A/D-rings-seco limonoids from the fruits of Aglaia edulis and their bioactivities

Yujin Sun; Letian Cui; Yunpeng Sun; Qiurong Li; Yongyi Li; Zefan Wang; Wenjun Xu; Lingyi Kong; Jun Luo

doi:10.1016/j.phytochem.2021.113049

A/D-rings-seco limonoids from the fruits of Aglaia edulis and their bioactivities

Phytochemistry. 2022 Mar:195:113049. doi: 10.1016/j.phytochem.2021.113049. Epub 2021 Dec 10.

Authors

Yujin Sun¹, Letian Cui¹, Yunpeng Sun¹, Qiurong Li¹, Yongyi Li¹, Zefan Wang¹, Wenjun Xu¹, Lingyi Kong², Jun Luo³

Affiliations

¹ Jiangsu Key Laboratory of Bioactive Natural Product Research, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China.
² Jiangsu Key Laboratory of Bioactive Natural Product Research, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China. Electronic address: cpu_lykong@126.com.
³ Jiangsu Key Laboratory of Bioactive Natural Product Research, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People's Republic of China. Electronic address: luojun@cpu.edu.cn.

PMID: 34902704
DOI: 10.1016/j.phytochem.2021.113049

Abstract

Agledulines A-K, eleven previously undescribed limonoids, including eight biogenic A/D-rings-seco limonoid analogs (agledulines A-H), one D-ring-seco limonoid (agleduline I) and two A-ring-seco limonoids with a rare Δ^4,28 moiety (agledulines J-K), together with twelve reported limonoids, were isolated from the fruits of Aglaia edulis. Their structures were determined by NMR data, HRESIMS, X-ray diffraction, ECD spectra and the CD exciton chirality method. Observably, the absolute configurations of agleduline A, agleduline C and nymania 2 were unambiguously elucidated by single-crystal X-ray diffraction analyses. The biological evaluation showed that agleduline C exhibited significant cytotoxic activities with IC₅₀ values of 10.05 μM, and 11α-acetoxygedunin showed notable anti-inflammatory activity (IC₅₀: 4.70 μM). In addition, agleduline I and 11α-acetoxygedunin reversed the multidrug resistance with IC₅₀ values of 5.05 and 1.49 μM (RI: 4.64 and 15.77) in the MCF-7/Dox cells.

Keywords: Aglaia edulis; Agledulines A-K; Biological activities; Limonoids; Meliaceae.

MeSH terms

Aglaia*
Fruit
Humans
Limonins* / pharmacology
Meliaceae*
Molecular Structure

Substances

Limonins