Literature DB >> 31640933

Polycyclic furanobutenolide-derived norditerpenoids from the South China Sea soft corals Sinularia scabra and Sinularia polydactyla with immunosuppressive activity.

Wan-Xiang Cui1, Min Yang2, Heng Li3, Song-Wei Li4, Li-Gong Yao5, Geng Li2, Wei Tang3, Chun-Hua Wang6, Lin-Fu Liang7, Yue-Wei Guo8.   

Abstract

One new polycyclic furanobutenolide-derived norcembranoid, xiguscabrolide H (1), together with eleven known related norditerpenoids 2-12 were isolated from South China Sea soft corals Sinularia scabra and S. polydactyla, respectively. Among them, compounds 1, 6, 8, and 12 were discovered from the former species, while compounds 2-5, 7, and 9-11 were obtained from the latter species. The structure of new compound 1 was elucidated by extensive spectroscopic analysis and by the comparison with the reported data. With the assistance of time-dependent density functional theory electronic circular dichroism (TDDFT-ECD) calculations, its absolute configuration was determined. Moreover, the absolute stereostructures of the known compounds 3, 4, and 9-12, of which only relative configurations were assigned, were established for the first time by X-Ray diffraction analysis and TDDFT-ECD calculations, respectively. In bioassay, several isolates exhibited potent inhibitory effects on the ConA-induced T lymphocytes and/or LPS-induced B lymphocytes proliferation.
Copyright © 2019 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  Absolute configuration; Immunosuppressive activity; Norditerpenoids; Sinularia

Mesh:

Substances:

Year:  2019        PMID: 31640933     DOI: 10.1016/j.bioorg.2019.103350

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN: 0045-2068            Impact factor:   5.275


  5 in total

1.  Bridging the gap between natural product synthesis and drug discovery.

Authors:  Nathanyal J Truax; Daniel Romo
Journal:  Nat Prod Rep       Date:  2020-10-26       Impact factor: 13.423

Review 2.  Chemistry and bioactivity of secondary metabolites from South China Sea marine fauna and flora: recent research advances and perspective.

Authors:  Jiao Liu; Yu-Cheng Gu; Ming-Zhi Su; Yue-Wei Guo
Journal:  Acta Pharmacol Sin       Date:  2022-09-14       Impact factor: 7.169

3.  Computational planning of the synthesis of complex natural products.

Authors:  Barbara Mikulak-Klucznik; Patrycja Gołębiowska; Alison A Bayly; Oskar Popik; Tomasz Klucznik; Sara Szymkuć; Ewa P Gajewska; Piotr Dittwald; Olga Staszewska-Krajewska; Wiktor Beker; Tomasz Badowski; Karl A Scheidt; Karol Molga; Jacek Mlynarski; Milan Mrksich; Bartosz A Grzybowski
Journal:  Nature       Date:  2020-10-13       Impact factor: 49.962

Review 4.  Chemical Diversity and Biological Activity of Secondary Metabolites from Soft Coral Genus Sinularia since 2013.

Authors:  Xia Yan; Jing Liu; Xue Leng; Han Ouyang
Journal:  Mar Drugs       Date:  2021-06-11       Impact factor: 5.118

5.  Total Syntheses of Scabrolide A and Nominal Scabrolide B.

Authors:  Zhanchao Meng; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2022-01-19       Impact factor: 15.419

  5 in total

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