Journal of Medicinal Materials, 2022, Vol. 27, No. 6 (pp. 336 - 343)

¹H AND ¹³C NMR ASSIGNMENTS OF PHENOLIC

AND OTHER CONSTITUENTS FROM MILIUSA SINENSIS LEAVES

AND THEIR CYTOTOXIC ACTIVITY

Cao Thi Hue¹, Pham Thanh Binh², Luc Quang Tan³, Hoang Van Hung³, Vu Thanh Trung², Nguyen Thi Lan Huong¹, Nguyen Manh Ha⁴, Nguyen Van Thanh², Nguyen Phuong Thao^2,*

¹Thuyloi University, Hanoi, Vietnam;

²Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, Hanoi, Vietnam;

³Thai Nguyen University-Lao Cai Campus, Lao Cai Province, Vietnam;

⁴University of Mining and Geology, Hanoi, Vietnam

*Corresponding author: thaonp@imbc.vast.vn

(Received August 31^st, 2022)

Summary

¹H and ¹³C NMR Assignments of Phenolic and other Constituents from Miliusa sinensis Leaves
and their Cytotoxic Activity

Phytochemical investigation of a methanolic extract of Miliusa sinensis leaves led to the isolation of eight compounds (1‒8), using various chromatographic separations. Their structures were elucidated to be pteleifoside C (1), melisimplexin (2), 3,5,6,7,3',4'-hexamethoxyflavone (3), 6'-O-β-D-apiofuranosylthalictoside (4), osmanthuside H (5), icariside D₁ (6), 3,4-dimethoxyphenol 1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (7), and 3,4,5-trimethoxyphenol 1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (8) by detailed analysis via spectroscopic techniques (1D, 2D NMR, and MS data) as well as comparison with those reported. All of the isolates were evaluated for their cytotoxicity against HepG2, DU145, A549, and MCF7 cancer cell lines, using the MTT assay. Compounds 1-8 showed weak or fewer effects against the tested cancer cell lines. This is the first time that glycoside constituents from M. sinensis leaves and their cytotoxic activity were reported.

Keywords: Miliusa sinensis; Annonaceae; Flavonoid; Megastigmane; Phenolic; Cytotoxic activity.

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