General Information of Natural Product (ID: NP0375)
  Natural Product Name
Cadina-1,4-Diene
  Synonyms
Cadina-1,4-diene; Cadina-1,4-diene, cis; Cadina-1(2),4-diene; (1S,4S,4aR)-4-Isopropyl-1,6-dimethyl-1,2,3,4,4a,7-hexahydronaphthalene; 4-Isopropyl-1,6-dimethyl-1,2,3,4,4a,7-hexahydronaphthalene-, [1S-(1.alpha.,4.alpha.,4a.alpha.)]-; Naphthalene, 1,2,3,4,4a,7-hexahydro-1,6-dimethyl-4-(1-methylethyl)-, [1S-(1.alpha.,4.alpha.,4a.alpha.)]-
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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)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h7,9-10,12-13,15H,5-6,8H2,1-4H3/t12-,13?,15?/m0/s1
  InChI Key JUQGWBAOQUBVFP-OPFPJEHXSA-N
  Isomeric SMILES C[C@H]1CCC(C2C1=CCC(=C2)C)C(C)C
  Canonical SMILES CC1CCC(C2C1=CCC(=C2)C)C(C)C
  External Links PubChem ID 6427091

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Echinacea purpurea
  Factor Name: Plant Pathogen Infection [1]
              Species Info Factor Info
               Experiment Detail
Plant selection and virological tests: Before effecting the collection procedure, heathy and infected plants of E. purpurea grown in the open field at the Herb Garden of Casola Valsenio were selected and labelled by visual inspection of their aerial parts. The infection by CMV was associated with symptoms on both leaves and flowers. The most characteristic symptoms are yellow mosaic, ring and line-patterns on crinkled and deformed leaves that drop prematurely. The flowers, which may be smaller than normal, show color breaking with white or pale stripes on red petals. Shortening of the internodes is also very common, giving the plant a bushy appearance known as stunting. In Italian environmental conditions, these symptoms are best visible in the summer. On the other hand, plants appeared symptom-free were collected as healthy material. Plant collection: About 3-4 Kg fresh aerial part materials (70% stems, 10% leaves and 20% flowers) of healthy E. purpurea plants were collected in June 2000 at almost the end of flowering. An equivalent quantity of CMV-infected plants (evaluated by DAS-ELISA) was also collected; the percentage of leaves in the infected infected was about 6.0% as due to CMV presence that caused the premature leaf drop.
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               Factor Function
The oil from healthy material was rich in germacrene D (57.8%) and was more abundant. The infected materials afforded a lower oil content and significant quantitative variations in the oil composition. In particular, the observed percentage of germacrene D (52.6%) was reduced as were other sesquiterpene hydrocarbons. These variations, tested to be significant for all the compound-class fractions and individual major components, were ascribed to the cucumber mosaic cucumovirus (CMV) infection, the only fixed-effect variable that might affect the oil composition.
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               Factor Part Location NP Content
 
Healthy plant
Aerial parts Italy
NP Content: 0.1 %
 
Infected plants (cucumber mosaic cucumovirus)
Aerial parts Italy
NP Content: 0.1 %
      Species Name: Mentha rotundifolia
  Factor Name: Altitude Variation [2]
              Species Info Factor Info
               Experiment Detail
Mentha rotundifolia leaves were collected in the second week of November 2004 in two localities of Algeria (Rouina: altitude 250 m, Miliana: altitude 780 m) within the region of Ain-Defla located in northern Algeria.
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               Factor Function
Thirty-nine compounds were identified in leaf oil of sample 1 (Rouina, Algeria), the main one being cis-piperitone oxide. Thirty-nine compounds were identified in leaf oil of sample 2 (Miliana, Algeria). The main one being piperitenone oxide.
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               Factor Part Location NP Content
 
Locality: Miliana, Algeria; Altitude 780 m
Leaves Algeria
NP Content: < 0.1 %
      Species Name: Pinus sylvestris
  Factor Name: Locality Variation [3]
              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: Jonava, Lithuania
Branches Jonava, Lithuania
NP Content: 0.2 %
 
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: Salacininkai, Lithuania
Branches Salacininkai, Lithuania
NP Content: 0.1 %
 
Locality: Silute, Lithuania
Branches Silute, Lithuania
NP Content: 0.2 %
 
Locality: Trakai, Lithuania
Branches Trakai, Lithuania
NP Content: 0.2 %
 
Locality: Ukmerge, Lithuania
Branches Ukmerge, Lithuania
NP Content: 0.2 %
 
Locality: Varena, Lithuania
Branches Varena, Lithuania
NP Content: 0.2 %
 
Locality: Vilnius, Lithuania
Branches Vilnius, Lithuania
NP Content: 0.2 %
 
Locality: Zarasai, Lithuania
Branches Zarasai, Lithuania
NP Content: 0.3 %
 
Locality: Zarsai (lmbradas), Lithuania
Branches Zarsai (lmbradas), Lithuania
NP Content: 0.3 %
 
Locality: Zarasai (Sunele), Lithuania
Branches Zarasai (Sunele), Lithuania
NP Content: 0.3 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [4]
              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: Corti, Corsica, France
Aerial parts France
NP Content: 0.2 %
 
Locality: Oristano, Sardinia, Italy
Aerial parts Italy
NP Content: 0.1 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [5]
              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 Characterization of the Essential Oils of Healthy and Virus Infected Echinacea purpurea (L.) Moench Plants
2 Chemical Composition of the Leaf Oil of Mentha rotundifolia (L.) from Algeria
3 Composition of Essential Oils of Pinus sylvestris L. from Different Locations of Lithuania
4 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia
5 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey