General Information of Natural Product (ID: NP0568)
  Natural Product Name
1,10-Di-Epcubenol
  Synonyms
1,10-epi-Cubenol; 1,10-Di-epcubenol
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  Formula C15H26O
  Weight 222.37
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H26O/c1-10(2)13-6-5-12(4)15(16)8-7-11(3)9-14(13)15/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14+,15-/m1/s1
  InChI Key COGPRPSWSKLKTF-APIJFGDWSA-N
  Isomeric SMILES C[C@@H]1CC[C@@H]([C@H]2[C@]1(CCC(=C2)C)O)C(C)C
  Canonical SMILES CC1CCC(C2C1(CCC(=C2)C)O)C(C)C
  External Links PubChem ID 91748749

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Eugenia chlorophylla
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
Plant material was collected at vegetative stage (stems and leaves,September 2005) and at flowering stage (leaves and flowers,December 2004), inCuritiba,Parana state, Brazil.
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               Factor Function
Thirty-four components were identified, representing more than 80% of total oil. The major components were beta-caryophyllene (flowers-12.8%), caryophyllene oxide (stems-17.2%), globulol (stems-16.5%; leaves-22.5% at vegetative stage and 18.9% at flowering stage), 1-epi-cubenol (stems-10.9%), epi-alpha-muurolol (stems-16.8%) and alpha-cadinol (stems-12.1%; flowers-10.1%).
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               Factor Part Location NP Content
 
Leaf: flowering stage
Leaves Brazil
NP Content: 2 %
 
Leaf: vegetative stage
Leaves Brazil
NP Content: 9.8 %
 
Stem: vegetative stage
Stems Brazil
NP Content: 1.6 %
      Species Name: Eugenia dysenterica
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Unripe, semi-ripe, and ripe fruits of E. dysenterica were collected in rural area of Abadia de Goias city (S 16° 45′ 1″, W 49° 25′ 5″, 850 m), Goias State, Brazil, in October 2002.
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               Factor Function
Limonene (25.8% and 24.6%), (E)-beta-ocimene (20.3% and 21.7%) and beta-pinene (12.0% and 14.2%) were the major compounds in the unripe and semi-ripe stages, respectively, while gamma-muurolene (25.8%), beta-caryophyllene (18.4%) and alpha-humulene (15.4%) became the major compounds in ripe fruits. The concentration of monoterpenes was high in the unripe and semi-ripe stages and decreased afterwards, while sesquiterpenes were intensively synthesized only in the last part of the ripening process.
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               Factor Part Location NP Content
 
Fruit: Ripe fruit stage
Ripe fruits Brazil
NP Content: 1.3 %
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
The plant material was collected in eastern Lithuania (July-August, 2002). Numbers of growing localities of H. arenarium with yellow (Y) and orange (O) flowers were as follows: Svencionys district (Zalavas) and Ukmerge district (Sventupe).
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               Factor Function
The 68 constituents identified comprised 73.8-90.7% of the total oil content. It was found that the principal constituents were: beta-caryophyllene (in three inflorescence and one leaf oil), delta-cadinene (in two leaf oils), octadecane (in one leaf oil) and heneicosane (in one inflorescence sample). Monoterpenes and oxygenated monoterpenes made up 4.0-13.9%, aliphatic hydrocarbons 0.4-35.3%, and sesquiterpenes 24.7-71.2% of the oils.
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               Factor Part Location NP Content
 
Inflorescence: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: < 0.05 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 1 %
 
Inflorescence: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 1.3 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.3 %
 
Leaf: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: < 0.05 %
 
Leaf: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 1.2 %
 
Leaf: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: < 0.05 %
 
Leaf: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 1.7 %
      Species Name: Ocimum basilicum L
  Factor Name: Cultivar Comparison [4]
              Species Info Factor Info
               Experiment Detail
The 36 'Genovese' and 24 'Foglia di Lattuga' samples preliminarily analysed were grown in Tavazzano (MI), and harvested at flowering, from 5th to 10th August 1998. The breeding program started in 1999, by crossing several selected lines of 'Genovese' with 'Foglia di Lattuga' and 'Compatto'. Selected F1 plants were selfpollinated in 2000. Plants of the F2 (2001), F3 (2002) and F4 (2003) generations were selected on the basis of agronomic and morphologic traits, and self-pollinated. Only the seeds from self pollinated plants with satisfactory essential oil content and composition were used to obtain the next generation. In 2004, some F4 plants were replanted in order to evaluate their stability in relation to environmental variations. All leaf harvests were carried out at flowering.
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               Factor Function
Genovese' showed higher essential oil and linalool content, with almost total absence of methyl chavicol, very abundant in 'Foglia di Lattuga'.
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               Factor Part Location NP Content
 
Ocimum basilicumcv. Foglia Lattuga
Leaves Italy
NP Content: 0.3 %
 
Ocimum basilicumcv. Genovese
Leaves Italy
NP Content: 0.2 %
      Species Name: Pinus sylvestris
  Factor Name: Locality Variation [5]
              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: 0.1 %
 
Locality: Jurbarkas, Lithuania
Branches Jurbarkas, Lithuania
NP Content: 0.2 %
 
Locality: Kaisiadorys, Lithuania
Branches Kaisiadorys, Lithuania
NP Content: 0.1 %
 
Locality: Moletai, Lithuania
Branches Moletai, Lithuania
NP Content: 0.1 %
 
Locality: Neringa (Smiltyne), Lithuania
Branches Neringa (Smiltyne), Lithuania
NP Content: 0.2 %
 
Locality: Radviliskis, Lithuania
Branches Radviliskis, Lithuania
NP Content: 0.1 %
 
Locality: Salacininkai, Lithuania
Branches Salacininkai, Lithuania
NP Content: 0.3 %
 
Locality: Silute, Lithuania
Branches Silute, Lithuania
NP Content: 0.1 %
 
Locality: Trakai, Lithuania
Branches Trakai, Lithuania
NP Content: 0.2 %
 
Locality: Ukmerge, Lithuania
Branches Ukmerge, Lithuania
NP Content: 0.1 %
 
Locality: Varena, Lithuania
Branches Varena, Lithuania
NP Content: 0.1 %
 
Locality: Vilnius, Lithuania
Branches Vilnius, 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 %
References
1 Chemical Composition and Antimicrobial Activity of Essential Oils of Eugenia chlorophylla (Myrtaceae)
2 Changes in Volatile Constituents During Fruit Ripening of Wild Eugenia dysenterica DC.
3 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
4 Biodiversity and selection of European basil (Ocimum basilicum L.) types
5 Composition of Essential Oils of Pinus sylvestris L. from Different Locations of Lithuania