General Information of Natural Product (ID: NP0274)
  Natural Product Name
Carvone
  Synonyms
CARVONE; 99-49-0; 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone; Karvon; 1-Carvone; dl-Carvone; Carvol; D-Cavone; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-; 2-Methyl-5-isopropenyl-2-cyclohexenone; 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one; 6,8(9)-p-Menthadien-2-one; p-Mentha-6,8-dien-2-one; NCI-C55867; 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one; 6,8-p-Menthadien-2-one; 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one; p-Mentha-6,8-dien-2-one, (R)-(-)-; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)-; CHEBI:38265; NSC6275; MFCD00062996; Carvone (natural); Carvone [ISO]; l-6,8(9)-p-Menthadien-2-one; FEMA Number 2249; 6,8-p-Menthadien-2-on; d-p-Mentha-1(6),8-dien-2-one; FEMA No. 2249; HSDB 707; (+-)-Carvone; NSC 6275; EINECS 202-759-5; delta(sup 6,8)-(9)-terpadienone-2; BRN 1364206; Carvon; a carvone; AI3-08877; d-p-Mentha-6,8,(9)-dien-2-one; .alpha.-Carvone; delta-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 5-isopropenyl-2-methylcyclohex-2-en-1-one; (+/-)-carvone; 5-isopropenyl-2-methyl-cyclohex-2-en-1-one; 2-Methyl-5-(1-propen-2-yl)-2-cyclohexenone; DSSTox_CID_27426; DSSTox_RID_82339; NCIOpen2_001348; DSSTox_GSID_47426; SCHEMBL39408; 4-07-00-00316 (Beilstein Handbook Reference); CHEMBL15676; DTXSID8047426; AMY4152; p-mentha-1(6),8-dien-2-one; HMS1789N08; NSC-6275; NSC93738; Tox21_302547; 6982AC; BBL010103; NSC-93738; STK801456; AKOS000121377; AKOS016843655; Carvone 100 microg/mL in Acetonitrile; MCULE-6744252540; CAS-99-49-0; NCGC00256915-01; WLN: L6V BUTJ B1 EY1 & U1; .delta.(sup 6,8)-(9)-Terpadienone-2; AS-10471; NCI60_008753; SY010704; SY012922; SY274718; 2-Methyl-5-isopropenyl-2-cyclohexen-1-one; DB-054736; CS-0033814; FT-0600385; FT-0605067; FT-0658046; O10834; (-)-2-Methyl-5-isopropenyl-2-cyclohexen-1-one; A858458; Q416800; .delta.-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one; 5-Isopropenyl-2-methyl-2-cyclohexen-1-one, (R)-; W-100036; 2-methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-one
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  Formula C10H14O
  Weight 150.22
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3
  InChI Key ULDHMXUKGWMISQ-UHFFFAOYSA-N
  Isomeric SMILES CC1=CCC(CC1=O)C(=C)C
  Canonical SMILES CC1=CCC(CC1=O)C(=C)C
  External Links PubChem ID 7439
CAS ID 99-49-0
NPASS ID NPC58970
HIT ID C0579
CHEMBL ID CHEMBL15676
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [1]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
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               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
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               Factor Part Location NP Content
 
Artemisia annua accessions Suraksha
Aerial parts India
NP Content: 0.1 %
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: <0.05 %
      Species Name: Artemisia verlotiorum
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Plant material of A. verlotiorum was harvested near Marseille (France) in May (before blooming) and November (full flowering) 2000.
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               Factor Function
For the oil from the vegetative plants, 50 compounds, representing 99.8% of the oil were characterized. Fifty-nine compounds, representing 99.6% of the oil were identified in the oil from flowering plants. In both cases, the constituents were mainly oxygenated monoterpenes (74% and 88%). The composition of each oil showed only a few differences, as the main components were alpha-thujone (55% and 44%), 1,8-cineole (5% and 15%), beta-caryophyllene (13% and 7%) and beta-thujone (5% and 11%), in the oils of the vegetative plant and flowering plant, respectively. The proportions of the oxygenated compounds seemed to increase during flowering.
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               Factor Part Location NP Content
 
Aerial part: before blooming stage
Aerial parts Marseille, France
NP Content: 0.3 %
 
Aerial part: full flowering stage
Aerial parts Marseille, France
NP Content: 1 %
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [3]
              Species Info Factor Info
               Experiment Detail
Aerial parts of endemic pichana were harvested in December 1996 at different localities of northern Patagonia. Origin: Planicie Banderita, Dept. Confluencia, Province of NeuquCn. Habitat: altitude, 327 m; average temperature in the station, 21.8 ℃; annual precipitation, 125 mm; sandy soils. Aerial parts (5 kg, 2 kg of dried material;humidity, 11%) from four well developed plants at the fullflowering stage (December, 1996). Sample 2 : Origin: RincBn de 10s; Sauces, Dept. of Pehuenclies, Province of Neuqukn. Habitat: altitude, 750 m; average temperature in the station, 20.9 ℃; annual precipitation, 147 mm; sandy and gritty salty soils. Aerial parts (5 kg, 1.85 kg of dried material, humidity, 10%), from two well developed plants at the full flowering stage, and after several days copious rains (December, 1996). Sample 3: Origin: Coronel GBmez, Dept. General Roca, Province of Rio Negro. Habitat: altitude, 242 m; average temperature in the station, 22.5 ℃; annual precipitation, 179 mm; sandy and stony soils. Aerial parts (4.5 kg, 1.3 kg of dried material, humidity, 9%), from 12 young plants at the beginning flowering stage (December, 1996).
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               Factor Function
Fifty-four components, representing approximately 84.6-97.4% of the oil samples, were identified. The samples consisted mainly of hydrocarbons and oxygenated monoterpenes. The major constituents were limonene (28.7-56.7%), 6R-7R-bisabolone (3.2-9.1%), sabinene (0.1-11.0%) and citronellal (2.4-5.2%). Significant differences among the content of the three samples could be the result of changes in the climatic conditions (sample 2: Rincon de los Sauces, Province of Neuquen, after strong rains) or by translocations in different parts of the plant (sample 3: Coronel Gomez, Province of Rio Negro, more leaves and less stems).
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               Factor Part Location NP Content
 
Locality: Planicie Banderita, Province of Neuquen; Altitude 327 m
Aerial parts Patagonia, Argentina
NP Content: 1.7 %
 
Locality: Rincon de los Sauces, Province of Neuquen; Altitude 750 m
Aerial parts Patagonia, Argentina
NP Content: 1.9 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
Aerial parts Patagonia, Argentina
NP Content: 1.9 %
      Species Name: Citrus sinensis (Hongjiang)
  Factor Name: Variety Comparison [4]
              Species Info Factor Info
               Experiment Detail
Four kinds of fresh sweet oranges were obtained in the same season, November 2000, in Guangzhou. Citrus sinensis var. Hongjiang (called 'hong jiang chen' in Chinese) and C. sinensis Osbeck var. Anliu (called 'luo gang chen') were obtained at an orchard in Luo gang in Guangzhou (25 km from the center of Guangzhou). Citrus sinensis var. Sihui (called 'sihui ju') was harvested at the Shigou Experimental Farm in Sihui City in Guangdong Province (75 km far away from Guangzhou). Citrus sinensis var. Washington navel (called 'qi chen') which was produced in Jiangxi Province (200 km from Guangzhou; bordering Guangdong Province), was purchased at the wholesale market in Guangzhou. All oranges were kept in a cold room until prepared a few days later.
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               Factor Function
The peel oil compositions of four kinds of sweet oranges in China, Citrus sinensis Osbeck var. Hongjian, C. sinensis Osbeck var. Anliu, C. sinensis Osbeck var. Sihui and C. sinensis Osbeck var. Washington navel, were investigated by GC and GC/MS. The essential oils were extracted by cold-pressing method. Forty-two to 53 compounds were quantitatively determined for each variety. Their percentages, respectively, were: > 97.3%, > 98.4%, > 97.5% and > 98.0% in hydrocarbons; > 1.5%, > 0.7%, > 0.8% and > 0.9% in total aldehydes; 0.8%, 0.5%, 0.5% and 0.5% in alcohols. Either cis-or trans-limonene oxide was detected in small amounts in each of the four samples, with Hongjiang containing both limonene oxides. delta-3-Carene was commonly quantified at a level of 0.1% in all the samples. The content of aliphatic aldehydes, including octanal, nonanal, decanal and dodecanal, exceeded that of terpene aldehydes, such as neral and geranial in Hongjiang (0.9%) and Washington navel (0.6%), whereas the aliphatic aldehydes in Anliu and Sihui were present to a lesser degree than the terpene aldehydes. Either alpha- or beta-sinensal was detected in trace amounts in each of the four samples. Linalool was the major alcohol in all the samples. Nootkatone was not detected.
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               Factor Part Location NP Content
 
Citrus sinensis var. Washington navel
Fruits China
NP Content: > 0.005; < 0.05 %
      Species Name: Coriandrum sativum
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Two samples (20 kg each) of mature coriander (Coriandrum sativum L.) fruits were used for this study. The first was purchased from a spice market of Korba in Tunisia (Tn), the second, from Canada (Can), was supplied by General Herboristerie Laboratory (Marseille, France).
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               Factor Function
The first from Tunisia (Tn) and the second from Canada (Can). The highest essential oil yield was observed for Can with 0.44% (w/w) and 0.37% (w/w) for Tn. Forty-five compounds were identified in the essential oils and the main compound of both samples was linalool. The total phenol contents varied between two coriander fruit samples; Can sample presented high polyphenol contents (15.16 mg GAE/g) compared with Tn one (12.10 mg GAE/g). Significant differences were also found in total tannin contents among representing 0.7 mg GAE/g in Can and 0.34 mg GAE/g in Tn. The highest contents of total flavonoids were observed in Can sample with 13.2 mg CE/g.
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               Factor Part Location NP Content
 
Locality: Canada
Fruits Canada
NP Content: 0.1 %
 
Locality: Korba, Tunisia
Fruits Tunisia
NP Content: 0.1 %
      Species Name: Fortunella japonica Lour. Swingle
  Factor Name: Heat Stress Treatment [6]
              Species Info Factor Info
               Experiment Detail
The investigation was carried out on kumquat [Fortunella japonica Lour. Swingle] cv. Ovale, grown in an experimental orchard located in central western Sardinia (Italy), receiving standard horticultural practices. Fruits were randomly harvested in March, when commercially mature (total soluble solids content/titratable acidity ratio = 5.24) and delivered to the laboratory immediately after harvest. Medium-size fruits free from defects were selected, placed into boxes (100 fruits per box), and grouped into two treatment groups of three boxes each (replications). The fruits of the first group were untreated (control fruit), whereas fruits of the second group were subjected to a standard treatment, water dipping at 50 &#8451 for 2 min, for extending the postharvest life of kumquat fruit. Dip treatment was performed as described previously. After treatments, fruits were allowed to dry at room temperature and stored for 21 days at 17 &#8451 and ca. 80% relative humidity (simulated shelf-life conditions). All analyses were performed following treatments and at the end of storage.
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               Factor Function
The concentration of the essential oil and the relative percentage of the individual components of the essential oil were not affected by HWD except for the minor compound p-menta-1,5-dien-1-ol, which increased after HWD.
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               Factor Part Location NP Content
 
Control: stored for 0 days
fruit Sardinia, Italy
NP Content: 0.23 %
 
HWD (Hot Water Dipping treatment: water dipping at 50 ℃ for 2 min) : stored for 0 days
fruit Sardinia, Italy
NP Content: 0.24 %
 
Control: stored for 21 days at 17 ℃
fruit Sardinia, Italy
NP Content: 0.15 %
 
HWD: stored for 21 days at 17 ℃
fruit Sardinia, Italy
NP Content: 0.21 %
      Species Name: Ichthyothere terminalis
  Factor Name: Locality Variation [7]
              Species Info Factor Info
               Experiment Detail
The leaves and stems of Ichthyothere terminalis were collected at Marapanim, PA (sample A) and Manaus, AM (sample B).
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               Factor Function
The chief constituent found in the leaf oil of sample of, I. terminalis collected at Marapanim (PA) was sabinene (18.0%). The leaf oil of I. terminalis collected at Manaus (AM) was dominated by alpha-pinene (19-8%), sabinene (14.8%) and limonene (35.8%), while the main components identified in the stem oil were alpha-pinene (13.9%) and limonene (20.0%).
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               Factor Part Location NP Content
 
Leaves: Manaus, Brazil
Leaves Brazil
NP Content: 1.8 %
 
Leaves: Marapanim, Brazil
Leaves Brazil
NP Content: 0.7 %
      Species Name: Lavandula latifolia
  Factor Name: Developmental Stage Variation [8]
              Species Info Factor Info
               Experiment Detail
Plant material: Samples of L. latifolia were collected in August 1998 during the full flowering period (L/La) and in October 1998 during the fruiting period (L/Lb) from three different spike lavender populations located into the Cazorla, Segura y Las Villas Natural Park (Jaen province, Spain). The plant material from each population consisted of the twigs of several single plants. L/La (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: August 14, 1998, Phenological stage: Flowering); L/Lb (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: October 15, 1998, Phenological stage: Fruiting).
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               Factor Function
The small amounts of linalool needed to match the standard can be reached in a natural way (from full flowering to fruiting) which means it is important to choose the most convenient time of harvest in the studied area.
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Whole plant Spain
NP Content: <0.1 %
      Species Name: Mentha longifolia
  Factor Name: Locality Variation [9]
              Species Info Factor Info
               Experiment Detail
Plants were collected in the Inner plain, the Sharon plain and the kava valley.
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               Factor Function
The major constituent of all three oils was found to be 1,8-cineole (26.4-34.5%) followed by menthone (10.0-16.7%), pulegone (7.0-7.5%), and isomenthone (4.7-7.8%). Despite some differences in the component proportions, the plants of all three populations clearly belong to the same chemotype.
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               Factor Part Location NP Content
 
Locality: Sharon plain, Israel
Aerial parts Israel
NP Content: 0.5 %
 
Locality: Arava valley, Israel
Aerial parts Israel
NP Content: 0.2 %
 
Locality: Inner plain, Israel
Aerial parts Israel
NP Content: 0.2 %
      Species Name: Mentha piperita
  Factor Name: Month Variation [10]
              Species Info Factor Info
               Experiment Detail
The peppermint material was obtained from ten cultivation sites (four growers) around Le Mayetde-Montagne, Allier, France (altitude 400 to 800 m). The individual surface areas ranged from 0.6 to 2.5 ha for an overall surface of 8 to 10 ha. Planting density was 30,000 plants/ha.
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               Factor Function
A marked inversion of the menthol/menthone ratio was observed according to harvesting time. The late blooming period gave oils rich in menthol. A second harvest gave a high-quality oil and increased overall yield. Pre-drying did not affect the chemical composition of the oil obtained but allowed larger amounts of plant material to be distilled. In particular, Bouverat-Bernier showed an increase in oil yield up to flowering and a fall thereafter and an increase of levels of menthol and menthyl acetate while those of menthone decreased from June to September. For Hungarian peppermint, the levels of menthone were always greater than those of menthol regardless of harvest time.
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               Factor Part Location NP Content
 
Harvesting time: 14-June
Whole plant Allier, France
NP Content: trace %
 
Harvesting time: 5-July
Whole plant Allier, France
NP Content: trace %
 
Harvesting time: 29-July
Whole plant Allier, France
NP Content: trace %
 
Harvesting time: 15-August
Whole plant Allier, France
NP Content: 0.2 %
 
Harvesting time: 15-September
Whole plant Allier, France
NP Content: 0.2 %
 
Harvesting time: 30-October
Whole plant Allier, France
NP Content: 0.5 %
  Factor Name: Cultivar Comparison [11]
              Species Info Factor Info
               Experiment Detail
Dry leaves of Menlba piperita L. 'Kliment-63' and 'Zefir' of 1997 crop were used.
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               Factor Function
The oil yield from 'Zefir' was 0.97% and that from 'Kliment-63' was 0.54%. The oil from 'Zefir' was found to be rich in menthol (46.2-50.2%) and menthyl acetate (16.8-22.5%). In the oil from 'Kliment-63,' the content of these components was lower, while the menthone content was higher (20.0-23.1%).
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               Factor Part Location NP Content
 
Mentha piperita cv. Kliment-63
Leaves Bulgaria
NP Content: 0.8 %
 
Mentha piperita cv. Zefir
Leaves Bulgaria
NP Content: <0.1 %
      Species Name: Micromeria biflora
  Factor Name: Seasonal Variation [12]
              Species Info Factor Info
               Experiment Detail
The aerial parts of M. biflora collected during November 1993 and June 1994 were used for the investigation.
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               Factor Function
The major constituents of the oil were neral (25.3-32.2%) and geranial (26.7-41.3%). The oil produced in the winter was found to contain higher amounts of oxygenated monoterpenes than the oil produced in the summer.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Aerial parts South India
NP Content: 0.07 %
 
Harvesting time: Winter
Aerial parts South India
NP Content: 0.07 %
      Species Name: Ocimum basilicum L
  Factor Name: Chemotype Comparison [13]
              Species Info Factor Info
               Experiment Detail
The study was conducted in North-Central Anatolia under semi arid conditions. Seeds of 18 basil landraces (O. basilicum L.) were collected from local farms and home gardens in Turkey. To examine essential oil composition of the basil landraces without environmental influences, the plants were grown under identical (same environmental and soil conditions) conditions. Seeds were sown on a medium (1:1:1 washed sand, horse manure and field soil) in greenhouse conditions on March 25, 2003. Seedlings were grown until the 3-5 leaf stage. The seedlings were transplanted into pilots in the Gaziosmanpasxa University Experimental Research Station on May 15, 2003. The plants were harvested at the full blooming stage and dried at 35 ℃ for essential oil isolation.
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               Factor Function
Variation of essential oils in the landraces was subjected to cluster analysis, and seven different chemotypes were identified. They were (1) linalool, (2) methyl cinnamate, (3) methyl cinnamate/linalool, (4) methyl eugenol, (5) citral, (6) methyl chavicol (estragol), and (7) methyl chavicol/citral. Methyl chavicol with high citral contents (methyl chavicol/citral) can be considered as a 'new chemotype' in the Turkish basils.
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               Factor Part Location NP Content
 
Chemotype (methyl eugenol-rich type)
Leaves Turkey
NP Content: 0.5 %
      Species Name: Rosmarinus eriocalyx
  Factor Name: Locality Variation [14]
              Species Info Factor Info
               Experiment Detail
The leaves of R. eriocalyx were harvested at random from two localities of the forest in the North and South ranges of Boutaleb in Algeria at different altitudes during the full flowering stage. Sample N3(Locality: Northern slope; Altitude (m): 850; Collection date: Mar 20,1993); Sample S3(Locality: Southern slope; Altitude (m): 850; Collection date: Mar 20,1993).
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               Factor Function
Concerning the alcohols, the highest amount of 1,8-cineole (11.4%) coincided with a very low amount of terpinen-4-ol(1.0%) in sample N3 as well as with a generally low concentration of hydrocarbons (apart from camphene and pinene) in all samples of R. eriocalyx.
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               Factor Part Location NP Content
 
Locality: Southern slope, Boutaleb range, Algeria; Altitude 850 m + Harvesting time: 20-Mar-1993
Leaves Algeria
NP Content: trace %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [15]
              Species Info Factor Info
               Experiment Detail
Aerial parts of both varieties(Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and Salvia euphratica Montbret et Aucher ex Benth. var. leiocalycina) were collected in Malatya, Turkey in June 1999.
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               Factor Function
Ninety-five compounds in var. euphratica and 94 compounds in var. leiocalycina were characterized representing 93% and 95% of the total components detected, respectively, with 1,8-cineole (13.8% and 15.2%) and myrtenyl acetate (15.9% and 13.9%) as main constituents.
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               Factor Part Location NP Content
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: 1.8 %
      Species Name: Satureja icarica
  Factor Name: Locality Variation [16]
              Species Info Factor Info
               Experiment Detail
The plant material was collected from different regions of Turkey. B = Canakkale: Gokceada, Ulukaya hill, August 1995; C = Canakkale: Gokceada, Doruktepe hill, August 1995; D = Canakkale: Gokceada, Kekliktepe hill, August 1995.
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               Factor Function
Carvacrol (52-56%) was found as the major component of these oils.
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               Factor Part Location NP Content
 
Locality: Doruktepe hill, Gokceada, Turkey
Aerial parts Turkey
NP Content: 0.2 %
 
Locality: Ulukaya hill, Gokceada, Turkey
Aerial parts Turkey
NP Content: 0.5 %
 
Locality: Kekliktepe hill, Gokceada, Turkey
Aerial parts Turkey
NP Content: 0.2 %
      Species Name: Satureja thymbra
  Factor Name: Month Variation; Developmental Stage Variation [17]
              Species Info Factor Info
               Experiment Detail
Fresh plant materials were obtained in 2004 and 2005. S. thymbra 1(vegetative stage: just before flowering, date: June 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 2(vegetative stage: full flowering, date: July 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 3(vegetative stage: after flowering, date: Aug 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 4(vegetative stage: fruiting, date: Sept 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 5(vegetative stage: fruiting, date: Nov 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 6(vegetative stage: fruiting, date: Feb 7, 2005, location: Mt. Immitos, altitude(m): 350); S. thymbra 7(vegetative stage: before flowering, date: May 7, 2005, location: Mt. Immitos, altitude(m): 350); S. parnassica 8(vegetative stage: before flowering, date: June 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 9(vegetative stage: just before flowering, date: July 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 10(vegetative stage: full flowering, date: Aug 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 11(vegetative stage: after flowering, date: Sept 16, 2004, location: Mt. Parnon, altitude(m): 1800).
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               Factor Function
It is evident that the phytochemical content of the essential oils for both Satureja species varied greatly, depending on the period examined, and showed large prevalence of phenolic content. It must also be pointed out that regardless of the vegetative stage of the plant collected, the sum of the two isomeric phenol monoterpenes (carvacrol and thymol) and their biosynthetic monoterpene precursors p-cymene and gamma-terpinene represented always the bulk of each essential oil (~76%). More specificallysfor both species-during their premature vegetative stage, gamma-terpinene constitutes the major component of their essential oils. The approach of the flowering period results in the simultaneous gradual diminishment of monoterpene precursors and the prevalence of their phenolic metabolites. Thus, essential oils obtained from plants collected during the 'just before their flowering' stage contain thymol as their major component, which constitutes 27.88 and 38.51% of the total oil content for S. thymbra and S. parnassica, respectively. On the other hand, during their full flowering period carvacrol prevails as the major component, accounting for 39.10% for S. thymbra and for 34.61% for S. parnassica. The end of the flowering stage delineates a sharp decrease of carvacrol levels and the predominance of thymol as the major component of the essential oils. A few months later, as the premature vegetative stage approached, the level of gamma-terpinene was restored. The content of p-cymenesthe other major monoterpene precursor-fluctuated seasonally in a manner similar to that shown by gamma-terpinene. Other monoterpene hydrocarbons such as myrcene and alpha-terpinene were also detected in smaller quantities, whereas various monoterpene alcohols such as linalool, borneol, and terpin-4-ol were found mainly in the oils obtained after the flowering stage. Finally, it is notable that the oils obtained during the just before the full flowering period contain beta-caryophyllene as one of their major components.
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               Factor Part Location NP Content
 
Harvesting time: full flowering satge; 7-June-2004
Leaves, stems and flowers Mt. Immitos, Continental Greece
NP Content: <0.05 %
 
Harvesting time: after flowering satge; 7-August-2004
Leaves, stems and flowers Mt. Immitos, Continental Greece
NP Content: 0.05 %
 
Harvesting time: fruiting satge; 7-September-2004
Leaves and stems Mt. Immitos, Continental Greece
NP Content: 0.09 %
 
Harvesting time: fruiting satge; 7-November-2004
Leaves and stems Mt. Immitos, Continental Greece
NP Content: <0.05 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [18]
              Species Info Factor Info
               Experiment Detail
Plant material and isolation procedure: Aerial parts of the plant were collected from two regions, from Kazeroon in southern Iran and Shahr-e-kord in western Iran at the time of flowering in June 2002.
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               Factor Function
The main components of the oil of S. pilifera collected from Kazeroon, in southern Iran, were spathulenol (15.8%), cis-chrysanthenol (15.3%), beta-caryophyllene (8.4%) and cis-chrysanthenyl acetate (6.9%), while for the plant collected from Shahr-e-kord, in western Iran, they were cis-chrysanthenyl acetate (21.8%), linalool (18.9%), terpinen-4-ol (11.9%) and cis-chrysanthenol (9.2%).
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               Factor Part Location NP Content
 
Locality: Kazeroon, southern Iran
Aerial parts Iran
NP Content: 0.2 %
      Species Name: Talauma ovata
  Factor Name: Month Variation [19]
              Species Info Factor Info
               Experiment Detail
Talauma ovata was collected from October 2003 to February 2005. Leaves and trunk bark from the same set of plants were collected in the four seasons: spring (October 15th, 2003), autumn (April 10th, 2004), winter (July 17th, 2004) and summer (February 15th, 2005). In addition, trunk bark was also collected on January 22nd, 2004 (summer). The plant material was harvested from wild-growing population in Santos Dumont City, Minas Gerais State, Brazil, (21° 28′ 03″ S, 43° 39′ 26″ W), at 1000 m of altitude.
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               Factor Function
In each season the composition of trunk bark oils was similar to leaf oils, with mainly quantitative differences. However considerable seasonal variation was observed. Significant levels of monoterpenes were found only in autumn. The content of oxygenated sesquiterpenes was highest in samples of spring (October) and decreased in summer (January and February), reaching the lowest level in autumn (April) and increasing again in winter (July). In trunk bark oils the main constituents were: spathulenol, alpha-eudesmol, linalool, trans-beta-guaiene and caryophyllene oxide. The major component in all samples of trunk bark was spathulenol. Its level was highest in October (46.8%), decreased in January (33.3%), remained stable in April and July (18.0%) and increased again in February of next year (27.7%). Levels of alpha-eudesmol were high in spring (13.0%) and autumn (11.5%). Linalool peaked only in April, while trans-beta-guaiane peaked in July (11.1%). Caryophyllene oxide ranged between 10.7-2.0%. The level was highest in January, decreased regularly until July and increased slightly again in October. In leaf oils the main components were: spathulenol, germacrene B, germacrene D, caryophyllene oxide and viridiflorol. Spathulenol was the major component in sample of spring (34.4%), but decreased gradually until winter, when reached the lowest level (9.4%). Caryophyllene oxide showed a similar pattern, varying from 14.1% (spring) to 2.4% (winter). An inverse effect was observed for viridiflorol, which increased from 0.1% in October to 13.7% in July. Important levels of alpha-eudesmol were observed in October (12.3%) and February (9.5%). The percentage of germacrene D was highest in summer, while germacrene B showed high amounts in autumn and winter. The seasonal changes in oil composition of T. ovata can be associated with cycle of life of plant (flowering, fruiting and vegetative stages) and climatic parameters such as intense raining in the spring and summer.
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               Factor Part Location NP Content
 
Leaf: (Harvesting time: April)
Leaves Brazil
NP Content: 0.7 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [20]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected during the flowering period in July 2002 from the Dumluca Mountain in the vicinity of Divrigi village of Sivas city at 1900 m altitude and Saksagan Gorge in Saimbeyli village of Adana city at 1900 m altitude.
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               Factor Function
The flower, stem and root oils of T. cadmeum ssp. orientale collected from the Adana location were characterized with alpha-thujone (25%, 5.2%), cis-linalool oxide (6.8%, 12.8%), trans-chrysanthenyl acetate (5.8%, 8.5%) for flower and stem oils, and beta-eudesmol (10.3%, 6.2%, 13.8%); in addition, stem oil contained 1,8-cineole (6.6%) and root oil contained hexadecanoic acid (6.0%), spathulenol (5.8%) and beta-muurolol (5.3%). The flower and stem oils of T. cadmeum ssp. orientale collected from the Sivas location were characterized with camphor (25.9%, 14.8%), borneol (15.4%, 25.8%) and alpha-thujone (7.8%, 5.5%); in addition, stem oil contained 1,8-cineole (7.4%) and root oil contained nonacosane (16.2%), spathulenol (6.8%) and hexadecanoic acid (5.8%).
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               Factor Part Location NP Content
 
Flower: (Locality: Adana, Turkey)
Flowers Adana, Turkey
NP Content: <0.1 %
 
Stem: (Locality: Adana, Turkey)
Stems Adana, Turkey
NP Content: 0.1 %
 
Flower: (Locality: Sivas, Turkey)
Flowers Sivas, Turkey
NP Content: 0.9 %
      Species Name: Thymus carnosus
  Factor Name: Month Variation; Developmental Stage Variation [21]
              Species Info Factor Info
               Experiment Detail
The aerial parts of samples from collective populations of T. carnosus were collected during the vegetative phase (February 2000), at the beginning of the flowering phase (May 2000) and during the flowering phase (July 2000) at Quinta do Lago (Algarve). AQLM: collected in May, beginning of flowering phase; AQLJ: collected in July, flowering stage; AQLF: collected in Feb, vegetative stage.
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               Factor Function
All the oil samples collected in Quinta do Lago (QL) were dominated by borneol (26-31%) and camphene (9-18%), but the third main component varied according to the harvesting period. Bornyl acetate was the third main component (9-13%) in the flower oil and in the aerial parts oils collected in May and July, whereas terpinen-4-ol (8%) was the third main component in oil collected in February from vegetative phase plant material. A fourth main component, alpha-pinene (4-9%), was also present in relative high amounts in the QL oils.
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               Factor Part Location NP Content
 
Harvesting time: Feb, vegetative stage
Aerial parts Quinta do Lago, Portugal
NP Content: 0.2 %
 
Harvesting time: May, beginning of flowering satge
Aerial parts Quinta do Lago, Portugal
NP Content: 0.1 %
 
Harvesting time: July, flowering stage
Aerial parts Quinta do Lago, Portugal
NP Content: 0.1 %
 
Harvesting time: July, flowering stage
Flowers Quinta do Lago, Portugal
NP Content: 0.1 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [22]
              Species Info Factor Info
               Experiment Detail
Aerial parts of the plant were collected from four localities: A = Kirklareli: Karadere in May 1991; B = Kirklareli: Karahamza Village in May 1990; C = Kirklareli: Evciler Village on 13 June 1993; D = Kirklareli: Korukoy on 25 May 1994
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               Factor Function
The four oils obtained from plants collected in different localities of the same region gave quite different compositions as follows: A: thymol (10.5%), 1,8-cineole (9.96%), p-cymene (9.48%), carvacrol (5.28%); B: beta-caryophyllene (29.50%), carvacrol(20.59%); C: thymol (34.7%), beta-caryophyllene (12.74%), carvacrol (5.24%); D: beta-caryophyllene (56.48%), germacrene D (11.12%), carvacrol (4.85%). Since the identities of the plant materials were checked repeatedly, any misidentification is ruled out. Except for A and C, all the other materials showed beta-caryophyllene as the major constituent. Carvacrol (20.59%) was present in good amount in the oil of B. In A, however, high percentages of 1,8-cineole (10%) and p-cymene (9.5%) were significant. This oil contained only a trace amount of beta-caryophyllene. Four isomeric caryophyllene alcohols were detected in the oil B. The results clearly indicate that the oil of T. striatus var. interruptus has no consistency and we can safely suggest that there are at least three chemotypes, namely thymol/1,8-cineole/p-cymene-type; thymol/beta-caryophyllene-type; and beta-caryophyllene-type, of this species.
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               Factor Part Location NP Content
 
Locality: Karadere, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.1 %
 
Locality: Evciler Village, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.4 %
References
1 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
2 Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
3 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
4 Volatile Constituents of the Peel Oils of Several Sweet Oranges in China
5 Chemical Composition and Antioxidant Activities of Tunisian and Canadian Coriander (Coriandrum sativum L.) Fruit
6 Influence of postharvest hot water treatment on nutritional and functional properties of kumquat (Fortunella japonica Lour. Swingle Cv. Ovale) fruit
7 Volatile Constituents of Ichthyothere terminalis and I. cunabi
8 Chemical Composition and Seasonal Variations of Spike Lavender Oil from Southern Spain
9 Volatile Extract of Mentha longifolia Growing in Israel. Aromatic Plants of the Holy Land and the Sinai. Part XIII
10 Variation of the Chemical Composition of Essential Oil of Mentha piperita L. during the Growing Time
11 A Comparative Investigation on the Essential Oil Composition of Two Bulgarian Cultivars of Mentha piperita L.
12 Composition of the Essential Oil of Micromeria biflora
13 Variability in essential oil composition of Turkish basils (Ocimum basilicum L.)
14 Comparative Study of the Essential Oils from Rosmarinus eriocalyx Jordan & Fourr. from Algeria and R. officinalis L. from Other Countries
15 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
16 The Essential Oils of Two New Satureja Species from Turkey: Satureja pilosa and S. icarica
17 Characterization of the essential oil volatiles of Satureja thymbra and Satureja parnassica: influence of harvesting time and antimicrobial activity
18 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
19 Chemical Composition, Seasonal Variation and Evaluation of Antimicrobial Activity of Essential Oils of Talauma ovata A. St. Hil. (Magnoliaceae)
20 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
21 Thymus carnosus Boiss.: Effect of Harvesting Period, Collection Site and Type of Plant Material on Essential Oil Composition
22 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey