Aglatestine A, a Rearranged Limonoid with a 3/6/6 Tricarbocyclic Framework from the Fruits of .

J Org Chem

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.

Published: August 2021

Aglatestine A (), an unprecedented 3/6/6 tricarbocyclic limonoid framework along with four biogenic A/D- limonoid analogues with rare β-substituents at C-6 (), was discovered from the fruits of . The structures of along with their absolute configurations were clarified using methods of HRMS(ESI), NMR, electronic circular dichroism, X-ray diffraction crystallography, and quantum chemical calculations. The plausible biogenetic speculation suggested that an electrophilic cyclization between C-1 carbocation from acetolysis and electron-rich C-5 from enolization of C═O of may play a key role. The biological evaluation showed that exhibited anti-inflammatory activity indicated by inhibiting NO release in LPS-activated RAW 264.7 macrophages (IC: 35.72 ± 1.96 μM).

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http://dx.doi.org/10.1021/acs.joc.1c00968DOI Listing

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