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)

Mar Drugs. 2020 Nov 6;18(11):554. doi: 10.3390/md18110554.

Authors

Yu-Chia Chang¹, Chih-Chao Chiang², Yuan-Shiun Chang³, Jih-Jung Chen⁴, Wei-Hsien Wang⁵, Lee-Shing Fang^{5

6

7}, Hsu-Ming Chung⁸, Tsong-Long Hwang^{1

9

10

11

12}, Ping-Jyun Sung^{5

13

14

15

16}

Affiliations

¹ Research Center for Chinese Herbal Medicine, Graduate Institute of Healthy Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333324, Taiwan.
² Graduate Institute of Clinical Medical Sciences, College of Medicine, Chang Gung University, Taoyuan 333323, Taiwan.
³ Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, College of Chinese Medicine, China Medical University, Taichung 404333, Taiwan.
⁴ Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 112304, Taiwan.
⁵ Department of Marine Biotechnology and Resources, College of Marine Sciences, National Sun Yat-sen University, Kaohsiung 804201, Taiwan.
⁶ Center for Environmental Toxin and Emerging-Contaminant Research, Cheng Shiu University, Kaohsiung 833301, Taiwan.
⁷ Super Micro Mass Research and Technology Center, Cheng Shiu University, Kaohsiung 833301, Taiwan.
⁸ Department of Applied Chemistry, College of Science, National Pingtung University, Pingtung 900393, Taiwan.
⁹ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333323, Taiwan.
¹⁰ Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 333423, Taiwan.
¹¹ Department of Chemical Engineering, College of Environment and Resources, Ming Chi University of Technology, New Taipei City 243303, Taiwan.
¹² Research Center for Food and Cosmetic Safety, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333324, Taiwan.
¹³ National Museum of Marine Biology and Aquarium, Pingtung 944401, Taiwan.
¹⁴ Graduate Institute of Marine Biology, College of Marine Sciences, National Dong Hwa University, Pingtung 944401, Taiwan.
¹⁵ Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404394, Taiwan.
¹⁶ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807378, Taiwan.

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 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.

Publication types

Comparative Study

MeSH terms

Animals
Anthozoa / metabolism*
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Humans
Leukocyte Elastase / metabolism
Molecular Structure
Neutrophils / drug effects*
Neutrophils / metabolism
Polycyclic Sesquiterpenes / isolation & purification
Polycyclic Sesquiterpenes / pharmacology*
Structure-Activity Relationship
Superoxides / metabolism

Substances

Anti-Inflammatory Agents
Polycyclic Sesquiterpenes
Superoxides
ELANE protein, human
Leukocyte Elastase

Grants and funding

MOST 107-2320-B-291-001-MY3; 109-2320-B-291-001-MY3/Ministry of Science Research and Technology