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This article was downloaded by: [Nipissing University]On: 09 October 2014, At: 04:57Publisher: Taylor & FrancisInforma Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House,37-41 Mortimer Street, London W1T 3JH, UK
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Abaco Bush Medicine: Chemical Composition of theEssential Oils of Four Aromatic Medicinal Plants fromAbaco Island, BahamasJennifer M. Schmidt a , Joseph A. Noletto a , Bernhard Vogler a & William N. Setzer aa Department of Chemistry , University of Alabama in Huntsville , Huntsville, ALPublished online: 04 Oct 2008.
To cite this article: Jennifer M. Schmidt , Joseph A. Noletto , Bernhard Vogler & William N. Setzer (2007) Abaco BushMedicine: Chemical Composition of the Essential Oils of Four Aromatic Medicinal Plants from Abaco Island, Bahamas, Journalof Herbs, Spices & Medicinal Plants, 12:3, 43-65, DOI: 10.1300/J044v12n03_04
To link to this article: http://dx.doi.org/10.1300/J044v12n03_04
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Abaco Bush Medicine:Chemical Composition of the Essential Oils
of Four Aromatic Medicinal Plantsfrom Abaco Island, Bahamas
Jennifer M. SchmidtJoseph A. NolettoBernhard Vogler
William N. Setzer
ABSTRACT. The leaf essential oils of four aromatic plants used in tradi-tional “bush” medicine on Abaco Island, Bahamas, were obtained byhydrodistillation and analyzed by GC-MS. The most abundant compo-nents of Amyris elemifera (Rutaceae) were limonene (45.0%), linalool(20.8%), �-caryophyllene (5.6%), 3-hexadecanone (5.3%), caryo-phyllene oxide (3.9%), and �-sesquiphellandrene (3.6%). Eugeniaaxillaris (Myrtaceae) leaf oil was largely composed of �-pinene (15.5%),
Jennifer M. Schmidt, Joseph A. Noletto, Bernhard Vogler, and William N. Setzerare affiliated with Department of Chemistry, University of Alabama in Huntsville,Huntsville, AL.
Address correspondence to: William N. Setzer, Department of Chemistry, Universityof Alabama in Huntsville, Huntsville, AL 35899 (E-mail: [email protected]).
The authors thank Dr. Michael A. Vincent (W. S. Turrell Herbarium, Miami Uni-versity, Oxford, Ohio) for plant identification; Rebecca Bifulco, Mary Setzer, RobertWerka, and Julie Collier for help with plant collection on Abaco; Amelia Boehme,Angela Rea-Ramsey, Benjamin Plummer, and Anita Bansal for assistance with the bio-logical assays; and Lauren Eiter for collecting GC-MS data. The authors would like toacknowledge the bush herbalist, Ms. Dolly Davis, for the plants and their uses; and For-est Heights Academy, Marsh Harbour, for allowing us the use of their laboratory facili-ties on Abaco.
The support for this work was provided by a generous grant from an anonymous pri-vate donor.
Received August 8, 2005.
Journal of Herbs, Spices & Medicinal Plants, Vol. 12(3) 2006Available online at http://jhsmp.haworthpress.com
© 2006 by The Haworth Press, Inc. All rights reserved.doi:10.1300/J044v12n03_04 43
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dihydroagarofuran (9.2%), �-caryophyllene (8.8%), �-humulene (6.9%),1,8-cineole (6.6%), and germacrene D (6.2%). The leaf essential oil ofLantana involucrata (Verbenaceae) was made up largely of germacrene D(21.1%), �-humulene (15.2%), and �-caryophyllene (13.7%). The mostabundant components of Myrica cerifera (Myricaceae) were 1,8-cineole(30.7%), �-terpineol (14.2%), 4-terpineol (9.0%), and �-caryophyllene(6.4%). The antimicrobial activity against Bacillus cereus, Pseudomonasaeruginosa, Escherichia coli, Pseudomonas aeruginosa, Candidaalbicans, and Aspergillus niger, and the in vitro cytotoxicity of the oils onMDA-MB-231, MCF7, Hs 578T, Hep G2, and PC-3 human tumor cellshave also been examined. The reported biological activities of the majorconstituents of A. elemifera leaf oil are consistent with the ethnopharmaco-logical uses of the plant in the Bahamas to reduce fever, treat symptoms offlu, treat sores, and wounds, and its use as a general tonic and bath. L.involucrata leaf oil shows slight antibacterial activity against B. cereusand Staph. aureus and is weakly cytotoxic against our panel of cell lines.The major components in the leaf oil and slight antimicrobial activity areconsistent with the ethnobotanical use of L. involucrata to treat itchingskin. Neither E. axillaris nor M. cerifera leaf essential oils are appreciablyantimicrobial or cytotoxic. In addition, none of the major componentsfrom these essential oils show notable activity in our antimicrobial orcytotoxicity assays. doi:10.1300/J044v12n03_04 [Article copies available fora fee from The Haworth Document Delivery Service: 1-800-HAWORTH.E-mail address: <[email protected]> Website: <http://www.HaworthPress.com> © 2006 by The Haworth Press, Inc. All rights reserved.]
KEYWORDS. Amyris elemifera, Eugenia axillaris, Lantanainvolucrata, Myrica cerifera, Bahamas, leaf essential oil, composition,antimicrobial activity, cytotoxic activity
INTRODUCTION
In earlier times, all drugs and medicinal agents were derived fromnatural substances, and most of these remedies were obtained fromhigher plants. Even today, about 80% of the world’s population reliespredominantly on plants and plant extracts for health care. For manygenerations, people living in remote locations of the Bahamas have uti-lized “bush medicine” to ameliorate their maladies (34). In this paper,we report on the chemical compositions, antimicrobial activities, andcytotoxic activities, of the leaf essential oils of four aromatic herbalmedicines used by the people of Abaco Island, Bahamas.
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Amyris elemifera L. (Rutaceae), “white torch,” is a shrub or tree 8-17m in height with light brown bark and slender, unarmed stems (42, 56).The compound leaves are generally trifoliate with ovate, pointed oppo-site leaflets, 3-8 cm long, glossy green above and pale green below.They emit an aromatic citrus-like odor when crushed. Flowers arewhite, 4-petaled, 12 mm wide, in terminal and axillary clusters. Fruit isa purple or black round or ovoid drupe, 5-8 mm long. In the Bahamas, aleaf decoction is taken as a febrifuge and applied to sores and wounds,to treat influenza, and as an external bath and general tonic (42).
Phytochemical analyses of Neotropical Amyris spp. have revealedthese plants to be rich in coumarins (10, 16, 23), sesquiterpenoids (50,61), lignans (6), and alkaloids (9, 21). Extracts of A. elemifera haveyielded a number of coumarins (11, 54). The leaf essential oil ofA. diatrypa from the Dominican Republic is composed largely ofpregeijerene with moderate amounts of 1,8-cineole, linalool, geijerene,sabinene, and �-caryophyllene (3).
Eugenia axillaris (Myrtaceae), “white stopper,” is a shrub or smalltree 6-10 m tall with thin, light gray bark (42, 56). Leaves are simple,entire, opposite, elliptic to ovate, 3-7 cm long, dark green above, palerbelow with numerous small pellucid oil dots. The leaves emit a skunk-like odor when crushed. Flowers are white, four-petaled, fragrant, withnumerous stamens, and occur in axillary racemes. The fruit is globular,berry-like, one-seeded, reddish-purple to black, 7-12 mm wide. In theBahamas, a decoction of the leafy branch tips of E. axillaris is used for“building up men’s energy and body” (i.e., as an aphrodisiac); it is alsoused to treat diarrhea and for bathing women after childbirth (34, 42).To our knowledge, there have been no phytochemical investigations ofE. axillaris reported.
Lantana involucrata (Verbenaceae), “wild sage,” is a highly aro-matic shrub native to the U.S. Gulf coast, Florida, Mexico, the Baha-mas, the West Indies, and Central America, up to 2 m tall with paleyellow bark (56). Leaves are pale green, oval, rough in texture, crenate,and give off a spicy aroma when crushed. Flowers are small, white, inclusters about 1-3 cm across. The fruit is a purple drupe, 3 mm wide.L. involucrata is used in the Bahamas to treat itching of the skin, mea-sles and chicken pox (34). Recently, the cytotoxic naphthoquinones,lantalucratins A-F, were isolated from the roots of the plant (32).
Myrica cerifera (Myricaceae), “wax myrtle” or “bayberry,” is ashrub or tree, 4-12 m tall with smooth light gray bark, native to the eastcoast of the U.S., Florida Keys, and West Indies (42, 56). Leaves are al-ternate, aromatic, linear to oblong-lanceolate, 5-10 cm long, 1.5-3 cm
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wide, irregularly toothed, aromatic when crushed. The flowers aredioecious, small, yellowish-green, in axillary clusters. Fruit is a round,waxy bluish-white drupe, 2.5-3 cm wide. In Bahamian bush medicine, atea made from the leafy branchlets of M. cerifera is taken as a generaltonic and diuretic (42). The root is used as an astringent. The fruits andleaves are used in Honduras to treat dental problems, stomachache, con-stipation, and as a skin cleanser (39). The methanol extract of M.cerifera has shown antithrombin activity (15), whereas the ethanol ex-tract has shown no antimicrobial activity (39). Previous phytochemicalanalyses have revealed the triterpenoids myricadiol, taraxerol, andtaraxerone from the root bark (46), myriceric acids (53), myrica acid(43), and the flavonoid glycoside myricitrin (46).
MATERIALS AND METHODS
A. elemifera. The plant was collected June 10, 2002 from Abaco Is-land, Bahamas (26� 34.5′ N, 77� 7.4′ W, 1-2 m a.s.l.) and was identifiedin the field by W. N. Setzer using appropriate field guides (44, 56) andverified by M. A. Vincent. A voucher specimen was deposited in theUniversity of Alabama in Huntsville herbarium. The essential oil wasobtained by hydrodistillation of freshly chopped leaves (209.9 g) anddichloromethane extraction of the distillate (yield: 7.309 g, 3.48%).
E. axillaries. The plant was collected June 10, 2002 from Abaco Is-land, Bahamas (26� 34′ N, 77� 8′ W, 1-2 m a.s.l.). The plant was identi-fied by M. A. Vincent by comparison with specimens at the W. S.Turrell Herbarium. A voucher specimen was deposited in the Univer-sity of Alabama in Huntsville herbarium. The essential oil was obtainedby hydrodistillation of the freshly chopped leaves (228.9 g) and di-chloromethane extraction of the distillate (yield: 2.642 g, 1.15%).
L. involucrata. The leaves of L. involucrata were collected Decem-ber 18, 2000, from Forest Heights Academy, Marsh Harbour, Abaco Is-land, Bahamas (26� 31.09′ N, 77� 4.26′ W, 13 m a.s.l.). The plant wasidentified in the field by W. N. Setzer using appropriate field guides (44,56) and verified by M. A. Vincent. The leaf essential oil was obtainedby hydrodistillation and dichloromethane extraction of 190.0 g freshlychopped leaves (yield: 125 mg, 0.0658%).
M. cerifera. Fresh leaves of M. cerifera were collected from Abaco Is-land, Bahamas (26� 34.55′ N, 77� 8.35′ W, 1-2 m a.s.l.) June 9, 2002. Theplant was identified in the field by W. N. Setzer using appropriate field
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guides (44, 56) and verified by M. A. Vincent. The essential oil was ob-tained by hydrodistillation of the freshly chopped leaves (141.8 g) and di-chloromethane extraction of the distillate (yield: 1.772 g, 1.25%).
Gas chromatographic-mass spectral analysis. The leaf essential oilswere subjected to GC-MS analysis on an Agilent system consisting of amodel 6890 gas chromatograph, a model 5973 mass selective detector(MSD), and an Agilent ChemStation data system. The GC column wasan HP-5ms fused silica capillary with a (5% phenyl)-methylpolysilo-xane stationary phase, film thickness of 0.25 µm, a length of 30 m, andan internal diameter of 0.25 mm. The carrier gas was helium with a col-umn head pressure of 7.07 psi and flow rate of 1.0 mL/min. Inlet tem-perature was 200�C and MSD temperature was 280�C. The GC oventemperature program was used as follows: 40�C initial temperature,hold for 10 min; increased at 3�/min to 200�C; increased 2�/min to220�C. The sample was dissolved in CH2Cl2 and a split injection tech-nique was used. Identification of oil components was achieved based ontheir retention indices (determined with reference to a homologous se-ries of normal alkanes), and by comparison of their mass spectral frag-mentation patterns (NIST database/ChemStation data system) (1). Gaschromatograms of the essential oils are shown in Figures 1-4, and thecomponents from the gas chromatographic-mass spectral analyses ofthe leaf oils of the studied plant species are listed in Tables 1-4.
Antimicrobial assays. The essential oils and the purified major com-ponents (see Figure 5) were screened for antimicrobial activity againstGram-positive bacteria, Bacillus cereus (ATCC No. 14579) and Staph-ylococcus aureus (ATCC No. 29213); Gram-negative bacteria, Pseudo-monas aeruginosa (ATCC No. 27853) and Escherichia coli (ATCCNo. 25922); and the fungi Candida albicans (ATCC No. 10231) andAspergillus niger (ATCC No. 16401). Minimum inhibitory concentra-tions (MIC) were determined using the microbroth dilution technique(52, 57, 58). The antimicrobial activities of the essential oils andcomponents are summarized in Table 5.
Cytotoxicity assays. The essential oils and purified major componentswere screened for cytotoxic activity against PC-3 (human prostatic adeno-carcinoma), MDA-MB-231 (human mammary adenocarcinoma), MCF7(human mammary adenocarcinoma), Hs 578T (human ductal carci-noma), and Hep G2 (human hepatocellular carcinoma), using the MTSassay as described previously (57, 58). Cytotoxic activities are summa-rized in Table 6.
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5.00 10.00 15.00 20.00 25.00 30.00 35.00 40.00 45.00 50.00 55.00
FIGURE 1. Gas chromatogram of A. elemifera leaf essential oil.
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5.00 10.00 15.00 20.00 25.00 30.00 35.00 40.00 45.00 50.00 55.00
FIGURE 2. Gas chromatogram of E. axillaris leaf essential oil.
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5.00 10.00 15.00 20.00 25.00 30.00 35.00 40.00 45.00 50.00 55.00 60.
FIGURE 3. Gas chromatogram of L. involucrata leaf essential oil.
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5.00 10.00 15.00 20.00 25.00 30.00 35.00 40.00 45.00 50.00 55.00
FIGURE 4. Gas chromatogram of M. cerifera leaf essential oil.
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RESULTS
A. elemifera. The essential oil of A. elemifera as revealed by GC-MSis made up of 71.3% monoterpenoids, 21.0% sesquiterpenoids, and7.7% other compounds. The most abundant compounds are limonene(45.0%), linalool (20.8%), �-caryophyllene (5.6%), 3-hexadecanone(5.3%), caryophyllene oxide (3.9%), and �-sesquiphellandrene (3.6%).In this study, we find neither the leaf oil nor its major components to benotably antimicrobial. However, linalool is slightly active against S.aureus, while caryophyllene and caryophyllene oxide show slight ac-tivity against B. cereus. Although A. elemifera leaf oil shows no cyto-toxic activity against our panel of tumor cell lines, �-caryophyllene and
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TABLE 1. Chemical composition of A. elemifera leaf essential oil.
RI1 Compound Area (%)
1027 Limonene 44.981045 trans-�-Ocimene trace1068 cis-Linalool oxide 1.461085 trans-Linalool oxide trace1097 Linalool 20.801115 trans-p-2,8-Menthadien-1-ol 2.131186 �-Terpineol 1.971240 Carvone trace1287 Unknown2 2.001400 cis-Jasmone 0.391419 trans-Caryophyllene 5.641453 �-Humulene 0.671458 trans-�-Farnesene 1.321481 Germacrene-D 0.941498 �-Zingiberene 1.581512 (E,E)-α-Farnesene 2.311526 �-Sesquiphellandrene 3.591555 Germacrene-B trace1577 Spathulenol 1.041580 Caryophyllene oxide 3.921591 Viridiflorol trace1616 Zingiberinol trace1803 3-Hexadecanone 5.271991 Seselin trace2022 Xanthotoxin trace2177 Bravelin traceTotal identified 98.01RI = Linear “Retention Index” based on a homologous series of n-alkanes on a HP-5ms column.2MS (EI): 197(13%), 179(3%), 155(17%), 137(23%), 136(22%), 94(100%), 79(26%), 68(50%), 59(24%),
55(33%).
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TABLE 2. Chemical composition of E. axillaris leaf essential oil.
RI1 Compound Area (%)
875 trans-2-Hexenal 3.0933 �-Pinene 15.5982 �-Pinene trace995 �-Myrcene trace1005 �-Phellandrene trace1027 Limonene 4.71028 1,8-Cineole 6.61046 trans-�-Ocimene 1.41055 -Terpinene trace1085 trans-Linalool oxide 0.61099 Linalool 1.01111 endo-Fenchol trace1138 trans-Pinocarveol 1.61146 Isopulegol trace1154 Citronellal trace1168 endo-Borneol trace1181 Terpinen-4-ol 1.11187 �-Terpineol 4.51215 trans-Carveol trace1227 Citronellol 0.61239 Neral 1.31254 Geraniol 0.51270 Geranial 1.71375 �-Copaene 0.61420 �-Caryophyllene 8.81434 -Elemene trace1454 �-Humulene 6.91482 Germacrene-D 6.21486 �-Selinene 0.51497 C15H22O2 3.11501 Dihydroagarofuran 9.21525 -Cadinene 1.21538 �-Cadinene trace1541 Selina-3,7(11)-diene trace1551 Elemol trace1556 Germacrene-B 0.31619 10-epi-γ-Eudesmol 5.91628 1-epi-Cubenol 0.61631 γ-Eudesmol 0.91635 Hinesol 1.31642 �-Cadinol 0.81649 �-Eudesmol 5.11651 �-Eudesmol 3.21656 7-epi-�-Eudesmol 1.21692 Juniper Camphor traceTotal identified 96.91RI = Linear “Retention Index” based on a homologous series of n-alkanes on a HP-5ms column.2Unidentified sesquiterpenoid, MS (EI): 222(4%), 207(100%), 204(23%), 189(45%), 179(16%), 161(26%),149(15%), 126(79%), 123(21%), 111(34%), 107(20%), 105(15%), 93(21%), 81(22%), 69(20%), 55(20%).
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TABLE 3. Chemical composition of L. involucrata leaf essential oil.
RI1 Compound Area (%)
850 trans-2-hexenal trace854 cis-3-Hexenol 0.7984 1-Octen-3-ol 1.31029 1,8-Cineole trace1098 Linalool 0.51189 �-Terpineol trace1375 �-Copaene trace1384 �-Bourbonene 2.41392 �-Elemene 3.61420 �-Caryophyllene 13.71438 �-Guaiene 0.61454 �-Humulene 15.21460 Alloaromadendrene 1.61477 -Muurolene 0.81481 Germacrene D 21.11486 2,4,6-Trimethoxytoluene 4.61496 Bicyclogermacrene 5.11504 Germacrene A 1.41514 Cubebol 1.11525 -Cadinene 0.61556 Germacrene-B 1.61565 Nerolidol trace1577 Spathulenol 4.01582 Caryophyllene oxide 5.31608 Humulene epoxide II 3.41615 C15H24O2 0.61630 C15H24O3 1.51634 Caryophylla-4(12),8(13)-dien-5-�-ol 1.41644 C15H24O4 0.51653 �-Cadinol 1.61654 Caryophylla-3,8(13)-dien-5-�-ol 0.61684 C15H24O5 3.92150 C20H34O6 1.3Total identified 92.21RI = Linear “Retention Index” based on a homologous series of n-alkanes on a HP-5ms column.2Unidentified sesquiterpenoid, MS (EI): 220(11%), 205(25%), 187(15%), 177(38%), 163(40%), 161(26%), 159(85%),
149(40%), 146(41%), 145(70%), 135(33%), 133(38%), 131(100%), 121(43%), 119(46%), 109(39%), 107(65%),105(80%), 93(66%), 91(67%), 81(48%), 79(46%), 77(45%), 67(33%), 55(34%).3Unidentified sesquiterpenoid, MS (EI): 220(15%), 205(11%), 202(10%), 187(19%), 177(17%), 159(28%), 145(23%),136(92%), 119(100%), 109(90%), 107(68%), 105(64%), 95(96%), 93(84%), 91(94%), 85(68%), 82(73%), 81(64%),79(76%), 77(46%), 69(85%), 67(91%), 55(49%), 53(32%).4Unidentified sesquiterpenoid, MS (EI): 220(13%), 205(25%), 204(19%), 187(23%), 177(65%), 161(67%), 159(35%),149(19%), 145(21%), 135(33%), 133(37%), 131(32%), 123(100%), 119(49%), 109(36%), 107(50%), 105(61%),95(61%), 93(53%), 91(60%), 82(58%), 81(64%), 79(51%), 67(47%), 55(33%).5Unidentified sesquiterpenoid, MS (EI): 220(15%), 202(23%), 187(11%), 177(28%), 159(83%), 149(18%), 145(18%),135(31%), 133(27%), 131(37%), 123(25%), 122(31%), 121(30%), 119(31%), 117(38%), 109(100%), 107(50%),105(48%), 95(32%), 93(51%), 91(79%), 81(46%), 79(64%), 77(44%), 69(24%), 67(33%), 55(31%).
6Unidentified diterpenoid, MS (EI): 272(14%), 257(8%), 191(38%), 178(18%), 163(8%), 148(14%), 134(100%), 119(51%),109(26%), 95(28%), 83(31%), 81(37%), 69(25%), 55(17%).
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TABLE 4. Chemical composition of M. cerifera leaf essential oil.
RI1 Compound Area (%)
876 cis-3-Hexenol 1.4938 �-Pinene trace961 Benzaldehyde trace1029 1,8-Cineole 30.71053 -Terpinene trace1060 Acetophenone trace1068 cis-Linalool oxide trace1085 trans-Linalool oxide trace1098 Linalool 2.01110 endo-Fenchol trace1119 cis-p-Menth-2-en-1-ol trace1137 trans-Pinocarveol trace1139 trans-p-Menth-2-en-1-ol trace1163 Pinocarvone trace1166 Borneol trace11692 -Terpineol 1.51177 4-Terpineol 9.01189 �-Terpineol 14.21215 trans-Carveol trace1225 Nerol trace1250 Piperitone trace1288 Thymol trace1297 Carvacrol trace1348 �-Cubebene trace1370 �-Ylangene 0.31375 �-Copaene 1.01384 �-Bourbonene trace1392 �-Elemene trace1400 cis-Jasmone trace1409 �-Gurjunene trace1420 �-Caryophyllene 6.41429 Calarene 0.41438 Aromadendrene trace1453 �-Humulene 3.21478 -Muurolene 1.51481 Germacrene D 0.61486 �-Selinene trace1494 �-Selinene trace1495 Epizonarene 0.81502 �-Muurolene 1.31508 -Cadinene trace15153 �-Cadinene 2.71525 -Cadinene 5.01533 Cadina-1,4-diene 0.31538 �-Cadinene 0.7
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caryophyllene oxide are active. The other major components, limoneneand linalool, are not cytotoxic, according to our study.
E. axillaris. GC-MS Analysis of the leaf oil of E. axillaris shows theoil to be composed of oxygenated sesquiterpenoids (31.6%), sesquiter-pene hydrocarbons (24.4%), monoterpene hydrocarbons (21.6%), andoxygenated monoterpenoids (19.4%). The most abundant constituents ofE. axillaris leaf oil are �-pinene (15.5%), �-dihydroagarofuran (9.2%),�-caryophyllene (8.8%), �-humulene (6.9%), 1,8-cineole (6.6%), andgermacrene D (6.2%). E. axillaris leaf oil is neither appreciably anti-microbial nor cytotoxic. In addition, none of the major components fromthe essential oil shows notable activity in our antimicrobial or cytotox-icity assays.
L. involucrata. The oil of L. involucrata is dominated by sesquiter-penoids with 67.6% sesquiterpene hydrocarbons and 24.0% oxygen-ated sesquiterpenoids. The most abundant components are germacreneD (21.1%), �-humulene (15.2%), �-caryophyllene (13.7%), and caryo-phyllene oxide (5.3%).
M. cerifera. M. cerifera leaf oil is made up of 57.4% oxygenatedmonoterpenoids, dominated by 1,8-cineole (30.7%), �-terpineol(14.2%), and 4-terpineol (9.0%); 24.4% sesquiterpene hydrocarbons,
56 JOURNAL OF HERBS, SPICES & MEDICINAL PLANTS
TABLE 4 (continued)
RI1 Compound Area (%)
1543 �-Calacorene 0.31565 Nerolidol 2.21577 Spathulenol 0.41582 Carophyllene oxide 2.31608 Humulene epoxide II 1.01614 1,10-di-epi-Cubenol 0.91627 1-epi-Cubenol 1.51631 C15H24O4 1.01635 Caryophylla-4(12),8(13)-dien-5β-ol 0.51640 �-Cadinol 3.51645 �-Muurolol 0.81653 �-Cadinol 2.3Total identified 99.01RI = Linear “Retention Index” based on a homologous series of n-alkanes on a HP-5ms column.2Reference RI (1167) from Adams (64).3Reference RI (1518) from Skaltsa et al. (65).4Unidentified sesquiterpenoid, MS (EI): 220(6%), 204(32%), 189(6%), 187(6%), 179(100%), 161(66%),136(25%), 119(66%), 109(55%), 107(34%), 105(45%), 95(54%), 93(44%), 91(43%), 82(36%), 81(37%),79(36%), 69(43%), 67(39%), 55(33%).
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mostly �-caryophyllene (6.4%) and -cadinene (5.0%); and 16.8% ox-ygenated sesquiterpenoids. Neither the volatile leaf oil of M. ceriferanor its major components exhibited either antimicrobial activity orantineoplastic activity in our assays.
DISCUSSION
A. elemifera. Linalool and �-caryophyllene are also moderately abun-dant constituents of A. diatrypa (3). Both A. diatrypa leaf oil (3) andA. balsamifera wood essential oil (61) contain moderate amounts of
Schmidt et al. 57
α-Pinene
α-Terpineol β-Caryophyllene
β-Dihydroagarofuran
β-Sesquiphellandrene
Limonene
OH
4-Terpineol
Germacrene D
Caryophyllene oxide
α-Humulene
δ-Cadinene
OH
O
O
H
H H
H
H
1,8-Cineole Linalool
OH
O
FIGURE 5. Major components of aromatic medicinal plants from Abaco dis-cussed in this work.
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�-sesquiphellandrene. Limonene is an abundant constituent of many es-sential oils of the Rutaceae, especially Citrus (5), and has exhibited can-cer chemopreventive activity (19, 25), possibly due to induction ofglutathione-S-transferase and glutathione peroxidase (62). In addition,limonene has been shown to have muscle relaxant and sedative activities(24). Linalool, abundant in rosewood (Aniba roseadora) (28) and sweetbasil (Ocimum basilicum) (30) essential oils, has been found to exhibitanti-inflammatory (48), antinociceptive (47), and sedative (8) effects. Inaddition, linalool inhibited the growth of bacteria and fungi (13, 45, 49)and showed antileukemic activity (14). �-Caryophyllene has shownanti-inflammatory (40) and anesthetic (29) effects in addition to anti-carcinogenic (65) and antineoplastic (38) activities. Caryophyllene oxideexhibited anti-dermatophytic activity (64) and smooth- muscle-relaxantactivity (41). �-Sesquiphellandrene has shown antirhinoviral (22) andantiulcer (63) activities. The reported biological activities of the majorconstituents of A. elemifera leaf oil are consistent with the ethnopharma-cological uses of the plant to reduce fever, treat symptoms of flu, treatsores and wounds, and its use as a general tonic and bath.
58 JOURNAL OF HERBS, SPICES & MEDICINAL PLANTS
TABLE 5. Antimicrobial activity (MIC, �g/mL) of leaf essential oils and their ma-jor components of Abaco bush medicinal plants.
Material Bacilluscereus
Staphylococcusaureus
Escherichiacoli
Pseudomonasaeruginosa
Candidaalbicans
Aspergillusniger
A. elemifera 625 1250 625 625 1250 625E. axillaris 625 625 625 625 625 625L. involucrata 312 312 625 625 625 625M. cerifera 625 625 312 625 625 625�-Pinene 625 312 312 625 156 625Limonene 625 312 625 1250 1250 25001,8-Cineole 156 625 625 625 312 312Linalool 625 156 625 1250 625 6254-Terpineol 1250 1250 1250 625 312 1250�-Terpineol 625 1250 1250 625 1250 625�-Caryophyllene 156 312 312 1250 1250 625�-Humulene 312 312 625 1250 625 78Germacrene D 625 156 625 1250 625 39Caryophylleneoxide
156 1250 1250 1250 625 625
Positive Control 1.221 0.611 2.441 1.221 0.612 0.612
1Gentamicin sulfate.2Amphotericin B.
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TA
BLE
6.C
ytot
oxic
activ
ityof
leaf
esse
ntia
loils
and
thei
rm
ajor
com
pone
nts
ofA
baco
med
icin
alpl
ants
.
Mat
eria
lC
ytot
oxic
ity
MD
A-M
B-2
31M
CF
7H
s57
8TP
C-3
Hep
-G2
A.e
lem
ifera
10
23.3
7(3.
34)
16.9
5(11
.49)
6.91
(28.
68)
19.4
1(6.
22)
E.a
xilla
ris0
11.9
9(3.
30)
8.77
(3.0
0)0
16.4
5(5.
63)
L.in
volu
crat
a42
.66(
19.8
0)30
.21(
1.76
)95
.79(
1.43
)67
.47(
6.38
)92
.21(
2.42
)M
.cer
ifera
00
2.74
(9.3
1)3.
23(4
.89)
14.7
6(18
.01)
�-P
inen
e2
735
73
5
1840
73
597
0(26
0)Li
mon
ene
73
5
735
18
40
735
1150
(110
)1,
8-C
ineo
le
650
65
0
1625
65
0
1625
Lina
lool
65
0
650
16
25
650
16
254-
Ter
pine
ol
650
65
0
1625
65
0
1625
�-T
erpi
neol
65
0
650
16
25
650
16
25�
-Car
yoph
ylle
ne15
5(1)
190(
26)
383(
41)
153(
6)34
7(74
)�
-Hum
ulen
e10
8(1)
131(
18)
251(
26)
49
026
0(23
)G
erm
acre
neD
331(
12)
341(
12)
270(
26)
127(
10)
272(
19)
Car
yoph
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neox
ide
324(
33)
178(
33)
350(
1)15
0(3)
116(
8)D
oxor
ubic
inhy
droc
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ide3
44.6
(4.1
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.4(3
.3)
17.9
(2.1
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.7(8
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2.28
(0.4
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ityfo
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250
µg/m
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dH
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lls;p
erce
ntag
eki
llat
100
�g/
mL
for
MD
A-M
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31,
MC
F7,
and
PC
-3ce
lls.S
tand
ard
devi
atio
nsar
esh
own
inpa
rent
hese
s.2 C
ytot
oxic
ityfo
rpu
reco
mpo
unds
isex
pres
sed
asLC
50va
lues
in�
M.S
tand
ard
devi
atio
nsar
esh
own
inpa
rent
hese
s.3 P
ositi
veco
ntro
l.
59
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E. axillaris. �-Pinene, �-caryophyllene, �-humulene, 1,8-cineole,and germacrene D are relatively common in Eugenia spp. Thus,�-pinene is abundant in the leaf oil of E. jambolana (18), 1,8-cineole isthe major component of E. haitiensis essential oil (36), �-caryophylleneand �-humulene are abundant constituents of E. disenterica leaf essen-tial oil (17), and germacrene D is abundant in E. stipitata fruits (27).�-Dihydroagarofuran has been found in the many essential oils, but hasapparently not been previously detected in Eugenia essential oils.
L. involucrata. The presence of germacrene D, �-humulene, and�-caryophyllene as major components is consistent with the ethno-pharmacological use of L. involucrata to treat skin problems. Thus, com-mercially marketed herbal treatments for skin problems include goldenrod(Solidago canadensis) oil, rich in germacrene D (60); salves from purpleconeflower (Echinacea purpurea) root extract, rich in germacrene D and�-caryophyllene (35); and lotions from extracts of hops (Humulus lupulus)“flowers,” rich in �-humulene and �-caryophyllene (26). Both Lantanacamara (20) and L. aculeata (55) are used in traditional medicine to treatitching and other skin problems. L. camara essential oil has abundantquantities of �-humulene and �-caryophyllene (4), and L. aculeata essen-tial oil is high in �-caryophyllene (55). L. xenica is also rich in �-caryophyllene and germacrene D (37). The essential oils of L. camara (4,20), L. aculeata (55), L. xenica (37), and L. achyranthifolia (33) have ex-hibited weak antimicrobial activity, consistent with the results of L.involucrata leaf oil.
M. cerifera. The large percentage of 1,8-cineole may account for itsuse in traditional herbal medicine. Eucalyptus oil and tea tree (Melaleucaalternifolia) oil are commercially important medicines, and these essen-tial oils are also rich in 1,8-cineole (7, 12). Further 1,8- Cineole has beenreported to exhibit insecticidal (36), antimicrobial (13), and antioxidant(51) activity, and may synergistically enhance the biological activitiesof other essential oil components (31).
REFERENCES
1. Adams, R. P., 1995. Identification of Essential Oil Components by Gas Chro-matography/Mass Spectrometry. Allured Publishing, Carol Stream, Illinois.
2. Adams, R. P., 2001. Geographic variation in leaf essential oils and RAPDs ofJuniperus polycarpos K. Koch in central Asia. Biochem. Systemat. Ecol. 29:609-619.DOI: 10.1016/S0305-1978(00)00098-3.
60 JOURNAL OF HERBS, SPICES & MEDICINAL PLANTS
Dow
nloa
ded
by [
Nip
issi
ng U
nive
rsity
] at
04:
57 0
9 O
ctob
er 2
014
3. Adams, R. P., T. A. Zanoni, T. A. van Beek, M. A. Posthumus, and C. van deHaar, 1998. Essential leaf oil of Amyris diatrypa Sprengel from the Dominican Repub-lic. J. Essent. Oil Res. 10:175-178.
4. Alitonou, G., F. Avlessi, I. Bokossa, E. Ahoussi, J. Dangou, and D. C. K.Sohounhloué, 2004. Composition chimique et activités biologiques de l’huileessentielle de Lantana camara Linn. (French. Chemical composition and biologicalactivity of the essential oil of Lantana camara Linn.) C. R. Chimie 7:1101-1105. DOI:10.1016/j.crci.2003.11.017.
5. Attaway, J. A., A. P. Pieringer, and L. J. Barabas, 1967. A study of the percent-age variations in peel and leaf oil terpenes during one season. Phytochemistry 6:25-32.
6. Badawi, M. M., A. A. Seida, A. D. Kinghorn, G. A. Cordell, and N. R.Farsworth, 1981. Potential anticancer agents. XVIII. Constituents of Amyris pinnata. J.Nat. Prod. 44:331-334.
7. Balacs, T., 1997. Cineole-rich Eucalyptus. Int. J. Aromather. 8:15-21. DOI:10.1016/S0962-4562(97)80020-3.
8. Buchbauer, G., L. Jirovetz, W. Jager, H. Dietrich, and C. Plank, 1991.Aromatherapy: Evidence for sedative effects of the essential oil of lavender after inha-lation. Z. Naturforschung C 46:1067-1072.
9. Burke, B. A., and H. Parkins, 1978. Amyris of Jamaica. Nicotinamides ofAmyris plumieri D.C., (Rutaceae). Tetrahedron Lett. 19:2723-2726. DOI: 10.1016/S0040-4039(01)91587-4.
10. Burke, B. A., and H. Parkins, 1979. Coumarins from Amyris balsamifera.Phytochemistry 18:1073-1075. DOI: 10.1016/S0031-9422(00)91488-2.
11. Burke, B. A., and P. Saleela, 1981. Amyris of Jamaica. Coumarins of Amyriselemifera D.C., (Rutaceae). Heterocycles 16:897-900.
12. Carson, C. F., B. J. Mee, and T. V. Riley, 2002. Mechanism of action ofMelaleuca alternifolia (tea tree) oil on Staphylococcus aureus determined by time-kill,lysis, leakage, and salt tolerance assays and electron microscopy. Antimicrob. AgentsChemother. 46:1914-1920. DOI: 10.1128/AAC.46.6.1914-1920.2002.
13. Carson, C. F., and T. V. Riley, 1995. Antimicrobial activity of the major com-ponents of the essential oil of Melaleuca alternifolia. J. Appl. Bacteriol. 78:264-269.
14. Chiang, L. C., W. Chiang, M. Y. Chang, L. T. Ng, and C. C. Lin, 2003.Antileukemic activity of selected natural products in Taiwan. Amer. J. Chinese Med.31:37-46.
15. Chistokhodova, N., C. Nguyen, T. Calvino, I. Kachirskaia, G. Cunningham, andD. H. Miles, 2002. Antithrombin activity of medicinal plants from central Florida.J. Ethnopharmacol. 81:277-280. DOI: 10.1016/S0378-8741(02)00097-1.
16. Cordova, H. E., and L. N. Garelli, 1974. A new coumarin in Amyrissimplicifolia. Phytochemistry 13:758-760. DOI: 10.1016/S0031-9422(00)91414-6.
17. Costa, T. R., O. F. L. Fernandes, S. C. Santos, C. M. A. Oliveira, L. M. Liao,P. H. Ferri, J. R. Paula, H. D. Ferreira, B. H. N. Sales, and M. d. R. R. Silva, 2000.Antifungal activity of volatile constituents of Eugenia dysenterica leaf oil. J.Ethnopharmacol. 72:111-117. DOI: 10.1016/S0378-8741(00)00214-2.
18. Craveiro, A. A., C. H. S. Andrade, F. J. A. Matos, J. W. Alencar, and M. I. L.Machado, 1983. Essential oil of Eugenia jambolana. J. Nat. Prod. 46:591-592.
Schmidt et al. 61
Dow
nloa
ded
by [
Nip
issi
ng U
nive
rsity
] at
04:
57 0
9 O
ctob
er 2
014
19. Crowell, P. L, 1999. Prevention and therapy of cancer by dietary monoterpenes.J. Nutrition 129:775S-778S.
20. Deena, M. J., and J. E. Thoppil, 2000. Antimicrobial activity of the essential oilof Lantana camara. Fitoterapia 71:453-455. DOI: 10.1016/S0367-326X(00)00140-4.
21. de la Fuente, G, M. Reina, and I. Timon, 1991. Chromene amides from Amyristexana. Phytochemistry 30:2677-2684. DOI: 10.1016/0031-9422(91)85122-G.
22. Denyer, C. V., P. Jackson, D. M. Loakes, M. R. Ellis, and D. A. Young, 1994.Isolation of antirhinoviral sesquiterpenes from ginger (Zingiber officinale). J. Nat.Prod. 57:658-662.
23. Dominguez, X. A., G. Cano, I. Luna, and A. Dieck, 1977. Two coumarinsfrom the aereal parts of Amyris madrensis. Phytochemistry 16:1096. DOI: 10.1016/S0031-9422(00)86749-7.
24. do Vale, T. G., E. C. Furtado, J. G. Santos, and G. S. Viana, 2002. Centraleffects of citral, myrcene and limonene, constituents of essential oil chemotypesfrom Lippia alba (Mill.) n.e. Brown. Phytomedicine 9:709-714. DOI: 10.1078/094471102321621304.
25. Elson, C. E., T. H. Maltzman, J. L. Boston, M. A. Tanner, and M. N. Gould,1988. Anti-carcinogenic activity of d-limonene during the initiation and promotion/progression stages of DMBA-induced rat mammary carcinogenesis. Carcinogenesis 9:331-332.
26. Eri, S., B. K. Khoo, J. Lech, and T. G. Hartman, 2000. Direct thermaldesorption-gas chromatography and gas chromatography-mass spectrometry profilingof hop (Humulus lupulus L.) essential oils in support of varietal characterization. J.Agric. Food Chem. 48:1140-1149. DOI: 10.1021/jf9911850.
27. Franco, M. R. B., and T. Shibamoto, 2000. Volatile composition of some Bra-zilian fruits: Umbu-caja (Spondias citherea), Camu-camu (Myrciaria dubia),Araça-boi (Eugenia stipitata), and Cupuaçu (Theobroma grandiflorum). J. Agric.Food Chem. 48:1263-1265. DOI: 10.1021/jf9900074.
28. Gaydou, E. M., and R. P. Randriamiharisoa, 1987. Gas chromatographicdiastereomer separation of linalool derivatives. Application to the determination of theenantiomeric purity of linalool in essential oils. J. Chromatogr. A 396:378-381. DOI:10.1016/S0021-9673(01)94078-6.
29. Ghelardini, C., N. Galeotti, L. Di Cesare Mannelli, G. Mazzanti, and A. Bartolini,2001. Local anaesthetic activity of �-caryophyllene. Farmaco 56:387-389. DOI: 10.1016/S0014-827X(01)01092-8.
30. Grayer, R. J., G. C. Kite, F. J. Goldstone, S. E. Bryan, A. Paton, and E. Putievsky,1996. Infraspecific taxonomy and essential oil chemotypes in sweet basil, Ocimumbasilicum. Phytochemistry 43:1033-1039. DOI: 10.1016/S0031-9422(96)00429-3.
31. Harris, R., 2002. Synergism in the essential oil world. Int. J. Aromather. 12:179-186. DOI: 10.1016/S0962-4562(02)00083-8.
32. Hayashi, K., F. R. Chang, Y. Nakanishi, K. F. Bastow, G. Cragg, A. T. McPhail,H. Nozaki, and K. H. Lee, 2004. Antitumor agents. 233. Lantalucratins A-F, newcytotoxic naphthoquinones from Lantana involucrata. J. Nat. Prod. 67:990-993. DOI:10.1021/np030450f.
33. Hernandez, T., M. Canales, J. G. Avila, A. M. Garcia, A. Martinez, J. Caballero,A. Romo de Vivar, and R. Lira, 2005. Composition and antibacterial activity of essential
62 JOURNAL OF HERBS, SPICES & MEDICINAL PLANTS
Dow
nloa
ded
by [
Nip
issi
ng U
nive
rsity
] at
04:
57 0
9 O
ctob
er 2
014
oil of Lantana achyranthifolia Desf. (Verbenaceae). J. Ethnopharmacol. 96:551-554.DOI: 10.1016/j.jep.2004.09.044.
34. Higgs, L., 1969. Bush Medicine in the Bahamas. Bahamas Nassau Guardian,Nassau, Bahamas.
35. Hudaib, M., J. Fiori, M. G. Bellardi, C. Rubies-Autonell, and V. Cavrini, 2002.GC-MS analysis of the lipophilic principles of Echinacea purpurea and evaluation ofcucumber mosaic cucumovirus (CMV) infection. J. Pharmaceut. Biomed. Anal. 29:1053-1060. DOI: 10.1016/S0731-7085(02)00146-2.
36. Jacobson, M., and H. L. Haller, 1947. The insecticidal component of Eugeniahaitiensis identified as 1,8-cineol. J. Am. Chem. Soc. 69:709-710.
37. Juliani, H. R., F. Biurrun, A. R. Koroch, M. M. Oliva, M. S. Demo, V. S. Trippi,and J. A. Zygadlo, 2002. Chemical constituents and antimicrobial activity of the essen-tial oil of Lantana xenica. Planta Med. 68:762-764. DOI: 10.1055/s-2002-33803.
38. Kubo, I., S. K. Chaudhuri, Y. Kubo, Y. Sanchez, T. Ogura, T. Saito, H.Ishikawa, and H. Haraguchi, 1996. Cytotoxic and antioxidative sesquiterpenoids fromHeterotheca inuloides. Planta Med. 62:427-430.
39. Lentz, D. L., A. M. Clark, C. D. Hufford, B. Meurer-Grimes, C. M. Passreiter,J. Cordero, O. Ibrahimi, and A. L. Okunade, 1998. Antimicrobial properties of Hon-duran medicinal plants. J. Ethnopharmacol. 63:253-263. DOI: 10.1016/S0378-8741(98)00100-7.
40. Martin, S., E. Padilla, M. A. Ocete, J. Galvez, J. Jimenez, and A. Zarzuelo,1993. Anti-inflammatory activity of the essential oil of Bupleurum fruticescens. PlantaMed. 59:533-536.
41. Mata, R., A. Rojas, L. Acevedo, S. Estrada, F. Calzada, I. Rojas, R. Bye, and E.Linares, 1997. Smooth muscle relaxing flavonoids and terpenoids from Conyzafilaginoides. Planta Med. 63:31-35.
42. Morton, J. F, 1981. Atlas of Medicinal Plants of Middle America. Thomas Pub-lishing, Springfield, Illinois.
43. Nagai, M., N. Sakurai, N. Yumoto, S. Nagumo, and S. Seo, 2000. Oleanane acidfrom Myrica cerifera. Chem. Pharm. Bull. (Tokyo) 48:1427-1428.
44. Nickrent, D. L., W. H. Eshbaugh, and T. K. Wilson, 1991. The Vascular Floraof Andros Island, Bahamas. Turrell Herbarium, Oxford, Ohio.
45. Pattnaik, S, V. R. Subramanyam, M. Bapaji, and C. R. Kole, 1997. Antibacterialand antifungal activity of aromatic constituents of essential oils. Microbios. 89:39-46.
46. Paul, B. D., G. S. Rao, and G. J. Kapadia, 1974. Isolation of myricadiol,myricitrin, taraxerol, and taraxerone from Myrica cerifera L. root bark. J. Pharm. Sci.63:958-959.
47. Peana, A. T., P. S. D’Aquila, M. L. Chessa, M. D. Moretti, G. Serra, andP. Pippia, 2003. (-)-Linalool produces antinociception in two experimental models ofpain. Eur. J. Pharmacol. 460:37-41. DOI: 10.1016/S0014-2999(02)02856-X.
48. Peana, A. T., P. S. D’Aquila, F. Panin, G. Serra, P. Pippia, and M. D. Moretti,2002. Anti-inflammatory activity of linalool and linalyl acetate constituents of essen-tial oils. Phytomedicine 9:721-726. DOI: 10.1078/094471102321621322.
49. Pitarokili, D., M. Couladis, N. Petsikos-Panayotarou, and O. Tzakou, 2002.Composition and antifungal activity on soil-borne pathogens of the essential oil of
Schmidt et al. 63
Dow
nloa
ded
by [
Nip
issi
ng U
nive
rsity
] at
04:
57 0
9 O
ctob
er 2
014
Salvia sclarea from Greece. J. Agric. Food Chem. 50:6688-6691. DOI: 10.1021/jf020422n.
50. Rohmer, M., A. C. Schwartz, and R. Anton, 1977. Sesquiterpenes from essen-tial oil of Amyris balsamifera. Phytochemistry 16:773-774. DOI: 10.1016/S0031-9422(00)89256-0.
51. Ruberto, G., and M. T. Baratta, 2000. Antioxidant activity of selected essentialoil components in two lipid model systems. Food Chem. 69:167-174. DOI: 10.1016/S0308-8146(99)00247-2.
52. Sahm, D. H., and J. A. Washington, 1991. Antibacterial susceptibility tests: Di-lution methods. In: A. Balows, W. J. Hausler, K. L. Herrmann, H. D. Isenberg, and H. J.Shamody, eds., Manual of Clinical Microbiology, 5th Ed., American Society for Mi-crobiology, Washington DC.
53. Sakurawi, K., F. Yasuda, T. Tozyo, M. Nakamura, T. Sato, J. Kikuchi, Y. Terui,Y. Ikenishi, T. Iwata, K. Takahashi, T. Konoike, S. Mihara, and M. Fujimoto, 1996.Endothelin receptor antagonist triterpenoid, myriceric acid A, isolated from Myricacerifera, and structure activity relationships of its derivatives. Chem. Pharm. Bull. (To-kyo) 44:343-351.
54. Saleela, P., and B. A. Burke, 1985. Amyris of Jamaica. New coumarins fromAmyris elemifera L. (Rutaceae). Heterocycles 23:1921-1923.
55. Saxena, V. K., and R. N. Sharma, 1999. Antimicrobial activity of the essential oilof Lantana aculeata. Fitoterapia 70:67-70. DOI: 10.1016/S0367-326X (98)00003-3.
56. Scurlock, J. P., 1987. Native Trees and Shrubs of the Florida Keys. Laurel &Herbert, Lower Sugarloaf Key, Florida.
57. Setzer, M. C., D. M. Moriarity, R. O. Lawton, W. N. Setzer, G. A. Gentry, andW. A. Haber, 2003. Phytomedicinal potential of tropical cloudforest plants fromMonteverde, Costa Rica. Rev. Biol. Trop. 51:647-674.
58. Setzer, M. C., W. N. Setzer, B. R. Jackes, G. A. Gentry, and D. M. Moriarity,2001. The medicinal value of tropical rainforest plants from Paluma, north Queens-land, Australia. Pharmaceut. Biol. 39:67-78.
59. Skaltsa, S. D., C. Demetzos, D. Lazari, and M. Sokovic, 2003. Essential oilanalysis and antimicrobial activity of eight Stachys species from Greece. Phytochemistry64:743-752. DOI: 10.1016/S0031-9422(03)00386-8.
60. Steliopoulos, P., M. W st, K. P. Adam, and A. Mosandl, 2002. Biosynthesis ofthe sesquiterpene germacrene D in Solidago canadensis: 13C and 2H labeling studies.Phytochemistry 60:13-20. DOI: 10.1016/S0031-9422(02)00068-7.
61. van Beek, T. A., R. Kleis, M. A. Posthumus, and A. van Veldhuizen, 1989. Es-sential oil of Amyris balsamifera. Phytochemistry 28:1909-1911. DOI: 10.1016/S0031-9422(00)97885-3.
62. van Lieshout, E. M., G. H. Posner, B. T. Woodard, and W. H. Peters, 1998. Ef-fects of the sulforaphane analog compound 30, indole-3-carbinol, D-limonene orrelafen on glutathione S-transferases and glutathione peroxidase of the rat digestivetract. Biochim. Biophys. Acta 1379:325-336. DOI: 10.1016/S0304-4165(97)00112-8.
63. Yamahara, J., S. Hatakeyama, K. Taniguchi, M. Kawamura, and M. Yoshi-kawa, 1992. Pungent and anti-ulcer effects of low polar constituents isolated from gin-ger, the dried rhizome of Zingiber officinale Roscoe cultivated in Taiwan. The absolutestereostructure of a new diarylheptanoid. Yakugaku Zasshi 112:645-655.
64 JOURNAL OF HERBS, SPICES & MEDICINAL PLANTS
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nloa
ded
by [
Nip
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ng U
nive
rsity
] at
04:
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9 O
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er 2
014
64. Yang, D., L. Michel, J. P. Chaumont, and J. Millet-Clerc, 1999. Use of caryo-phyllene oxide as an antifungal agent in an in vitro experimental model of onycho-mycosis. Mycopathologia 148:79-82. DOI: 10.1023/A:1007178924408.
65. Zheng, G. Q., P. M. Kenney, and L. K. Lam 1992. Sesquiterpenes fromclove (Eugenia caryophyllata) as potential anticarcinogenic agents. J. Nat. Prod. 55:999-1003.
doi:10.1300/J044v12n03_04
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