Isosarcophytoxide Derivatives with a 2,5-Dihydrofuran Moiety from the Soft Coral Sarcophyton cinereum

Chih-Hua Chao; Yuan-Jhong Wu; Tzu-Yin Huang; Chi-Jen Tai; Yi-Ju Chen; Chiung-Yao Huang; Chi-Chien Lin; Chang-Feng Dai; Hui-Chi Huang; Jyh-Horng Sheu

doi:10.3390/molecules28020641

Isosarcophytoxide Derivatives with a 2,5-Dihydrofuran Moiety from the Soft Coral Sarcophyton cinereum

Molecules. 2023 Jan 8;28(2):641. doi: 10.3390/molecules28020641.

Authors

Chih-Hua Chao^{1

2}, Yuan-Jhong Wu³, Tzu-Yin Huang⁴, Chi-Jen Tai^{3

5}, Yi-Ju Chen³, Chiung-Yao Huang³, Chi-Chien Lin⁶, Chang-Feng Dai⁷, Hui-Chi Huang⁸, Jyh-Horng Sheu^{3

9

10}

Affiliations

¹ School of Pharmacy, China Medical University, Taichung 404, Taiwan.
² Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan.
³ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
⁴ Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan.
⁵ National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan.
⁶ Institute of Biomedical Science, National Chung-Hsing University, Taichung 402, Taiwan.
⁷ Institute of Oceanography, National Taiwan University, Taipei 112, Taiwan.
⁸ Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan.
⁹ Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 404, Taiwan.
¹⁰ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan.

Abstract

The present chemical investigation on the organic extract of the soft coral Sarcophyton cinereum has contributed to the isolation of four new cembranoids: 16β- and 16α-hydroperoxyisosarcophytoxides (1 and 2), 16β- and 16α-methoxyisosarcophytoxides (3 and 4), and a known cembranoid, lobocrasol (5). The structures of all isolates were elucidated by detailed spectroscopic analysis. Their structures were characterized by a 2,5-dihydrofuran moiety, of which the relative configuration was determined by DU8-based calculation for long-range coupling constants (⁴J_H,H). The cytotoxicity and immunosuppressive activities of all isolates were evaluated in this study.

Keywords: 16-hydroperoxyisosarcophytoxide; 16-methoxyisosarcophytoxide; 2,5-dihydrofuran; DU8; Sarcophyton cinereum; cytotoxicity; immunosuppressive.

Isosarcophytoxide Derivatives with a 2,5-Dihydrofuran Moiety from the Soft Coral Sarcophyton cinereum

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