Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral Sinularia hirta

Chemical investigation of the Hainan soft coral resulted in the isolation and identification of a library of sixteen structurally diverse terpenoids, including a dinorditerpenoid with an uncommon 17,19-dinorxeniaphyllane skeleton, namely sinuhirtone A ( ), six new xeniaphyllane-type diterpenoids ( -...

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Published in:Marine drugs 2022-04, Vol.20 (4), p.272
Main Authors: Chen, Zi-Hui, Lu, Si-Qi, Han, Guan-Ying, Li, Xu-Wen, Guo, Yue-Wei
Format: Article
Language:English
Subjects:
Animals
Anthozoa - chemistry
Cancer
Carbon
Cell lines
Circular dichroism
Corals
Cytotoxicity
Density Functional Theory
Dichroism
Diterpenes
Diterpenes - chemistry
Diterpenes - pharmacology
Experiments
Metabolites
Molecular Structure
NMR
norditerpenoids
Nuclear magnetic resonance
Optical rotatory dispersion
Quantum chemistry
Quantum mechanics
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Sesquiterpenoids
Sinularia
Sinularia hirta
soft coral
Spectrum analysis
stereochemistry
Terpenes
Terpenes - chemistry
Terpenes - pharmacology
Toxicity
Tumor cell lines
xeniaphyllanes
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Summary:Chemical investigation of the Hainan soft coral resulted in the isolation and identification of a library of sixteen structurally diverse terpenoids, including a dinorditerpenoid with an uncommon 17,19-dinorxeniaphyllane skeleton, namely sinuhirtone A ( ), six new xeniaphyllane-type diterpenoids ( - ), one new norxeniaphyllanoid ( ), two new norcaryophyllene-type sesquiterpenoids ( and ), together with six known related compounds ( - ). Compounds - are three new furanone-containing xeniaphyllane-type diterpenoids. The structures of the new compounds, including their absolute configurations, were determined by extensive spectroscopic analysis and a series of quantum chemical calculations, including quantum mechanical-nuclear magnetic resonance (QM-NMR), time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD), and optical rotatory dispersion (ORD) methods. A plausible biosynthetic connection between new compounds - was also proposed. New compounds - , , and were evaluated for in vitro cytotoxicity against four cancer cell lines.
ISSN:1660-3397
1660-3397
DOI:10.3390/md20040272