General Information of Natural Product (ID: NP0478)
  Natural Product Name
Gamma-Gurjunene
  Synonyms
gamma-Gurjunene; 1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene; 1,4-dimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,6,7-octahydroazulene; 1.beta.,4.beta.H,10.beta.H-Guaia-5,11-diene; (+)-gamma-Gurjunene; 22567-17-5; Azulene, 1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, [1R-(1.alpha.,3a.beta.,4.alpha.,7.beta.)]-; EINECS 245-084-1; .gamma.-Gurjunene; DTXSID80275870; CHEBI:178033; (1R-(1alpha,3Abeta,4alpha,7beta))-1,2,3,3a,4,5,6,7-octahydro-7-isopropenyl-1,4-dimethylazulene; 915104-82-4; FT-0699685; Q67880022; 7-Isopropenyl-1,4-dimethyl-1,2,3,3a,4,5,6,7-octahydroazulene #; 1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene; Azulene, 1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1R,3aR,4R,7R)-
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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/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h9,11-14H,1,5-8H2,2-4H3
  InChI Key DUYRYUZIBGFLDD-UHFFFAOYSA-N
  Isomeric SMILES CC1CCC(C=C2C1CCC2C)C(=C)C
  Canonical SMILES CC1CCC(C=C2C1CCC2C)C(=C)C
  External Links PubChem ID 90805
CAS ID 22567-17-5

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia nilagirica var. Septentrionalis
  Factor Name: Altitude Variation [1]
              Species Info Factor Info
               Experiment Detail
Leaves from mature plants of Artemisia nilagirica var. septentrionalis, before flowering, were collected from different altitudes in Himachal Pradesh such as Shimla (2210 m), Mandi (1044 m) and Manali (2050 m) in June 2005.
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               Factor Function
The major constituents of the oil show variation with changes in altitude. At lower, middle and higher altitudes, the major constituents of the oil were caryophyllene oxide (28.6%), borneol (35.8%) and camphor (46.9%), respectively. The percentages of alpha-humulene and trans-beta-guaiene also increased, but the percentage of sabinene, trans-sabinene hydrate, 4-terpineol, caryophyllene oxide and humulene epoxide-II decreased with an increase in altitude. The characteristic compounds observed in the plants from lower altitudes were 2-hexene-1-ol, beta-thujone, thujanol, myrtenol and linalyl acetate, while the higher altitude plants were characterized by the presence of alpha-pinene, beta-pinene, limonene, linalool, gamma-gurijunene, germacrene-D and farnesol.
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               Factor Part Location NP Content
 
Locality: Shimla, Himachal Pradesh, India; Altitude 2210 m
Leaves Himachal Pradesh, India
NP Content: 3.6 %
      Species Name: Pinus sylvestris
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
The branches of pine were collected in July, 1996 in 15 different locations in Lithuania in the following regions: Western part (Silute, Jurbarkas, Kursiu Nerija), Eastern part (Salcininkai, Zarasai, Moletai), Southern part (Varena, Trakai, Radviliskis) and central part (Ukmerge, Jonava, Kaisiadorys). The branches in each location were collected from the trees in approximately 1 km radius.
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               Factor Function
More than 70 constituents were identified (64 positively and 10 tentatively) in the oils. alpha-Pinene (18.5-33.0%) and delta-3-carene (9.1-24.6%) were dominating constituents with the only one exception when the germacrene-4-ol content in one of the samples was 13.2%. The important bornyl acetate content varied from 0.5% to 3.0%. The main sesquiterpenes were beta-caryophyllene, germacrene D, bicyclogermacrene, delta-cadinene, gamma-cadinene, germacrene D-4-ol, cubenol (2.0-5.1%) and alpha-cadinol (1.9-7.7%).
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               Factor Part Location NP Content
 
Locality: Jurbarkas, Lithuania
Branches Jurbarkas, Lithuania
NP Content: 0.2 %
 
Locality: Kaisiadorys, Lithuania
Branches Kaisiadorys, Lithuania
NP Content: 0.2 %
 
Locality: Moletai, Lithuania
Branches Moletai, Lithuania
NP Content: 0.2 %
 
Locality: Neringa (Smiltyne), Lithuania
Branches Neringa (Smiltyne), Lithuania
NP Content: 0.3 %
 
Locality: Radviliskis, Lithuania
Branches Radviliskis, Lithuania
NP Content: 0.2 %
 
Locality: Trakai, Lithuania
Branches Trakai, Lithuania
NP Content: 0.1 %
 
Locality: Ukmerge, Lithuania
Branches Ukmerge, Lithuania
NP Content: 0.2 %
 
Locality: Varena, Lithuania
Branches Varena, Lithuania
NP Content: 0.2 %
 
Locality: Zarasai, Lithuania
Branches Zarasai, Lithuania
NP Content: 0.1 %
 
Locality: Zarsai (lmbradas), Lithuania
Branches Zarsai (lmbradas), Lithuania
NP Content: 0.1 %
 
Locality: Zarasai (Sunele), Lithuania
Branches Zarasai (Sunele), Lithuania
NP Content: 0.1 %
      Species Name: Salvia mirzayanii
  Factor Name: NaCl Treatment [3]
              Species Info Factor Info
               Experiment Detail
To break the seed dormancy, they were soaked in boiling water for 10 min and were then placed in Petri dishes moistened with distilled water and kept in a refrigerator (4 ℃) for 7 days. Seeds were then sown in plastic pots containing sands and powdered leaves (1:2) and were allowed to grow in the greenhouse with the mean day/night temperature and relative humidity of 29 ℃ , 38 % and 17 ℃ , 50 % respectively. Sixty days after seed germination, uniform seedlings with two nodes and four opposite leaves were transplanted into big plastic pots (30 × 50 cm). Each pot was filled with 10 kg of air-dried soil and two seedlings were used per pot for all treatments.Eight weeks after transplanting, plants were subjected to different levels of salinity supplied with irrigation water. In order to prevent osmotic shock, salt solutions were added gradually at several stages and so, lasting for three weeks. To keep the levels of soil salt concentration constant, distilled water was used in subsequent irrigations. At the end of salt treatment, total soil electrical conductivities including control were determined by EC meter (0.40, 2.3, 4.5, 6.8 and 9.1 dS/m). Salt stress symptoms (leaf tip chlorosis and necrosis) in plants treated with high salt concentrations appeared after three weeks. At this time, seedlings were harvested. A total of 10 g of fresh leaf material was harvested per plant, 3.5 g of which was used for HGC-MS analysis and the rest was allowed to dry at room temperature.
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               Factor Function
Moderate salinity could induce S. mirzayanii to produce high amounts of some valuable volatile oils and total phenolic compounds.
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               Factor Part Location NP Content
 
0.4 dS/m NaCl (control)
Fresh leaves Shiraz, Iran
NP Content: 0.34 ± 0.04 % fresh weight
 
2.3 dS/m NaCl
Fresh leaves Shiraz, Iran
NP Content: 0.25 ± 0.00 % fresh weight
 
4.5 dS/m NaCl
Fresh leaves Shiraz, Iran
NP Content: 0.18 ± 0.01 % fresh weight
 
9.1 dS/m NaCl
Fresh leaves Shiraz, Iran
NP Content: 0.07 ± 0.00 % fresh weight
      Species Name: Sphagneticola trilobata (L.)
  Factor Name: Seasonal Variation [4]
              Species Info Factor Info
               Experiment Detail
Fresh aerial parts of the S. trilobata were collected from CSIR-Central Institute of Medicinal and Aromatic Plants, Research Centre Pantnagar (Uttarakhand) in summer (vegetative stage), rainy (vegetative stage), autumn (flowering stage) and winter (flowering stage) seasons. The experimental site is located between coordinates 29.02° N, 79.31° E and an altitude of 243 m in foothills of northern India.
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               Factor Function
Volatile oil yield varied from 0.18 to 0.25% in different seasons, with the maximum in winter season. Altogether, 43 constituents, representing 96.1-97.3% of the total oil composition were identified. Major constituents of the oils were alpha-pinene (78.6-83.3%), alpha-phellandrene (1.3-4.1%), sabinene (1.4-1.9%), limonene (1.2-1.9%), beta-pinene (1.0-1.6%), camphene (0.7-2.0%), 10-nor-calamenen-10-one (<0.05-1.5%), germacrene D (0.1-1.4%) and gamma-amorphene (<0.05-1.3%). The comparative results showed no big differences in the oil composition of this plant due to season of collection.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Aerial parts India
NP Content: 0.2 %
 
Harvesting time: Autumn
Aerial parts India
NP Content: 0.1 %
 
Harvesting time: Winter
Aerial parts India
NP Content: <0.05 %
 
Harvesting time: Rainy
Aerial parts India
NP Content: 0.1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [5]
              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: <0.05 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities in north western Turkey. A = Trabzon: Caykara, Soganli dag on July 28, 1994; B = Bayburt: Caykara, Mohakambo yaylasi on July 25, 1994; C = Trabzon: Koprubasi, Vizara yaylasi on July 20, 1994.
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               Factor Function
One hundred and four compounds were identified representing 97.5-99.5% of the total components detected in thymol/carvacrol (50.14/10.67%), thymol/linalool (23.14/20.24%) and linalool/alpha-terpinyl acetate/geraniol (21.55/16.70/11.17%) rich oils.
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               Factor Part Location NP Content
 
Locality: Soganli dag, Caykara, Trabzon, Eskisehir, Turkey
Aerial parts Eskisehir, Turkey
NP Content: <0.1 %
References
1 Oil Constituents of Artemisia nilagirica var. septentrionalis Growing at Different Altitudes
2 Composition of Essential Oils of Pinus sylvestris L. from Different Locations of Lithuania
3 Effects of salt stress on volatile compounds, total phenolic content and antioxidant activities of Salvia mirzayanii
4 Essential oil composition of Sphagneticola trilobata (L.) Pruski from India
5 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
6 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey