New 8,17-epoxybriaranes from octocoral Briareum stechei (Kükenthal, 1908)

Yeh, Yao‐Tsung; Chen, Chun-Yu; Chen, Po‐Jen; Hsieh, Yin-Cheng; Chien, Su‐Ying; Liu, Chia-Jung; Wen, Zhi‐Hong; Hwang, Tsong‐Long; Chen, Nan‐Fu; Sung, Ping‐Jyun

doi:10.1016/j.tetlet.2022.153997

Cited by 4 publications

(8 citation statements)

References 10 publications

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“…It was clear that 1 was found to be the 12-epi-compound of 2. However, we found that the 13 C NMR data and specific rotation value for briacavatolide B differed slightly from those of 2 reported in this article.…”

contrasting

confidence: 90%

“…The 13 24 D -6.1 (c 0.09, CHCl3)). The structure of briacavatolide B is not in question; we suggested that the differences in the 13 C NMR data and rotation values were arose from conformational flexibility.…”

mentioning

confidence: 99%

“…The IR absorptions were observed at νmax 3500, 1779, and 1732 cm -1 , suggesting the presence of hydroxy, γ-lactone, and ester groups in 1, respectively. From the 13 C NMR data (Table 1), together with DEPT and HSQC spectra, illustrated the presence of 28 carbons in 1, including five ester carbonyls (δC 171.6, OAc-16; 170.6, OAc-2; 170. as well as seven methyls, two aliphatic sp 3 methylenes, one aliphatic sp 3 methine, and one aliphatic sp 3 nonprotonated carbon. Analysis of the 1 H (Table 1), 13 C, and HSQC spectra confirmed that 1 possessed a tetrasubstituted epoxide (δC 70.…”

mentioning

confidence: 99%

“…From the 13 C NMR data (Table 1), together with DEPT and HSQC spectra, illustrated the presence of 28 carbons in 1, including five ester carbonyls (δC 171.6, OAc-16; 170.6, OAc-2; 170. as well as seven methyls, two aliphatic sp 3 methylenes, one aliphatic sp 3 methine, and one aliphatic sp 3 nonprotonated carbon. Analysis of the 1 H (Table 1), 13 C, and HSQC spectra confirmed that 1 possessed a tetrasubstituted epoxide (δC 70. The gross structure of 1 was determined by 2D NMR studies including COSY, HSQC, and HMBC experiments.…”

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confidence: 99%

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12-epi-Briacavatolide B, a New Briarane Diterpenoid from the Octocoral Briareum stechei

Sung¹,

Liu²,

Liu³

et al. 2023

HETEROCYCLES

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A new briarane-type diterpenoid, 12-epi-briacavatolide B (1), along with its known epimer, briacavatolide B (2), were purified from an octocoral identified as Briareum stechei. Spectroscopic approaches were used to reveal the structure of new briarane 1.Octocorals are invertebrates extensively distributed in coastal waters, especially the coasts of tropical and subtropical Indo-Pacific Ocean regions. The creatures have been shown to be rich sources of an array of diterpenoid derivatives with characteristic carbon skeletons that have various bioactivities. 1,2 The octocorals belonging to genus Briareum (phylum: Cnidaria, sub-phylum: Anthozoa, class: Octocorallia,

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confidence: 90%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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12-epi-Briacavatolide B, a New Briarane Diterpenoid from the Octocoral Briareum stechei

Sung¹,

Liu²,

Liu³

et al. 2023

HETEROCYCLES

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“…These briarane-skeleton compounds were reported to possess cytotoxicity 2) and anti-inflammatory activity. [3][4][5] We previously conducted substantial examinations of B. stechei, both wildand cultured-type, [4][5][6] via which a new highly-oxygenated briarane, briastecholide M (1), and its known analogue, brianodin B (2), 7) were isolated (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Briastecholide M, a New Polyoxygenated Briarane from <i>Briareum stechei</i>

Huynh

Wen

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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A formerly unpublicized briarane diterpenoid, briastecholide M (1), and its established analogue, brianodin B (2), were purified from Briareum stechei, an octocoral collected from Okinawan waters. Using spectroscopic methods, the structure of 1 was established. Functional study showed that 1 can reducing the release of inducible nitric oxide synthase (iNOS) but enhancing cyclooxygenase-2 (COX-2) protein expression.

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