The essential oils from the leaves of Artemisia dubia, A. indica, and A. vulgaris growing wild in Nepal were obtained by hydrodistillation and analyzed by GC-MS. The major components in A. dubia oil were chrysanthenone (29.0%), coumarin (18.3%), and camphor (16.4%). A. indica oil was dominated by ascaridole (15.4%), isoascaridole (9.9%), trans-p-mentha-2,8-dien-1-ol (9.7%), and trans-verbenol (8.4%). The essential oil of Nepalese A. vulgaris was rich in α-thujone (30.5%), 1,8-cineole (12.4%), and camphor (10.3%). The essential oils were screened for phytotoxic activity against Lactuca sativa (lettuce) and Lolium perenne (perennial ryegrass) using both seed germination and seedling growth, and all three Artemisia oils exhibited notable allelopathic activity. A. dubia oil showed in-vitro cytotoxic activity on MCF-7 cells (100% kill at 100 μg/mL) and was also marginally antifungal against Aspergillus niger (MIC = 313 μg/mL). DFT calculations (B3LYP/6-31G*) revealed thermal decomposition of ascaridole to be energetically accessible at hydrodistillation and GC conditions, but these are spin-forbidden processes. If decomposition does occur, it likely proceeds by way of homolytic peroxide bond cleavage rather than retro-Diels-Alder elimination of molecular oxygen.
MabberlyDJ. (1997) The Plant Book, 2nd Ed. Cambridge University Press, Cambridge, UK, 57.
2.
GewaliMB. (2008) Aspects of Traditional Medicine in Nepal. Institute of Natural Medicine, University of Toyama, Japan, 17–20.
3.
TamangG. (2003) An ethnobiological study of the Tamang people. Our Nature, 1, 37–41.
4.
HussainS, HoreDK. (2007) Collection and conservation of major medicinal plants of Darjeeling and Sikkim Himalayas. Indian Journal of Traditional Knowledge, 6, 352–357.
5.
TurinM. (2003) Ethnobotanical notes on Thangmi plant names and their medicinal and ritual uses. Contributions to Nepalese Studies, 30, 19–52.
6.
ZhengW, TanR, LiuZ. (1996) Chemical constituents of essential oil of two varieties of Artemisia dubia Wall. ex Bess. Acta Phytotaxonomica Sinica, 34, 410–414.
7.
BhattLR, LimJA, BaekSH. (2005) Antimicrobial activity of Nepalese medicinal plants on skin microbial inflammation pathogens. Journal of Cosmetic and Public Health, 1, 6–9.
8.
ParajuliRR, TiwariRD, ChaudharyRP, GuptaVN. (2005) Fungitoxicity of the essential oils of some aromatic plants of Manang against Alternaria brassicicola. Scientific World, 3, 39–43.
9.
WuH, WeiZ, LiY, LiangC, LiangH. (2009) Analysis of the constituents of volatile oil in Artemisia indica from Guangxi. China Pharmacy 2009-09 doi: CNKI:SUN:ZGYA.0.2009.09.024.
10.
NanoGM, BicchiC, FrattiniC, GallinoM. (1976) On the composition of some oils from Artemisia vulgaris. Planta Medica, 30, 211–215
11.
MichaelisK, VostrowskyO, PauliniH, ZintlR, KnoblochK. (1982) Das ätherische Öl aus Blüten von Artemisia vulgaris L. Zeitschrift für Naturforschung, 37c, 152–158
12.
AokiT, ShigetakaH. (1985) Seasonal variations and geographical differences of volatile constituents from Artemisia vulgaris L. var. indica Maxim. Bulletin of Suzugamine Women's College of Natural Science, 26, 9–14
13.
MisraLN, SinghSP. (1986) α-Thujone, the major component of the essential oil from Artemisia vulgaris growing wild in Nilgiri hills. Journal of Natural Products, 49, 941–941
14.
DüngNX, NamVV, HuongHT, LeclercqPA. (1992) Chemical composition of the essential oil of Artemisia vulgaris L. var. indica Maxim. from Vietnam. Journal of Essential Oil Research, 4, 433–434
15.
MilhauG, ValentinA, BenoitF, MalliéM, BastideJM, PélissierY, BessièreJM. (1997) In vitro antimalarial activity of eight essential oils. Journal of Essential Oil Research, 9, 329–333
16.
AboutablEA, El- AzzounyA, El DahmySI. (1998) Composition of the essential oil of Artemisia vulgaris L. grown in Egypt. Journal of Essential Oil-Bearing Plants, 1, 21–27
17.
PinoJA, RosadoA, FuentesV. (1999) Composition of the essential oil of Artemisia vulgaris L. herb from Cuba. Journal of Essential Oil Research, 11, 477–478
18.
HaggagMY, El TantawyME, AhmedFI, ShamsMM. (2000) Study of chemical composition, antimicrobial and anthelmintic activities of the essential oils of Artemisia vulgaris L. and Santolina chamaecyparissus L. cultivated in Egypt. Azerbaijan Journal of Pharmaceutical Sciences, 26, 23–39
19.
HaiderF, DwivediPD, NaqviAA, BagchiGD. (2003) Essential oil composition of Artemisia vulgaris harvested at different growth periods under Indo-Gangetic Plain conditions. Journal of Essential Oil Research, 15, 376–378
20.
JerkovicI, MastelicJ, MilosM, JuteauF, MasottiV, VlanoJ. (2003) Chemical variability of Artemisia vulgaris L. essential oils originated from the Mediterranean are of France and Croatia. Flavour and Fragrance Journal, 28, 436–440
21.
SefidkonF, JahiliA, RabieM, HamzeheeB, AsriY. (2003) Chemical composition of essential oil of five Artemisia species from Iran. Journal of Essential Oil-Bearing Plants, 6, 41–45
22.
ThaoNTP, ThuyNT, HoiTM, ThaiTH, MuselliA, BighelliA, CastolaV, CasanovaJ. (2004) Artemisia vulgaris L. from Vietnam: Chemical variability and composition of the oil along the vegetative life of the plant. Journal of Essential Oil Research, 16, 358–361
23.
BlagojevićP, RadulovićN, PalićR, StojanovićG. (2006) Chemical composition of the essential oils of Serbian wild-growing Artemisia absinthium and Artemisia vulgaris. Journal of Agricultural and Food Chemistry, 54, 4780–4789
24.
JudžentienėA, BuzelytėJ. (2006) Chemical composition of essential oils of Artemisia vulgaris L. (mugwort) from north Lithuania. Chemija, 17, 12–15
25.
LohaniH, SahS, SinghA, SatiM, YadavRK. (2007) Chemical composition of essential oil of Artemisia vulgaris L. from three different areas of Uttaranchal. Fafai Journal, 9, 69–72
26.
GovindarajS, KumariBDR, CioniPL, FlaminiG. (2008) Mass propagation and essential oil analysis of Artemisia vulgaris. Journal of Bioscience and Bioengineering, 105, 176–183
27.
Baykan ErelS, ReznicekG, ŞenolSG, Karabay YavaşoğulNU, KonyalioğluS, ZeybekAU. (2011) Antimicrobial and antioxidant properties of Artemisia L. species from western Anatolia. Turkish Journal of Biology, 35, doi:10.3906/biy-0912-27
28.
ZhuL, LiY, LiB, LuB, ZhangW. (1995) Artemisia vulgaris Linn. (Compositae). In Aromatic Plants and Essential Constituents (Supplement). Hai Feng Publishing Co., Hong Kong, 135.
29.
BarneyJN, HayAG, WestonLA. (2005) Isolation and characterization of allelopathic volatiles from mugwort (Artemisia vulgaris). Journal of Chemical Ecology, 31, 247–265.
30.
WangJ, ZhuF, ZhouXM, NiuCYLeiCL. (2006) Repellent and fumigant activity of essential oil from Artemisia vulgaris to Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). Journal of Stored Products Research, 42, 339–347.
31.
BhattLR, LimJA, ChaiKY, KangJI, OhHK, BaekSH. (2006) Antioxidative and antimicrobial activities of essential oil from Artemisia vulgaris. Natural Product Sciences, 12, 226–231.
32.
KovátsN, GölöncsérF, ÁcsA, RefaeyM. (2010) Quantification of the antibacterial properties of Artemisia absinthium, A. vulgaris, Chrysanthemum leucanthemum and Achillea millefolium using the Vibrio fischeri bacterial biassay. Acta Botanica Hungarica, 52, 137–144.
33.
DobT, BenabdelkaderT. (2006) Chemical composition of the essential oil of Artemisia herba-alba grown in Algeria. Journal of Essential Oil Research, 18, 685–690.
34.
OuachikhO, BouyanzerA, BouklahM, DesjobertJM, CostaJ, HammoutiB, MajidiL. (2009) Application of essential oil of Artemisia herba alba as green corrosion inhibitor for steel in 0.5 M H2SO4. Surface Review and Letters, 16, 49–54.
35.
KostykBC, BordenJH, GriesG. (1993) Photoisomerization of antiaggregation pheromone verbenone: Biological and practical implications with respect to the mountain pine beetle, Dendroctonus poderosae Hopkins (Coleoptera: Scolytidae). Journal of Chemical Ecology, 19, 1749–1759.
36.
AsfawN, StoresundHJ, SkattebølL, AasenAJ. (2001) Coexistence of chrsanthenone, filifolone and (Z)-isogeranic acid in hydrodistillates. Artefacts! Phytochemistry, 58, 489–492.
37.
CarnatAP, LamaisonJL. (1992) Composition of the essential oil of Artemisia molinieri Quézel, Barbero et R. Loisel. Journal of Essential Oil Research, 4, 635–637
38.
MasottiV, JuteauF, BessièreJM, VianoJ. (2003) Seasonal and phenological variations of the essential oil from the narrow endemic species Artemisia molinieri and its biological activities. Journal of Agricultural and Food Chemistry, 51, 7115–7121.
39.
MirjaliliBF, MeybodyMHH, ArkakaniMM, RustaiyanA, AmeriN, MasoudiS, BamoniriA. (2006) Chemical composition of the essential oil from aerial parts, leaves, flowers and roots of Artemisia persica Boiss. from Iran. Journal of Essential Oil Research, 18, 544–547.
40.
Monzote FidalgoL. (2007) Essential oil from Chenopodium ambrosioides as a promising antileishmanial agent. Natural Product Communications, 2, 1257–1262
41.
MonzoteL, NanceMR, GarciaM, ScullR, SetzerWN. (2011) Comparative chemical, cytotoxicity and antileishmanial properties of essential oils from Chenopodium ambrosioides. Natural Product Communications, 6, 281–286.
42.
CavalliJF, TomiF, BernardiniAF, CasanovaJ. (2004) Combined analysis of the essential oil of Chenopodium ambrosioides by GC, GC-MS and 13C-NMR spectroscopy: Quantitative determination of ascaridole, a heat-sensitive compound. Phytochemical Analysis, 15, 275–279.
43.
WestonLA, BarneyJN, Di TommasoA. (2005) A review of the biology and ecology of three invasive perennials in New York State: Japanese knotweed (Polygonum cuspidatum), mugwort (Artemisia vulgaris) and pale swallow-wort (Vincetoxicum rossicum). Plant and Soil, 277, 53–69.
44.
YamamotoY. (1995) Allelopathic potential of Anthoxanthum odoratum for invading Zoysia-grassland in Japan. Journal of Chemical Ecology, 21, 1365–1373.
45.
AbenavoliMR, SorgonàA, SidariM, BadianiM, FuggiA. (2003) Coumarin inhibits the growth of carrot (Daucus carota L. cv. Saint Valery) cells in suspension culture. Journal of Plant Physiology, 160, 227–237.
46.
AbenavoliMR, SorgonàA, AlbanoS, CaccoG. (2004) Coumarin differentially affects the morphology of different root types of maize seedlings. Journal of Chemical Ecology, 30, 1871–1883.
47.
NishidaN, TamotsuS, NagataN, SaitoCSakaiA. (2005) Allelopathic effects of volatile monoterpenoids produced by Salvia leucophylla: Inhbition of cell proliferation and DNA synthesis in the root apical meristem of Brassica campestris seedlings. Journal of Chemical Ecology, 31, 1187–1203.
48.
YumiO, KeikoY, KatsuichiroK. (2011) Allelopathic activity of camphor released from camphor tree (Cinnamomum camphora). Allelopathy Journal, 27, 123–232.
49.
KennedyJE, DavéPC, HarbinLN, SetzerWN. (2011) Allelopathic potential of Sassafras albidum and Pinus taeda essential oils. Allelopathy Journal, 27, 111–122.
50.
YenYP, YehMJ, HsiaoWF. (2007) Synthesis and nematicidal activity of ascaridole derivatives against Meloidogyne incognita and Aphelenchoides besseyi. Journal of Pesticide Science, 32, 49–52
51.
TorresMCM, AssunçãoJC, SantiagoGMP, Andrade-NetoM, SilveiraER, Costa-LotufoLV, BezerraDP, FilhoJDBM, VianaFA, PessoaODL. (2008) Larvicidal and nematicidal activities of the leaf essential oil of Croton regelianus. Chemistry and Biodiversity, 5, 2724–2728
52.
MonzoteL, StambergW, StaniekK, GilleL. (2009) Toxic effects of carvacrol, caryophyllene oxide, and ascaridole from essential oil of Chenopodium ambrosioides on mitochondria. Toxicology and Applied Pharmacology, 240, 337–347
53.
ChuSS, HuJF, LiuZL. (2011) Composition of essential oil of Chinese Chenopodium ambrosioides and insecticidal activity against maize weevil, Sitophilus zeamais. Pest Management Science, 67, 714–718
54.
BaiCQ, LiuZL, LiuQZ. (2011) Nematicidal constituents from the essential oil of Chenopodium ambrosioides aerial parts. E. Journal of Chemistry, 8, S143–S148.
55.
Jiménez-OsornioFMVZJ, KumamotoJ, WasserC. (1996) Allelopathic activity of Chenopodium ambrosioides L. Biochemical Systematics and Ecology, 24, 195–205.
56.
De MartinoL, ManciniE, Rolim de AlmeidaLF, De FeoV. (2010) The antigerminative activity of twenty-seven monoterpenes. Molecules, 15, 6630–6637.
57.
KoitabashiR, SuzukiT, KawazuT, SakaiA, KuroiwaH, KuroiwaT. (1997) 1,8-Cineole inhibits root growth and DNA synthesis in the root apical meristem of Brassica campestris L. Journal of Plant Research, 110, 1–6
58.
RomagniJG, AllenSN, DayanFE. (2000) Allelopathic effects of volatile cineoles on two weedy plant species. Journal of Chemical Ecology, 26, 303–313
59.
SinghHP, BatishDR, KaurS, AroraK, KohliRK. (2002) Allelopathic effect of two volatile monoterpenes against bill goat weed (Ageratum conyzoides L.)Crop Protection, 21, 347–350.
60.
HalliganJP. (1975) Toxic terpenes from Artemisia californica. Ecology, 56, 999–1003
61.
JassbiAR, ZamanizadehnajariS, BaldwinIT. (2010) Phytotoxic volatiles in the roots and shoots of Artemisia tridentata as detected by headspace solid-phase microextraction and gas chromatographic-mass spectrometry analysis. Journal of Chemical Ecology, 36, 1398–1407.
62.
SteinfeldJI, FranciscoJS, HaseWL. (1999) Chemical Kinetics and Dynamics, 2nd Ed. Prentice Hall, Upper Saddle River, New Jersey, USA, 247–250.
63.
KobaK, CatherineG, RaynaudC, ChaumontJP, SandaK, LaurenceN. (2009) Chemical composition and cytotoxic activity of Chenopodium ambrosioides L. essential oil from Togo. Bangladesh Journal of Scientific and Industrial Research, 44, 435–440.
64.
NelsonEK. (1920) The composition of oil of Chenopodium from various sources. Journal of the American Chemical Society, 42, 1204–1208
65.
ZandR, MesrobianRB. (1955) Polymerization of methacrylonitrile initiated by ascaridole and dihydroascaridole. Journal of the American Chemical Society, 77, 6523–6524.
66.
ToncerO, BasbagS, KaramanS, DirazE, BasbagM. (2010) Chemical composition of the essential oils of some Achillea species growing wild in Turkey. International Journal of Agriculture and Biology, 12, 527–530.
67.
AdamsRP. (2007) Identification of Essential Oil Components by Gas Chromatography / Mass Spectrometry, 4th Ed. Allured Publishing, Carol Stream, Illinois.
68.
ZarJH. (1996) Biostatistical Analysis, 3rd Ed. Prentice Hall, Upper Saddle River New Jersey, 123–137.
69.
ReedLJ, MuenchH. (1938) A simple method of estimating fifty percent end points. American Journal of Hygiene, 27, 493–497.
70.
SahmDH, WashingtonJA. (1991) Antibacterial susceptibility tests: Dilution methods. In Manual of Clinical Microbiology. BalowsA, HauslerWJ, HerrmannKL, IsenbergHD, ShamodyHJ (Eds.). American Society for Microbiology, Washington DC, USA.
71.
SouleHD, VazguezJ, LongA, AlbertS, BrennanM. (1973) A human cell line from a pleural effusion derived from a breast carcinoma. Journal of the National Cancer Institute, 51, 1409–1416.
72.
SetzerWN, SetzerMC, HopperAL, MoriarityDM, LehrmanGK, NiekampKL, MorcombSM, BatesRB, McClureKJ, StessmanCC, HaberWA. (1998) The cytotoxic activity of a Salacia liana species from Monteverde, Costa Rica, is due to a high concentration of tingenone. Planta Medica, 64, 583.
73.
FerrariM, FornasieroMC, IsettaAM. (1990) MTT colorimetric assay for testing macrophage cytotoxic activity in vitro. Journal of Immunological Methods, 31, 165–172.
74.
RohlfJF. (2005) NTSYSpc, Numerical Taxonomy and Multivariate Analysis System. Applied Biostatistics Inc., New York.
75.
Spartan ‘10 for Windows (2010) Wavefunction, Inc., Irvine, California.
76.
BeckeAD. (1993) Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 98, 5648–5652
77.
LeeC, YangW, ParrRG. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785–789.
78.
HehreWJ, RadomL, SchleyerPvR. (1986) Ab initio Molecular Orbital Theory. Wiley, New York.
