Structures of two oleanane-type triterpenoids from an extract of Cyrilla racemiflora housed in a repository

Y Ren; A VanSchoiack; HB Chai; M Goetz; AD Kinghorn

doi:10.1055/s-0035-1556481

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Planta Med 2015; 81 - PX37
DOI: 10.1055/s-0035-1556481

Structures of two oleanane-type triterpenoids from an extract of Cyrilla racemiflora housed in a repository

Y Ren ¹, A VanSchoiack ², HB Chai ¹, M Goetz ³, AD Kinghorn ¹

¹Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy
²Mass Spectrometry and Proteomics Facility, Campus Chemical Instrument Center, The Ohio State University, Columbus, OH 43210, United States
³Natural Products Discovery Institute (NPDI), Baruch S. Blumberg Institute (BSBI), Doylestown, PA 18902, United States

Congress Abstract

Two new oleanane-type triterpenoids were isolated from a small-scale sample of a dichloromethane partition of an ethanol-soluble extract of Cyrilla racemiflora L. (Cyrillaceae) collected in Dominica. This extract repository was donated to BSBI by Merck Research Laboratories, Rahway, NJ, USA. The structures of these compounds were elucidated by interpretation of their spectroscopic data, with an unusual compound containing a di-angelated glucose residue being confirmed by its MS² and MS³ mass spectra. The conformation of the pentacyclic ring system of these triterpenoids was characterized based on the published single-crystal structure of 3-O-acetyloleanolic acid, and the absolute configuration of these two compounds was ascertained by analysis of their electronic circular dichroism (ECD) induced with [Mo₂(OAc)₄] and NOESY 2D NMR spectra.