Abstract
Three new ursane triterpenes, 3α,19α-dihydroxy-2-nor-urs-12-en-23,28-dioic acid-23-methyl ester (1), 19α,23-dihydroxy-3-oxo-2-nor-urs-12-en-28-oic acid (2), and 2,3-seco-3-methoxy-3,19α,23-trihydroxy-urs-12-en-2-al-28-oic acid (3), were isolated from the MeOH extract of the branch barks of Davidia involucrata, together with six known compounds. Their structures were elucidated by means of various spectroscopic analyses. The isolated triterpenes provide important evolutionary and chemotaxonomic knowledge about the monotypic genus Davidia. Five of the identified compounds showed moderate cytotoxicities against the cell proliferation of SGC-7901, MCF-7, and BEL-7404 with IC50 range from 7.26 to 47.41 μM.
Highlights
Davidia involucrata Baill., the only species in the genus Davidia Baill., is a famous ornamental tree known as the Chinese dove tree or handkerchief tree
Our continuing efforts of the phytochemical study of this plant have led to the isolation of two new nor-ursane type triterpenoids with a five-membered A ring and a novel 2,3-seco-ursane triterpene, which were named davinvolunic acids A-C
Betulinic acid (8), one of such compounds that possess several medicinal properties including anticancer, antimalarial, antimicrobial and anti-HIV activities, was initially considered to be melanoma-specific, but recent studies suggest that it shows anticancer activity against a broad panel of cancers [22,23,24,25]
Summary
Davidia involucrata Baill., the only species in the genus Davidia Baill., is a famous ornamental tree known as the Chinese dove tree or handkerchief tree. Our continuing efforts of the phytochemical study of this plant have led to the isolation of two new nor-ursane type triterpenoids with a five-membered A ring and a novel 2,3-seco-ursane triterpene, which were named davinvolunic acids A-C (compounds 1–3). Two known ursane triterpenoids, euscaphic acid (4) [7] and myrianthic acid (5) [8], as well as four lupane triterpenes, including lupeol (6) [9], betulin (7) [10], betulinic acid (8) [11] and platanic acid (9) [12] were obtained in the current study (Figure 1). This paper deals with the isolation and structure elucidation of the new compounds on the basis of spectroscopic methods, including 1D. All of the isolated triterpenoids except compound 2 were evaluated for their in vitro cytotoxic activities against three tumor cell lines (SGC-7901, MCF-7 and BEL-7404)
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