Briavioids A–C, discovery of new polyacetoxybriaranes from octocoral Briareum violaceum (Quoy & Gaimard, 1833)

Three new polyacetoxybriarane diterpenoids, briavioids A–C (1–3), as well as two known analogues, briaexcavatin M (4) and excavatolide F (5), were isolated from a cultured soft coral Briareum violaceum. The structures and relative stereochemistry of new metabolites 1–3 were assigned on the basis of...

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Published inTetrahedron Vol. 125; pp. 133037 - 133042
Main Authors Huynh, Thanh Hao, Wen, Zhi-Hong, Chien, Su-Ying, Chung, Hsu-Ming, Su, Jui-Hsin, Fang, Lee-Shing, Wu, Yu-Jen, Lin, Shih-Hsiung, Sung, Ping-Jyun
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.10.2022
Elsevier
Subjects
Briarane
Briareum violaceum
Briavioid
Chemistry
Chemistry, Organic
iNOS
Physical Sciences
Science & Technology
X-ray
Briavioid
Briareum violaceum
iNOS
Briarane
X-ray
DITERPENOIDS
CORALS
DIVERSITY
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Summary:Three new polyacetoxybriarane diterpenoids, briavioids A–C (1–3), as well as two known analogues, briaexcavatin M (4) and excavatolide F (5), were isolated from a cultured soft coral Briareum violaceum. The structures and relative stereochemistry of new metabolites 1–3 were assigned on the basis of NMR studies. Single-crystal X-ray diffraction analysis was performed to identify the structure of 1. Briaranes 1–5 were assessed in terms of their inflammation activity by screening their inhibition abilities against iNOS protein in LPS-stimulated RAW264.7 macrophage cells. [Display omitted] •Three previously-undescribed briaranes, briavioids A–C (1–3), were isolated from a cultured octocoral Briareum violaceum.•The structure of briavioid A was confirmed by a single-crystal X-ray diffraction analysis.•Excavatolide F reduced the release of iNOS.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2022.133037