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Keywords = juncenolide

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10 pages, 5185 KiB  
Article
11β,20β-Epoxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae)
by Tung-Pin Su, Tsu-Jen Kuo, San-Nan Yang, Gene-Hsiang Lee, Yen-Tung Lee, Yi-Chen Wang, Jih-Jung Chen, Zhi-Hong Wen, Tsong-Long Hwang and Ping-Jyun Sung
Mar. Drugs 2020, 18(4), 183; https://doi.org/10.3390/md18040183 - 31 Mar 2020
Cited by 3 | Viewed by 2942
Abstract
Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1 [...] Read more.
Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells. Full article
(This article belongs to the Special Issue Bioactive Compounds from Coral Reef Organisms 2021)
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12 pages, 848 KiB  
Article
Four New Briarane Diterpenoids from Taiwanese Gorgonian Junceella fragilis
by Chia-Ching Liaw, Yu-Chi Lin, Yun-Sheng Lin, Chung-Hsiung Chen, Tsong-Long Hwang and Ya-Ching Shen
Mar. Drugs 2013, 11(6), 2042-2053; https://doi.org/10.3390/md11062042 - 10 Jun 2013
Cited by 21 | Viewed by 6411
Abstract
Four new 8-hydroxybriarane diterpenoids, frajunolides P–S (1–4), together with umbraculolide A, juncenolide C, junceellonoid A and juncin R, were isolated from the acetone extract of the gorgonian Junceella fragilis, collected from the southeast coast of Taiwan. Compound 1 [...] Read more.
Four new 8-hydroxybriarane diterpenoids, frajunolides P–S (1–4), together with umbraculolide A, juncenolide C, junceellonoid A and juncin R, were isolated from the acetone extract of the gorgonian Junceella fragilis, collected from the southeast coast of Taiwan. Compound 1 contains an unusual pivaloyloxy group at C-2, while 3 is a rare compound having a chlorine atom on the olefinic carbon (C-6). The structures of the isolated compounds were established by extensive spectroscopic analysis, including 1D- and 2D-NMR, as well as HRMS data. Compound 1 was further confirmed by X-ray crystallographic analysis. In the anti-inflammatory test, compounds 1 and 2 exhibited moderate inhibition on superoxide anion generation and elastase release by human neutrophils in response to formylmethionylleucyl-phenylalanine/dihydrocytochalasin B (fMLP/CB). Full article
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18 pages, 802 KiB  
Article
Chemistry and Tumor Cell Growth Inhibitory Activity of 11,20-Epoxy-3Z,5(6)E-diene Briaranes from the South China Sea Gorgonian Dichotella gemmacea
by Cui Li, Mei Jiang, Ming-Ping La, Tie-Jun Li, Hua Tang, Peng Sun, Bao-Shu Liu, Yang-Hua Yi, Zhiyong Liu and Wen Zhang
Mar. Drugs 2013, 11(5), 1565-1582; https://doi.org/10.3390/md11051565 - 15 May 2013
Cited by 18 | Viewed by 6291
Abstract
Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA–AR (1–18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the [...] Read more.
Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA–AR (1–18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the South China Sea gorgonian Dichotella gemmacea. The structures of the compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was determined based on the ECD experiment. In the in vitro bioassay, compounds 1–3, 5, 6, 8–12, and 14–19 exhibited different levels of growth inhibition activity against A549 and MG63 cell lines. Preliminary structure-activity analysis suggests that 12-O-isovalerate may increase the activity whereas 13- or 14-O-isovalerate may decrease the activity. Contribution of substitutions at C-2 and C-16 remains uncertain. Full article
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10 pages, 688 KiB  
Article
New Briarane Diterpenoids from the Gorgonian Coral Junceella juncea
by Jiun-Yang Chang, Chia-Ching Liaw, Ahmed Eid Fazary, Tsong-Long Hwang and Ya-Ching Shen
Mar. Drugs 2012, 10(6), 1321-1330; https://doi.org/10.3390/md10061321 - 7 Jun 2012
Cited by 22 | Viewed by 7490
Abstract
Chemical investigation of Junceella juncea has resulted in the isolation of three new briaranes designated juncenolides M–O (1–3). The structures of these compounds were determined by spectroscopic analysis including 2D-NMR (COSY, HMBC and NOESY) and HRMS. Compound 1 is [...] Read more.
Chemical investigation of Junceella juncea has resulted in the isolation of three new briaranes designated juncenolides M–O (1–3). The structures of these compounds were determined by spectroscopic analysis including 2D-NMR (COSY, HMBC and NOESY) and HRMS. Compound 1 is a new chlorinated briarane while compound 3 contains a rare methyl ester at C-16. The anti-inflammatory activities tested on superoxide anion generation and elastase release by human neutrophils in response to FMLP/CB were evaluated. Full article
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16 pages, 1292 KiB  
Article
Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea
by Cui Li, Ming-Ping La, Peng Sun, Tibor Kurtan, Attila Mandi, Hua Tang, Bao-Shu Liu, Yang-Hua Yi, Ling Li and Wen Zhang
Mar. Drugs 2011, 9(8), 1403-1418; https://doi.org/10.3390/md9081403 - 16 Aug 2011
Cited by 29 | Viewed by 9129
Abstract
Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N–S (1–6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7–10), from the South China Sea gorgonian Dichotella [...] Read more.
Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N–S (1–6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7–10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1. The cytotoxic and antimicrobial activities of these compounds were evaluated. In preliminary in vitro bioassays, compounds 4, 5, 6, 8 and 9 showed cytotoxicity against A549 and MG63, while compounds 1, 2, 4, 7–10 showed antimicrobial activity against the fungus Septoria tritici and the bacterium Escherichia coli. Full article
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