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

doi:10.3390/md18050271

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^*

^*Corresponding author for this work

School of Traditional Chinese Medicine

Research output: Contribution to journal › Journal Article › peer-review

13 Scopus citations

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 language	English
Article number	271
Journal	Marine Drugs
Volume	18
Issue number	5
DOIs	https://doi.org/10.3390/md18050271
State	Published - 05 2020

Bibliographical note

Publisher Copyright:
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

Keywords

Antineutrophilic inflammation
Elastase
Secosteroids
Sinularia leptoclados
Superoxide anion

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10.3390/md18050271

Cite this

@article{15fb4221becc49829fc8fc6ef38f3e83,

title = "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 (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.",

keywords = "Antineutrophilic inflammation, Elastase, Secosteroids, Sinularia leptoclados, Superoxide anion",

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

note = "Publisher Copyright: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).",

year = "2020",

month = may,

doi = "10.3390/md18050271",

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volume = "18",

journal = "Marine Drugs",

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T1 - 1H NMR-based isolation of anti-inflammatory 9,11-secosteroids from the octocoral sinularia leptoclados

AU - Chang, Yu Chia

AU - Lai, Kuei Hung

AU - Kumar, Sunil

AU - Chen, Po Jen

AU - Wu, Yi Hsuan

AU - Lai, Ching Long

AU - Hsieh, Hsi Lung

AU - Sung, Ping Jyun

AU - Hwang, Tsong Long

N1 - Publisher Copyright: © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

PY - 2020/5

Y1 - 2020/5

N2 - 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.

AB - 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.

KW - Antineutrophilic inflammation

KW - Elastase

KW - Secosteroids

KW - Sinularia leptoclados

KW - Superoxide anion

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DO - 10.3390/md18050271

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