General Information of Natural Product (ID: NP0144)
  Natural Product Name
Alpha-Curcumene
  Synonyms
alpha-Curcumene; Curcumene; 1-methyl-4-(6-methylhept-5-en-2-yl)benzene; 2-Methyl-6-p-tolyl-2-heptene; Ar-Curcumene; 644-30-4; aryl-curcumene; aromatic curcumene; 1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene; 2-Heptene, 2-methyl-6-p-tolyl-; Benzene, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-; alpha-Cucurmene; .alpha.-Curcumene; Curcumene <AR>; CHEMBL4210821; CHEBI:62757; DTXSID90862351; FT-0778157; 1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene #; 1-(1,5-dimethyl-hex-4-enyl)-4-methyl-benzene; Q27132148
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  Formula C15H22
  Weight 202.33
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3
  InChI Key VMYXUZSZMNBRCN-UHFFFAOYSA-N
  Isomeric SMILES CC1=CC=C(C=C1)C(C)CCC=C(C)C
  Canonical SMILES CC1=CC=C(C=C1)C(C)CCC=C(C)C
  External Links PubChem ID 92139
CAS ID 644-30-4
CHEMBL ID CHEMBL4210821
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia campestris
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
The aerial parts (~20 cm, 15-100 g) of A. campestris L. from ten different wild populations of Lithuania were gathered at the full flowering stage. Plant material was dried at room temperature (20-25 ℃). Oils (samples 1-10) obtained from Artemisia campestris plants collected at sampling sites (A-I,Y) characterized by locality, city (c.) or district (d.), soil type (Or, ordo; Sn, sand; Sl, sandy loam; Gr, gravel; Lm, loam) and description of natural habitat (Af, abandoned field; Fe, forest edge; Ct, cutting area; Mw, meadow; Rs, roadside; Rv, river valley): A (1) Birstonas c. (Or, Ct); B (2) Palanga c. (Sn, Fe); C (3) Nociunai, Kedainai d. (Or, Mw); D (4) Alytus c. (Sl, Rs); E (5) Moletai c. (Lm, Af); F (6) Kaltanenai, Sencionys d. (Gr, Fe); G (7) Merkine, Alytus d. (Sl, Ct); H (8) Trakai c. (Gr, Af); I (9) Druskininkai c. (Or, Rv); Y (10) Vilnius c. (Gr, Af).
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               Factor Function
The main chemical profile (ten samples) was characterized by the predominance of germacrene D (9.8-31.2%), while spathulenol, humulene epoxide II and caryophyllene oxide were found as the first major compounds in another three oils. One oil was determined as a mixed chemotype. Some compounds such as gamma-curcumene, alpha-cadinol, (E,E)-alpha-farnesene, beta-ylangene, beta-selinene and humulene epoxide II have been mentioned for the first time among three principal constituents in A. campestris oils. The fifty-six components made up 73.6.1-98.5% of the total content, while the remaining twenty-six volatile compounds were identified in insignificant amounts in the A. campestris essential oils.
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               Factor Part Location NP Content
 
Locality: Merkine, Alytus district, Lithuania (soil type: sandy loam; natural habitat: cutting area)
Aerial parts Lithuania
NP Content: 0.9 %
 
Locality: Trakai city, Lithuania (soil type: gravel; natural habitat: abandoned field)
Aerial parts Lithuania
NP Content: 1.4 %
 
Locality: Druskininkai city, Lithuania (soil type: ordo; natural habitat: river valley)
Aerial parts Lithuania
NP Content: 1.3 %
 
Locality: Vilnius city, Lithuania (soil type: gravel; natural habitat: abandoned field)
Aerial parts Lithuania
NP Content: 1.1 %
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [2]
              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: 1.3 %
 
Locality: Rincon de los Sauces, Province of Neuquen; Altitude 750 m
Aerial parts Patagonia, Argentina
NP Content: 1 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
Aerial parts Patagonia, Argentina
NP Content: 0.7 %
      Species Name: Pulicaria dysenterica
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
Aerial parts of P. dysenterica were collected during the flowering stage from two different locations in Greece in August 2002. Sample A: Katara (Perfecture Trikala). Sample B: Arahova (Perfecture Viotia).
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               Factor Function
Fifty-four components were identified representing 80.5% (sample A) and 72.6% (sample B) of the total oils. The main components in sample A were (Z)-nerolidol (11.2%), caryophyllene oxide (9.1%) and (E)-nerolidol (6.6%), while those of sample B were beta-caryophyllene (12.8%), caryophyllene oxide (12.8%) and (E)-nerolidol (6.9%).
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               Factor Part Location NP Content
 
Locality: Katara, Perfecture Trikala, Greece
Aerial parts Greece
NP Content: 4.9 %
 
Locality: Arahova, Perfecture Viotia, Greece
Aerial parts Greece
NP Content: 3 %
      Species Name: Salvia aucheri
  Factor Name: Variety Comparison [4]
              Species Info Factor Info
               Experiment Detail
S. aucheri var. aucheri was collected in Karaman: Ermenek to Mutt Road on July 19,1995; Salvia aucheri var. canescens was collected in Karaman: Ermenek, Tekecati Valley on July 19,1995.
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               Factor Function
Eighty components were characterized in the Salvia aucheri var. aucheri oil, with camphor (21.1%), 1, 8-cineole (20.3%), borneol (7.8%), spathulenol (6.3%) and camphene (5.3%) as major constituents. 1, 8-Cineole (25.2%), camphor (17.9%), borneol (10.6%), alpha-pinene (5.4%) and camphene (5.3%) were identified as major constituents among the 88 components characterized in the oil of Salvia aucheri var. canescens.
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               Factor Part Location NP Content
 
Salvia aucheri var. canescens
Aerial parts Karaman, Turkey
NP Content: 0.1 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [5]
              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. euphratica
Flowering aerial parts Turkey
NP Content: 0.1 %
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: < 0.1 %
      Species Name: Sideritis pusilla
  Factor Name: Variety Comparison; Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
The aerial parts (~35 cm) of each taxa growing wild in eight localities of Almeria province were collected in May 1996. All samples were collected at full flowering. Sideritis pusilla (Lange) Pau ssp. pusilla var. typica, Population/location (UTM): Los Matarines (30SWF7992); Sideritis pusilla ssp. pusilla var. carthaginensis Font Quer, Population/location (UTM): Rambla del Hacho (30SWF7178); Sideritis pusilla ssp. pusilla var. granatensis (Pau) Font Quer, Population/location (UTM): Gafarillos (30SWG8702); Sideritis pusilla ssp. almeriensis (Pau) Malagarriga var. typica, Population/location (UTM): Sierra de Gador, Cerro de los Lobos (30SWF3575); Sideritis pusilla ssp. almeriensis var. littoralis Font Quer, Population/location (UTM): Los Morales (30SWF6775); Sideritis pusilla ssp. almeriensis var. salina Font Quer, Population/location (UTM): Los Pedregales (30SWG7835); Sideritis pusilla ssp. flavovirens (Rouy) Malagarriga, Population/location (UTM): Velez Rubio, Cerro del Huezno (30SWG8965); Sideritis pusilla ssp. osteoxylla (Pau) Pallares, Population/location (UTM): Cabo de Gata, Cerro de S. Miguel (30SWF7165)
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               Factor Function
Monoterpene hydrocarbons, alcohols, sesquiterpenes and diterpenes were the main constituents in all samples. Among these, alpha-pinene (7.1-25.4%), sabinene (5.9-20.4%), fenchone (0.9-19.3%), limonene (1.2-7.4%) and 1,8-cineole (1.8-15.6%) were the major compounds. The results confirm that there are differences between varieties and subspecies, while cluster analysis revealed that the oil composition potentially has chemotaxonomical significance for this taxon.
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               Factor Part Location NP Content
 
Sideritis pusilla (Lange) Pau ssp. pusilla var. typica (Locality: Los Matarines)
Aerial parts Los Matarines, Spain
NP Content: 2 %
 
Sideritis pusilla ssp. almeriensis var. littoralis Font Quer (Locality: Los Morales)
Aerial parts Los Morales, Spain
NP Content: 0.2 %
 
Sideritis pusilla ssp. almeriensis var. salina Font Quer (Locality: Los Pedregales)
Aerial parts Los Pedregales, Spain
NP Content: 0.6 %
 
Sideritis pusilla ssp. almeriensis (Pau) Malagarriga var. typica (Locality: Sierra de Gador, Cerro de los Lobos)
Aerial parts Sierra de Gador, Cerro de los Lobos, Spain
NP Content: 0.4 %
 
Sideritis pusilla ssp. flavovirens (Rouy) Malagarriga (Locality: Velez Rubio, Cerro del Huezno)
Aerial parts Velez Rubio, Cerro del Huezno, Spain
NP Content: 0.8 %
 
Sideritis pusilla ssp. pusilla var. carthaginensis Font Quer (Locality: Rambla del Hacho)
Aerial parts Rambla del Hacho, Spain
NP Content: 1.2 %
 
Sideritis pusilla ssp. pusilla var. granatensis (Pau) Font Quer (Locality: Gafarillos)
Aerial parts Gafarillos, Spain
NP Content: 1.3 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [7]
              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: Shahr-e-kord, western Iran
Aerial parts Iran
NP Content: 2.6 %
      Species Name: Tanacetum dolichophyllum
  Factor Name: Altitude Variation [8]
              Species Info Factor Info
               Experiment Detail
Wild growing Tanacetum dolichophyllum samples were collected during the period of full flowering, between September-October 2009 from high alpine meadows of Western Himalaya (Uttarakhand, India): Sample I (Dayara, altitude 3200 m) and Sample II (Tungnath, altitude 3800 m).
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               Factor Function
Plant collected from Dayara meadow (Sample I) afforded cis-lanceol (11.8%), beta-pinene (10.7%), (E)- beta-farnesene (7.4%), alpha-bisabolol (7.2%), beta-eudesmol (5.2%) and terpinen-4-ol (5.1%) as the major constituents, whereas in the sample collected from Tungnath (Sample II) beta-eudesmol (31.4%), alpha-bisabolol (10.7%) were the most abundant components followed by neryl acetate (5.8%) and (E)-beta-farnesene (5.7%). The composition was dominated by sesquiterpene hydrocarbons and oxygen containing sesquiterpenes (49.2-71.1%). The oils are clearly different from those of all other previously reported T. dolichophyllum oils.
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               Factor Part Location NP Content
 
Locality: Dayara; Altitude 3200m
Aerial parts Himalyas, Uttarakhand, India
NP Content: 1.5 %
 
Locality: Tungnath; Altitude 3800m
Aerial parts Himalyas, Uttarakhand, India
NP Content: 1 %
References
1 Variability of Artemisia campestris L. essential oils from Lithuania
2 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
3 Chemical Composition of Pulicaria dysenterica (L.) Bernh. from Greece
4 Composition of Essential Oils from Two Varieties of Salvia aucheri Benth. Growing in Turkey
5 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
6 Essential Oil Composition of Sideritis pusilla (Lange) Pau ssp.
7 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
8 Variation in the Constituents of Tanacetum dolichophyllum (Kitam.) Kitam. from Different Locations of Uttarakhand Himalaya (India)