Cytotoxic quinazoline alkaloids from the seeds of Peganum harmala

Bioorg Med Chem Lett. 2018 Jan 15;28(2):103-106. doi: 10.1016/j.bmcl.2017.12.003.

Sheng-Ge Li ¹, Kai-Bo Wang ¹, Chi Gong ¹, Yu Bao ², Ning-Bo Qin ¹, Da-Hong Li ¹, Zhan-Lin Li ¹, Jiao Bai ³, Hui-Ming Hua ⁴

Affiliations

1 Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
2 School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
3 Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address: baijiao@hotmail.com.
4 Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address: huimhua@163.com.

PMID: 29229205 DOI: 10.1016/j.bmcl.2017.12.003

Abstract

Seventeen Quinazoline Alkaloids and derivatives, containing two pairs of new epimers, named as (S)- and (R)-1-(2-aminobenzyl)-3-hydroxypyrrolidin-2-one β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside (1, 2), (S)- and (R)-vasicinone β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside (3, 4), and a new enantiomer (12b), together with six known ones (5-8, 10, and 12a), and three pairs of known enantiomers (9, 11, and 13), were isolated from the ethanol extracts of the seeds of Peganum harmala L.. Their structures including the absolute configuration were elucidated by using 1D and 2D NMR, and ECD calculation approaches. The cytotoxic activities of all isolated compounds were evaluated. 11 showed moderate cytotoxicity against PC-3 cells with an IC₅₀ value of 15.41 μM.

Keywords

Cytotoxicity; Peganum harmala; Quinazoline alkaloids.

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