Planta Med 2018; 84(12/13): 964-970
DOI: 10.1055/a-0624-9538
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Limonoids from Aphanamixis polystachya Leaves and Their Interaction with Hsp90[*]

César Muñoz Camero
1  Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
,
Antonio Vassallo
2  Dipartimento di Scienze, Università degli Studi della Basilicata, Potenza, Italy
,
Marinella De Leo
1  Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
3  Centro Interdipartimentale di Ricerca “Nutraceutica e Alimentazione per la Salute”, Università di Pisa, Pisa, Italy
,
Abeer Temraz
4  Department of Pharmacognosy, Faculty of Pharmacy, Umm Al-Qura University, Saudi Arabia
5  Faculty of Pharmacy, Al Azhar University, Cairo, Egypt
,
Nunziatina De Tommasi
6  Dipartimento di Farmacia, Università di Salerno, Fisciano (SA), Italy
,
Alessandra Braca
1  Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
3  Centro Interdipartimentale di Ricerca “Nutraceutica e Alimentazione per la Salute”, Università di Pisa, Pisa, Italy
› Author Affiliations
Further Information

Publication History

received 05 February 2018
revised 26 April 2018

accepted 01 May 2018

Publication Date:
15 May 2018 (online)

Abstract

A phytochemical study of n-hexane, CHCl3, and CHCl3-MeOH extracts of Aphanamixis polystachya leaves led to the isolation of 10 compounds. Five of them turned out to be new natural compounds, including two mexicanolide-type (1, 2) and three polyoxyphragmalin-type (35) limonoids, together with two known andirobin-type limonoids (6, 7) and three phenolic derivatives. The structures of the new compounds were established on the basis of spectroscopic methods to be 8-hydro-14,15-en-cabralin (1), 3-deacetyl-8-hydro-cabralin-14,15-en-3-one (2), 20,22-dihydroxy-21,23-dimethoxytetrahydrofuran khayanolide A (3), 1-deacetyl-3-dehydroxy-3-oxokhaysenelide E (4), and meliaphanamixin A (5). All compounds were isolated for the first time from this species. The ability of the isolated limonoids to interact with the molecular chaperone Hsp90 was tested. Compounds 6 and 7 were the most active.

* Dedicated to Professor Dr. Robert Verpoorte in recognition of his outstanding contribution to natural products research.


Supporting Information