General Information of Natural Product (ID: NP1122)
  Natural Product Name
(1R,4Z,9R)-4,11,11-Trimethyl-8-Methylenebicyclo[7.2.0]Undec-4-Ene
  Synonyms
9-Epi-beta-caryophyllene; ZINC49538668; (1R,4Z,9R)-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+/m0/s1
  InChI Key NPNUFJAVOOONJE-ULKYWBSGSA-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 5498519

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Eucalyptus grandis
  Factor Name: Seasonal Variation [1]
              Species Info Factor Info
               Experiment Detail
Eucalyptus urophylla and E. grandis were collected in January (summer) and August (winter) 2006 at the mature vegetative state from Goiania city Brazil, and identified by one of the authors (E.P.F.). Leaves from 5-11 randomized individual plants of the same age representing the local population were collected as homogenous samples in each season, dried at room temperature.
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               Factor Function
The results were submitted to Principal Components and Clusters Analysis which enabled four groups of oils to be distinguished with regard to specimens and harvest seasons: clusters I and II with only E. grandis samples collected in the cold and dry winter and the hot and humid summer, which were characterized by a high percentage of isoleptospermone (9.6% and 13.2%), alpha-pinene (12.2% and 24.7%), p-cymene (20.5% and 14.5%), and alpha-terpineol (14.3% and 4.9%), respectively; clusters III and IV only associated with E. urophylla samples collected in summer and winter with 1,8-cineole (36.6% and 44.7%) and alpha-terpinyl acetate (7.0% and 11.7%) rich oils.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Whole plant Brazil
NP Content: 0.9 %
 
Harvesting time: Winter
Whole plant Brazil
NP Content: 0.8 %
      Species Name: Pimenta pseudocaryophyllus
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Two samples were collected in Sao Goncalo do Abaete, one in July 2000 and the other in November 2005, in periods of post-anthesis and preanthesis, respectively.
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               Factor Function
Thirty compounds were detected in the samples collected in Sao Goncalo do Abaete. Among the identified compounds, 53.8% are sesquiterpenes and 42.3% are monoterpenes. The majority components in the two samples were neral and geranial. The sample in anthesis presented a lower percentage of neral (21.4%) and geranial (36.5%) than the sample in pre-anthesis, whose percentages of neral and geranial were 33.6% and 47.2%, respectively.
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               Factor Part Location NP Content
 
post-anthesis stage
Leaves Sao Goncalo do Abaete, Brazil
NP Content: 0.5 %
      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
 
Harvesting time: February; pre-flowering stage
Leaves Italy
NP Content: 0.3 %
 
Harvesting time: December; vegetative stage
Leaves Italy
NP Content: 0.3 %
 
Fruit oil
Fruits Italy
NP Content: 0.3 %
References
1 Seasonal Influence on the Essential Oil Compositions of Eucalyptus urophylla S. T. Blake and E. grandis W. Hill ex Maiden from Brazilian Cerrado
2 Chemical Differences in the Essential Oil of Pimenta pseudocaryophyllus (Gomes) L. R. Landrum Leaves from Brazil
3 Seasonal Variations of Teucrium flavum L. Essential Oil