Discovery and photosynthesis of sinuaustones A and B, diterpenoids with a novel carbon scaffold isolated from soft coral <i>Sinularia australiensis</i> from Hainan

Wu, Meng-Jun; Yu, Dan-Dan; Su, Ming-Zhi; Wang, Jian‐Rong; Gong, Lei; Zhang, Zaiyong; Wang, Hong; Guo, Yue‐Wei

doi:10.1039/d2qo01265k

Cited by 10 publications

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“…The structure of sinuaustone A 7 , from the soft coral Sinularia australiensis , was also confirmed by X-ray analysis. 7 Sinuaustone A 7 has a novel diterpenoid skeleton and the authors propose it is formed by [2+2] cyclisation of the co-occurring lobophytumin A 8 . It is proposed that the novel sesquiterpenoid skeleton of seritranin A 9 , from Seriphidium transiliense , is formed by [2+2] cyclisation of a guaiane precursor.…”

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Hill

Sutherland

2023

Nat. Prod. Rep.

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Hill

Sutherland

2023

Nat. Prod. Rep.

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“…The usual work-up, as described previously, [16][17][18][19][20] afforded the crude acetone extract of S. tortuosum. The Et 2 O-soluble portion of the extract was subjected to preliminary analysis by LC-MS/ MS.…”

Section: Resultsmentioning

confidence: 99%

Guided Isolation of An Uncommon Cembranoid Orthoester, Sarcotortin A, and Three Skeletal Diverse Terpenoids from the Hainan Soft Coral Sarcophyton tortuosum Based on Molecular Networking Strategy

Chen

Yu²,

Liu

et al. 2023

Chemistry A European J

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Applying the emerging molecular networking strategy, an uncommon cembranoid orthoester, sarcotortin A (1), featuring a 3/14/8/5-fused scaffold, an unusual eunicellane-type diterpenoid, sarcotorolide A (2), and two new biscembranoids, ximaolides M and N (7 and 8), along with nine known terpenoids 3-6 and 9-13 were isolated from the Hainan soft coral Sarcophyton tortuosum. The structure and absolute configuration of all new compounds were established by a combination of spectroscopic data, X-ray diffraction analysis, and/or quantum chemical computational approaches. The plausible biogenetic relationship among these skeletally different terpenoids was proposed and discussed. In in vitro bioassay, new compound 7 exhibited a remarkable inhibitory activity against protein tyrosine phosphatases 1B (PTP1B) with the IC 50 value of 8.06 μM. In addition, compounds 4 and 10 displayed significant inhibitory effects on lipopolysaccharide (LPS)-induced inflammatory responses in RAW264.7 macrophages cells with the IC 50 values of 19.13 and 16.45 μM, respectively. Compound 9 showed interesting cytotoxicity against H1975, MDA-MB231, A549, and H1299 cancer cell lines with IC 50 values of 31.59, 34.96, 43.87, and 27.93 μM, respectively.

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“…504 Unusual tricyclic diterpenoids sinuaustones A 1268 and B 1269 and a spartane-type diterpenoid isolobophytumin E 1270 were isolated from a Hainan collection of Sinularia australiensis. 505 The structures and absolute congurations of both sinuaustones were secured by XRD. Mercury lamp irradiation of a methanolic solution of co-metabolite lobophytumin A afforded a mixture containing the three new NPs, suggesting they either derive from photochemical reactions in nature or could be considered artefacts of isolation.…”

Section: Cnidariansmentioning

confidence: 99%