General Information of Natural Product (ID: NP0091)
  Natural Product Name
Zingiberene
  Synonyms
Zingiberene; 495-60-3; UNII-8XOC63EI5F; 8XOC63EI5F; [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene; (S-(R*,S*))-5-(1,5-Dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene; (5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene; Zingiberene from ginger; EINECS 207-804-2; (-)-alpha-zingiberene; .alpha.-Sesquiphellandrene; CHEBI:10115; DTXSID00197808; 1,3-Cyclohexadiene, 5-[(1S)-1,5-dimethyl-4-hexenyl]-2-methyl-, (5R)-; LMPR0103060002; HY-14618; CS-0003477; C09750; Q4117486; (R)-2-Methyl-5-((S)-6-methylhept-5-en-2-yl)cyclohexa-1,3-diene; (5r)-2-methyl-5-[(2s)-6-methylhept-5-en-2yl] cyclohexa-1,3-diene; (5R)-5-[(1S)-1,5-dimethyl-4-hexenyl]-2-methyl-1,3-cyclohexadiene
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  Formula C15H24
  Weight 204.35
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15+/m0/s1
  InChI Key KKOXKGNSUHTUBV-LSDHHAIUSA-N
  Isomeric SMILES CC1=CC[C@@H](C=C1)[C@@H](C)CCC=C(C)C
  Canonical SMILES CC1=CCC(C=C1)C(C)CCC=C(C)C
  External Links PubChem ID 92776
CAS ID 495-60-3
HIT ID C0630

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [1]
              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: 0.1 %
 
Locality: Rincon de los Sauces, Province of Neuquen; Altitude 750 m
Aerial parts Patagonia, Argentina
NP Content: 0.6 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
Aerial parts Patagonia, Argentina
NP Content: 0.2 %
      Species Name: Glechoma hederacea
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
Samples of Glechoma hederacea were collected at full flowering in seven localities in Vilnius district (Lithuania) at 2005: A - Salininkai, B -Zolyno, C - Mistunai, D -Antakalnis, E - Nemencine, F - Seskine, G -Zujunai.
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               Factor Function
More than half of the oils were rich in sesquiterpene hydrocarbons (56.5-67.9%). The most predominant compound was germacrene D (14.1-20.7%). The other main constituents were gamma-elemene (9.0-16.0%), beta-elemene (8.7-12.9%), phytols (2.8-15.6%), (Z)-beta-ocimene (2.2-8.5%), 1,8-cineole (92.2-5.4%), beta-ylangene (2.7-4.1%) and germacrene B (2.2-3.9%). Forty-three identified compounds made up 89.1-96.2%. Four oils (A, D-G) might be attributed to germacrene / elemene chemotype and three samples (A-C) containing marked amounts of phytols beside above compounds were of germacrene/elemene/phytols chemotype.
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               Factor Part Location NP Content
 
Locality: Zolyno, Lithuania
Aerial parts Lithuania
NP Content: <0.05 %
 
Locality: Mistunai, Lithuania
Aerial parts Lithuania
NP Content: 3.8 %
 
Locality: Antakalnis, Lithuania
Aerial parts Lithuania
NP Content: 20.7 %
 
Locality: Nemencine, Lithuania
Aerial parts Lithuania
NP Content: 3.4 %
 
Locality: Zujunai, Lithuania
Aerial parts Lithuania
NP Content: 2.5 %
      Species Name: Heteropappus altaicus
  Factor Name: Altitude Variation [3]
              Species Info Factor Info
               Experiment Detail
Aerial parts of H. altaicus Willd. (Novopokr.) plants were randomly collected from the wild at four different altitudes, as described below, during the 1999-2001 vegetation periods. All the collections of the plant samples were carried out during massive bud formation and the beginning of flowering. Sample # 1 (3.4 kg) was collected on July 14, 1999 from LAT: 53° 05′ LON: 85° 00′, 330 m, Altai Region, Troiszkii Raion, around the village of Taldinka, 4-5 km below the Bolshoi Rechke, facing southwestern Sopki, Tipchakovo-Heteropalusovo-Pavilnaya steppe. Sample # 2 (10.5 kg) was collected on July 28, 1999 from LAT: 51°, LON: 86° 40′, 600 m, Altai Republic, Ongudaiskii Raion, at the right side of the delta of Lake Ursup, surrounding Stepushka village, along the roadside. Sample # 3 (8.5 kg) was collected on July 30, 2000 from LAT: 51° 39′ LON:79° 59′, 120 m of Altaiskii Krai, Litovskii Raion, 2 km southwest of the Ustianka village, along the roadside. Sample # 4 (6.5 kg) was collected on August 2, 2001 at LAT 50° 11′ LON 87° 53′, 1550 m of Altai Republic, Kosh-Agachiskii Raion, 24 km away from Kurai village, towards North-Tchuiskoe mountain chain following the right side of lake Tete where there is a mixture of heavy weeds.
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               Factor Function
The oil obtained from 330 m had alpha-pinene (18.6%), myrcene (18.6%), beta-phellandrene (17.2%), (E)-beta-ocimene (12.9%) and germacrene D (11.9%), while samples from 600 m consisted of myrcene (26.4%), alpha-pinene (23.2%), beta-phellandrene (18.0%), (E)-beta-ocimene (9.9%), germacrene D (4.3%) and sabinene (4.2%). The oil from 120 m had -pinene (22.0%), beta-phellandrene (21.6%), myrcene (19.5%), trans-beta-ocimene (11.3%), germacrene D (7.2%) and limonene (4.5%) as major components. At 1550 m the major components were germacrene D (22.0%), myrcene (18.0%), beta-phellandrene (14.0%), alpha-pinene (11.3%) and (E)-beta-ocimene (9.2%).
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               Factor Part Location NP Content
 
Locality: Kosh-Agachiskii Raion, Altai Republic, Russia; Altitude 1550 m
Flowers Altai, Russia
NP Content: 0.3 %
      Species Name: Ocimum basilicum L
  Factor Name: Chemotype Comparison [4]
              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 (linalool-rich type)
Leaves Turkey
NP Content: 1.3 %
 
Chemotype (methyl (E)-cinnamate-rich type)
Leaves Turkey
NP Content: 1.2 %
 
Chemotype (methyl (E)-cinnamate-rich and linalool-rich type)
Leaves Turkey
NP Content: 3.4 %
 
Chemotype (methyl eugenol-rich type)
Leaves Turkey
NP Content: 2.2 %
 
Chemotype (citral-rich type)
Leaves Turkey
NP Content: 2.8 %
 
Chemotype (methyl chavicol-rich type)
Leaves Turkey
NP Content: 1 %
 
Chemotype (methyl chavicol and citral-rich type)
Leaves Turkey
NP Content: 1.1 %
      Species Name: Persea americana
  Factor Name: Variety Comparison; Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Experimental: Two hundred grams of healthy mature intact leaves were harvested from each of the taxa growing on their own rootstocks at the UC South Coast Research and Extension Center. flocc = P. americana var. floccosa from Mexico D-7; stey = P. americana var. steyermarkii from Mexico El Salvador 3-22-16; nubi = P. americana var. nubigena from Guatemala 45-C-1; mex = P. americena var. drymfolia from Tasco, Mexico; guat = P. americana var. guatemalensis cult. Nimlioh from Florida; bwl = P. ameticana var. americana cult. Trapp from Florida.
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               Factor Function
Analysis of oils showed the presence of over 90 components, of which 76 were identified. P. schiedeana oil was found to contain alpha-pinene (23.7%), beta-pinene (23.2%) and beta-caryophyllene as major components. The major constituents of P. americana var. floccosa and P. americana var. steyermarkii were alpha-pinene (10.9%, 7.6%), beta-pinene (20.6%, 10.4%), alpha-terpineol (9.6%, 7.9%), beta-caryophyllene (12.6%, 8.4%), viridiflorene (0.1%, 10.3%) and globulol (0.1%, 9.2%), respectively. The oils of P. americana var. nubigena and P. americana var. drymifolia contained alpha-terpineol (18.4%, 393%) and methylchavicol (12.4%, 40.2%), as major components, respectively. P. americana var. guatemalensis was found to be rich in beta-caryophyllene (38.3%), while the oils of P. americana var. americana and P. primatogena contained alpha-pinene (27.5%) and beta-pinene (40.9%), and alpha-pinene (24.6%), beta-caryophyllene (20.7%) and germacene D (10.1%).
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               Factor Part Location NP Content
 
Persea americana var. drymfolia (Locality: Tasco)
Leaves Tasco, Mexico
NP Content: 0.01 %
 
Persea americana var. floccosa (Locality: Mexico)
Leaves Mexico
NP Content: 0.1 %
 
Persea americana var. nubigena (Locality: Guatemala)
Leaves Guatemala
NP Content: 0.2 %
      Species Name: Solidago virgaurea
  Factor Name: Altitude Variation [6]
              Species Info Factor Info
               Experiment Detail
Aerial parts of Solidago virgaurea plants were randomly collected from the wild at two different altitudes, as described below, during the 2000 vegetation period. All the collections of the plant samples were carried out during massive bud formation and the beginning of flowering stage. Sample # 1, LTS00-46; 10 kg of the sample was collected on July 31, 2000 at LAT: 51° 07′ LON: 81° 10′ HEI 290 m from Altai land, Lokteev district, near the village of NovoMikhaylovskoe, on the left bank of the Aley River, outskirts of pine forest, fire area, sandy soils. Sample # 2, LTS00-57; 5.6 kg of the sample was collected on August 3, 2000 at LAT 51° 14′ LON 82° 28′ HEI 650 m from Altai land, Kur'in district, around the Kolyvanm quarries, with diverse turf grasses, along the river bank of Aley.
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               Factor Function
The main components from 290 m were alpha-pinene (36.5%), myrcene (14.8%), beta-caryophyllene (10.5%), germacrene D (8.2%), beta-pinene (7.1%) and limonene+beta-phellandrene (6.4%). The oil from the sample collected at 650 m had benzyl benzoate (57.0%), beta-caryophyllene (6.3%), germacrene D (6.0%), alpha-pinene (4.4%) and alpha-humulene (4.0%) as major components, suggesting polymorphism or the existence of different chemoytpes.
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               Factor Part Location NP Content
 
Locality: Lokteev district, Russia; Altitude 290 m
Flowers Russia
NP Content: 0.4 %
 
Locality: Kur'in district, Russia; Altitude 650 m
Flowers Russia
NP Content: 1.1 %
References
1 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
2 The Essential Oil of Ground Ivy (Glechoma hederacea L) Growing Wild In Eastern Lithuania
3 Chemical Screening of Volatile Oil-bearing Flora of Siberia IX. Variations in Chemical Composition of the Essential Oil of Heteropappus altaicus Willd. (Novopokr.) Growing Wild at Different Altitudes of Altai Region, Russia
4 Variability in essential oil composition of Turkish basils (Ocimum basilicum L.)
5 Essential Oils of Persea subgenus Persea (Lauraceae)
6 Volatile Oil-Bearing Flora of Siberia VIII: Essential Oil Composition and Antimicrobial Activity of Wild Solidago virgaurea L. from the Russian Altai