Pentacylic triterpenes from Lavandula coronopifolia: structure related inhibitory activity on α-glucosidase

Marwa Elsbaey, Rogers Mwakalukwa, Kuniyoshi Shimizu, Tomofumi Miyamoto

研究成果: Contribution to journalArticle査読

1 被引用数 (Scopus)

抄録

Ten pentacyclic triterpenes (1-10) were isolated from Lavandula coronopifolia. We evaluated their α-glucosidase inhibitory activity, and found that the aglycones, 1, 2, 3, 4, 7 and 10 showed superior IC50 values to the positive control. In order to explain the structural requirements for α-glucosidase inhibitory activity, eleven derivatives were prepared, including one new compound, 2-formyl-(A)1–19α-hydroxy-1-norursane-2, 12-dien-28-oic acid 10c. The results demonstrated that a free hydroxyl at ring-A and a free carboxylic group at position 28 are key structural features for the α-glucosidase inhibitory activity, also that an ursane skeleton is optimum for the activity. Additionally, enzyme kinetic analysis of pomolic acid 2, the most potent compound, revealed that it inhibited α-glucosidase in a mixed-type manner. The molecular docking simulation validated this type of inhibition and highlighted the role of the C-3 hydroxyl and C-28 carboxylic groups in interaction with the enzyme in silico.

本文言語英語
ページ(範囲)1436-1444
ページ数9
ジャーナルNatural Product Research
35
9
DOI
出版ステータス出版済み - 2021

All Science Journal Classification (ASJC) codes

  • 分析化学
  • 生化学
  • 植物科学
  • 有機化学

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