PDF herunterladen
Planta Med 2011; 77(14): 1597-1599
DOI: 10.1055/s-0030-1270960
Biological and Pharmacological Activity
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic and Anti-infective Phenolic Compounds Isolated from Mikania decora and Cremastosperma microcarpum

José C. Aponte1 , 2 , Zhuang Jin1 , Abraham J. Vaisberg3 , Denis Castillo3 , Edith Málaga3 , Walter H. Lewis4 , Michel Sauvain5 , Robert H. Gilman6 , Gerald B. Hammond1
  • 1Department of Chemistry, University of Louisville, Louisville, KY, USA
  • 2Current address: Department of Geological Sciences, Brown University, Providence, RI, USA
  • 3Departamento de Microbiología y Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, Lima, Perú
  • 4Department of Biology, Washington University, St. Louis, MO, USA
  • 5Universidad de Toulouse III – IRD, UMR 152 (Pharma-Dev), France, and UPCH, Lima, Peru
  • 6Johns Hopkins School of Public Health, Baltimore, MD, USA
Weitere Informationen

Publikationsverlauf

received December 16, 2010 revised March 10, 2011

accepted March 12, 2011

Publikationsdatum:
06. April 2011 (online)

Auch verfügbar auf
    Lizenzen und Reprints

Abstract

An anticancer-bioassay guided isolation of the ethanol extract and fractions of two plants from the Peruvian rainforest, Mikania decora and Cremastosperma microcarpum, led to the characterization of one abundant diterpene, ent-pimara-8(14),15-dien-19-oic acid (1), three thymol derivatives, 10-acetoxy-8,9-dehydro-6-methoxythymol butyrate (2), 10-acetoxy-8,9-epoxy-6-methoxythymol isobutyrate (3), and acetylschizoginol (4), as well as one neolignan, (±)-trans-dehydrodiisoeugenol (5). Only the latter was isolated from C. microcarpum. These compounds exhibited significant cytotoxic activity against a panel of human tumor cell lines. Compounds 3 and 4 were also investigated for their in vitro antileishmanial and trypanocidal activity against Leishmania amazonensis axenic amastigotes and Trypanosoma cruzi trypomastigotes.

Key words

Mikania decora - Compositae - Cremastosperma microcarpum – Annonaceae - anticancer - antileishmania - trypanoside

References

  • 1 Altmann K H, Gertsch J. Anticancer drugs from nature-natural products as a unique source of new microtubule-stabilizing agents.  Nat Prod Rep. 2007;  24 327-357
    CrossrefPubMedSuche in Google Scholar
  • 2 Koehn F E, Carter G T. The evolving role of natural products in drug discovery.  Nat Rev Drug Discov. 2005;  4 206-220
    CrossrefPubMedSuche in Google Scholar
  • 3 Paterson I, Anderson E A. The renaissance of natural products as drug candidates.  Science. 2005;  310 451-453
    CrossrefPubMedSuche in Google Scholar
  • 4 Cordell G A, Colvard M D. Some thoughts on the future of ethnopharmacology.  J Ethnopharmacol. 2005;  100 5-14
    CrossrefPubMedSuche in Google Scholar
  • 5 Lewis W H, Lamas G, Vaisberg A, Corley D G, Sarasara C, Albán J, Apanú R, Castro R, Crandall C, Elvin-Lewis M, Fritz W, Hammond G, Klueh P, Millán B, Okunade A, Pacheco V, Tovar O, Yarupaitán G. Peruvian medicinal plant sources of new pharmaceuticals (International Cooperative Biodiversity Group-Peru).  Pharm Biol. 1999;  37 69-83
    CrossrefPubMedSuche in Google Scholar
  • 6 Aponte J C, Vaisberg A J, Rojas R, Sauvain M, Lewis W H, Lamas G, Sarasara C, Gilman R H, Hammond G B. A multipronged approach to the study of Peruvian ethnomedicinal plants: a legacy of the ICBG-Peru Project.  J Nat Prod. 2009;  72 524-526
    CrossrefPubMedSuche in Google Scholar
  • 7 Aponte J C, Yang H, Vaisberg A J, Castillo D, Málaga E, Verástegui M, Casson L K, Stivers N, Bates P J, Rojas R, Fernandez I, Lewis W H, Sarasara C, Sauvain M, Gilman R H, Hammond G B. Cytotoxic and anti-infective sesquiterpenes present in Plagiochila disticha (Plagiochilaceae) and Ambrosia peruviana (Asteraceae).  Planta Med. 2010;  76 705-707
    Thieme ConnectPubMedSuche in Google Scholar
  • 8 Aponte J C, Vaisberg A J, Rojas R, Caviedes L, Lewis W L, Lamas G, Sarasara C, Gilman R H, Hammond G B. Isolation of cytotoxic metabolites from targeted Peruvian Amazonian medicinal plants.  J Nat Prod. 2008;  71 102-105
    CrossrefPubMedSuche in Google Scholar
  • 9 Aponte J C, Estevez Y, Gilman R H, Lewis W H, Rojas R, Sauvain M, Vaisberg A J, Hammond G B. Anti-infective and cytotoxic compounds present in Blepharodon nitidum.  Planta Med. 2008;  74 407-410
    Thieme ConnectPubMedSuche in Google Scholar
  • 10 Catalán C A N, Cuenca M R, Hernández L R, Joseph-Nathan P. cis,cis-Germacranolides and melampolides from Mikania thapsoides.  J Nat Prod. 2003;  66 949-953
    CrossrefPubMedSuche in Google Scholar
  • 11 Krautmann M, de Riscala E C, Burgueno-Tapia E, Mora-Perez Catalán C A N, Joseph-Nathan P. C-15-Functionalized eudesmanolides from Mikania campanulata.  J Nat Prod. 2007;  70 1173-1179
    CrossrefPubMedSuche in Google Scholar
  • 12 Cava M P, Wakisaka K, Noguchi I, Edie D L. Phlebicine, a new biphenylbisbenzylisoquinoline alkaloid from Cremastosperma polyphlebum.  J Org Chem. 1974;  39 3588-3591
    CrossrefPubMedSuche in Google Scholar
  • 13 Mihashi S, Yanagisawa I, Tanaka O, Shibata S. Further study on the diterpenes of Aralia spp.  Tetrahedron Lett. 1969;  21 1683-1686
    PubMedSuche in Google Scholar
  • 14 Matsuo A, Uto S, Nakayama M, Hayashi S, Yamasaki K, Kasai R, Tanaka O. (−)-Thermarol, a new ent-pimarane-class diterpene diol from Jungermannia thermarum (Liverwort).  Tetrahedron Lett. 1976;  28 2451-2454
    PubMedSuche in Google Scholar
  • 15 González A G, Bermejo Barrera J, Estévez Rosas F, Yanes Hernandez A C, Espiñeira J, Josep-Nathan P. Thymol derivatives from Schizogyne glaberrima.  Phytochemistry. 1986;  25 2889-2891
    CrossrefPubMedSuche in Google Scholar
  • 16 Bohlmann F, Jakupovic J, Lonitz M. Über Inhaltsstoffe der Eupatorium-Gruppe.  Chem Ber. 1977;  110 301-314
    CrossrefPubMedSuche in Google Scholar
  • 17 González A G, Bermejo J, Estévez F, Yanes A C, Joseph-Nathan P. Derivados fenolicos del genero Schizogyne.  Rev Latinoam Quím. 1986;  17 54-56
    PubMedSuche in Google Scholar
  • 18 González A G, Bermejo Barrera J, Castaneda Acosta J, Estévez Rosas F. Anti-inflammatory activity of Schizogyne species.  Fitoterapia. 1988;  59 476-478
    PubMedSuche in Google Scholar
  • 19 Aiba C J, Correa R G C, Gottlieb O R. Natural occurrence of Erdtman's dehydrodiisoeugenol.  Phytochemistry. 1973;  12 1163-1164
    CrossrefPubMedSuche in Google Scholar
  • 20 Enriquez R G, Chaves M A. Phytochemical investigations of plant of the genus Aristolochia, 1. Isolation and NMR spectral characterization of eupomatenoid derivatives.  J Nat Prod. 1984;  47 896-899
    CrossrefPubMedSuche in Google Scholar
  • 21 Bortolomeazzi R, Verardo G, Liessi A, Callea A. Formation of dehydrodiisoeugenol and dehydrodieugenol from the reaction of isoeugenol and eugenol with DPPH radical and their role in the radical scavenging activity.  Food Chem. 2010;  118 256-265
    CrossrefPubMedSuche in Google Scholar
  • 22 Atsumi T, Fujisawa S, Satoh K, Sakagami H, Iwakura I, Uehai T, Sugita Y, Yokoe I. Cytotoxicity and radical intensity of eugenol, isoeugenol or related dimers.  Anticancer Res. 2000;  20 2519-2524
    PubMedSuche in Google Scholar
  • 23 Le Quesne P W, Larrahondo J E, Raffauf R F. Antitumor plants. X. Constituents of Nectandra rigida.  J Nat Prod. 1980;  43 353-359
    CrossrefPubMedSuche in Google Scholar
  • 24 Meyer I, Koch O, Krutmann J. Use of dihydrodehydrodiisoeugenol as skin care preparations. PCT Int Appl 2010; WO 2010070152 A2 20100624. 

Univ.-Prof. Dr. Gerald B. Hammond

Department of Chemistry
University of Louisville

2308 S. Brook St

Louisville, KY 40292

USA

Telefon: +1 50 28 52 59 98

Fax: +1 50 28 52 38 99

eMail: gb.hammond@louisville.edu

    www.thieme-connect.de/ejournals/toc/plantamedica