Download PDF
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)

Also available at
   Permissions and Reprints

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

  • 1 Aristeguieta L. Familias y géneros de los árboles de Venezuela. Edición special del Instituto botánico. Caracas: 1973: 841
    Search in Google Scholar
  • 2 Oga S, Sertié JA, Brasile AC, Hanada S. Antiinflammatory effect of crude extract from Guarea guidonia . Planta Med 1981; 42: 310-312
    Thieme ConnectPubMedSearch in Google Scholar
  • 3 Garcez FR, Nuñez CV, Garcez WS, Almeida RM, Roque NF. Sesquiterpenes, limonoid and coumarin from the wood bark of Guarea guidonia . Planta Med 1998; 64: 79-80
    Thieme ConnectPubMedSearch in Google Scholar
  • 4 Lago JHG, Brochini CB, Roque NF. Terpenoids from Guarea guidonia . Phytochemistry 2002; 60: 333-338
    CrossrefPubMedSearch in Google Scholar
  • 5 Dal Piaz F, Malafronte N, Romano A, Gallotta D, Belisario MA, Bifulco G, Gualtieri MJ, Sanogo R, De Tommasi N, Pisano C. Structural characterization of tetranortriterpenes from Pseudrocedrela kotschyi and Trichilia emetica and study of their activity towards the chaperone Hsp90. Phytochemistry 2012; 75: 78-89
    CrossrefPubMedSearch in Google Scholar
  • 6 Gualtieri MJ, Malafronte N, Vassallo A, Braca A, Cotugno R, Vasaturo M, De Tommasi N, Dal Piaz F. Bioactive limonoids from the leaves of Azadirachta indica (Neem). J Nat Prod 2014; 77: 596-602
    CrossrefPubMedSearch in Google Scholar
  • 7 Kamperdick C, Lien TP, Adam G, Sung TV. Apotirucallane and tirucallane triterpenoids from Luvunga sarmentosa . J Nat Prod 2003; 66: 675-678
    CrossrefPubMedSearch in Google Scholar
  • 8 Zheng Q, Guan B, Qin JJ, Wang CH, Cheng XR, Ren J, Yan SK, Jin HZ, Zhang WD. 2, 3-seco- and 3, 4-seco-tirucallane triterpenoid derivatives from the stems of Aphanamixis grandifolia Blume. Phytochemistry 2012; 80: 148-155
    CrossrefPubMedSearch in Google Scholar
  • 9 Kim KH, Choi SU, Kim YC, Lee KR. Tirucallane triterpenoids from Cornus walteri . J Nat Prod 2011; 74: 54-59
    CrossrefPubMedSearch in Google Scholar
  • 10 Guang-Yi L, Gray AI, Waterman PG. Chemistry of the Burseraceae. Part 9. Tirucallane and oleanane triterpenes from the resin of Aucoumea klaineana . Phytochemistry 1988; 27: 2283-2286
    CrossrefPubMedSearch in Google Scholar
  • 11 Ahmed FR, Ng AS, Fallis AG. 7α-Acetoxydihydronomilin: isolation, spectra, and crystal structure. Can J Chem 1978; 56: 1020-1025
    CrossrefPubMedSearch in Google Scholar
  • 12 Xu J, Xiao D, Lin QH, He JF, Liu WY, Xie N, Feng F, Qu W. Cytotoxic tirucallane and apotirucallane triterpenoids from the stems of Picrasma quassioides . J Nat Prod 2016; 79: 1899-1910
    CrossrefPubMedSearch in Google Scholar
  • 13 Wang YG, Ren J, Wang AG, Yang JB, Ji TF, Ma QG, Tian J, Su YL. Hepatoprotective prenylaromadendrane-type diterpenes from the gum resin of Boswellia carterii . J Nat Prod 2013; 76: 2074-2079
    CrossrefPubMedSearch in Google Scholar
  • 14 Brochini CB, Roque NF. Two new cneorubin related diterpenes from the leaves of Guarea guidonia (Meliaceae). J Braz Chem Soc 2000; 11: 361-364
    CrossrefPubMedSearch in Google Scholar
  • 15 De Leo M, Peruzzi L, Granchi C, Tuccinardi T, Minutolo F, De Tommasi N, Braca A. Constituents of Polygala flavescens ssp. flavescens and their activity as inhibitors of human lactate dehydrogenase. J Nat Prod 2017; 80: 2077-2087
    CrossrefPubMedSearch in Google Scholar
  • 16 Jimenez-Usuga N, Malafronte N, Cotugno R, De Leo M, Osorio E, De Tommasi N. New sesquiterpene lactones from Ambrosia cumanensis Kunth. Fitoterapia 2016; 113: 170-174
    CrossrefPubMedSearch in Google Scholar