General Information of Natural Product (ID: NP0572)
  Natural Product Name
Epi-Cubenol
  Synonyms
Epicubenol; epi-Cubenol; 19912-67-5; Ent-Epicubenol; (-)-epicubenol; (-)-epi-cubenol; CHEBI:156227; 4a(2H)-Naphthalenol, 1,3,4,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-(1alpha,4beta,4aalpha,8aalpha))-; (1S,4R,4aS,8aR)-4,7-dimethyl-1-propan-2-yl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-4a-ol; (1S,4R,4aS,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,3,4,5,6,8a-hexahydronaphthalen-4a(2H)-ol
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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-QPSCCSFWSA-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 12046149
CAS ID 19912-67-5

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Melaleuca quinquenervia (Cav.) S.T. Blake
  Factor Name: Chemotype Comparison [1]
              Species Info Factor Info
               Experiment Detail
One hundred grams of mature leaves were collected from 2 to 10 widely spaced trees per site and sent to Sydney for analysis as soon as possible after collection. Samples usually arrived in the laboratory within 48 h of collection. The majority of the sampling was done between December 1998 and October 1999. Seasonal trends in oil yields and composition are confounded in the data on geographic variation, but these were considered minor in the context of this study.
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               Factor Function
Chemotype 1 is comprised of E-nerolidol (74-95%) and linalool (14-30%) and is found from Sydney, north along the east coast of Australia to Selection Flat, New South Wales, with an isolated occurrence near Maryborough, Queensland. Two divisions occur in this chemotype which are based on the presence or absence of significant proportions of linalool (14-40%). Chemotype 2 contains 1,8-cineole (10-75%), viridiflorol (13-66%), alpha-terpineol (0.5-14%) and beta-caryophyllene (0.5-28%) in varying proportions and order of dominance in the oils. It is found throughout the distribution of the species, from Sydney to Papua New Guinea and New Caledonia. Within chemotype 2 there appears to be a continuous spread of oil composition without formation of any further discrete divisions as in chemotype 1. Analyses have shown that M. quinquenervia trees that occur at latitudes south of 25d S have high oil yields (1-3% w/w%, fresh leaves) and comprise chemotypes 1 and 2. North of 25d S, however, chemotype 1 does not occur and oil yields amongst the Australian populations are uniformly low (0.1-0.2%).
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               Factor Part Location NP Content
 
Chemotype (E-nerolidol in large concentration type)
Leaves Australia and Papua New Guinea
NP Content: 0.1 %
      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: Jonava, Lithuania
Branches Jonava, Lithuania
NP Content: 6 %
 
Locality: Jurbarkas, Lithuania
Branches Jurbarkas, Lithuania
NP Content: 5 %
 
Locality: Kaisiadorys, Lithuania
Branches Kaisiadorys, Lithuania
NP Content: 5.3 %
 
Locality: Moletai, Lithuania
Branches Moletai, Lithuania
NP Content: 6.2 %
 
Locality: Neringa (Smiltyne), Lithuania
Branches Neringa (Smiltyne), Lithuania
NP Content: 3.8 %
 
Locality: Radviliskis, Lithuania
Branches Radviliskis, Lithuania
NP Content: 5 %
 
Locality: Salacininkai, Lithuania
Branches Salacininkai, Lithuania
NP Content: 4.8 %
 
Locality: Silute, Lithuania
Branches Silute, Lithuania
NP Content: 4.1 %
 
Locality: Trakai, Lithuania
Branches Trakai, Lithuania
NP Content: 3.1 %
 
Locality: Ukmerge, Lithuania
Branches Ukmerge, Lithuania
NP Content: 5 %
 
Locality: Varena, Lithuania
Branches Varena, Lithuania
NP Content: 3.3 %
 
Locality: Vilnius, Lithuania
Branches Vilnius, Lithuania
NP Content: 5.6 %
 
Locality: Zarasai, Lithuania
Branches Zarasai, Lithuania
NP Content: 5.2 %
 
Locality: Zarsai (lmbradas), Lithuania
Branches Zarsai (lmbradas), Lithuania
NP Content: 2.1 %
 
Locality: Zarasai (Sunele), Lithuania
Branches Zarasai (Sunele), Lithuania
NP Content: 5.3 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. flavum were collected in different periods from December to July 2006, from plants growing along the Ionic coast of Sicily (Italy). LF 1-LF 2-LF 3: represent the composition of leaf oils of plant samples collected in December (vegetative stage), February (pre-flowering stage) and April (budding stage) respectively; FL: flower oil; FR: fruit oil.
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               Factor Function
Some components, in all investigated plant parts, remained more or less constant during all the different phases of the plant cycle life. Worthy of note, considering the leaf oils, was that beta-pinene, limonene and germacrene D increased in the pre-flowering stage, while a series of esters and alpha-copaene, beta-caryophyllene, viridiflorol, Tmuurolol and phytol increased in the budding stage (LF3); the vegetative stage oil is generally characterized by a rich chemical composition and some constituents such as isoamyl hexanoate, alpha-humulene, bicyclogermacrene, beta-bisabolene and alpha-bisabolol reached their highest levels in this oil. In the flower oil, linalool and 1-octen-3-yl acetate were the main components compared to the amounts found in the other oils. Fruit oil composition was relatively oil poor, with beta-bisabolene, caryophyllene oxide, cadin-4-en-1-ol and phytone as the major constituents.
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               Factor Part Location NP Content
 
Flower oil
Flowers Italy
NP Content: 0.3 %
 
Fruit oil
Fruits Italy
NP Content: 0.5 %
References
1 Chemical variation in the leaf essential oil of Melaleuca quinquenervia (Cav.) S.T. Blake
2 Composition of Essential Oils of Pinus sylvestris L. from Different Locations of Lithuania
3 Seasonal Variations of Teucrium flavum L. Essential Oil