Phyllospongianes A–E, Dinorscalarane Sesterterpenes from the Marine Sponge Phyllospongia foliascens

• Published in: Journal of natural products (Washington, D.C.) Vol. 86; no. 7; pp. 1754 - 1760
• Main Authors: Yu, Hao-Bing, Hu, Bo, Wu, Gai-Fang, Ning, Zhe, He, Ying, Jiao, Bing-Hua, Liu, Xiao-Yu, Lin, Hou-Wen
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 28.07.2023; Amer Chemical Soc
• Subjects: Animals; Anti-Bacterial Agents - pharmacology; Antineoplastic Agents - chemistry; Bacillus subtilis; Chemistry, Medicinal; Escherichia coli; Life Sciences & Biomedicine; Molecular Structure; Pharmacology & Pharmacy; Plant Sciences; Porifera - chemistry; Science & Technology; Sesterterpenes - chemistry; SCALARANE SESTERTERPENES; SP
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.3c00218

Phyllospongianes A–E (1–5), five new scalarane derivatives featuring an unprecedented 6/6/6/5 tetracyclic dinorscalarane scaffold, along with the known probable biogenetic precursor, 12-deacetylscalaradial (6), were isolated from the marine sponge Phyllospongia foliascens. The structures of the isolated compounds were determined by analysis of spectroscopic data and electronic circular dichroism experiments. Compounds 1–5 are the first 6/6/6/5 tetracyclic scalarane derivatives to be reported within the scalarane family. Compounds 1, 2, and 4 exhibited antibacterial activity against Vibrio vulnificus, Vibrio parahemolyticus, Escherichia coli, Staphylococcus aureus, Enterococcus faecalis, Bacillus subtilis, and Pseudomonas aeruginosa with MIC values ranging from 1 to 8 μg/mL. Furthermore, compound 3 exhibited significant cytotoxic activity on MDA-MB-231, HepG2, C4-2-ENZ, MCF-7, H460, and HT-29 cancer cell lines with IC50 values in the range between 0.7 and 13.2 μM.