A New Apotirucallane from Walsura trichostemon Leaves and Its Antibacterial and α-Glucosidase Inhibitory Activities

Nattawut Suchaichit; Siripit Pitchuanchom; Kwanjai Kanokmedhakul; Panawan Moosophon; Apiwat Chompoosor; Somdej Kanokmedhakul; Natcha P Suchaichit

doi:10.1002/cbdv.202100134

A New Apotirucallane from Walsura trichostemon Leaves and Its Antibacterial and α-Glucosidase Inhibitory Activities

Chem Biodivers. 2021 Jun 17. doi: 10.1002/cbdv.202100134. Online ahead of print.

Authors

Nattawut Suchaichit¹, Siripit Pitchuanchom², Kwanjai Kanokmedhakul³, Panawan Moosophon³, Apiwat Chompoosor⁴, Somdej Kanokmedhakul³, Natcha P Suchaichit¹

Affiliations

¹ Department of Applied Chemistry, Faculty of Sciences and Liberal Arts, Rajamangala University of Technology Isan, Nakhon Ratchasima, 30000, Thailand.
² Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahasarakham University, Maha Sarakham, 44150, Thailand.
³ Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, 40002, Thailand.
⁴ Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkapi, Bangkok, 10240, Thailand.

PMID: 34145750
DOI: 10.1002/cbdv.202100134

Abstract

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.

Keywords: Walsura trichostemon; antibacterial activity; apotirucallane; molecular docking; α-glucosidase inhibition.

Abstract

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