Subergorgines A-E, five new suberosanone-purine hybrids from the South China Sea gorgonian Subergorgia suberosa

Gang Zhang; Xuli Tang; Lianzhong Luo; Xingwang Zhang; Pinglin Li; Guoqiang Li

doi:10.1016/j.bioorg.2022.106040

Subergorgines A-E, five new suberosanone-purine hybrids from the South China Sea gorgonian Subergorgia suberosa

Bioorg Chem. 2022 Nov:128:106040. doi: 10.1016/j.bioorg.2022.106040. Epub 2022 Jul 26.

Authors

Gang Zhang¹, Xuli Tang², Lianzhong Luo³, Xingwang Zhang⁴, Pinglin Li⁵, Guoqiang Li⁶

Affiliations

¹ Xiamen Key Laboratory of Marine Medicinal Natural Product Resources, Xiamen Medical College, Xiamen 361023, People's Republic of China; Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
² College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao 266100, People's Republic of China.
³ Xiamen Key Laboratory of Marine Medicinal Natural Product Resources, Xiamen Medical College, Xiamen 361023, People's Republic of China.
⁴ State Key Laboratory of Microbial Technology, Shandong University, Qingdao, Shandong 266237, China.
⁵ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China. Electronic address: lipinglin@ouc.edu.cn.
⁶ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China. Electronic address: liguoqiang@ouc.edu.cn.

PMID: 36049320
DOI: 10.1016/j.bioorg.2022.106040

Abstract

Five new suberosanone-purine hybrids, namely subergorgines A-E (1-5), were isolated from the South China Sea gorgonian Subergorgia suberosa. Their structures were elucidated on the basis of extensive spectroscopic data and the absolute configurations were clarified by the theoretical ECD calculation. Compounds 1-5 were rare purine alkaloids merged with the same suberosanone moiety via different C (6)-N bridges. Cytotoxic activities of the isolates were tested. Compound 4 was found to be the most active against the HL-60 cancer cell line with an IC₅₀ value of 14.3 μM. A plausible biosynthetic pathway for suberosanone-purine hybrids was also discussed.

Keywords: Cytotoxicity; Gorgonian; Subergorgia suberosa; Suberosanone-purine hybrids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anthozoa* / chemistry
Antineoplastic Agents* / chemistry
Antineoplastic Agents* / pharmacology
Molecular Structure
Purines / chemistry
Sesquiterpenes* / chemistry

Substances

Antineoplastic Agents
Purines
Sesquiterpenes
suberosanone