A PHYTOCHEMICAL SURVEY OF 21 SPECIES OF THE GENUS BURSERA (BURSERACEAE) NATIVES OF MEXICO Xorge Alejandro Dominguez, Jerzy Rzedowki*, Magdalena Gutiérrez, Maria Ester Gomez. Departamento de Quimica, Escuela de Ciencias, Instituto Tecnolégico de Monterrey. Monterrey, N. L. México Recibido, Mayo 8 de 1972 SUMMARY. A phytochemical survey of twenty one mexican species of Bursera was under- taken, Besides chemical methods, thin layer chromatographic techniques were used to confirm the chemical information and detect the number on interesting compounds. The results are reported in a table, RESUMEN. Se hizo el estudio de veintidin especies mexicanas de Bursera. Ademés de las pruebas quimicas usuales, se usaron técnicas de cromatografia en capa delgada para confir- mar los resultados previos. Los datos se resumen en una tabla, The Burseraceae is a family of about 20 generat. The family is distinguished from the Rutaceae and Simaroubaceae by the presence of resin ducts in the bark. Some members of the family have some value as source of gums and resins as frankincense and myrrh. In Mexico, by steam distillation of the wood of old and damaged trees of Bursera species, particularly Bursera delpechiana, the linaloe wood oil is obtained?. The genus Bursera, that has about 60 species, is native of tropical America, largely and primarily Mexican and the history of the evolution of this genus is closely related to the vegetation of western Mexico.3, Many Burseraceae have been used with medicinal purposes, some of them in the treatment of cancerous tumors, particularly seven species of Bursera*. Several triter- penes have been obtained from this genus. From B. graveolens® a tricarboxylic acid was isolated, which suggests a biochemical link with the bitter compounds of the Rutaceae, From the resin of B. * Departamento de Boténica, Escuela Nacional de Ciencias Bidlogicas Instituto Politecnico Nacional. México, D.F. bipinnata, B. galeotiana, B. gorullensis and B. sessiliflora, «-amyrin and epilupeol were obtained®. Besides the known linalol, linaly! acetate and other terpenoids from the linaloe wood oil, the steam distillation of B. microphylla has produced an oil with phellandran and tetrahydrocumin acid? and from the chloroformic extract dioxypodophylotoxin. The genus Bursera has presented some taxonomical problems, because the flowering material of many species is hardly known, so the botanists have depended chiefly upon leaf characters This work had the aim to learn more about the principal groups of possible physiological active compounds present in the mexican Bursera species and also to obtain information of some value for the chemotaxonomy of this genus. To accomplish our goal, the plant material collected in the western states of southern Mexico, Michoacdn, Guerrero, Jalisco, and Baja California, were identified by one of us (J.R.) The chemical survey was a combination of clasical spot test for alkaloids, saponins tannins and flavonoids and thin layer chromatographic methods which helped to confirm the chemical results and gave an idea of the number ofcompounds and on basis of their colors, RE are compared with known chemicals, which maybe are present in the plant material? The results are summarized in Table I. Experimental, Extraction procedures.— The — aerial part of the Bursera species were separately dried at 60°C powderized and a 100 g. sample was placed in a Soxhlet apparatus. Succesive 6 hours extractions with petroleum ether (b. p. 30-60 °C), ethanol and water gave solutions from which the solvents were removed by distillation under reduced pressure. The residues were weighed and a portion of the residue was taken in a convenient solvent (p. eth., ethanol or water) for further tests. Cromatographic methods.— Thin layer plates were prepared with silica gel G (Merck) (30 g) and water (60 g) aplied with a Desaga device. The solvents were: (A) benzene/n— heptane/ethanol (50:50:5) v/v (B) n-butanol/acetic acid/water (75:10:15) v/v. Visualization.—(UV) Ultraviolet light (260-400 nm); 20% antimony trichloride. in chloroform: iodine vapor; modified Dragendroff reagent!°. Chemical tests~ On a spot plate three drops of the ethanolic or water extract were mixed with one drop of 1N hydrochloric acid and one drop of the alkaloid detecting reagent was added, and the formation of — precipitate was taken as a positive result. The reagents used were Mayer’s (potassium mercuric iodide), Wagner’s (iodine potassium iodide), Dragendorff (bismuth potasssium iodide) and silicotungstic acid. Tannins were detected with one drop of a 10% ferric chloride solution added to 3 drops of the ethanolic or water extract. For saponins, about one mililiter of the ethanolic or water extract were mixed 109 with one mililiter of water and the mixture was shaken one minute. A froth test was positive when the froth has a characteristic honeycomb structure and was stable for twenty minutes. A flavonoid test was positive when one mililiter of the ethanolic or water extract gave an organe to red froth when mixed with 30-50 mg. of powderized magnesium and one ml. of 6N hydrochloric acid. The presence of carbohydrates was detected boiling on a steam bath 2 ml. of ethanolic or water extracts with 2 ml. of Fehling’s mixture. The anthrone sulfuric acid solution was added to the extracts as a confirmation text. Discussion of Results, — Most of the Bursera species were found to contain fluorescent compounds soluble in pe- troleum ether and in ethanol, also se- veral compounds reacting with antimony trichloride, wich on basis of their violet or grey color are indicative of the presence of sterols and di or triterpenoids. B-sitosterol was observed in B. fagoroides,— B. submoniliformis, B. lancifolia, B. morelensis and B. grandifolia. Several ethanolic extracts (from B. grandifolia, B. cuneata, B. var. elongata B. fagaroide var, purpusii) gave positive: all the alkaloidal tests, but the t.l.c. with modified Dragendorff as cromogenic agent observed 29 hs. after spraying, failed to detect alkaloids. Also the water extracts gave negative results. False po’ alkaloid reactions had been reported by Farnsworth1© to be due to compounds having conjugated carbonyl or lactone functions, which may be present on those Bursera sp. extracts. All the ethanolic and water extracts gave positive the tests for tannins and carbohydrates and negative the tests for detecting saponins and flavonoids. The negative flavonoids reaction may be due to the absence of flowers on all the plant material studied.110 sygorpueseig “G ‘xousey ‘A ‘rece SR (aeraxe or poueyse “HOI ‘ay8zT oqoraezatn “GA ‘30er9Ke royz0 unsqoseg “Fa 18830 Hor rt 2 eae tt T 2.0 Ged 9: GE z €0'c (WDE) BsTeoxe “33e “E OS SE - o> RG = eS + One Fe PD HORP Ee enettes zen CeowT) Troured ~g re eo or Bee ee Ge eS) Ong eet 06% YE 1 try “C3FTeO elegy rreqey |g tie eh 5 Sse sae ft ee eee ee Thiel Ser ORE etre z 4e°% — (FFTPO"a) PUETSTPUTY “gE Rog gt - Sobre FE et t+ Claes Se Tiel oe It STsUSTIe “Gg ee hr rete ee ee a) ah a Care e Taba atest € rz ‘Fayouog “gE Hest - Shek oe Fo oN Ee - Oe Vee SREEME gn oe oz"t FOTOEG “E Hott POT HH Ht Ca a tae s. 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