Abstract
Two new compounds, caryopristimerin and 2α,3α,22β-trihydroxy-21-oxo-29-nor-friedelan-24-oic acid, were isolated from the hexane/ethyl ether extract of Salacia crassifolia roots. Caryopristimerin represents the first example of a homo Diels-Alder adduct of a sesquiterpene and a triterpene, and the new 29-nor-friedelane displays a highly oxygenated A ring with a carboxylic group at the unusual C-5 position. The new compounds were elucidated by infrared (IR), high-resolution-atmospheric pressure chemical ionization-mass spectrometry (HR-APCI-MS), 1D/2D nuclear magnetic resonance (NMR) and single crystal X-ray diffraction analysis. Additionally, the known compounds 3-oxo-29-hydroxyfriedelane, pristimerin, tingenone and netzahualcoyonol are herein reported for the first time as constituents of S. crassifolia. Their structures were established by spectroscopic analysis.
Highlights
The genus Salacia comprises more than 100 species and belongs to the Celastraceae family.[1]
The phytochemical study led to two novel and unusual compounds: a dimer named as caryopristimerin (1) and the 2α,3α,22β-trihydroxy-21-oxo-29-nor-friedelan24-oic acid (2)
The 1H nuclear magnetic resonance (NMR) spectrum of 1 revealed the presence of ten methyl singlets, one of which was due to an OCH3 group, and two singlets for a methylidene at dH 4.88 and 5.01 ppm
Summary
The genus Salacia comprises more than 100 species and belongs to the Celastraceae family.[1] It has been used in traditional medicine around many regions of the world, from South America to Asia.[2,3] Phytochemical studies on Salacia species reported different bioactive secondary metabolites such as alkaloids, flavonoids, steroids and triterpenes.[4,5,6,7] The isolated triterpenoids display a variety of skeletons like friedelane,[6,7,8] ursane, oleanane and quinonemethide.[6,8,9] The latter is only found in the roots and serves as a biomarker for the Celastraceae family.[10,11]. This is the first time that a dimer between a quinonemethidederivative and the sesquiterpene caryophyllene (1) linked
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