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Search Results (6)

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Keywords = capnosane

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13 pages, 1658 KiB  
Article
Six Undescribed Capnosane-Type Macrocyclic Diterpenoids from South China Sea Soft Coral Sarcophyton crassocaule: Structural Determination and Biological Evaluation
by Hanyang Peng, Yanbo Zeng, Hao Wang, Wenjun Chang, Huiqin Chen, Fengjuan Zhou, Haofu Dai and Xiachang Wang
Mar. Drugs 2023, 21(12), 645; https://doi.org/10.3390/md21120645 - 18 Dec 2023
Viewed by 1798
Abstract
Six undescribed capnosane-type macrocyclic diterpenes sarcocrassolins A–F (1–6) and one related known analog pavidolide D (7) were isolated from Sarcophyton crassocaule, a soft coral collected off the Nansha Islands, in the South China Sea. Their complete [...] Read more.
Six undescribed capnosane-type macrocyclic diterpenes sarcocrassolins A–F (1–6) and one related known analog pavidolide D (7) were isolated from Sarcophyton crassocaule, a soft coral collected off the Nansha Islands, in the South China Sea. Their complete structures, relative configurations and absolute configurations were established through comprehensive spectroscopic analysis, quantum mechanical nuclear magnetic resonance (QM-NMR) and single-crystal X-ray diffraction. Sarcocrassolins D (4) and E (5) showed inhibitory activity against lipopolysaccharide (LPS)-stimulated inflammatory responses in RAW264.7 cells with IC50 values of 76.8 ± 8.0 μM and 93.0 ± 3.8 μM, respectively. Full article
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14 pages, 3308 KiB  
Article
Structurally Diverse Diterpenes from the South China Sea Soft Coral Sarcophyton trocheliophorum
by Yu-Ting Song, Dan-Dan Yu, Ming-Zhi Su, Hui Luo, Jian-Guo Cao, Lin-Fu Liang, Fan Yang and Yue-Wei Guo
Mar. Drugs 2023, 21(2), 69; https://doi.org/10.3390/md21020069 - 20 Jan 2023
Cited by 5 | Viewed by 2439
Abstract
The present investigation of the South China Sea soft coral Sarcophyton trocheliophorum resulted in the discovery of six new polyoxygenated diterpenes, namely sartrocheliols A–E (1, 3, 5–8) along with four known ones, 2, 4, 9 [...] Read more.
The present investigation of the South China Sea soft coral Sarcophyton trocheliophorum resulted in the discovery of six new polyoxygenated diterpenes, namely sartrocheliols A–E (1, 3, 5–8) along with four known ones, 2, 4, 9, and 10. Based on extensive spectroscopic data analysis, sartrocheliol A (1) was identified as an uncommon capnosane diterpene, while sartrocheliols B–E (3, 5–8) were established as cembrane diterpenes. They displayed diverse structural features not only at the distinctly different carbon frameworks but also at the various types of heterocycles, including the epoxide, γ-lactone, furan, and pyran rings. Moreover, their absolute configurations were determined by a combination of quantum mechanical-nuclear magnetic resonance (QM-NMR) approach, modified Mosher’s method, and X-ray diffraction analysis. In the anti-tumor bioassay, compound 4 exhibited moderate cytotoxic activities against A549, H1975, MDA-MB-231, and H1299 cells with the IC50 values ranging from 26.3 to 47.9 μM. Full article
(This article belongs to the Special Issue A Theme Issue Honoring Professor Peter Proksch's 70th Birthday: Bioactive Compounds from the Ocean)
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14 pages, 2371 KiB  
Article
Uncommon Capnosane Diterpenes with Neuroprotective Potential from South China Sea Soft Coral Sarcophyton boettgeri
by Ye-Qing Du, Jing Chen, Meng-Jun Wu, Hai-Yan Zhang, Lin-Fu Liang and Yue-Wei Guo
Mar. Drugs 2022, 20(10), 602; https://doi.org/10.3390/md20100602 - 25 Sep 2022
Cited by 9 | Viewed by 2083
Abstract
The first investigation of the South China Sea soft coral Sarcophyton boettgeri afforded five new capnosane diterpenes, sarboettgerins A–E (1–5), together with one known related compound, pavidolide D (6). Their structures, including absolute configurations, were elucidated by [...] Read more.
The first investigation of the South China Sea soft coral Sarcophyton boettgeri afforded five new capnosane diterpenes, sarboettgerins A–E (1–5), together with one known related compound, pavidolide D (6). Their structures, including absolute configurations, were elucidated by the extensive spectroscopic analysis, 13C NMR calculations, and X-ray diffraction. Among them, new compounds 1–5 were featured by the rarely encountered Z-geometry double bond Δ1 within the 5/11-fused bicyclic capnosane carbon framework. Plausible biogenetic relationships of all isolates were proposed, and they might give an insight into future biomimetic synthesis of these novel compounds. In an in vitro bioassay, compound 5 displayed potent anti-neuroinflammatory activity against LPS-induced NO release in BV-2 microglial cells, which might be developed as a new type of potential neuroprotective agent in future. Full article
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10 pages, 2381 KiB  
Article
Mililatensols A–C, New Records of Sarsolenane and Capnosane Diterpenes from Soft Coral Sarcophyton mililatensis
by Qing Bu, Min Yang, Xian-Yun Yan, Song-Wei Li, Zeng-Yue Ge, Ling Zhang, Li-Gong Yao, Yue-Wei Guo and Lin-Fu Liang
Mar. Drugs 2022, 20(9), 566; https://doi.org/10.3390/md20090566 - 6 Sep 2022
Cited by 10 | Viewed by 2065
Abstract
Three unusual diterpenes with rare sarsolenane and capnosane skeletons, namely mililatensols A–C (1–3), were isolated from the South China Sea soft coral Sarcophyton mililatensis, leading to the first record of sarsolenane and capnosane diterpenes from the title animal. [...] Read more.
Three unusual diterpenes with rare sarsolenane and capnosane skeletons, namely mililatensols A–C (1–3), were isolated from the South China Sea soft coral Sarcophyton mililatensis, leading to the first record of sarsolenane and capnosane diterpenes from the title animal. The structures of compounds 1–3 were established by extensive spectroscopic analysis and comparison with the literature data. Moreover, the absolute configuration of 2 was determined by TDDFT ECD calculations. In an in vitro bioassay, none of the isolated compounds showed obvious anti-inflammatory activity on LPS-induced TNF-α release in RAW264.7 macrophages. In the preliminary virtual screening of inhibitory potential against SARS-CoV-2 by molecular docking, the results showed these three diterpenes were potential SARS-CoV-2 Mpro inhibitors. Full article
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11 pages, 1680 KiB  
Article
Bioactive Capnosanes and Cembranes from the Soft Coral Klyxum flaccidum
by Wan-Ru Tseng, Atallah F. Ahmed, Chiung-Yao Huang, Yi-Ying Tsai, Chi-Jen Tai, Raha S. Orfali, Tsong-Long Hwang, Yi-Hsuan Wang, Chang-Feng Dai and Jyh-Horng Sheu
Mar. Drugs 2019, 17(8), 461; https://doi.org/10.3390/md17080461 - 7 Aug 2019
Cited by 15 | Viewed by 3565
Abstract
Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral [...] Read more.
Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral Klyxum flaccidum, collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus Klyxum for the first time. The cytotoxicity of compounds 1 to 7 against the proliferation of a limited panel of cancer cell lines was assayed. The isolated diterpenoids also exhibited anti-inflammatory activity through suppression of superoxide anion generation and elastase release in the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-stimulated human neutrophils. Furthermore, 1 and 7 also exhibited cytotoxicity toward the tested cancer cells, and 7 could effectively inhibit elastase release. It is worth noting that the biological activities of 7 are reported for the first time in this paper. Full article
(This article belongs to the Special Issue Marine Natural Products Discovery: In Memory of Late Prof. Tatsuo Higa)
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10 pages, 2001 KiB  
Article
Further New Diterpenoids as PTP1B Inhibitors from the Xisha Soft Coral Sinularia polydactyla
by Fei Ye, Zheng-Dan Zhu, Yu-Cheng Gu, Jia Li, Wei-Liang Zhu and Yue-Wei Guo
Mar. Drugs 2018, 16(4), 103; https://doi.org/10.3390/md16040103 - 25 Mar 2018
Cited by 25 | Viewed by 4163
Abstract
A new prenyleudesmane type diterpene, sinupol (8), and a new capnosane type diterpenoid, sinulacetate (9), were isolated from the Xisha soft coral Sinularia polydactyla along with five known related diterpenes (4–7 and 10). Their structures, [...] Read more.
A new prenyleudesmane type diterpene, sinupol (8), and a new capnosane type diterpenoid, sinulacetate (9), were isolated from the Xisha soft coral Sinularia polydactyla along with five known related diterpenes (4–7 and 10). Their structures, including absolute configurations, were determined by extensive spectroscopic analysis, the comparison of their NMR data with those of related compounds, and time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculations. Both new compounds (8 and 9) exhibited promising inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a potential drug target for the treatment of type II diabetes and obesity. Full article
(This article belongs to the Special Issue Natural Products from Coral Reef Organisms)
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