BJOC - Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

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Supporting Information File 1: HPLC chromatograms of 4 and 5, chiral separation of 4 and 5, X-ray crystallographic data for 2, spectra of compounds (+)-1, 4 and 5, TDDFT-ECD calculation of compound (+)-1.
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Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

Shou-Mao Shen, Qing Yang, Yi Zang, Jia Li, Xueting Liu and Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925. https://doi.org/10.3762/bjoc.18.91

How to Cite

Shen, S.-M.; Yang, Q.; Zang, Y.; Li, J.; Liu, X.; Guo, Y.-W. Beilstein J. Org. Chem. 2022, 18, 916–925. doi:10.3762/bjoc.18.91

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TY  - JOUR
A1  - Shen, Shou-Mao
A1  - Yang, Qing
A1  - Zang, Yi
A1  - Li, Jia
A1  - Liu, Xueting
A1  - Guo, Yue-Wei
T1  - Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 916
EP  - 925
SN  - 1860-5397
DO  - 10.3762/bjoc.18.91
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.91
KW  - Acanthella cavernosa
KW  - anti-inflammatory
KW  - biosynthetic pathway
KW  - chiral separation
KW  - marine sponge
KW  - sesquiterpenoid
N2  - One new aromadendrane-type sesquiterpenoid, namely ximaocavernosin P [(+)-1], and three new cadinane-type sesquiterpenoids, namely (+)-maninsigin D [(+)-4], (+)- and (−)-ximaocavernosin Q [(+)- and (−)-5], together with five related known ones [2, 3, (−)-4, 6, and 7], were isolated from the Hainan sponge Acanthella cavernosa. Compounds 4 and 5 were isolated as racemic forms, which were further separated to the corresponding enantiomers [(+)-4/(−)-4 and (+)-5/(−)-5], respectively, by using chiral-phase HPLC. The structures of new compounds were elucidated by extensive spectroscopic analysis and comparison with the reported data. In addition, the absolute configuration of optically pure (+)-1 and 2 were determined by time-dependent density functional theory/electronic circular dichroism (TDDFT-ECD) calculations or X-ray diffraction analysis. A plausible biosynthetic pathway of these sesquiterpenoids and their internal correlation were proposed and discussed. In an in vitro bioassay, (+)-aristolone (3) exhibited promising anti-inflammatory activity by the inhibition of LPS-induced TNF-α and CCL2 release in RAW 264.7 macrophages.
ER  -

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