β-Carboline alkaloids from the roots of Peganum harmala L

Shengge Li; Qin Zhang; Yuetong Wang; Bin Lin; Dahong Li; Huiming Hua; Xu Hu

doi:10.1016/S1875-5364(24)60583-2

β-Carboline alkaloids from the roots of Peganum harmala L

Chin J Nat Med. 2024 Feb;22(2):171-177. doi: 10.1016/S1875-5364(24)60583-2.

Authors

Shengge Li¹, Qin Zhang², Yuetong Wang³, Bin Lin⁴, Dahong Li⁵, Huiming Hua⁶, Xu Hu⁷

Affiliations

¹ Henan Key Laboratory of Zhang Zhongjing Formulate and Herbs for Immunoregulation, Zhang Zhongjing Traditional School of Chinese Medicine, Nanyang Institute of Technology, Nanyang 473004, China.
² Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
³ Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang 110016, China.
⁴ School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China.
⁵ Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China. Electronic address: lidahong0203@163.com.
⁶ Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China. Electronic address: huimhua@163.com.
⁷ Henan Key Laboratory of Zhang Zhongjing Formulate and Herbs for Immunoregulation, Zhang Zhongjing Traditional School of Chinese Medicine, Nanyang Institute of Technology, Nanyang 473004, China. Electronic address: huxu105@163.com.

PMID: 38342569
DOI: 10.1016/S1875-5364(24)60583-2

Abstract

This study reports the isolation of four new β-carboline alkaloids (1-4) and six previously identified alkaloids (5-10) from the roots of Peganum harmala L. Among these compounds, 1 and 2 were characterized as rare β-carboline-quinazoline dimers exhibiting axial chirality. Compound 3 possessed a unique 6/5/6/7 tetracyclic ring system with an azepine ring, and compound 4 was a novel annomontine β-carboline. The structures of these compounds were elucidated by spectroscopic data and quantum mechanical calculations. The biosynthetic pathways of 1-3 were proposed. Additionally, the cytotoxicity of some isolates against four cancer cell lines (HL-60, A549, MDA-MB-231, and DU145) was evaluated. Notably, compound 4 exhibited significant cytotoxicity against HL-60, A549, and DU145 cells with IC₅₀ values of 12.39, 12.80, and 30.65 μmol·L^-1, respectively. Furthermore, compound 2 demonstrated selective cytotoxicity against HL-60 cells with an IC₅₀ value of 17.32 μmol·L^-1.

Keywords: Cytotoxic activity; Peganum harmala; Structure elucidation; β-Carboline alkaloids.

MeSH terms

Alkaloids* / chemistry
Carbolines / chemistry
HL-60 Cells
Humans
Peganum* / chemistry
Peganum* / metabolism

Substances

Alkaloids
Carbolines