A new oleanane-skeleton triterpene isolated from Coffea canephora

Extensive fractionation of n-hexane extract from the dried powdered-trunks of Coffea canephora Pierre ex A.Froehner (Rubiaceae) led to the isolation of a new oleanane-skeleton triterpene, coffecanolic acid (1), along with three known analogues sumaresinolic acid (2), oleanolic acid (3), and 3-O-acet...

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Bibliographic Details
Published in:Natural product research 2022-10, Vol.36 (20), p.5161-5167
Main Authors: Hoang, Minh Hao, Nguyen, Thi Anh Tuyet, Pham, Nguyen Kim Tuyen, Dang, Van Son, Vo, Thi Nga
Format: Article
Language:English
Subjects:
Acarbose
Coffea canephora
Data analysis
Fractionation
Glucosidase
Hexanes
n-Hexane
NMR
NMR analysis
Nuclear magnetic resonance
oleanane skeleton
Oleanolic acid
triterpene
Two dimensional analysis
α-Glucosidase
α-glucosidase inhibition
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Summary:Extensive fractionation of n-hexane extract from the dried powdered-trunks of Coffea canephora Pierre ex A.Froehner (Rubiaceae) led to the isolation of a new oleanane-skeleton triterpene, coffecanolic acid (1), along with three known analogues sumaresinolic acid (2), oleanolic acid (3), and 3-O-acetyloleanolic acid (4). The chemical structures were elucidated using FT-IR, 1D and 2D NMR and HR-ESI-MS data analysis. The isolated compounds were assayed for in vitro α-glucosidase inhibitory activity by determining their half-maximal inhibitory concentration (IC 50 , µM). Compounds 1-4 exhibited higher inhibitory activities when compared with acarbose, a positive control. Compound 1 was found to be the most potent molecule against α-glucosidase, with the IC 50 = 83.0 ± 1.2 µM, which improved by 2.5-fold over acarbose (IC 50 = 209.8 ± 0.3 µM) in this assay.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2021.1921767