-nitroaniline, 2-methyl-4-nitroaniline and para-acetylaniline) as electron-acceptor substituents in the benzol ring results in stable products resulting from substitution of the hydrogen atom in the amino group of aromatic amines, namely: 4-nitro-N-(1'-cyclohepta-2'

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18

Kuanhut, Wichuta, Thammarat Aree, Surachai Pornpakakul, and Pattara Sawasdee. "Novel Cucurbitane Triterpenoids and Anti-cholinesterase Activities of Constituents from Momordica charantia L." Natural Product Communications 9, no. 6 (2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900609.

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The C-19 epimers of 5β,19-epoxycucurbita-6,23( E),25(26)-triene-3β,19-diol (1) and 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (2) along with (19 R, 23 E)-5β,19-epoxy-19-methoxycucurbita-6,23,25-trien-3β-ol (3), (23 E)-5β,19-epoxycucurbita-6,23-diene-3β,25-diol (4), ligballinol (5), charantin (6) and momordicoside K (7) were isolated from the green fruits of Momordica charantia. The ( S)-epimers of 1 and 2 are the first reports in nature. The acetyl- and butyryl-cholinesterase inhibitory activities of the isolated compounds were evaluated, and 5 showed the highest activity of these c

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19

Xu, Dongbo, Erli Tian, Fandong Kong, and Kui Hong. "Bioactive Molecules from Mangrove Streptomyces qinglanensis 172205." Marine Drugs 18, no. 5 (2020): 255. http://dx.doi.org/10.3390/md18050255.

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Five new compounds 15R-17,18-dehydroxantholipin (1), (3E,5E,7E)-3-methyldeca-3,5,7-triene-2,9-dione (2) and qinlactone A–C (3–5) were identified from mangrove Streptomyces qinglanensis 172205 with “genetic dereplication,” which deleted the highly expressed secondary metabolite-enterocin biosynthetic gene cluster. The chemical structures were established by spectroscopic methods, and the absolute configurations were determined by electronic circular dichroism (ECD). Compound 1 exhibited strong anti-microbial and antiproliferative bioactivities, while compounds 2–4 showed weak antiproliferative

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20

Kofujita, Hisayoshi, Youji Fujino, Michikazu Ota, and Kouetsu Takahashi. "Antifungal diterpenes from the bark of Cryptomeria japonica D. Don." Holzforschung 60, no. 1 (2006): 20–23. http://dx.doi.org/10.1515/hf.2006.004.

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Abstract Bioassay-guided isolation of compounds from n-hexane extracts of the bark of Cryptomeria japonica resulted in six abietane- and two pimarane-type diterpenoids, including a new compound, 12-methoxy-6α,11-dihydroxyabieta-8,11,13-triene. The structure of the new substance was established by spectral analyses and comparison with related compounds. The antifungal activities of these diterpenes were evaluated against the phytopathogenic fungi Alternaria alternata, Pyricularia oryzae, Rhizoctonia solani and Fusarium oxysporum. The diterpenes showed moderate antifungal activity against the fu

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21

Szöllösy, Aron, George Kotovych, Gábor Tóth та Albert Lévai. "The synthesis and the nuclear magnetic resonance study of β-lactam derivatives of 1,5-benzothiazepines". Canadian Journal of Chemistry 66, № 2 (1988): 279–82. http://dx.doi.org/10.1139/v88-047.

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The synthesis and stereochemistry of seven β-lactam derivatives of 1,5-benzothiazepines are presented. The configurational and conformational analysis is based on nuclear Overhauser effect experiments, together with analysis of the vicinal proton–proton coupling constants. In the preferred conformation, the seven-membered ring is in a half-chair. Only for one compound, 2-aza-4-bromo-4-methyl-5,7-diphenyl-8-thiatricyclo[7.4.0.02,5]trideca-Δ1,9,10,12-trien-3-one, were two diastereomers isolated (compounds 6a and 6b). Six of the compounds have the 4S*, 5R*, 7R* configuration while compound 6b has

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22

Chang, Chi-I., Cheng-Chi Chen, Chiy-Rong Chen, et al. "Bioactive Dimeric Abietanoid Peroxides from the Bark of Cryptomeria japonica." Molecules 24, no. 11 (2019): 2178. http://dx.doi.org/10.3390/molecules24112178.

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Three new dimeric abietane-type diterpenoids, abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7α-yl peroxide (1), abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7β-yl peroxide (2), and 12-hydroxyabieta-8,11,13-trien-7β-yl 7-oxoabieta-5,8,11,13-tetraen-12-yl peroxide (3), together with four known abietane-type diterpenoids (4–7) were isolated from the methanol extract of the bark of Cryptomeria japonica. Their structures were elucidated on the basis of spectroscopic analysis and comparison of NMR data with those of known analogues. At a concentration of 50 μM, compo

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23

Layne, Tanya H., William F. Reynolds, Stewart McLean, and Winston F. Tinto. "Secondary Metabolites from Clerodendrum Chinense." Natural Product Communications 3, no. 11 (2008): 1934578X0800301. http://dx.doi.org/10.1177/1934578x0800301108.

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Chemical studies carried out on Clerodendrum chinense yielded three new compounds including the steroid (22E, 24S)-stigmasta-4, 22, 25-trien-3-one (1), the flavone glycoside 7, 8, 4′-trihydroxyflavone-6-O-β-D-glucuronopyranoside (2) and the epimeric neo-clerodane 14, 15-dihydro-15ξ-hydroxyclerodendrin A (3). Two acetylated derivatives of compound 3-, 2α-acetoxy-14, 15-dihydro-15ξ-hydroxyclerodendrin A (4) and 2α-acetoxy-14, 15-dihydro-15ξ-methoxyclerodendrin A (5) were also prepared, which have not been reported previously. The structure of each compound was elucidated by spectroscopic means.

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24

Jagadeesh, Raman, Gajandran Babu, Hariprasath Lakshmanan, et al. "Bioactive Sterol Derivatives Isolated from the Pleurotus djamor var. Roseus Induced Apoptosis in Cancer Cell Lines." Cardiovascular & Hematological Agents in Medicinal Chemistry 18, no. 2 (2020): 124–34. http://dx.doi.org/10.2174/1871525718666200303123557.

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Objective: The aim of the present study is to isolate and characterize the bioactive compounds from Pleurotus djamor against human breast cancer (MDA-MD-231) and mouse T cell lymphoma (EL4) cell lines. Materials and methods: Sequential fractionization and column chromatography methods were involved in compound isolation. The structures of the isolated compound were determined by NMR, GC/MS, and X-ray crystallography studies. Results: The isolated compounds 1- 4 [D-mannitol (C1), ergosta-5,7,22-trien-3β-ol (C2), 5,8- epidioxy-ergosta-6-22-dien-3β-ol (C3), and palmitic acid (C4)] are white cryst

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25

Shiyanga, Aina N., Michael Knott, and Petrina Kapewangolo. "In vitro Anti-HIV and Antimicrobial Activities of a Halogenated Monoterpene from a Namibian Plocamium Species of Marine Algae." Current Bioactive Compounds 16, no. 3 (2020): 363–67. http://dx.doi.org/10.2174/1573407215666190111153845.

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Background: The marine red alga Plocamium naturally produces halogenated monoterpenes with varied biological activities. In our continuing efforts to discover new lead compounds for the treatment of HIV/AIDS as well as novel antibacterial compounds, various Namibian Plocamium species have been investigated. Methods: A rare but known compound namely 1E,3R,4S,5E,7Z-1-bromo-3,4,8-trichloro-7- (dichloromethyl)-3-methylocta-1,5,7-triene (1) was isolated from a Namibian Plocamium red alga. The anti-HIV activity of compound 1 was investigated against three HIV enzymes namely, HIV protease, reverse tr

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26

Bérubé, Gervais, and Pierre Deslongchamps. "Synthesis and transannular Diels–Alder reaction of a 13-membered macrocyclic triene having a tetrasubstituted enol ether as dienophile." Canadian Journal of Chemistry 68, no. 3 (1990): 404–11. http://dx.doi.org/10.1139/v90-062.

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The syntheses of the acyclic triene trans–trans–cis27 and trans–trans–trans31 are described. Macrocyclization and concomitant transannular Diels–Alder reaction were performed with the chloride derivative obtained from the trans–trans–cis triene alcohol 27 yielding a mixture of the tricyclic compounds trans–syn–trans33 and cis–syn–cis34. On the other hand, macrocyclization of the chloride derived from trans–trans–trans triene 31 was not successful. Keywords: transannular process, Diels–Alder reaction, macrocyclic triene, macrocyclization, tricyclic compounds, organic synthesis.

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27

Ali, Sami I., Chuan-Rui Zhang, Amal A. Mohamed, et al. "Major Constituents of Boswellia Carteri Resin Exhibit Cyclooxygenase Enzyme Inhibition and Antiproliferative Activity." Natural Product Communications 8, no. 10 (2013): 1934578X1300801. http://dx.doi.org/10.1177/1934578x1300801005.

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Aromatic gum from Boswellia carteri (olibanum oleogum) has long been used in Egyptian traditional medicine. Cyclooxygenase-1 (COX-1) enzyme inhibitory assay guided purification of the extracts of this resin resulted in five bioactive compounds, 3α- O-acetyl-8,24-dien-tirucallic acid (1), verticilla-4(20),7,11-triene (2), cembrene A (3), incensole acetate (4), and incensole (5). The pure isolates were investigated for their inhibitory effects on COX-1 and −2 enzymes and human tumor cell lines Hep-G2, MCF-7 and RAW 264.7. Compounds 1–5 inhibited COX-2 enzyme by 39.0, 32.7, 60.0, 46.3, and 49.8%,

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28

Herberhold, Max, Wolfgang Milius, and Nilgün Akkus. "The Structure of the Ligand Tri(1-cyclohepta-2,4,6-trienyl)phosphane, P(C7H7)3, in the Hexafluoroacetylacetonato Copper(I) Complexes, (hfac)Cu[P(C7H7)3]n (n = 1, 2)." Zeitschrift für Naturforschung B 59, no. 8 (2004): 843–49. http://dx.doi.org/10.1515/znb-2004-0801.

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AbstractThe reaction of CuCl[P(C7H7)3] (1a) with sodium hexafluoroacetylacetonate, Na(hfac), leads to (hfac)Cu[P(C7H7)3] (2a), which in the presence of excess P(C7H7)3 (a) gives (hfac)Cu[P(C7H7)3]2 (3a). Whereas the 1:2 compound 3a is a pseudo-tetrahedral copper(I) complex with relatively long Cu-P (224.85(10) and 223.75(10) pm) and Cu-O (212.7(3) and 212.0(3) pm) distances, the 1:1 complex 2a may be described as having a distorted pseudo-trigonal coordination sphere (Cu-P 214.32(11) pm, Cu-O 196.6(3) and 208.1(3) pm), although one of the cyclohepta-2,4,6-trienyl substituents develops a weak a

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29

Hanuš, Lumír O., Arieh Moussaieff, Tomáš Řezanka, Saleh Abu-Lafi, and Valery M. Dembitsky. "Phytochemical Analysis and Comparison for Differentiation of Boswellia Carterii and B. Serrata." Natural Product Communications 2, no. 2 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200206.

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Frankincense (Boswellia carterii) and olibanum (B. serrata) were chemically analyzed to determine compounds that would enable the differentiation of the two products. Typical compounds for both species were identified. Three new compounds, 24-noroleana-3,9(11),12-triene, 24-norursa-3,9(11),12-triene, and 24-norursa-3,12-diene-11-one, were identified in olibanum; these may be either naturally occuring or pyrolytic products.

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30

Li, Wei, Xue-Qiong Yang, Ya-Bin Yang, et al. "A Novel Steroid Derivative and a New Steroidal Saponin from Endophytic Fungus Xylaria sp." Natural Product Communications 12, no. 6 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200617.

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Two new steroids, (24 R)-22, 23-dihydroxy-ergosta-4,6,8(14)-trien-3-one 23-β-D-glucopyranoside (1), and xylarester (2), together with 16 known compounds were isolated from the extract of endophytic Xylaria sp. solid culture. Their structures were elucidated by spectroscopic methods. Compound 2 has an unprecedent ergosta skeleton with a six-membered lactonic group in A ring. The X-ray single crystal diffraction data of 4,7-dihydroxy-13-tetradeca-2,5,8-trienolide (4) were also reported for the first time. The antibacterial, anti-acetylcholinesterase, nitric oxide inhibition and cytotoxic activit

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31

Horinouchi, Masae, Toshiaki Hayashi, Hiroyuki Koshino, Michal Malon, Takako Yamamoto, and Toshiaki Kudo. "Identification of Genes Involved in Inversion of Stereochemistry of a C-12 Hydroxyl Group in the Catabolism of Cholic Acid by Comamonas testosteroni TA441." Journal of Bacteriology 190, no. 16 (2008): 5545–54. http://dx.doi.org/10.1128/jb.01080-07.

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ABSTRACT Comamonas testosteroni TA441 degrades steroids such as testosterone via aromatization of the A ring, followed by meta-cleavage of the ring. In the DNA region upstream of the meta-cleavage enzyme gene tesB, two genes required during cholic acid degradation for the inversion of an α-oriented hydroxyl group on C-12 were identified. A dehydrogenase, SteA, converts 7α,12α-dihydroxyandrosta-1,4-diene-3,17-dione to 7α-hydroxyandrosta-1,4-diene-3,12,17-trione, and a hydrogenase, SteB, converts the latter to 7α,12β-dihydroxyandrosta-1,4-diene-3,17-dione. Both enzymes are members of the short-c

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32

Choi, Byeoung-Kyu, Song-Hee Jo, Dong-Kug Choi, et al. "Anti-Neuroinflammatory Agent, Restricticin B, from the Marine-Derived Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells." Marine Drugs 18, no. 9 (2020): 465. http://dx.doi.org/10.3390/md18090465.

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A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2–5) were obtained from the EtOAc extract of the marine-derived fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via the analyses of NOESY spectroscopy data, the comparison of optical rotation values with those of reported restricticin derivatives and electronic circular dichroism (ECD). All the compounds were sc

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33

Alvarenga, Tavane Aparecida, Osvaine Júnior Alvarenga Alves, Mariana Cintra Pagotti, et al. "In vitro antileishmanial activity of Anacardium othonianum and isolated compounds against Leishmania amazonensis." Acta Brasiliensis 5, no. 1 (2021): 44. http://dx.doi.org/10.22571/2526-4338429.

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This study analyzes the antileishmanial activity of the crude ethanol extract, fractions, and isolated compounds of A. othonianum nuts. Antileishmanial activity was evaluated against Leishmania amazonensis promastigotes in vitro. The phytochemical study was performed by high-performance liquid chromatography-high-resolution mass spectrometry-diode array detector (HPLC-HRMS-DAD) and by preparative HPLC. HPLC-HRMS-DAD analysis of the bioactive extract confirmed the presence of ten alkyl phenol derivatives that had previously been isolated from A. occidentale. Bioassay-guided isolation afforded c

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34

Ayyildiz, Hamide Filiz. "Evaluation of Chemical Properties of Cold Pressed Ficus Carica Seed Oil." Pakistan Journal of Analytical & Environmental Chemistry 22, no. 1 (2021): 35–43. http://dx.doi.org/10.21743/pjaec/2021.06.05.

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Free fatty acid, peroxide value , conjugated diene and triene, chlorophyll, β-carotene, fatty acid composition, triglyceride, tocol (tocopherol and tocotrienol) compositions, sterol, wax and total polymeric compound amounts of cold pressed Ficus carica seed oil were evaluated by using chromatographic and spectrometric methods in this study. While the % free fatty acid of cold pressed ficus carica seed oil was 0.76±0.06, the peroxide value was found as 1.06 ± 0.09 meqO2/kg. It also had low content of conjugated diene and triene amounts, chlorophyll, wax and total polymeric compounds. The obtain

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35

Cantin, Michel, Yao-Chang Xu, and Pierre Deslongchamps. "Stereocontrolled construction of A.B.C.[6.6.6] tricycle via transannular Diels–Alder reaction of 14-membered triene macrocycle." Canadian Journal of Chemistry 68, no. 12 (1990): 2144–52. http://dx.doi.org/10.1139/v90-329.

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The synthesis of the four acyclic trienes 11a, b and 20a, b is reported. The tandem macrocyclization and stereoselective transannular Diels–Alder reaction of acyclic trienes 11b (trans-trans-cis) and 20b (trans-trans-trans) were observed in the presence of Cs2CO3 at 85 °C to give tricycles 30 (TST) and 32 (CAT) respectively. However, treatment of acyclic trienes 11a (cis-trans-cis) and 20a (cis-trans-trans) under the same conditions yielded the 14-membered macrocycles 21 and 23, which were stereoselectively transformed at 250 °C into tricycles 22 (CST) and 24 (CAT) respectively in excellent yi

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36

D'Souza, Mervyn C., та Morris Ingle. "A RAPID METHOD FOR EVALUATING α-FARNESENE, TRIENE AND ANTIOXIDANT LEVELS IN APPLE SCALD PHYSIOLOGY STUDIES". HortScience 26, № 5 (1991): 480a—480. http://dx.doi.org/10.21273/hortsci.26.5.480a.

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Superficial scald on apples is effectively controlled by the currently registered inhibitors, diphenylamine and ethoxyquin. However, the availability of these chemicals as scald inhibitors in the future is uncertain. There is renewed interest and need for scald research to develop prediction systems and non-chemical control measures. Scald is believed to be caused by the oxidation of α-farnesene into trienes. The reaction is partially inhibited by the presence of antioxidants in the peel. We have developed a new method to evaluate scald reaction compounds. This method was used to show that dif

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37

Lian, Danhong, Xin Zhong, Yimei Zheng, Sha Zhou, Li Gu, and Xin Liu. "A New Sterol From Sporoderm-Broken Ganoderma sinense Spores and Its Anticancer Activity." Natural Product Communications 14, no. 12 (2019): 1934578X1989512. http://dx.doi.org/10.1177/1934578x19895123.

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A new sterol, ganodermaside E (1), and 4 known sterols, (22 E,24 R)-3β,5α-dihydroxyergosta-7,22-dien-6-one (2), (22 E,24 R)-3β,5α,9α-trihydroxyergosta-7,22-diene-6-one (3), (22 E,24 R)-ergosta-7,9(11),22-triene-3β,5α,6β-triol (4), and (22 E,24 R)-ergosta-7,22-diene-3β,5α,6α-triol (5), were isolated for the first time from the sporoderm-broken spores of Ganoderm sinense Zhao, Xu et Zhang. Their structures were determined by spectroscopic techniques such as nuclear magnetic resonance spectroscopy and mass spectrometry. Furthermore, all the compounds were evaluated for their in vitro cytotoxicity

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38

Jovanovic-Santa, Suzana, Sanja Gaborov, and Julijana Petrovic. "Synthesis of 3-benzyloxyl-17-maleyloxy-16, 17-secoestra- 1, 3, 5 (10)-triene-16-nitrile - Sinteza 3-benziloksi-17-maleiloksi- 16, 17-sekoestra-1, 3, 5 (10)-trien-16-nitrila." Zbornik Matice srpske za prirodne nauke, no. 103 (2002): 5–9. http://dx.doi.org/10.2298/zmspn0201005j.

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Under the conditions of Beckmann fragmentation reaction 3-benzyloxy-17(-hydroxyestra-1, 3, 5, (10)-triene-16-one oxime (2) gave the D-seco derivative 3. Sodium borohydride reduction of this compound afforded 3-benzyloxy-17-hydroxy-16, 17-secoestra-1, 3, 5 (10)-triene-16-nitrile (4). The esterification of seco-cyanoalcohol 4 was achieved by action of maleic acid anhydride in dry pyridine, yielding 3-benzyloxy-17-maleyloxy-16 17-secoestra-1, 3, 5 (10)-triene-16-nitrile (5).

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39

Musa, Weny, Hersanti Hersanti, Achmad Zainuddin та Roekmi-ati Tjokronegoro. "THE PORIFERASTA COMPOUND-5,22E,25-TRIEN-3-Oβ FROM Clerodendrum paniculatum LEAF AS INDUCER AGENT OF SYSTEMIC RESISTANCE ON RED CHILLI PLANT Capsicum annuum L FROM CUCUMBER MOSAIC VIRUS (CMV". Indonesian Journal of Chemistry 9, № 3 (2010): 487–90. http://dx.doi.org/10.22146/ijc.21521.

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The poriferasta-5.22E.25-trien-3β-ol compound of leaves of this plant Clerodendrum paniculatum has activity as an inducer agent of plant systemic resistance of red plant toward Cucumber Mosaic Viruses (CMV), the inhibition activity compound shows 82% inhibition activity at 300 ppm. The structure of these compound were determined on the basis of spectroscopic data including UV, IR, 1H-NMR, 13C-NMR and 2D-NMR Keywords: Poriferasta-5.22E.25-trien-3β-ol, Clerodendrum paniculatum, induction of systemic resistance, CMV

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40

Saragih, Magdalena, Trizelia Trizelia, Nurbailis Nurbailis, and Yusniwati Yusniwati. "Profil GCMS Senyawa Kimia Ekstrak Metanol Isolat Cendawan Entomopatogen Beauveria Bassiana Dan Akar Cabai Sebagai Pemacu Pertumbuhan Cabai." Agrotekma: Jurnal Agroteknologi dan Ilmu Pertanian 4, no. 2 (2020): 106–18. http://dx.doi.org/10.31289/agr.v4i2.3840.

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The aim of this study was to identify the chemical compound methanol extract of entomopathogenic fungus Beauveria bassiana from insect walang sangit and the chemical compound roots of red chili plants that were able to stimulate the growth of chilli plants after being applied with entomopathogenic fungus B. bassiana through seed immersion inoculation using GCMS method. The chemical compound identified as a growth booster in B. bassiana fungus isolates from the insect walang sangit is an Acetic acid Ethanoic acid Ethylic acid Glacial acetic acid CH3COOH, Hexadecanoic acid, methyl ester (CAS) Me

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41

Ndibwami, Alexis, Serge Lamothe, Pierre Soucy, Solo Goldstein, and Pierre Deslongchamps. "Transannular Diels–Alder reactions on 14-membered macrocyclic trienes. Part II: formation of macrocycles and thermal conversion into tricyclic systems." Canadian Journal of Chemistry 71, no. 5 (1993): 714–25. http://dx.doi.org/10.1139/v93-095.

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In the preceding paper (Part I) we described the synthesis of eight isomeric acyclic trienes. These compounds could be transformed into the corresponding macrocyclic trienes, which were further converted into tricyclic A.B.C.[6.6.6] products by a thermal transannular Diels–Alder reaction. The experimental results of this study and their analysis are reported in the present paper. The comparison with theoretical predictions is also discussed.

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42

Qi, Zhiwen, Chengzhang Wang, Jianxin Jiang, and Caie Wu. "Novel C15 Triene Triazole, D-A Derivatives Anti-HepG2, and as HDAC2 Inhibitors: A Synergy Study." International Journal of Molecular Sciences 19, no. 10 (2018): 3184. http://dx.doi.org/10.3390/ijms19103184.

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A series of novel C15 urushiol derivatives were designed by introducing a pechmann structure and F-, Cl-, and Br-nitro substituents with different electronic properties into its alkyl side chain, as well as a triazolyl functional group in its aromatic oxide. Their chemical structures were determined based on the analysis of the NMR (nuclear magnetic resonance) spectroscopic and mass spectrometric data. The results showed that compound 4 exhibited a strong inhibition of the HepG2 cell proliferation (half maximal inhibitory concentration (IC50): 2.833 μM to human hepatocellular carcinoma (HepG2)

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43

Tai, Chi-Jen, Chiung-Yao Huang, Atallah F. Ahmed, et al. "An Anti-Inflammatory 2,4-Cyclized-3,4-Secospongian Diterpenoid and Furanoterpene-Related Metabolites of a Marine Sponge Spongia sp. from the Red Sea." Marine Drugs 19, no. 1 (2021): 38. http://dx.doi.org/10.3390/md19010038.

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Chemical investigation of a Red Sea Spongia sp. led to the isolation of four new compounds, i.e., 17-dehydroxysponalactone (1), a carboxylic acid, spongiafuranic acid A (2), one hydroxamic acid, spongiafuranohydroxamic acid A (3), and a furanyl trinorsesterpenoid 16-epi-irciformonin G (4), along with three known metabolites (−)-sponalisolide B (5), 18-nor- 3,17-dihydroxy-spongia-3,13(16),14-trien-2-one (6), and cholesta-7-ene-3β,5α-diol-6-one (7). The biosynthetic pathway for the molecular skeleton of 1 and related compounds was postulated for the first time. Anti-inflammatory activity of thes

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44

Betalleluz-Pallardel, I., R. Chirinos, H. Rogez, R. Pedreschi, and D. Campos. "Phenolic compounds from Andean mashua (Tropaeolum tuberosum) tubers display protection against soybean oil oxidation." Food Science and Technology International 18, no. 3 (2012): 271–80. http://dx.doi.org/10.1177/1082013211427794.

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Phenolic compounds from mashua tuber were evaluated as potential antioxidants to retard the oxidation of crude soybean oil submitted to accelerated storage and frying. During the accelerated storage, an ethanolic crude extract, a purified extract, an aqueous fraction and an ethyl acetate fraction from mashua containing different gallic acid equivalent concentrations (100, 300 and 600 ppm) in oil were evaluated at 55 °C. After 15 days of storage, better effects were evidenced against soybean oil oxidation at 300 and 600 ppm of ethyl acetate fraction in comparison to 200 ppm butylated hydroxytol

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45

Marinier, Anne, and Pierre Deslongchamps. "Stereocontrolled chiral synthesis of a trans-anti-trans tricycle by a transannular Diels–Alder reaction." Canadian Journal of Chemistry 70, no. 9 (1992): 2350–64. http://dx.doi.org/10.1139/v92-297.

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The racemic and chiral synthesis of trans-cis-cis macrocyclic triene 5 is described. Heating this compound at 262 °C leads via a transannular Diels–Alder reaction to the tricyclic structure 6, which can be further transformed into tricyclic compound 7. This work constitutes a preliminary study for the synthesis of corticoids.

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46

Wang, H. Y., та H. Schulz. "β-oxidation of polyunsaturated fatty acids with conjugated double bonds. Mitochondrial metabolism of octa-2,4,6-trienoic acid". Biochemical Journal 264, № 1 (1989): 47–52. http://dx.doi.org/10.1042/bj2640047.

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The mitochondrial beta-oxidation of octa-2,4,6-trienoic acid was studied with the aim of elucidating the degradation of unsaturated fatty acids with conjugated double bonds. Octa-2,4,6-trienoic acid was found to be a respiratory substrate of coupled rat liver mitochondria, but not of rat heart mitochondria. Octa-2,4,6-trienoyl-CoA, the product of the inner-mitochondrial activation of the acid, was chemically synthesized and its degradation by purified enzymes of beta-oxidation was studied spectrophotometrically and by use of h.p.l.c. This compound is a substrate of NADPH-dependent 2,4-dienoyl-

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47

Mayaka, Regina Kemunto, Alice Wanjiku Njue, Moses Kiprotich Langat, Peter Kiplagat Cheplogoi, and Josiah Ouma Omolo. "Antimicrobial compounds from the Kenyan Ganoderma adspersum (Schulz.) Donk species." International Journal of Biological and Chemical Sciences 13, no. 7 (2020): 3390–97. http://dx.doi.org/10.4314/ijbcs.v13i7.33.

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The emergence of antibiotic resistant pathogens has continuously increased, leading to a growing worldwide health threat due to infectious diseases. And therefore in our search for antibacterial and antifungal compounds from the polypore Ganoderma adspersum, the dried, ground fruiting bodies of G. adspersum were extracted with methanol and solvent removed in a rotary evaporator. The extract was suspended in distilled water, then partitioned using ethyl acetate solvent to obtain an ethyl acetate extract. The extract was fractionated and purified using column chromatographic method and further p

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48

Greve, Hippolyt, Marcel Kaiser, Reto Brun, and Thomas Schmidt. "Terpenoids from the Oleo-Gum-Resin of Boswellia serrata and Their Antiplasmodial Effects In Vitro." Planta Medica 83, no. 14/15 (2017): 1214–26. http://dx.doi.org/10.1055/s-0043-116943.

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AbstractIn the course of our ongoing search for new natural products as leads against protozoal diseases, the dichloromethane extract of Indian frankincense, the oleo-gum-resin obtained from Boswellia serrata, showed in vitro activity against Plasmodium falciparum. Bioactivity-guided fractionation led to the isolation of eight diterpenes: (1S,3E,7E,11R)-verticilla-3,7,12(18)-triene (1), cembrene A (2), serratol (3), 1S,3E,7R,8R,11E-7,8-epoxy-cembra-3,11-dien-1-ol (4), incensole oxide (5), rel (1S,3R,7E,11S,12R)-1,12-epoxy-4-methylenecembr-7-ene-3, 11-diol (6), isoincensole oxide (7), and isode

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49

Choudhary, Muhammad I., Syed G. Musharraf, Rahat A. Ali, Muhammad Atif та Atta-ur Rahman. "Microbial Transformation of Antifertility Agents, Norethisterone and 17α-Ethynylestradiol". Zeitschrift für Naturforschung B 59, № 3 (2004): 319–23. http://dx.doi.org/10.1515/znb-2004-0314.

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The microbial transformation of oral contraceptive norethisterone (1) by Cephalosporium aphidicola afforded an oxidized metabolite, 17α-ethynylestradiol (2), while the microbial transformation of 2 by Cunninghamella elegans yielded several metabolites, 19-nor-17α-pregna-1,3,5 (10)- trien-20-yne-3,4,17β -triol (3), 19-nor-17α-pregna-1,3,5 (10)-trien-20-yne-3,7α,17β -triol (4), 19- nor-17α-pregna-1,3,5 (10)-trien-20-yne-3,11α,17β -triol (5), 19-nor-17α-pregna-1,3,5 (10)-trien-20- yne-3,6β ,17β -triol (6) and 19-nor-17α-pregna-1,3,5 (10)-trien-20-yne-3,17β -diol-6β -methoxy (7). Metabolite 7 was

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50

R., Soorya, Dhamodaran P., Rajesh Kumar R., and Duraisamy B. "IN SILICO STUDIES OF THE SECONDARY METABOLITES OF SOLANUM TORVUM SW. FOR THEIR ANTIASTHMATIC ACTIVITY." International Journal of Current Pharmaceutical Research 9, no. 4 (2017): 38. http://dx.doi.org/10.22159/ijcpr.2017v9i4.20759.

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Objective: Solanum torvum Sw., Family: Solanaceae, commonly known as Turkey Berry is used by the traditional tribes for the treatment of cold, cough, tuberculosis, hepatotoxicity, cancer, etc. The action of the plant towards the treatment of these diseases has been proven except for asthma. The present study is to prove the antiasthmatic activity of methanolic extract and the secondary metabolites of Solanum torvum Sw using in silico docking studies in compare to reference standard Dexamethasone, a synthetic cortisone derivative.Methods: The GC-MS analysis of the dried methanolic extract of th

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