Pseudoceranoids A-J, Sesquiterpene-Based Meroterpenoids with Cytotoxicity from the Sponge Pseudoceratina purpurea

  • J Nat Prod. 2023 Dec 22;86(12):2710-2717. doi: 10.1021/acs.jnatprod.3c00877.
Xiaoli Yu  1 ,  Xiao Han  1  2 ,  Yongpeng Cui  1 ,  Anran Fu  1 ,  Kun Liu  1 ,  Wenjie Zhang  1 ,  Xuli Tang  2 ,  Guoqiang Li  1  3
Affiliations
  • 1. 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. Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China.
PMID: 38064664 DOI: 10.1021/acs.jnatprod.3c00877
Abstract

Pseudoceranoid A (1), a rare merosesquiterpene featuring a rearranged 4,9-friedodrimane-type core with a crotonolactone moiety, two new rearranged 4,9-friedodrimane-type sesquiterpene cyclopentanones (2 and 3), and three new rearranged 4,9-friedodrimane-type sesquiterpene hydroquinones (4-6), along with two new drimane-type sesquiterpene derivatives (7 and 8), as well as two new 4,9-friedodrimane-type sesquiterpene Quinones (9 and 10), were isolated from the South China Sea Sponge Pseudoceratina purpurea. The structures of compounds were established by analysis of spectroscopic data, as well as by single-crystal X-ray diffraction, DP4+ probability analyses, and calculated electronic circular dichroism. Compound 4 showed weak cytotoxicity against K562, H69AR, and MDAMB-231 cell lines with IC50 values of 3.01, 7.74, and 9.82 μM, respectively. Compound 5 exhibited cytotoxicity against the H69AR cell line with an IC50 value of 2.85 μM.