Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)

Yu Chia Chang; Chih Chao Chiang; Yuan Shiun Chang; Jih Jung Chen; Wei Hsien Wang; Lee Shing Fang; Hsu Ming Chung; Tsong Long Hwang; Ping Jyun Sung

doi:10.3390/MD18110554

Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)

Yu Chia Chang, Chih Chao Chiang, Yuan Shiun Chang, Jih Jung Chen, Wei Hsien Wang, Lee Shing Fang, Hsu Ming Chung^*, Tsong Long Hwang^*, Ping Jyun Sung^*

^*Corresponding author for this work

School of Traditional Chinese Medicine

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

13 Scopus citations

Abstract

Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated Mar. Drug554; www.mdpi.com/journal/marinedrugs that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC₅₀ values of 11.22 and 23.53 µM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC₅₀ value of 7.63 µM.

Original language	English
Article number	554
Journal	Marine Drugs
Volume	18
Issue number	11
DOIs	https://doi.org/10.3390/MD18110554
State	Published - 11 2020

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© 2020 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

Rumphella antipathes
antipacid
caryophyllane
clovane
elastase
rumphellolide
superoxide anion

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title = "Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)",

abstract = "Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated Mar. Drug554; www.mdpi.com/journal/marinedrugs that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC50 values of 11.22 and 23.53 µM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC50 value of 7.63 µM.",

keywords = "Rumphella antipathes, antipacid, caryophyllane, clovane, elastase, rumphellolide, superoxide anion",

author = "Chang, {Yu Chia} and Chiang, {Chih Chao} and Chang, {Yuan Shiun} and Chen, {Jih Jung} and Wang, {Wei Hsien} and Fang, {Lee Shing} and Chung, {Hsu Ming} and Hwang, {Tsong Long} and Sung, {Ping Jyun}",

note = "Publisher Copyright: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2020",

month = nov,

doi = "10.3390/MD18110554",

language = "英语",

volume = "18",

journal = "Marine Drugs",

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AU - Chang, Yu Chia

AU - Chiang, Chih Chao

AU - Chang, Yuan Shiun

AU - Chen, Jih Jung

AU - Wang, Wei Hsien

AU - Fang, Lee Shing

AU - Chung, Hsu Ming

AU - Hwang, Tsong Long

AU - Sung, Ping Jyun

PY - 2020/11

Y1 - 2020/11

N2 - Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated Mar. Drug554; www.mdpi.com/journal/marinedrugs that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC50 values of 11.22 and 23.53 µM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC50 value of 7.63 µM.

AB - Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated Mar. Drug554; www.mdpi.com/journal/marinedrugs that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC50 values of 11.22 and 23.53 µM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC50 value of 7.63 µM.

KW - Rumphella antipathes

KW - antipacid

KW - caryophyllane

KW - clovane

KW - elastase

KW - rumphellolide

KW - superoxide anion

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DO - 10.3390/MD18110554

M3 - 文章

C2 - 33172193

AN - SCOPUS:85096030776

SN - 1660-3397

VL - 18

JO - Marine Drugs

JF - Marine Drugs

IS - 11

M1 - 554

ER -

Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)

Abstract

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Keywords

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