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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)

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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.

Key words

Guarea guidonia - Meliaceae - tirucallane triterpenes - cytotoxicity - antiproliferative activity

Supporting Information

    NMR spectra of compounds 1–3 and data for the EC50 determination of cytotoxic activity are available as Supporting Information.

  • Supporting Information
 

  • References

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