Rukamtenol, a new spiro compound isolated from Flacourtia rukam Zoll. & Moritzi growing in Vietnam

Abstract

Chemical investigation of chloroform extract of Flacourtia rukam Zoll. & Moritzi stems led to the isolation of one new compound namely rukamtenol together with four known compounds, viz., chaulmooric acid, flacourtin, 3,4,5-trimethoxyphenyl β-D-glucopyranoside, and daucosterol. Their structures and relative stereochemistry have been determined by 1D and 2D NMR analysis, high resolution mass spectroscopy, and compared with those in literatures. Rukamtenol represented the first 2-oxaspiro[4.4]non-8-en-3-one in nature. The relative configuration of rukamtinol was defined using DFT-NMR chemical shift calculations and subsequent DP4 probability method. Rukamtenol, flacourtin, and 3,4,5-trimethoxyphenyl β-D-glucopyranoside were tested for cytotoxic activity toward three MDA-MB-231, HepG2, and RD cancer cell lines. However, they failed to reveal any activity (IC₅₀ > 100 μM) on these cell lines.

Graphical Abstract

Keywords:

• Rukamtenol
• flacourtin
• Flacourtia rukam
• spiro
• DP4 probability

Disclosure statement

No potential conflict of interest was reported by the authors.