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Planta Med 2017; 83(03/04): 341-350
DOI: 10.1055/s-0042-117114
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

New Structurally Diverse Limonoids from the Seeds of Khaya senegalensis

Xiaomeng Tian   *
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, Peopleʼs Republic of China
,
Hui Li   *
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, Peopleʼs Republic of China
,
Faliang An
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, Peopleʼs Republic of China
,
Ruijun Li
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, Peopleʼs Republic of China
,
Miaomiao Zhou
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, Peopleʼs Republic of China
,
Minghua Yang
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, Peopleʼs Republic of China
,
Lingyi Kong
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, Peopleʼs Republic of China
,
Jun Luo
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 09 May 2016
revised 24 August 2016

accepted 06 September 2016

Publication Date:
20 September 2016 (online)

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Abstract

Twelve new limonoids (khasenegasins O–Z; 1–12) with three different kinds of skeletons, including eight mexicanolides, two gedunins, and two andirobins, together with four known limonoids (13–16) were isolated from the seeds of Khaya senegalensis. Their structures were determined by extensive spectroscopic analyses (HR-ESI-MS, 1D/2D NMR), and the absolute configurations of 1 and 2 were established by the electronic circular dichroism exciton chirality method. Moreover, a new andirobin-type limonoid (12) showed significant neuroprotective activity against glutamate-induced injury in primary rat cerebellar granule neuronal cells with increased viability of 83.3 ± 6.0 % at 10 µM and 80.3 ± 3.2 % at 1 µM.

Key words

Khaya senegalensis - Meliaceae - limonoids - ECD exciton chirality - neuroprotective activity

* These authors contributed equally to this work.


Supporting Information

 

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