Triterpenoids from the fruits of Melia azedarach L. and their cytotoxic activities

Min Song; Ging Chan; Li-Gen Lin; Derong Li; Kehan Zhang; Xiao-Qi Zhang; Wen-Cai Ye; Na Li; Qing-Wen Zhang

doi:10.1016/j.phytochem.2022.113280

Triterpenoids from the fruits of Melia azedarach L. and their cytotoxic activities

Phytochemistry. 2022 Sep:201:113280. doi: 10.1016/j.phytochem.2022.113280. Epub 2022 Jun 15.

Authors

Min Song¹, Ging Chan¹, Li-Gen Lin², Derong Li³, Kehan Zhang³, Xiao-Qi Zhang⁴, Wen-Cai Ye⁴, Na Li⁵, Qing-Wen Zhang⁶

Affiliations

¹ State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, Macao, PR China.
² State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, Macao, PR China; Department of Pharmaceutical Sciences, Faculty of Health Sciences, University of Macau, Macao, PR China.
³ Macau Anglican College, Macao, PR China.
⁴ Center for Bioactive Natural Molecules and Innovative Drugs Research, And Guangdong Provincial Engineering Research Center for Modernization of TCM, College of Pharmacy, Jinan University, Guangzhou, 510632, PR China.
⁵ State Key Laboratory of Quality Research in Chinese Medicine, Macau University of Science and Technology, Macao, PR China. Electronic address: nli@must.edu.mo.
⁶ State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, Macao, PR China; Department of Pharmaceutical Sciences, Faculty of Health Sciences, University of Macau, Macao, PR China. Electronic address: qwzhang@um.edu.mo.

PMID: 35716716
DOI: 10.1016/j.phytochem.2022.113280

Abstract

Eleven undescribed tetracyclic triterpenoids, meliazedarachins A-K, along with twenty-six known compounds were isolated from the fruits of Melia azedarach L.. Their structures were determined by HRESIMS, UV, IR, NMR, X-ray diffraction, electronic circular dichroism (ECD) spectra, and the modified Mosher's method. The cytotoxic activities of all the isolates were measured. Meliazedarachin K and mesendanin N showed cytotoxicity against five human cancer cell lines with IC₅₀ values ranging from 9.02 to 31.31 μM. Meliazedarachin K showed significant cytotoxicity against HCT116 cell line with IC₅₀ value of 9.02 ± 0.84 μM. 21α-methylmelianodiol showed significant cytotoxicity against HCT116 and RKO cell lines with IC₅₀ values of 10.16 ± 1.22 and 8.57 ± 0.80 μM, respectively.

Keywords: Cytotoxicity; Melia azedarach L.; Meliaceae; Tetracyclic triterpenoids.

MeSH terms

Antineoplastic Agents*
Fruit / chemistry
Humans
Melia azedarach* / chemistry
Molecular Structure
Neoplasms*
Triterpenes* / chemistry

Substances

Antineoplastic Agents
Triterpenes