Ursane Triterpenes and Norisoprenoids from Anchusa italica Retz. and Their Chemotaxonomic Significance

来自意大利紫草(Anchusa italica Retz.)的熊果烷型三萜和降异戊二烯类化合物及其化学分类学意义

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Abstract

A total of 31 compounds were isolated from the ethyl acetate and n-butanol fractions of Anchusa italica Retz., which contained one ursane triterpenoid, 2α,3β,19α-trihydroxy-23-formyl-urs-12-en-28,21β-olide (1), and five norisoprenoids: (2R,6R,9S)-9-hydroxy-4-megastigmen-3-one-2-O-β-D-glucopyranoside (3); (2R,6S,9S)-9-hydroxy-megastigman-4,7-dien-3-one-2-O-β-D-glucopyranoside (4); (+)-isololiolide β-D-glucopyranoside (5); (2S,8R)-loliolide β-D-glucopyranoside (6a); and (2R,8S)-loliolide β-D-glucopyranoside (6b). It also contained 25 known compounds (2 and 7-30). The chemical structures of the compounds, inclusive of their absolute configurations, were ascertained using spectroscopic methods such as NMR, HR-MS, and quantum chemical calculations (computational NMR and ECD), in combination with relevant literature data. Moreover, the chemotaxonomic significance of the isolated substances was discussed, with compounds 1, 2, and 7-13 potentially broadening the application of triterpenes as taxonomic markers for the classification of the genus Anchusa.

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