Cytotoxic activity of Brazilian Cerrado plants used in traditional medicine against cancer cell lines

Journal of Ethnopharmacology

Volumn 123, Issue 3, 2009, Pages 439-445

  de Mesquita, Mariana Laundry ^a   de Paula, José Elias ^a   Pessoa, Cláudia ^b   de Moraes, Manoel Odorico ^b   Costa Lotufo, Letícia Veras ^b   Grougnet, Raphael ^c   Michel, Sylvie ^c   Tillequin, François ^c   Espindola, Laila Salmen ^a  

^a UNIVERSITY OF BRASILIA   (Brazil)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^c UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Brazilian Cerrado plants; Cytotoxic activity; Glaucarubinone; MTT assay; Traditional use

Indexed keywords

ALCOHOL; CASEARIA SYLVESTRIS EXTRACT; DICHLOROMETHANE; GLAUCARUBINONE; HEXANE; PLANT EXTRACT; SIMAROUBA VERSICOLOR EXTRACT; UNCLASSIFIED DRUG;

ANACARDIACEAE; ANNONACEAE; APOCYNACEAE; ARTICLE; BARK; BIOASSAY; BRAIN TUMOR; BRAZIL; CANCER CELL CULTURE; CANCER INHIBITION; CELL PROLIFERATION; CELL STRAIN HL 60; COLON CARCINOMA; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG ISOLATION; FLACOURTIACEAE; FRACTIONATION; GUTTIFERAE; HUMAN; HUMAN CELL; HUMAN TISSUE; IC 50; LEUKEMIA CELL; MELANOMA CELL; PLANT ROOT; PLANT STEM; SAPINDACEAE; SAPOTACEAE; SIMAROUBACEAE; TRADITIONAL MEDICINE; ZINGIBERACEAE;

ANGIOSPERMS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BRAZIL; CASEARIA; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ECOSYSTEM; GLAUCARUBIN; HUMANS; INHIBITORY CONCENTRATION 50; MEDICINE, TRADITIONAL; NEOPLASMS; PHYTOTHERAPY; PLANT COMPONENTS; PLANT EXTRACTS; PLANTS, MEDICINAL; SIMAROUBA;

ANACARDIACEAE; ANNONACEAE; APOCYNACEAE; CASEARIA SYLVESTRIS; CLUSIACEAE; FLACOURTIACEAE; SAPINDACEAE; SAPOTACEAE; SIMAROUBA VERSICOLOR; SIMAROUBACEAE; ZINGIBERACEAE;

EID: 67349129685     PISSN: 03788741     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jep.2009.03.018     Document Type: Article

References (82)

1. Abe F., Nagafuji S., Okawa M., Kinjo J., Akahane H., Ogura T., Martinez-Alfaro M.A., and Reyes-Chilpa R. Trypanocidal constituents in plants 5. Evaluation of some Mexican plants for their trypanocidal activity and active constituents in the seeds of Persea Americana. Biological & Pharmaceutical Bulletin 28 (2005) 1314-1317
2. Allen J.D., Dort S.C.V., Buitelaar M., Tellingen O.V., and Schinkel A.H. Mouse breast cancer resistance protein (Bcrp1/Abcg2) mediates etoposide resistance and transport, but etoposide oral availability is limited primarily by p-glycoprotein. Cancer Research 63 (2005) 1339-1344
3. Arriaga A.C., De Mesquita A.C., Pouliquen Y.B., De Lima R.A., Cavalcante S.H., De Carvalho M.G., De Siqueira J.A., Alegrio L.V., and Braz-Filho R. Chemical constituents of Simarouba versicolor. Anais da Academia Brasileira de Ciências 74 (2002) 415-424
4. Bermejo A., Figadere B., Zafra-Polo M.C., Barrachina I., Estornell E., and Cortes D. Acetogenins from Annonaceae. Recent progress in isolation, synthesis, and mechanisms of action. Natural Product Reports 22 (2005) 269-303
5. Blair, S., Correa, A., Madrigal, B., Zuluaga, C.B., Franco, H.D., 1991. Plantas antimaláricas, una revisíon bibliográfica. Universidad de Antioquia, Medellín, p. 214. In: Osorio, E., Arango, G.J., Jiménez, N., Alzate, F., Ruiz, G., Gutiérrez, D., 2007. Antiprotozoal and cytotoxic activities in vitro of colombian Annonaceae. Journal of Ethnopharmacology, 111, 630-635.
6. Braga F.G., Bouzada M.L., Fabri R.L., de O., Matos M., Moreira F.O., Scio E., and Coimbra E.S. Antileishmanial and antifungal activity of plants used in traditional medicine in Brazil. Journal of Ethnopharmacology 111 (2007) 396-402
7. Brandão M.G., Zanetti N.N., Oliveira P., Grael C.F., Santos A.C., and Monte-Mór R.L. Brazilian medicinal plants described by 19th century European naturalists and in the official Pharmacopoeia. Journal of Ethnopharmacology 120 (2008) 141-148
8. Chandrika P.M., Yakaiah T., Rao A.R., Narsaiah B., Reddy N.C., Sridhar V., and Rao J.V. Synthesis of novel 4, 6- disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U937 leukemia cell lines. European Journal of Medicinal Chemistry 43 (2008) 846-852
9. Chen C.-Y., Cheng Y.-B., Chen S.-Y., Chien C.T., Kuo Y.-H., Guh J.-H., Khalil A.T., and Shen Y.-C. New bioactive clerodane diterpenoids from the roots of Casearia membranacea. Chemistry & Biodiversity 5 (2008) 162-167
10. Choi H.J., Cho B.C., Shin S.J., Cheon S.H., Jung J.Y., Chang J., Kim S.K., Sohn J.H., and Kim J.H. Combination of topotecan and etoposide as a salvage treatment for patients with recurrent small cell lung cancer following irinotecan and platinum first-line chemotherapy. Cancer Chemotherapy and Pharmacology 61 (2008) 309-313
11. Cragg G.M., Schepartz S.A., Suffness M., and Grever M.R. The taxol supply crisis. New NCI policies for handling the large-scale production of novel natural product anticancer and anti-HIV agents. Journal of Natural Products 56 (1993) 1657-1668
12. Cragg G.M., Boyd M.R., Cardellina J.H., Newman D.J., Snader K.M., and McCloud T.G. Ethnobotany and drug discovery experience of the US National Cancer Institute. In: Chadwick D.J., and Marsh J. (Eds). Ciba Foundation "Ethnobotany and the search for new drugs" Symposium 185 (1994), Wiley and Sons, Chichester, UK 178-196
13. Cragg G.M., and Newman D.J. Antineoplastic agents from natural sources: achievements and future directions. Expert Opinion on Investigational Drugs 9 (2000) 1-15
14. da Silva S.L., Chaar J.S., Figueiredo P.M.S., and Yano T. Cytotoxic evaluation of essential oil from Casearia sylvestris Sw. on human cancer cells and erythrocytes. Acta Amazonica 38 (2008) 107-112
15. de Lima M.R., de Souza Luna J., dos Santos A.F., de Andrade M.C., Sant'Ana A.E., Genet J.-P., Márquez B., Neuville L., and Moreau N. Anti-bacterial activity of some Brazilian medicinal plants. Journal of Ethnopharmacology 105 (2006) 137-147
16. de Mesquita M.L., Grellier P., Blond A., Brouard J.-P., Paula J.E., Espindola L.S., and Mambu L. New ether diglycosides from Matayba guianensis with antiplasmodial activity. Bioorganic and Medicinal Chemistry 13 (2005) 4499-4506
17. de Mesquita M.L., Desrivot J., Bories C., Fournet A., de Paula J.E., Grellier P., and Espindola L.S. Antileishmanial and trypanocidal activity of Brazilian Cerrado plants. Memórias do Instituto Oswaldo Cruz 100 (2005) 783-787
18. de Mesquita M.L., Grellier P., Mambu L., de Paula J.E., and Espindola L.S. In vitro antiplasmodial activity of Brazilian Cerrado plants used as traditional remedies. Journal of Ethnopharmacology 110 (2007) 165-170
19. de Souza C.D., and Felfili M.J. Uso de plantas medicinais na região de Alto Paraíso de Goiás, GO, Brasil. Acta Botânica Brasileira 20 (2006) 135-142
20. Espindola, L.S., de Paula, J.E., Silveira, C.E.S., 2000. Curso de Fitoterapia. Produção de Remédios Caseiros com Qualidade. NEPAVI/CEAM/Universidade de Brasília, 208 p.
21. Espindola L.S., Vasconcelos Jr. J.R., de Mesquita M.L., Marquié P., de Paula J.E., Mambu L., and Santana J.M. Trypanocidal activity of a new diterpene from Casearia sylvestris var. lingua. Planta Medica 70 (2004) 1093-1095
22. Fenner R., Betti A.H., Mentz L.A., and Rates S.M.K. Plantas utilizadas na medicina popular brasileira com potencial atividade antifúngica. Brazilian Journal of Pharmaceutical Science 42 (2006) 369-394
23. 50) do extrato aquoso da Simarouba versicolor St. Hill, em camundongos. Revista Brasileira de Plantas Medicinais 6 (2004) 48-51
24. Ficker C.E., Smith M.L., Susiarti S., Leamanb D.J., Irawati C., and Arnason J.T. Inhibition of human pathogenic fungi by members of Zingiberaceae used by the Kenyah (Indonesian Borneo). Journal of Ethnopharmacology 85 (2003) 289-293
25. Garcia Cortez D.A., Young M.C.M., Marston A., Wolfender J.-L., and Hostettmann K. Xanthones, triterpenes and a biphenyl from Kielmeyera coriacea. Phytochemistry 47 (1998) 1367-1374
26. Garcia Cortez D.A., Abreu Filho B.A., Vataru Nakamura C., Dias Filho B.P., Marston A., and Hostettmann K. Antibacterial Activity of a Biphenyl and Xanthones from Kielmeyera coriacea. Pharmaceutical Biology 40 (2002) 485-489
27. Gaudemer A., and Polonsky J. Structure de la glaucarubinone nouveau principe amer isolé de Simarouba glauca. Phytochemistry 4 (1965) 149-153
28. Ghosh P.C., Larrahondo J.E., Le Quesne P.W., and Raffauf R.F. Antitumor plants. IV. Constituents of Simarouba versicolor. Lloydia 40 (1977) 364-369
29. Grieco P.A., Collins J.L., Moher E.D., Fleck T.J., and Gross R.S. Synthetic studies on quassinoids: total synthesis of (-)-chaparrinone, (-)-glaucarubolone, and (+)-glaucarubinone. Journal of the American Chemical Society 115 (1993) 6078-6093
30. Guimarães, E.F., Mautone, L., Rizzini, C.T., Mattos Filho, A., 1993. Árvores do Jardim Botânico do Rio de Janeiro. Jardim Botânico, Rio de Janeiro, pp. 99-100. In: Sartori, N.T., Canepelle, D., De Sousa Jr., P.T., Martins, D.T.O., 1999. Gastroprotective effect from Calophyllum brasiliense Camb. bark on experimental gastric lesions in rats and mice. Journal of Ethnopharmacology 67, 149-156.
31. Hall I.H., Liou Y.F., Lee K.H., Chaney S.G., and Willingham. Antitumor agents. LIX: effects of quassinoids on protein synthesis of a number of murine tumors and normal cells. Journal of Pharmaceutical Sciences 72 (1983) 626-630
32. Huerta-Reyes M., Basualdo M.Del.C., Abe F., Jimenez-Estrada M., Soler C., and Reyes-Chilpa R. HIV-1 inhibitory compounds from Calophyllum brasiliense leaves. Biological & Pharmaceutical Bulletin 27 (2004) 1471-1475
33. Ishimaru C., Takeuchi T., Yonezawa Y., Kuriyama I., Takemura M., Kato I., Sugawara F., Yoshida H., and Mizushina Y. Inhibitory effect of acetogenins on mammalian DNA polymerase and human cancer cell growth. Letters in Drug Design & Discovery 4 (2007) 239-245
34. Ito C., Murata T., Itoigawa M., Nakao K., Kaneda N., and Furukawa H. Apoptosis inducing activity of 4 - substituted coumarins from Calophyllum brasiliense in human leukaemia HL- 60 cells. Journal of Pharmacy and Pharmacology 58 (2006) 975-980
35. Joshi B.C., Pandey A., Sharma R.P., and Khare A. Quassinoids from Ailanthus excelsa. Phytochemistry 62 (2003) 579-584
36. Kanokmedhakul S., Kanokmedhakul K., Kanarsa T., and Buayairaksa M. New bioactive clerodane diterpenoids from the bark of Casearia grewiifolia. Journal of Natural Products 68 (2005) 183-188
37. Kanokmedhakul S., Kanokmedhakul K., and Buayairaksa M. Cytotoxic clerodane diterpenoids from fruits of Casearia grewiifolia. Journal of Natural Products 70 (2007) 1122-1126
38. Kelland L.R. Emerging drugs for ovarian cancer. Expert Opinion Emerging Drugs 10 (2005) 413-424
39. Kingston D.G., and Newman D.J. Taxoids: cancer-fighting compounds from nature. Current Opinion in Drug Discovery & Development 10 (2007) 130-144
40. Kupchan S.M., Uchida I., and Branfman A.R. Antileukemic principles isolated from euphorbiaceae plants. Science 191 (1976) 571-572
41. Kupchan S.M., and Lacadie J.A. Tumor inhibitors. 101. Dehydroailanthinone, a new antileukemic quassinoid from Pierreodendron kerstingii. The Journal of Organic Chemistry 40 (1975) 654
42. Kviecinski M.R., Felipe K.B., Schoenfelder T., de Lemos Wiese L.P., Rossi M.H., Goncalez E., Felício J.D., Filho D.W., and Pedrosa R.C. Study of the antitumor potential of Bidens pilosa (Asteraceae) used in Brazilian folk medicine. Journal of Ethnopharmacology 117 (2008) 69-75
43. Leskinen V., Polonsky J., and Bhatnagar S. Antifeedant activity of quassinoids. Journal of Chemical Ecology 10 (1984) 1497-1507
44. Levêque D., and Jehl F. Molecular pharmacokinetics of Catharanthus (vinca) alkaloids. Journal of Clinical Pharmacology 47 (2007) 579-588
45. Liaw C.-C., Yang Y.-L., Chen M., Chang F.-Rong., Chen S.-Li., Wu S.-H., and Wu Y.-C. Mono-tetrahydrofuran annonaceous acetogenins from Annona squamosa as cytotoxic agents and calcium ion chelators. Journal of Natural Products 71 (2008) 764-771
46. Liu X.-X., Alali F.Q., Pilarinou E., and McLaughlin J.L. Two bioactive mono-tetrahydrofuran acetogenins, annoglacins A and B, from Annona glabra. Phytochemistry 50 (1999) 815-821
47. Lucena P.L., Ribas Filho J.M., Mazza M., Czeczko N.G., Dietz U.A., Correa Neto M.A., Henriques G.S., Santos O.J., Ceschin A.P., and Thiele E.S. Evaluation of the aroeira (Schinus terebinthifolius Raddi) in the healing process of surgical incision in the bladder of rats. Acta Cirurgica Brasileira 21 (2006) 46-51
48. Magnotta M., Murata J., Chen J., and De Luca V. Expression of deacetylvindoline-4-O-acetyltransferase in Catharanthus roseus hairy roots. Phytochemistry 68 (2007) 1922-1931
49. Mendes F.R., and Carlini E.A. Brazilian plants as possible adaptogens: an ethnopharmacological survey of books edited in Brazil. Journal of Ethnopharmacology 109 (2007) 493-500
50. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods 16 (1983) 55-63
51. Napolitano D.R., Mineo J.R., de Souza M.A., de Paula J.E., Espindola L.S., and Espindola F.S. Down-modulation of nitric oxide production in murine macrophages treated with crude plant extracts from the Brazilian Cerrado. Journal of Ethnopharmacology 99 (2005) 37-41
52. Noldin V.F., Isaias D.B., and Cechinel Filho V. Gênero Calophyllum: importância química e farmacológica. Química Nova 29 (2006) 549-554
53. Núñez V., Otero F., Barona J., Fonnegra R., Jiménez S., Osorio R.G., Quintana J.C., and Díaz A. Inhibition of the toxic effects of Lachesis muta. Crotalus durissus cumanensis and Micrurus mipartitus snake venoms by plant extracts. Pharmaceutical Biology 42 (2004) 49-54
54. O'Neill M.J., Bray D.H., Boardman P., Wright C.W., Phillipson J.D., Warhurst D.C., Gupta M.P., Correya M., and Solis P. Plants as sources of antimalarial drugs, Part 6: Activities of Simarouba amara fruits. Journal of Ethnopharmacology 22 (1988) 183-190
55. Obici S., Otobone F.J., da Silva S.V.R., Ishida K., da Silva J.C., Nakamura C.V., Garcia C.D.A., and Audi E.A. Preliminary toxicity study of dichloromethane extract of Kielmeyera coriacea stems in mice and rats. Journal of Ethnopharmacology 115 (2008) 131-139
56. Ono M. Molecular links between tumor angiogenesis and inflammation: inflammatory stimuli of macrophages and cancer cells as targets for therapeutic strategy. Cancer Science 99 (2008) 1501-1506
57. 50) of the fruit of the Brazilian black pepper (Schinus terebinthifolius Raddi) and black pepper (Piper nigrum L.). Acta Farmaceutica Bonaerense 23 (2004) 176-182
58. Polonsky J., Baskévitch Z., Gottlieb H.E., Hagaman E.W., and Wenkert E. Carbon-13 Nuclear Magnetic Resonance Spectral Analysis of Quassinoid Bitter Principles. Journal of Organic Chemistry 40 (1975) 2499-2504
59. Polonsky J., Bhatnagar S.C., Griffiths D.C., Pickett J.A., and Woodcock C.M. Activity of quassinoids as antifeedants against aphids. Journal of Chemical Ecology 15 (1989) 993-998
60. Pretto J.B., Cechinel-Filho V., Noldin V.F., Sartori M.R.K., Isaias D.E.B., and Cruz A.B. Antimicrobial activity of fractions and compounds from Calophyllum brasiliense (Clusiaceae/Guttiferae). Zeitschrift fuer Naturforschung C59 (2004) 657-662
61. Reyes-Chilpa R., Estrada-Muniz E., Ramirez Apan T., Amekraz B., Aumelas A., Jankowski C.K., and Vazquez-Torres M. Cytotoxic effects of mammea type coumarins from Calophyllum brasiliense. Life Sciences 75 (2004) 1635-1647
62. Rodrigues, V.E.G., Carvalho, D.A., 2001. Levantamento etnobotânico de plantas medicinais no domínio cerrado na Região do Alto Rio Grande - Minas Gerais. Ciência e Agrotecnologia 25, 102-123. In: Tempone, A.G., Borborema, S.E.T., de Andrade, H.F.Jr., de Amorim Gualda, N.C., Yogi, A., Carvalho, C.S., Bachiega, D., Lupo, F.N., Bonotto, S.V., Fischer, D.C.H., 2005. Antiprotozoal activity of Brazilian plant extracts from isoquinoline alkaloid-producing families. Phytomedicine 12, 382-390.
63. Rodrigues E., and Carlini E.A. Ritual use of plants with possible action on the central nervous system by the Krahô Indians. Brazil. Phytotherapy Research 19 (2005) 129-135
64. Rodrigues A.M.S., De Paula J.E., Degallier N., Molez J.E., and Espindola L.S. Larvicidal activity of some Cerrado plant extracts against Aedes aegypti. Journal of the American Mosquito Control Association 22 (2006) 314-317
65. Rodrigues A.M.S., de Paula J.E., Roblot F., Fournet A., and Espíndola L.S. Larvicidal activity of Cybistax antisyphilitica against Aedes aegypti larvae. Fitoterapia 76 (2005) 755-757
66. Sai Prakash C.V., Hoch J.M., and Kingston D.G.I. Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascar rainforest. Journal of Natural Products 65 (2002) 100-107
67. Santos O.J., Ribas Filho J.M., Czeczko N.G., Castelo Branco Neto M.L., Naufel Jr. C., Ferreira L.M., Campos R.P., Moreira H., Porcides R.D., and Dobrowolski S. Evaluation of aroeira (Schinus terebinthifolius Raddi) extract on the healing process of gastroraphy in rats. Acta Cirurgica Brasileira 21 (2006) 39-45
68. Schmourlo G., Mendonça-Filho R.R., Alviano C.S., and Costa S.S. Screening of antifungal agents using ethanol precipitation and bioautography of medicinal and food plants. Journal of Ethnopharmacology 96 (2005) 563-568
69. Shen Y.-C., Wang L.-T., Wang C.-H., Khalil A.T., and Guh J.-H. Two new cytotoxic clerodane diterpenoids from Casearia membranacea. Chemical & Pharmaceutical Bulletin 52 (2004) 108-110
70. Shen Y.-C., Cheng Y.-B., Ahmed A.F., Lee C.L., Chen S.-Y., Chien C.-T., Kuo Y.-H., and Tzeng G.-L. Cytotoxic Clerodane Diterpenoids from Casearia membranacea. Journal of Natural Products 68 (2005) 1665-1668
71. Silva, F.M., de Paula, J., Espindola, L.S., 2009. Evaluation of the antifungal potential of brazilian Cerrado medicinal plants. Mycoses, doi:10.1111/j.1439-0507.2008.01647.x.
72. Suffness M., and Pezzuto J.M. Assays related to cancer drug discovery. In: Hostettmann K. (Ed). Methods in Plant Biochemistry: Assays for Bioactivity 6 (1990), Academic Press, London 71-133
73. Suffredini I.B., Paciência M.L.B., Varella A.D., and Younes R.N. In vitro cytotoxic activity of Brazilian plant extracts against human lung, colon and CNS solid cancers and leukemia. Fitoterapia 78 (2007) 223-226
74. Takahashi S., Yonezawa Y., Kubota A., Ogawa N., Maeda K., Koshino H., Nakata T., Yoshida H., and Mizushina Y. Pyranicin, a non-classical annonaceous acetogenin, is a potent inhibitor of DNA polymerase, topoisomerase and human cancer cell growth. International Journal of Oncology 32 (2008) 451-458
75. Wang H.K. Plant-derived anticancer agents currently in clinical use or clinical trials. The Investigation Drugs Journal 1 (1998) 92-102
76. Waterman P.G., and Ampofo S.A. Cytotoxic quassinoids from Odyendyea gabonensis stem bark: isolation and high-field NMR. Planta Medica 50 (1984) 261-263
77. Williams R.B., Norris A., Miller J.S., Birkinshaw C., Ratovoson F., Andriantsiferana R., Rasamison V.E., and Kingston D.G.I. Cytotoxic clerodane diterpenoids and their hydrolysis products from Casearia nigrescens from the rainforest of Madagascar. Journal of Natural Products 70 (2007) 206-209
78. Wright C.W., Anderson M.M., Allen D., Phillipson J.D., Kirby G.C., Warhurst D.C., and Chang H.R. Quassinoids exhibit greater selectivity against Plasmodium falciparum than against Entamoeba histolytica. Giardia intestinalis or Toxoplasma gondii in vitro. The Journal of Eukaryotic Microbiology 40 (1993) 244-246
79. Yeh S.H., Chang F.R., Wu Y.C., Yang Y.L., Zhuo S.K., and Hwang T.L. An anti-inflammatory ent-kaurane from the stems of Annona squamosa that inhibits various human neutrophil functions. Planta Medica 71 (2005) 904-909
80. Zagoto J.N., Bracht A., Pagadigorria C.L.S., Ishii-Iwamoto E.L., Cortez D.A.G., and Yamamoto N.S. Effects of the Kielmeyera coriacea extract on energy metabolism in the rat liver. Journal of Ethnopharmacology 105 (2006) 47-54
81. Zeng L., Ye Q., Oberlies N.H., Shi G., Cu Z.-M., and He K. Recent advances in annonaceous acetogenins. Natural Products Reports 13 (1996) 275-306
82. Zhou B.N., Baj N.J., Glass T.E., Malone S., Werkhoven M.C., van Troon F., David, Wisse J.H., and Kingston D.G. Bioactive labdane diterpenoids from Renealmia alpinia collected in the Suriname rainforest. Journal of Natural Products 60 (1997) 1287-1293