General Information of Natural Product (ID: NP0646)
  Natural Product Name
14-Hydroxy-9-Epi-Beta-Caryophyllene
  Synonyms
14-Hydroxy-9-epi-.beta.-Caryophyllene; (1R,4E,9R)-11-(Hydroxymethyl)-4,11-dimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene
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  Formula C15H24O
  Weight 220.35
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H24O/c1-11-5-4-6-12(2)13-9-15(3,10-16)14(13)8-7-11/h5,13-14,16H,2,4,6-10H2,1,3H3/b11-5-/t13-,14+,15?/m0/s1
  InChI Key DFMBJBXEHZSTJQ-KVBBHTPDSA-N
  Isomeric SMILES C/C/1=C/CCC(=C)[C@@H]2CC([C@@H]2CC1)(C)CO
  Canonical SMILES CC1=CCCC(=C)C2CC(C2CC1)(C)CO
  External Links PubChem ID 91747230

 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: 6.6 %
 
Sliced fresh Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 4.7 %
 
Whole dried Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 2.8 %
 
Sliced dried Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 2.6 %
 
Whole fresh Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 8.2 %
 
Whole dried Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 7 %
 
Sliced dried Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 5.2 %
 
Whole dried Leaves: (Locality: Tiradentes, Brazil)
Leaves Brazil
NP Content: 2.3 %
 
Sliced dried Leaves: (Locality: Tiradentes, Brazil)
Leaves Brazil
NP Content: 2.1 %
 
Whole dried Stems: (Locality: Tiradentes, Brazil)
Stems Brazil
NP Content: 4.1 %
 
Sliced dried Stems: (Locality: Tiradentes, Brazil)
Stems Brazil
NP Content: 4.3 %
      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: 0.8 %
      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: 2.6 %
 
Locality: Arahova, Perfecture Viotia, Greece
Aerial parts Greece
NP Content: 1 %
      Species Name: Talauma ovata
  Factor Name: Month Variation [4]
              Species Info Factor Info
               Experiment Detail
Talauma ovata was collected from October 2003 to February 2005. Leaves and trunk bark from the same set of plants were collected in the four seasons: spring (October 15th, 2003), autumn (April 10th, 2004), winter (July 17th, 2004) and summer (February 15th, 2005). In addition, trunk bark was also collected on January 22nd, 2004 (summer). The plant material was harvested from wild-growing population in Santos Dumont City, Minas Gerais State, Brazil, (21° 28′ 03″ S, 43° 39′ 26″ W), at 1000 m of altitude.
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               Factor Function
In each season the composition of trunk bark oils was similar to leaf oils, with mainly quantitative differences. However considerable seasonal variation was observed. Significant levels of monoterpenes were found only in autumn. The content of oxygenated sesquiterpenes was highest in samples of spring (October) and decreased in summer (January and February), reaching the lowest level in autumn (April) and increasing again in winter (July). In trunk bark oils the main constituents were: spathulenol, alpha-eudesmol, linalool, trans-beta-guaiene and caryophyllene oxide. The major component in all samples of trunk bark was spathulenol. Its level was highest in October (46.8%), decreased in January (33.3%), remained stable in April and July (18.0%) and increased again in February of next year (27.7%). Levels of alpha-eudesmol were high in spring (13.0%) and autumn (11.5%). Linalool peaked only in April, while trans-beta-guaiane peaked in July (11.1%). Caryophyllene oxide ranged between 10.7-2.0%. The level was highest in January, decreased regularly until July and increased slightly again in October. In leaf oils the main components were: spathulenol, germacrene B, germacrene D, caryophyllene oxide and viridiflorol. Spathulenol was the major component in sample of spring (34.4%), but decreased gradually until winter, when reached the lowest level (9.4%). Caryophyllene oxide showed a similar pattern, varying from 14.1% (spring) to 2.4% (winter). An inverse effect was observed for viridiflorol, which increased from 0.1% in October to 13.7% in July. Important levels of alpha-eudesmol were observed in October (12.3%) and February (9.5%). The percentage of germacrene D was highest in summer, while germacrene B showed high amounts in autumn and winter. The seasonal changes in oil composition of T. ovata can be associated with cycle of life of plant (flowering, fruiting and vegetative stages) and climatic parameters such as intense raining in the spring and summer.
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               Factor Part Location NP Content
 
Leaf: (Harvesting time: April)
Leaves Brazil
NP Content: 0.9 %
 
Leaf: (Harvesting time: July)
Leaves Brazil
NP Content: 5.6 %
 
Leaf: (Harvesting time: October)
Leaves Brazil
NP Content: 5.8 %
 
Trunk Bark: (Harvesting time: January)
Trunk bark Brazil
NP Content: 0.6 %
 
Trunk Bark: (Harvesting time: July)
Trunk bark Brazil
NP Content: 3.1 %
References
1 Composition and Chemical Variability in the Essential Oil of Hyptis marrubioides Epl.
2 Chemical Differences in the Essential Oil of Pimenta pseudocaryophyllus (Gomes) L. R. Landrum Leaves from Brazil
3 Chemical Composition of Pulicaria dysenterica (L.) Bernh. from Greece
4 Chemical Composition, Seasonal Variation and Evaluation of Antimicrobial Activity of Essential Oils of Talauma ovata A. St. Hil. (Magnoliaceae)