Tributelosides A-D: Four Undescribed Spirostan Glycosides Isolated from the Branches and Leaves of Tribulus terrestris with Their NO Production Inhibitory Activity in LPS Activated RAW 264.7 Cells

Nguyen Van Quoc; Nguyen Huy Hoang; Bui Huu Tai; Pham Hai Yen; Nguyen Thi Cuc; Phan Thi Thanh Huong; Duong Thi Dung; Do Thi Trang; Nguyen The Cuong; Le Duc Giang; Phan Van Kiem

doi:10.1002/cbdv.202401049

Tributelosides A-D: Four Undescribed Spirostan Glycosides Isolated from the Branches and Leaves of Tribulus terrestris with Their NO Production Inhibitory Activity in LPS Activated RAW 264.7 Cells

Chem Biodivers. 2024 May 16:e202401049. doi: 10.1002/cbdv.202401049. Online ahead of print.

Authors

Affiliations

¹ Vinh University, school of chemistry, biology and environment, Vinh, Vinh, VIET NAM.
² Vietnam Academy of Science and Technology, Institute of Marine Biochemistry, Hoang Quoc Viet, Hanoi, 10072, Hanoi, VIET NAM.
³ Vietnam Academy of Science and Technology, Institute of Marine Biochemistry, 18 Hoang Quoc Viet, Hanoi, 10072, Hanoi, VIET NAM.
⁴ Vietnam Academy of Science and Technology, Institute of Marine Biochemistry, 18 Hoang Quoc Viet, Hanoi, Hanoi, 10072, Hanoi, VIET NAM.
⁵ Vietnam Academy of Science and Technology, Institute of Marine Biochemistry, 18 Hoang Quoc Viet, Cau Giay,, Hanoi, Hanoi, VIET NAM.
⁶ Vietnam Academy of Science and Technology, Institute of Marine Biochemistry, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam, Hanoi, 10072, Hanoi, VIET NAM.
⁷ Vietnam Academy of Science and Technology, Institute of Ecology and Biological Resources, 18 Hoang QUoc Viet, Hanoi, 10072, Hanoi, VIET NAM.
⁸ Vinh University, Department of Chemistry, Vinh, Vinh, VIET NAM.
⁹ Vietnam Academy of Science and Technology, Department of Structural Research, 18 Hoang Quoc Viet, 10000, Hanoi, VIET NAM.

PMID: 38757233
DOI: 10.1002/cbdv.202401049

Abstract

Four undescribed spirostan glycosides, (25S)-5α-spirostan-12-one-2α,3β-diol-3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1), (25S)-5α-spirostan-12-one-2α,3β-diol-3-O-β-D-galatopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2), (25S)-5α-spirostan-12-one-2α,3β-diol-3-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (3), and hecogenin 3-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-galactopyranoside (4), together with eleven known compounds (5-15) were isolated from the branches and leaves of Tribulus terrestris. Their chemical structures were established through spectroscopic methods. including HR-ESI-MS, 1D-, and 2D-NMR spectra. Preliminary biological evaluation on NO production inhibitory activity in LPS activated RAW 264.7 cells showed that compounds 1-3, 5, and 6 had significant inhibitory effects with IC50 values ranging from 2.4 to 18.3 µM, compared to that of the positive control compound, dexamethazone (IC50 13.6 µM).

Keywords: NO inhibitory activity; Tribulus terrestris; Zygophyllaceae; spirostan glycoside; tributeloside.