REVISTA BOLIVIANA DE QUÍMICA The Bolivian Journal Of Chemistry VOLUMEN 19, No.1 - 2002 FIRST BIOGUIDED PHYTOCHEMICAL APPROACH TO CAVANILLESIA AFF. HYLOGEITON José Antonio Bravo; a * Catherine Lavaud; b Geneviève Bourdy; c Alberto Giménez, d Michel Sauvain c a Laboratorio de Química de Productos Naturales, Instituto de Investigaciones Químicas-IRD, Universidad Mayor de San Andrés, CP 303, La Paz Bolivia; b Laboratoire de Pharmacognosie UMR 6013 CNRS Bâtiment 18, BP 1039, 51097 Reims, Cedes 2, France; c Institut de Recherche pour le Développement (ex-ORSTOM), 213 rue Lafayette, 75480 Paris cedex 10, France; d Instituto de Investigaciones Fármaco Bioquímicas, Universidad Mayor de San Andrés, CP 20606, La Paz, Bolivia *Corresponding author: jbravo@red-sol.net Key Word Index: Cavanillesia aff. hylogeiton; Bombacaceae; stem-bark; sterols; sterone; glycoside; fatty acids; glycerol derivatives; Plasmodium falciparum RESUMEN En nuestro programa de estudios de especies vegetales bolivianas reportadas por su uso etnofarmacológico contra síntomas de enfermedades tropicales ampliamente expandidas en Bolivia como el paludismo, la leishmaniasis o la enfermedad de Chagas, hemos recolectado plantas expresamente descritas contra tales enfermedades. También de las mismas farmacopeas se colectaron plantas descritas para otros usos como Cavanillesia aff. hylogeiton; Bombacaceae, usada por los Tacanas para lograr el aumento de peso en humanos y animales y usada también como contraceptivo. El estudio de la planta permitió la descripción de compuestos grasos comunes que no manifestaron sin embargo ninguna actividad antipalúdica. Los compuestos fueron identificados principalmente mediante el uso de técnicas de RMN. Este constituye el primer reporte químico de la especie. ABSTRACT Among the minor bolivian ethnic groups that we have studied for their tropical illnesses pharmacopoeia, like malaria, leishmaniasis or Chagas’ disease, we harvested medicinal plants reported for their antiparasitic activity as well as other species reported for other pharmacological applications. Cavanillesia aff. hylogeiton; Bombacaceae, is a plant reported by the Tacanas ethnic group for its gaining weight induction properties in animals and humans as well as for its contraceptive use. 1 The bioguided separation of the extract afforded fatty common compounds like fatty acids and triglyceride mixtures, a triterpen, steroids and a steroid glycoside. None of these substances manifested any antimalarial activity. This constitutes the first chemical survey of the species and also a first evaluation of its biological activities. Compounds were structurally described mainly by the use of NMR. INTRODUCTION The tropical genus Cavanillesia 2 is composed of three species. Cavanillesia aff. hylogeiton 2 is a 25 m high tree, natural from ecological stages from 250 to 850 m over sea level of the amazonic rain forests. The phytochemical study of genus Cavanillesia, has not been undertaken profoundly enough yet. The chemistry of the family Bombacaceae 3,4,5 is actually described in many genus and it can be characterized by the presence of fatty products, mainly fatty acids like palmitic, oleic and linoleic acid that have been found in Ceiba pentandra and Bombax sessile. As another example we can also mention sterculic and malvalic acid extracted from Adansonia digitata, Bombax oleagineum and Ceiba pentandra and C. Acuminata as well. CH 2 CH 2 CH 3 (CH 2 ) 7 -C = C-(CH 2 ) 6 -COOH CH 3 (CH 2 ) 7 -C = C-(CH 2 ) 7 -COOH Sterculic and malvalic acids Glycolipids and polyphenols like quercetin, kaempferol and caffeic acid have been reported in Ceiba pentandra. Quinones and naphtoquinones are present in Bombax malabaricum. 3 RESULTS AND DISCUSSION The quest of the antimalarial responsible active principles in the initial active extract and subsequent chromatographic fractions from C. aff. Hylogeiton, guided us to the isolation and identification of a terpenoid and three sterols besides the obtention of mixtures of lipid substances. The dried and then pulverized stem bark of C. aff hylogeiton was macerated in a 30% hydroethanolic mixture. After elimination of alcohol, the extract was tested against chloroquine- resistant and sensitive strains of Plasmodium falciparum with an activity index of an IC 50 of 1 µg/ml. The extract was then diluted in water and mixed with methylene chloride. The organic layer after solvent elimination demonstrated to maintain the same activity index. The methylene 18