General Information of Natural Product (ID: NP0650)
  Natural Product Name
Caryophylla-4(14),8(15)-Dien-5Beta-Ol
  Synonyms
Caryophylla-4(14),8(15)-dien-5.beta.-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-/m1/s1
  InChI Key MRNBNSIHBSPJFJ-CQSZACIVSA-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 6429048

 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: 16.4 %
 
Sliced fresh Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 14 %
 
Whole dried Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 9.8 %
 
Sliced dried Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 10.9 %
 
Whole fresh Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 16.5 %
 
Whole dried Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 19 %
 
Sliced dried Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 17.5 %
 
Whole dried Leaves: (Locality: Tiradentes, Brazil)
Leaves Brazil
NP Content: 8.9 %
 
Sliced dried Leaves: (Locality: Tiradentes, Brazil)
Leaves Brazil
NP Content: 7.9 %
 
Whole dried Stems: (Locality: Tiradentes, Brazil)
Stems Brazil
NP Content: 11.2 %
 
Sliced dried Stems: (Locality: Tiradentes, Brazil)
Stems Brazil
NP Content: 13.7 %
      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: 2 %
 
Harvesting time: Summer
Aerial parts Brazil
NP Content: 1.4 %
 
Harvesting time: Autumn
Aerial parts Brazil
NP Content: 1.1 %
 
Harvesting time: Winter
Aerial parts Brazil
NP Content: 0.9 %
      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: 4.4 %
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