General Information of Natural Product (ID: NP0480)
  Natural Product Name
Isocaryophyllene
  Synonyms
Isocaryophyllene; (-)-ISOCARYOPHYLLENE; 118-65-0; UNII-NRY8I0KNIR; gamma-caryophyllene; Isocaryophyllene (80per cent); 87-44-5; NRY8I0KNIR; CHEBI:5993; beta-Caryophyllen; trans-Caryophyllene; (1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene; g-Caryophyllene; FEMA No. 2252; NSC 11906; .beta.-cis-Caryophyllene; Caryophyllene (VAN); UNII-BHW853AU9H; BHW853AU9H; beta-Caryophyllene (natural); 8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene; E-Caryophyllene; ss-Caryophyllene; Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-; Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4Z,9S)-; Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R-(1R*,4E,9S*))-; EINECS 201-746-1; EINECS 204-267-6; (-)--caryophyllene; (-)-E-Caryophyllene; AI3-36121; 4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene #; CCRIS 8094; CHEMBL448700; 2-Methylene-6,10,10-trimethylbicyclo(7.2.0)undec-5-ene; DTXSID10881246; ZINC30726969; (-)-Caryophyllene sum of enantiomers; LMPR0103120002; 4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene, (1R-(1R*,4E,9S))-; BS-48823; CARYOPHYLLENE, ALPHA + BETA MIXT.; C09691; E75762; Q27106968; (1beta,9alpha)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene; (1R-(1R*,4Z,9S*))-4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene
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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/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m1/s1
  InChI Key NPNUFJAVOOONJE-FLFDDASRSA-N
  Isomeric SMILES C/C/1=C/CCC(=C)[C@H]2CC([C@@H]2CC1)(C)C
  Canonical SMILES CC1=CCCC(=C)C2CC(C2CC1)(C)C
  External Links PubChem ID 5281522
CAS ID 118-65-0
NPASS ID NPC60556
HIT ID C0547
CHEMBL ID CHEMBL448700
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [1]
              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 [2]
              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: February)
Leaves Brazil
NP Content: 4 %
 
Leaf: (Harvesting time: April)
Leaves Brazil
NP Content: 1.6 %
 
Leaf: (Harvesting time: July)
Leaves Brazil
NP Content: 1.7 %
 
Leaf: (Harvesting time: October)
Leaves Brazil
NP Content: 1.9 %
 
Trunk Bark: (Harvesting time: January)
Trunk bark Brazil
NP Content: 1 %
 
Trunk Bark: (Harvesting time: February)
Trunk bark Brazil
NP Content: 3.7 %
 
Trunk Bark: (Harvesting time: April)
Trunk bark Brazil
NP Content: 3.1 %
 
Trunk Bark: (Harvesting time: July)
Trunk bark Brazil
NP Content: 2.4 %
 
Trunk Bark: (Harvesting time: October)
Trunk bark Brazil
NP Content: 1 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. chamaedrys were collected at the flowering stage in June 2004 near Corti, Corsica, France and near Oristano, Sardinia, Italy
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               Factor Function
The Corsican and Sardinian oils of T. chamaedrys investigated in this study were qualitatively similar but they differed by the amount of their major components. The major components were beta-caryophyllene (29.0% and 27.4%, respectively) and germacrene D (19.4% and 13.5%, respectively), followed by alpha-humulene (6.8%) and delta-cadinene (5.4%) in the Corsican oil and by caryophyllene oxide (12.3%) and alpha-humulene (6.5%) in the Sardinian oil. These quantitative differences are also noticeable on the amounts of the different class compounds. Especially, the monoterpene hydrocarbons amounted for 10.3% and 4.1% in Sardinian and Corsican oils respectively and the oxygenated sesquiterpenes amounted for 18.9% and only 7.4% in both oils, respectively. Both oils were qualitatively rather similar in comparison with those reported in the literature from various geographic regions. However, among the 87 components identified in this study, 47 minor components (< 0.6%) reported were identified for the first time in T. chamaedrys oil. This study confirms the quantitative variability of the major components according to the plant origin.
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               Factor Part Location NP Content
 
Locality: Oristano, Sardinia, Italy
Aerial parts Italy
NP Content: 0.1 %
References
1 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
2 Chemical Composition, Seasonal Variation and Evaluation of Antimicrobial Activity of Essential Oils of Talauma ovata A. St. Hil. (Magnoliaceae)
3 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia