Arthur O. Tucker,* Michael J. Maciarello and Rebecca C. Brown,. Department of Agriculture and Natural Resources, Delaware State University, Dover, DE ...
B. microphylla
Essential Oils from the Oleo-gum-resins of Elephant Tree or Torote (Bursera microphylla A. Gray, Burseraceae) from Arizona Arthur O. Tucker,* Michael J. Maciarello and Rebecca C. Brown, Department of Agriculture and Natural Resources, Delaware State University, Dover, DE 19901-2277
Leslie R. Landrum and Daryl Lafferty, School of Life Sciences, Arizona State University, Tempe, AZ 85287-4501
Abstract The essential oils isolated from the oleo-gum-resins of elephant tree or torote (Bursera microphylla A. Gray, Burseraceae) collected in Arizona were analyzed by GC and GC/MS. The major components of the oil were bcaryophyllene (35.7–72.9%) and myrcene (0.4–14.4%). Key Word Index Bursera microphylla, Burseraceae, essential oil composition, b-caryophyllene, myrcene.
Introduction The genus Bursera includes approximately 100 species, ranging from the southwestern United States to Peru. Bursera microphylla, variously called elephant tree, torote, torote blanco, copal, or cuajiote colorado, is native to the Sonoran Desert, from southwestern Arizona to southeastern California, western Mexican mainland and Baja California (1–4). One previous publication examined the monoterpene composition of dimethyl ether extracts of exudates from B. microphylla from Mexico and found a-pinene (1.0–61.3%), a-pinene (1.0–68.9%), phellandrene (trace–78.6%) and cineole (trace–16.8% ) (5).
Experimental Plant material: Four collections were made from South Mountain Park, Maricopa Co., Arizona, Landrum & Lafferty #11151 (near southwest corner of park near end of Pecos Road, 404 m, Oct 8, 2006), #11152 (near southwest corner of park near end of Pecos Road, 413 m, Oct 8, 2006), #11153 (above ruin in southwest portion of Park, 488 m, Oct 15, 2006), and #11154 (above ruin in southwest portion of Park, 488 m, Oct 8, 2006). Vouchers of the plants are filed at the Herbarium of Arizona State University (ASU) and the Claude E. Phillips Herbarium (DOV); vouchers of the oleo-gum-resins are also filed at DOV. Oil isolation: Oleo-gum-resins were distilled over Whatman #1 filter paper with a neo-Clevenger-type apparatus of Moritz after Kaiser and Lang with the modification of He-
fendehl (6,7). GC/MS/FID: Mass spectra were recorded with an Agilent Technologies 5973 Mass Selective Detector coupled to an Agilent Technologies 6890N GC equipped with FID and dual injectors. Chromatography for MS and FID analysis was done simultaneously with separate columns in parallel under the same oven parameters: temperature was programmed 60°C for 1 min to 115°C at 2.0°C/min, then to 210°C at 0.9°C/min and held for 75 min, the total run time is 209 min. The columns were Agilent 50 m x 0.2 mm fused silica column coated with 0.33 m thick FFAP (crosslinked) film. The temperature of the FID injector was 250°C, with a split ratio of 50/1, with a He carrier and sample size of 5 mL. The quantitative data were obtained electronically from FID area percents without the use of correction factors. The injection temperature of the MSD was 250°C, with a split ratio of 100/1, with a He carrier and sample size of 1 mL. MSD source temperature was 230°C, scanning masses between 44 and 550 with a scan rate of 2.9. Identifications were from our proprietary MS library and Retention Indices.
Results and Discussion The isolated oil from the oleo-gum-resins of torote (Bursera microphylla A. Gray) collected in Arizona contains 35.7–72.9% β-caryophyllene and 0.4–14.4% myrcene. This is the first report of the full oil from an oleo-gum-resin of a Herbarium-vouchered Bursera species. Case et al. (8) did identify a-copaene (14.5%) Received: March 2007
*Address for correspondence
Revised: April 2007 1041-2905/09/0001-057$14.00/0—© 2009 Allured Business Media Vol. 21, January/February 2009
Accepted: June 2007 Journal of Essential Oil Research/57
Tucker et al.
Table I. Percentage composition of the oils from the oleo-gum-resins of Bursera microphylla collected in Arizona Component & Oil Yield
RI*
Oil Yield (%) α-pinene β-pinene sabinene δ-3-carene myrcene α-phellandrene α-terpinene limonene p-cymene terpinolene 6-methyl-5-hepten-2-one α-cubebene α-copaene β-bourbonene β-elemene β-caryophyllene α-humulene δ-cadinene γ-cadinene cis-calamenene α-calacorene caryophyllene oxide octanoic acid cembrene neocembrene A caryophylla-2(12),6-dien-5-ol
1070 1119 1130 1157 1165 1174 1190 1209 1281 1292 1344 1425 1497 1523 1603 1615 1683 1766 1770 1843 1926 1997 2063 2194 2254 2382
#11151
Percentage
#11152
#11153
#11154
4.7
2.1
0.2
1.1
n.d.** n.d. n.d. 7.5 14.4 2.0 0.2 0.4 1.6 n.d. 1.0 n.d. 0.3 0.2 n.d. 35.7 2.1 0.9 0.2 0.3 0.4 5.5 1.0 n.d. 2.4 0.4
n.d. n.d. n.d. 0.1 0.4 n.d. n.d. < 0.1 0.1 n.d. 0.5 n.d. n.d. n.d. n.d. 72.9 3.9 < 0.1 n.d. n.d. 0.1 8.8 0.2 1.2 0.7 0.7
0.2 0.3 n.d. 8.3 3.9 0.9 0.1 0.4 0.2 0.8 n.d. 0.1 n.d. n.d. 0.1 51.3 3.0 0.1 n.d. n.d. n.d. 4.8 0.1 1.7 1.4 0.1
n.d. 0.6 0.1 0.1 8.2 0.1 n.d. 0.1 0.2 n.d. 0.2 0.1 < 0.1 < 0.1 n.d. 70.8 4.0 < 0.1 < 0.1 n.d. < 0.1 6.5 0.1 0.3 0.3 0.6
*RI = Retention Indices on an FFAP column; **n.d. = not detected.
and germacrene (13.8%) in commercial copal blanco, postulated to be from B. bipinnata (Sessé et Moc. ex DC.) Engl., but no Herbarium voucher could be filed. Bursera penicillata (DC.) Engl. (B. delpechiana Poiss. ex Engl.), linaloe-tree, native to Mexico but raised in India, has been reported to contain linalool (47.7%) and linalyl acetate (40.8%) in the leaf oil (9). The oil from the fruits of B. simaruba (L.) Sarg. from Costa Rica was found to contain 26.2% a-terpinene, g-terpinene (20.4%) and a-pinene (18.2%) (10). The diethyl ether extract from the wood of B. graveolens (Kunth) Triana et Planch. from Mexico has agarofuran eudesmanes and other rare mono- and sesquiterpenoids (11–13). The oil from the leaves and fruits of B. tonkinensis Guill. from Vietnam has a-phellandrene (70.1%) (14). Acknowledgments
Analytical research was supported by the State of Delaware and the Cooperative State Research, Education, and Extension Service (USDA-CSREES, Project No: DELX-0020-04-1, ACCESSION NO: 0201162). References 1. J.X. Becerra and D.L. Venable, Nuclear Ribosomal DNA Phylogeny and its Implications for Evolutionary Trends in Mexican Bursera (Burseraceae). Amer. J. Bot., 86, 1047–1057 (1999). 2. D. Daley, Notes on Bursera in South America, Including a New Species. Studies in Neotropical Burseraceae VII. Brittonia, 45, 240–246 (1993).
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3. J. Rzedowsski and H. Kruse, Algunas Tendencias Evolutivas en Bursera (Burseraceae). Taxon, 28, 103–116 (1979). 4. P.C. Standley, Trees and Shrubs of Mexico. Contr. U. S. Natl. Herb., 23, 1–1721 (1920–1926). 5. H.A. Mooney and W.A. Emboden, The Relationships of Terpene Composition, Morphology, and Distribution of Populations of Bursera microphylla (Burseraceae). Brittonia, 20, 44–51 (1968). 6. H. Kaiser and W. Lang, Ueber die Bestimmung des ätherischen Oels in Drogen. Deutsch. Apotheker-Z./Süddeutsch. Apotheker-Z., 91, 163–166 (1951). 7. E. von Rudloff, Scope and Limitations of Gas Chromatography of Terpenes in Chemosystematic Studies. Rec. Adv. Phytochem., 2, 127–162 (1969). 8. R.J. Case, A.O. Tucker, M.J. Maciarello and K.A. Wheeler, Chemistry and Ethnobotany of Commercial Incense Copals, Copal Blanco, Copal Oro, and Copal Negro, of North America. Econ. Bot., 57, 189–202 (2003). 9. K. Narayana and S. Dutt, Mysore Linaloe Leaf Oil. Indian Soap J., 10, 47–50 (1945). 10. K. Rosales and J.F. Cicció, The Volatile Oil of the Fruits of Bursera simaruba (L.) Sarg. (Burseraceae) from Costa Rica. Ing. Ci. Quim., 20, 60–61 (2002). 11. C. Yukawa, H. Iwabuchi, T. Kamikawa, S. Kimemush and A. Sawabe, Terpenoids of the Volatile Oil of Bursera graveolens. Flav. Fragr. J., 19, 565–570. 12. C. Yukawa, H. Iwabuchi, S. Kimemushi and A. Sawabe, Mono- and Sesquiterpeniods of the Volatile Oil of Bursera graveolens. Flav. Fragr. J., 20, 653–658. 13. C. Yukawa, Y. Imayoshi, H. Iwabuchi, S. Komemushi and A. Sawabe, Chemical Composition of Three Extracts of Bursera graveolens. Flav. Fragr. J., 21, 234–238. 14. Tran Minh Hoi, Tran Huy Thai, D. Lesueur, A. Bighelli and J. Casanova, Volatile Components of Bursera tokinensis Guill. J. Essent. Oil Bear. Plants, 7, 228–231 (2004).
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