General Information of Natural Product (ID: NP0649)
  Natural Product Name
Caryophylla-4(14),8(15)-Dien-5A-Ol
  Synonyms
Caryophylla-4(14),8(15)-dien-5a-ol; Caryophylla-4(14),8(15)-dien-5.alpha.-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/c1-12-7-8-14(16)13(2)6-5-10-15(3,4)11-9-12/h14,16H,1-2,5-11H2,3-4H3/t14-/m0/s1
  InChI Key MRNBNSIHBSPJFJ-AWEZNQCLSA-N
  Isomeric SMILES CC1(CCCC(=C)[C@H](CCC(=C)CC1)O)C
  Canonical SMILES CC1(CCCC(=C)C(CCC(=C)CC1)O)C
  External Links PubChem ID 6429047

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Hyptis marrubioides
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
Hyptis marrubioides were collected in March 2003 at the mature vegetative stage from their natural habitat; 20 randomised individual plants at the same age representing the local population were collected as homogenous samples from each locality: (A) Lavras (21° 14′ S/44° 59′ W), at an altitude of 919 m; (B) Tiradentes (21° 6′ S/44° 10 m W), 927 m.
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               Factor Function
The results were submitted to Principal Component and Cluster analysis which allowed three groups of oils to be distinguished with respect to sampling site and post-harvested process: cluster I (fresh leaves and fresh or dried stems from Lavras site) with high percentage of caryophylla-4(14),8(15)-dien-5beta-ol (16.7%) and eudesma-4(15),7-dien-1beta-ol (12.8%); cluster II (dried leaves and stems from Tiradentes site) with epi-longipinanol (16.2%) rich oil, and cluster III (dried leaves from Lavras) containing a high content of beta-caryophyllene (17.4%) and alpha-copaene (10.1%). Canonical discriminant analysis showed that is possible to accurately predict 100% well-classification in the original clusters using beta-caryophyllene, epi-longipinanol and caryophylla-4(14),8(15)-dien-5beta-ol as predictor variables. The whole or sliced plant materials resulted in similar chemical composition.
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               Factor Part Location NP Content
 
Whole fresh Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 4.3 %
 
Sliced fresh Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 3.8 %
 
Whole dried Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 3.3 %
 
Sliced dried Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 2.4 %
 
Whole fresh Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 4.9 %
 
Whole dried Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 5 %
 
Sliced dried Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 4.8 %
 
Whole dried Leaves: (Locality: Tiradentes, Brazil)
Leaves Brazil
NP Content: 2.2 %
 
Sliced dried Leaves: (Locality: Tiradentes, Brazil)
Leaves Brazil
NP Content: 2.8 %
 
Whole dried Stems: (Locality: Tiradentes, Brazil)
Stems Brazil
NP Content: 2.9 %
 
Sliced dried Stems: (Locality: Tiradentes, Brazil)
Stems Brazil
NP Content: 4.1 %
      Species Name: Lychnophora pinaster
  Factor Name: Seasonal Variation [2]
              Species Info Factor Info
               Experiment Detail
Plants from Horto de Plantas Medicinais of Universidade Federal de Lavras (UFLA) were cultivated in the form of a randomized block with six replications in an experimental field at Setor de Horticultura, UFLA, in Lavras city (S 21° 14′, W 44° 59′, 920 m). Samples were collected four times at 3-month intervals from March to December 2004.
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               Factor Function
There was a significant difference for oil contents in the different seasons. The lowest oil content was obtained in the summer (about 50% inferior to the other seasons). Methyl (E)-cinnamate was obtained as the major compound (86-90%) of the 14 identified components.
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               Factor Part Location NP Content
 
Harvesting time: Spring
Aerial parts Brazil
NP Content: 0.8 %
 
Harvesting time: Summer
Aerial parts Brazil
NP Content: 0.7 %
 
Harvesting time: Autumn
Aerial parts Brazil
NP Content: 0.6 %
 
Harvesting time: Winter
Aerial parts Brazil
NP Content: 0.5 %
      Species Name: Pulicaria dysenterica
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
Aerial parts of P. dysenterica were collected during the flowering stage from two different locations in Greece in August 2002. Sample A: Katara (Perfecture Trikala). Sample B: Arahova (Perfecture Viotia).
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               Factor Function
Fifty-four components were identified representing 80.5% (sample A) and 72.6% (sample B) of the total oils. The main components in sample A were (Z)-nerolidol (11.2%), caryophyllene oxide (9.1%) and (E)-nerolidol (6.6%), while those of sample B were beta-caryophyllene (12.8%), caryophyllene oxide (12.8%) and (E)-nerolidol (6.9%).
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               Factor Part Location NP Content
 
Locality: Katara, Perfecture Trikala, Greece
Aerial parts Greece
NP Content: <0.1 %
 
Locality: Arahova, Perfecture Viotia, Greece
Aerial parts Greece
NP Content: 1.4 %
      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: 0.3 %
 
Locality: Oristano, Sardinia, Italy
Aerial parts Italy
NP Content: 0.6 %
References
1 Composition and Chemical Variability in the Essential Oil of Hyptis marrubioides Epl.
2 Seasonal Variation in Essential Oils of Lychnophora pinaster Mart.
3 Chemical Composition of Pulicaria dysenterica (L.) Bernh. from Greece
4 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia