1H NMR-based isolation of anti-inflammatory 9,11-secosteroids from the octocoral sinularia leptoclados

Yu Chia Chang, Kuei Hung Lai, Sunil Kumar, Po Jen Chen, Yi Hsuan Wu, Ching Long Lai, Hsi Lung Hsieh, Ping Jyun Sung, Tsong Long Hwang

Research output: Contribution to journalArticle

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 (8αH-3β,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (3), 8βH-3β,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (4), leptosterol A (5), (24S)-3β,11-dihydroxy-24-methyl-9,11-secocholest-5-en-9-one (6), and 3β,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 µM, respectively.

Original languageEnglish
Article number271
JournalMarine Drugs
Volume18
Issue number5
DOIs
Publication statusPublished - May 2020
Externally publishedYes

Keywords

  • Antineutrophilic inflammation
  • Elastase
  • Secosteroids
  • Sinularia leptoclados
  • Superoxide anion

ASJC Scopus subject areas

  • Drug Discovery

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    Chang, Y. C., Lai, K. H., Kumar, S., Chen, P. J., Wu, Y. H., Lai, C. L., Hsieh, H. L., Sung, P. J., & Hwang, T. L. (2020). 1H NMR-based isolation of anti-inflammatory 9,11-secosteroids from the octocoral sinularia leptoclados. Marine Drugs, 18(5), [271]. https://doi.org/10.3390/md18050271