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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)

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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 (3–5) 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.

Key words

Aphanamixis polystachya - Meliaceae - limonoids - surface plasmon resonance - Hsp90

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


Supporting Information

    NMR spectra of compounds 1–5 and SPR sensorgrams of tested compounds are available as Supporting Information.

  • Supporting Information
 

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