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A New Apotirucallane from Walsura trichostemon Leaves and Its Antibacterial and α‐Glucosidase Inhibitory Activities
Author(s) -
Suchaichit Nattawut,
Pitchuanchom Siripit,
Kanokmedhakul Kwanjai,
Moosophon Panawan,
Chompoosor Apiwat,
Kanokmedhakul Somdej,
Suchaichit Natcha P.
Publication year - 2021
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202100134
Subject(s) - acarbose , chemistry , phytochemical , bacillus cereus , antibacterial activity , minimum inhibitory concentration , terpene , stereochemistry , pseudomonas aeruginosa , in vitro , triterpenoid , enzyme , biochemistry , bacteria , biology , genetics
Phytochemical investigation of Walsura trichostemon leaves led to the isolation of a new apotirucallane‐type triterpenoid, 11,25‐dideacetyl‐16‐hydroxytrichostemonate ( 1 ), along with two known apotirucallane‐type triterpenoids ( 2 and 3 ), two known tirucallane‐type triterpenes ( 4 and 5 ), and two known steroids ( 6 and 7 ). Their structures were identified by intensive analysis of 1D and 2D nuclear magnetic resonance, infrared, and mass spectrometry data, which were compared with data reported in the literature. Compounds 2 , 3 , and 5 exhibited moderate antibacterial activity against Pseudomonas aeruginosa (minimum inhibitory concentration (MIC) value: 64 μg/mL), and compound 4 showed weak antibacterial activity against P. aeruginosa (MIC: 128 μg/mL). Furthermore, compound 5 displayed activity against Bacillus cereus (MIC: 64 μg/mL). In addition, compound 4 showed stronger α‐glucosidase inhibitory activity than the control, acarbose. The active compound 4 was subjected to molecular docking experiments using AutoDock4 and revealed precise interactions with the active gorge of the enzyme through hydrogen bonding, supporting the in vitro results.