Psammocindoles A–C: Isolation, Synthesis, and Bioactivity of Indole-γ-lactams from the Sponge Psammocinia vermis

• DOI: 10.1021/acs.orglett.1c01410
• Publication Date: 2021-06-01T18:01:55Z
• Authors: Oh-Seok Kwon; Sungjin Ahn; Ju-eun Jeon; In Guk Park; Tae Hyung Won; Chung J. Sim; Hyeung-geun Park; Dong-Chan Oh; Ki-Bong Oh; Minsoo Noh; Jongheon Shin
• Keywords: Biological Products; Lactams; Molecular Structure; Animals; Humans; Mesenchymal Stem Cells; Stereoisomerism; 01 natural sciences; Indole Alkaloids; Porifera; 0104 chemical sciences

Psammocindoles A-C (1-3), a new class of indole alkaloids, were isolated from a Psammocinia vermis sponge. By combined spectroscopic analyses, the structures of these compounds were determined to be the indole-γ-lactams derived from three amino acid residues. In addition, an enantiomer psammocindole D (4), and the N-lactam isomers isopsammocindoles A-D (5-8) were also synthesized. These natural products and synthetic analogues were found to significantly stimulate adiponectin secretion in human bone marrow mesenchymal stem cells.