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1H NMR-Based Isolation of Anti-Inflammatory 9,11-Secosteroids from the Octocoral Sinularia leptoclados.

ABSTRACT: Octocoral Sinularia leptoclados has been identified as a source of bioactive 9,11-secosteroids. This study adopted a targeted isolation approach to the discovery and analysis of five 9,11-secosteroids, including two novel compounds named sinleptosterols A (1) and B (2) as well as five known analogues (8?H-3?,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (3), 8?H-3?,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (4), leptosterol A (5), (24S)-3?,11-dihydroxy-24-methyl-9,11-secocholest-5-en-9-one (6), and 3?,11-dihydroxy-9,11-secogorgost-5-en-9-one (7)) in terms of 1H-NMR patterns and potency against neutrophilic inflammation. The structure of secosteroids 1 and 2 was deduced from general spectroscopic analysis and an examination of NMR spectra. Among the above-mentioned isolates, compound 4 had the most pronounced effect in inhibiting elastase release and superoxide anion generation, with the IC50 values of 2.96 and 1.63 ?M, respectively.

SUBMITTER: Chang YC 

PROVIDER: S-EPMC7281107 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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<sup>1</sup>H NMR-Based Isolation of Anti-Inflammatory 9,11-Secosteroids from the Octocoral <i>Sinularia leptoclados</i>.

Chang Yu-Chia YC   Lai Kuei-Hung KH   Kumar Sunil S   Chen Po-Jen PJ   Wu Yi-Hsuan YH   Lai Ching-Long CL   Hsieh Hsi-Lung HL   Sung Ping-Jyun PJ   Hwang Tsong-Long TL  

Marine drugs 20200521 5

Octocoral <i>Sinularia leptoclados</i> has been identified as a source of bioactive 9,11-secosteroids. This study adopted a targeted isolation approach to the discovery and analysis of five 9,11-secosteroids, including two novel compounds named sinleptosterols A (<b>1</b>) and B (<b>2</b>) as well as five known analogues (8<i>α</i>H-3<i>β</i>,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (<b>3</b>), 8<i>β</i>H-3<i>β</i>,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (<b>4</b>), le  ...[more]

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