Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata

Journal of Natural Products
You-Sheng CaiSheng-Ping Yang

Abstract

Four new monoterpenoid bisindole alkaloids, flabellipparicine (1), 19,20-dihydrovobparicine (2), 10'-demethoxy-19,20-dihydrovobatensine D (3), and 3'-(2-oxopropyl)ervahanine A (4), and 10 known monoterpenoid indole alkaloids were isolated from the stems of Tabernaemontana divaricata. All structures were elucidated based on spectroscopic methods, and the absolute configuration of 1 was established using conformational analysis and TDDFT-ECD calculation of selected stereoisomers. Compound 1 represents the first flabelliformide-apparicine-type bisindole alkaloid, in which the flabelliformide-like unit connects to the apparicine-like unit with a C-3-C-22' bond and an N-1-C-16' bond to form an uncommon five-membered ring between the two monomers. All alkaloids were evaluated for their cytotoxicity against two human cancer cell lines, MCF-7 and A-549. Compounds 2, 4, and 14 exhibited cytotoxicity against MCF-7 and A-549 with IC50 values in the range of 2 nM to 8 μM.

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Citations

Nov 27, 2018·Natural Product Reports·Robert A Hill, Andrew Sutherland
Jun 23, 2020·Current Topics in Medicinal Chemistry·Dan Xu, Zhi Xu
Jan 23, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Afrah E MohammedWalied M Alarif
Aug 17, 2020·Accounts of Chemical Research·Maribel O MarcarinoAriel M Sarotti

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