Volatile Oils of Illicium floridanum and I. parviflorum (Illiciaceae) of the Southeastern UnitedStates and Their Potential Economic UtilizationAuthor(s): Arthur O. Tucker and Michael J. MaciarelloReviewed work(s):Source: Economic Botany, Vol. 53, No. 4 (Oct. - Dec., 1999), pp. 435-438Published by: Springer on behalf of New York Botanical Garden PressStable URL: http://www.jstor.org/stable/4256227 .Accessed: 16/12/2011 11:02

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VOLATILE OILS OF ILLICIUM FLORIDANUM AND I. PARVIFLORUM (ILLICIACEAE) OF THE SOUTHEASTERN UNITED STATES AND THEIR POTENTIAL ECONOMIC UTILIZATION1

ARTHUR 0. TUCKER AND MICHAEL J. MACIARELLO

Arthur 0. Tucker and Michael J. Maciarello (Department of Agriculture and Natural Re- sources, Delaware State University, Dover, DE 19901-2277). VOLATILE OILS OF ILLICIUM FLOR-

IDANUM AND I. PARVIFLORUM (ILLICIACEAE) OF THE SOUTHEASTERN UNITED STATES AND THEIR POTENTIAL ECONOMIC urILIZATION. Economic Botany 53(4):435-438, 1999. The essential oilfrom leaves and branches of cultivated Illicium floridanum is dominated by 22.53 ? 2.23% linalool and 13.93 ? 1.61% linalyl acetate. The essential oil from leaves and branches of cultivated I. parviflorum is dominated by 68.14 ? 0.88% safrole, 13.18 ? 1.01% linalool, and 11.89 ? 0.87% methyl eugenol. Besides the Lauraceae and Piperaceae, the Illiciaceae is another natural source of safrole.

ACEITES VOLATILES DE ILLICIUM FLORIDANUMY L PARVIFLORUM (ILLICIACEAE) DE LOS ESTADOS UNIDOS MERIDIONAL Y LOS USOS ECONOMICOS POTENTCIALES. El aceite esencial de las hojas y las ramas del Illicium floridanum cultivado esta dominado por linalool (22,53 + 2,23%) y el acetato de linalyl. El aceite esencial de las hojas y las ramas de I. parviflorum estd dominado por safrole (68,14 + 0,88%), linalool (13,18 + 1,01%), y el metilo de eugenol (11,89 + 0,87%). Ademas del las familias Lauraceae y Piperaceae, la familia Illiciaceae es otra fuente del safrole.

Key Words: Illicium floridanum; I. Parviflorum; linalool; linalyl acetate; safrole; methyl eu- genol.

The genus Illicium includes about 42 species in southeastern Asia and southeastern North America (Smith 1947). In North America, Flor- ida anise-tree, I. floridanum Ellis, occurs along the coastal plain of northwestern Florida to cen- tral Alabama, southern Mississippi, and south- eastern Louisiana with a disjunct population in northeastern Mexico (Cullen and Howe 1989; Harper 1928; Little 1979). Florida anise-tree has one cultivar, 'Halley's Comet,' with deep red flowers and long petals; one botanical fonna, f. album F G. Mey. & Mazzeo, with white flowers (and a clonal selection of f. album named 'Semmes'); and an unnamed pink-flowered cul- tivar (Crown 1993; Isaacson 1989; Meyer and Mazzeo 1992).

Yellow anise-tree, I. parviflorum Michx. ex Vent., is rare and local in central Florida (Kral 1983; Little 1979). Yellow anise-tree is also cul- tivated (Cullen and Howe 1989), and Uphof (1968) even reports that the "Bark is source of

'Received 16 October 1998; accepted 13 July 1999.

an oil, known as Anise Oil." A chemical anal- ysis of yellow anise-tree found over 90% safrole (Foote 1938).

MATERIALS AND METHODS

Plants acquired from commercial U.S. nurs- eries were raised on Sassafras sandy loam, pH 5.5, in Camden, Delaware. The top 0.5 m leafy branches were harvested on October 1995. Vouchers were filed with the Claude E. Phillips Herbarium, Delaware State University (DOV). Oils were distilled with a neo-Clevenger of Mo- ritz after Kaiser and Lang with the modification of Hefendehl (Kaiser and Lang 1951; von Rud- loff 1969). Mass spectra were recorded with a 5970 Hewlett-Packard Mass Selective detector coupled to a HP 5890 GC using a HP 50 m X 0.2 mm fused silica column coated with 0.33 mm FFAP (crosslinked). The GC was operated under the following conditions: injector temp.: 250?C; oven temp. programmed: 60?C held for one min to 1 15?C at 2.5?C per min, then to 210?C at L.0?C per min and held for 30 min;

Economic Botany 53(4) pp. 435-438. 1999 ? 1999 by The New York Botanical Garden Press, Bronx, NY 10458-5126 U.S.A.

436 ECONOMIC BOTANY [VOL. 53

TABLE 1. MEAN PERCENTAGE AND STANDARD DEVIATIONS OF COMPOUNDS IN ESSENTIAL OILS FROM

LEAVES AND BRANCHES OF ILLICIUM FLORIDANUM AND L PARVIFLORUM (MEAN ? SD%, N = 3, N.D. =

NOT DETECTED).

Compound & oil yield L. floridanum L parviflorum

Oil yield 0.07 + 0.01 0.34 ? 0.26 Tricyclene 0.04 + 0.05 n.d. o-pinene 1.67 + 0.62 n.d. Camphene 0.84 + 0.89 n.d. f-pinene 0.49 ? 0.24 n.d. Sabinene n.d. 0.03 + 0.02 Myrcene 5.81 ? 0.81 0.16 + 0.07 cx-terpinene 4.14 ? 3.21 n.d. Limonene 5.83 + 0.56 0.18 + 0.22 1,8-cineole n.d. 0.32 ? 0.07 3-phellandrene 0.20 n.d.

(Z)-,-ocimene 0.23 + 0.40 0.14 ? 0.08 y-terpinene 5.32 + 3.73 <0.01 + 0.01 p-cymene 3.33 + 0.46 <0.01 + 0.01 Terpinolene 0.83 ? 0.73 0.09 + 0.02 Linalool 22.53 + 2.33 13.16 + 1.01 Linalyl acetate 13.93 + 1.61 n.d. Bornyl acetate 7.64 ? 0.27 n.d. 3-elemene 0.31 ? 0.29 n.d.

Terpinene-4-ol 1.26 ? 0.03 n.d. ,B-caryophyllene 2.07 + 0.92 1.95 ? 0.64 Terpinen-1 -ol 0.14 + 0.12 n.d. (E)-P-farnesene 1.35 + 0.56 n.d. Estragole n.d. 0.02 ? 0.02 x-humulene 0.76 ? 0.46 0.04 + 0.06 ox-amorphene n.d. 0.01 + 0.02 ox-terpineol 3.87 ? 0.74 0.18 + 0.16 -y-muurolene n.d. <0.01 + 0.01 Germacrene D 0.03 + 0.06 0.06 ? 0.05 Neryl acetate 0.56 + 0.49 n.d. Piperitone 3.01 + 0.53 n.d. Geranyl acetate 2.00 + 0.24 0.09 + 0.03 b-cadinene 0.17 ? 0.30 0.09 + 0.05 y-cadinene n.d. 0.02 + 0.03 Nerol 0.66 + 0.17 n.d. ,B-phenylethyl acetate 1.04 + 0.16 n.d. Geraniol 1.16 ? 0.27 n.d. Safrole n.d. 68.14 ? 0.88 Caryophyllene oxide 0.03 ? 0.05 n.d. Methyl eugenol n.d. 11.89 ? 0.87 (Z)-nerolidol 0.50 ? 0.52 n.d. (E)-isosafrole n.d. 0.02 ? <0.01 T-cadinol 0.05 ? 0.08 n.d. Eugenol n.d. 2.16 ? 0.12 (E)-methyl isoeugenol 0.04 ? 0.07 n.d. Elemicin n.d. 0.66 ? 0.07

1999] TUCKER & MACIARELLO: VOLATILE OILS, ILLICIUM 437

injection size: 1 pL (-50% solution in spec- troscopy grade n-pentane) split 1:10. The MSD El was operated under the following conditions: electron impact source 70 eV, 250?C. Identifi- cations were made by Kovats Indices and library searches of our volatile oil library supplemented with those of NBS, NIST, and Wiley.

RESULTS AND CONCLUSIONS The essential oils are presented in Table 1.

The essential oil from leaves and branches of Illicium floridanum is dominated by 22.53 ? 2.23% linalool and 13.93 + 1.61% linalyl ace- tate, providing a spicy lavender-like odor. The essential oil from leaves and branches of I. par- viflorum is dominated by 68.14 ? 0.88% safrole, 13.18 + 1.01% linalool, and 11.89 ? 0.87% methyl eugenol, providing a spicy sassafras-like odor.

Within the genus Illicium, 1. floridanum and I. parviflorum are representatives of two clearly distinct sections [sect. Illicium (Badiana) and sect. Cymbostemon, respectively] (Smith 1947). Also, the former has 2n = 26, while the latter has 2n = 28 (Stone and Freeman 1968). In ad- dition, we note that both species may be distin- guished by their essential oils and the presence or absence of linalyl acetate, methyl eugenol, and/or safrole.

At first glance, the claim of Uphof (1968) that the rare and endemic I. parviflorum was a source of "anise oil" might indicate confusion with the Chinese star anise, I. verum Hook., a species whose fruits yield an essential oil rich in 71.2- 91.8% trans-anethole (Bernard et al. 1989; Chen et al. 1986; Cu, Perineau and Goepfert 1990; Li et al. 1985; Sun 1990). However, anethole and safrole are similar in chemical structure and odor, and the presence of 68.14 ? 0.88% safrole in I. parviflorum lends credence to this claim. Safrole, also the chief constituent of the essential oil from sassafras roots [Sassafras albidum (Nutt.) Nees], is a hepatocarcinogen upon me- tabolism in humans and its consumption is to be avoided (Tucker and Maciarello 1998; Tucker, Maciarello, and Broderick 1994). However, saf- role is used commercially to synthesize heliotro- pine and piperonyl butoxide (as well as MDMA, methylenedioxymethamphetamine, an illegal "designer" drug). Outside of Sassafras albidum, the primary commercial source of safrole used to be the Brazilian sassafras, Ocotea pretiosa (Nees) Mez. In 1992 a moratorium on the har-

vesting of Brazilian sassafras trees in Brazil steered buyers to China in search of Cinnamo- mum species rich in safrole. Then, in 1994 China placed restrictions on the cutting of its sassafras trees, and in 1997 the Vietnamese government banned the exportation of sassafras oils. Tam et al. (1998) have also reported safrole in trunk- and root-bark oils (60.2 and 77.7%, respective- ly) of an unidentified species of Illicium (similar to I. griffithii Hook. f. et Thomson) from Ninh Binh Province of North Vietnam. Thus, while commercial sources of safrole have traditionally been derived from species in the Lauraceae and Piperaceae, the Illiciaceae is another family to explore for this raw material (De Assis Brasil e Silva et al. 1979; Floreno 1995, 1997; French 1995; Gallagher 1994; Lawrence 1992; Maia et al. 1993; Mollan 1961a,b,c; Molleken and Bauer 1980; Santos 1992).

ACKNOWLEDGMENTS Analytical research was supported by the State of Delaware and the

Cooperative State Research, Education, and Extension Service (#801-15- OlC).

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