Planta Med 2018; 84(09/10): 716-720
DOI: 10.1055/s-0044-100524
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

New Tirucallane-Type Triterpenoids from Guarea guidonia

Vanessa Hernandez
1  Departamento de Farmacognosia y Medicamentos Organicos, Universidad de los Andes, Mérida, Venezuela
,
Marinella De Leo
2  Dipartimento di Farmacia, Università di Pisa, Italy
3  Centro Interdipartimentale di Ricerca “Nutraceutica e Alimentazione per la Salute,” Università di Pisa, Italy
,
Roberta Cotugno
4  Dipartimento di Farmacia, Università di Salerno, Fisciano (SA), Italy
,
Alessandra Braca
2  Dipartimento di Farmacia, Università di Pisa, Italy
3  Centro Interdipartimentale di Ricerca “Nutraceutica e Alimentazione per la Salute,” Università di Pisa, Italy
,
Nunziatina De Tommasi
4  Dipartimento di Farmacia, Università di Salerno, Fisciano (SA), Italy
,
Lorella Severino
5  Dipartimento di Medicina Veterinaria e Produzione Animale, Università di Napoli Federico II, Napoli, Italy
› Author Affiliations
Further Information

Publication History

received 13 November 2017
revised 22 December 2017

accepted 04 January 2018

Publication Date:
16 January 2018 (online)

Abstract

The aerial parts of Guarea guidonia afforded three new tirucallane-type triterpenoids: 3,4-seco-tirucalla-4(28),8(9),24(25)-trien-7α,11α-dihydroxy-21,23-epoxy-3,11-olide, named guareolide (1), 3,4-seco-tirucalla-4(28),7(8),24(25)-trien-21-hydroxy-21,23-epoxy-3-oic acid, named guareoic acid A (2), and 3,4-seco-tirucalla-4(28),7(8),24(25)-trien-21,23-epoxy-3-oic acid, named guareoic acid B (3), of which 1 possessed an unusual seven-membered lactone ring. Seven known terpenes were also isolated and characterized as flindissone, 7-acetyldihydronomilin, picroquassin E, boscartol C, and cneorubins A, B, and X. Their structures were determined by spectroscopic methods including one-dimensional and two-dimensional nuclear magnetic resonance analysis and high-resolution mass spectrometry. The isolates were investigated for their potential cytotoxic activity on Jurkat, HeLa, and MCF7 cancer cell lines. Flindissone and compound 2 showed an antiproliferative activity in all cell lines. Further studies revealed that flindissone, the most active compound, induced in Jurkat and HeLa cells both cytostatic and cytotoxic responses.

Supporting Information