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Montecrinanes A-C: Triterpenes With an Unprecedented Rearranged Tetracyclic Skeleton From Celastrus Vulcanicola. Insights Into Triterpenoid Biosynthesis Based on DFT Calculations

Montecrinanes A-C: Triterpenes With an Unprecedented Rearranged Tetracyclic Skeleton From Celastrus Vulcanicola. Insights Into Triterpenoid Biosynthesis Based on DFT Calculations

Martín Purino, Alejandro E Ardiles, Oliver Callies, Ignacio A Jiménez, Isabel L Bazzocchi

Chemistry. 2016 May 23;22(22):7582-91.

PMID: 27106132

Abstract:

Three new triterpenoids with an unprecedented 6/6/6/6-fused tetracyclic carbon skeleton, montecrinanes A-C (1-3), were isolated from the root bark of Celastrus vulcanicola, along with known D:B-friedobaccharanes (4-6), and lupane-type triterpenes (7-12). The stereostructures of the new metabolites were elucidated based on spectroscopic (1D and 2D NMR) and spectrometric (HR-EIMS and HR-ESIMS) techniques. Their absolute configurations were determined by both NMR spectroscopy, with (R)-(-)-α-methoxyphenylacetic acid as a chiral derivatizing agent, and biogenetic considerations. Biogenetic pathways for montecrinane and D:B-friedobaccharane skeletons were proposed and studied by DFT methods. The theoretical results support the energetic feasibility of the putative biogenetic pathways, in which the 1,2-methyl shift from the secondary baccharenyl cation represents a novel and key reaction step for a new montecrinane skeleton.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3966323	(R)-(-)-α-Methoxyphenylacetic acid		3966-32-3	Price

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