General Information of Natural Product (ID: NP0137)
  Natural Product Name
(1R,3S,5R)-6,6-Dimethyl-2-Methylidenebicyclo[3.1.1]Heptan-3-Ol
  Synonyms
(1r,3s,5r)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol; trans-Pinocarveol; UNII-993483H55R; 19894-98-5; 993483H55R; (1alpha,3alpha,5alpha)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol; [1R-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol; l-Pinocarveol; 1674-08-4; L-trans-Pinocarveol; (1alpha,3alpha,5alpha)-6,6-Dimethyl-2-methylenebicyclo(3.1.1)heptan-3-ol; Pinocarveol, trans-(+)-; (1R-(1alpha,3beta,5alpha))-6,6-Dimethyl-2-methylenebicyclo(3.1.1)heptan-3-ol; trans-(-)-Pinocarveol; (1S)-(-)-trans-Pinocarveol; trans-Isopinocarveol; EINECS 216-813-0; EINECS 243-410-7; (+)-trans-Pinocarveol; Pinocarveol, trans-(+/-)-; (1R,3S,5R)-3-Hydroxy-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane; SCHEMBL14484474; ZINC5455871; (-)-trans-2(10)-Pinen-3-ol; AKOS026742394; (1S,3R,5S)-(-)-2(10)-Pinen-3-ol; UNII-0WG2C7KI43 component LCYXQUJDODZYIJ-VGMNWLOBSA-N; UNII-20ZI248IAP component LCYXQUJDODZYIJ-VGMNWLOBSA-N
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  Formula C10H16O
  Weight 152.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9+/m1/s1
  InChI Key LCYXQUJDODZYIJ-VGMNWLOBSA-N
  Isomeric SMILES CC1([C@@H]2C[C@H]1C(=C)[C@H](C2)O)C
  Canonical SMILES CC1(C2CC1C(=C)C(C2)O)C
  External Links PubChem ID 88302
CAS ID 19894-98-5

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [1]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
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               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
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               Factor Part Location NP Content
 
Artemisia annua accessions Suraksha
Aerial parts India
NP Content: 0.5 %
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: 1 %
      Species Name: Artemisia verlotiorum
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Plant material of A. verlotiorum was harvested near Marseille (France) in May (before blooming) and November (full flowering) 2000.
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               Factor Function
For the oil from the vegetative plants, 50 compounds, representing 99.8% of the oil were characterized. Fifty-nine compounds, representing 99.6% of the oil were identified in the oil from flowering plants. In both cases, the constituents were mainly oxygenated monoterpenes (74% and 88%). The composition of each oil showed only a few differences, as the main components were alpha-thujone (55% and 44%), 1,8-cineole (5% and 15%), beta-caryophyllene (13% and 7%) and beta-thujone (5% and 11%), in the oils of the vegetative plant and flowering plant, respectively. The proportions of the oxygenated compounds seemed to increase during flowering.
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               Factor Part Location NP Content
 
Aerial part: before blooming stage
Aerial parts Marseille, France
NP Content: 0.7 %
 
Aerial part: full flowering stage
Aerial parts Marseille, France
NP Content: 1.3 %
      Species Name: Callistemon salignus
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
Fresh leaf samples of C. salignus were collected on the campus of University of Zululand, KwaDlangezwa and Empangeni (Both in KwaZulu-Natal Province) , South Africa.
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               Factor Function
1,8-Cineole (63.4%), alpha-pinene (17.8%) and E-(beta)-ocimene (6.7%) were the major constituents identified in the KwaDlangezwa sample (Sample A). The Empangeni sample (Sample B) contained only 1,8-cineole (85.4%) and alpha-pinene (6.2%) as the main compounds present in the oil.
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               Factor Part Location NP Content
 
Locality: Empangeni, KwaZulu-Natal Province, South Africa
Leaves South Africa
NP Content: 0.5 %
      Species Name: Chamaemelum nobile
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
Two different Roman chamomile oils were obtained from Giardino Officinale in Casola Valsenio (RA - Italy). One oil was distilled from chamomile plants grown in the Emilia-Romagna region (E), and the other one came from the Piemonte region (P) in Northern Italy
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               Factor Function
No significant differences were found in the composition of the two oils which were characterized by a high content of isobutyl angelate (36.3-38.5%), 2-methylbutyl angelate (18.2-20.3%) and other angelate esters.
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               Factor Part Location NP Content
 
Locality: Emilia-Romagna region, Italy
Whole plant Italy
NP Content: 3.1 %
 
Locality: Piemonte region, Italy
Whole plant Italy
NP Content: 4.5 %
      Species Name: Cistus ladanifer
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Cistus ladanifer was collected from two sites, in July-August 2001, after the flowering season. The major quantity was brought from the wild, where the plant was growing in the mountainous region of the center-interior of the country (site 1). A smaller amount was harvested from a cultivated plant in the north of Portugal (site 2) that was propagated from a wild plant found in the dry plain region in the South of Portugal.
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               Factor Function
Considering the oil composition of cistus plants from different sites, there were found some differences. The cistus oil of site 2 had a high content on the ocimenone isomers, an absence of trans-pinocarveol and unknown (compound 17) and a higher quantity of less volatile compounds such as sclareol oxide and 15-nor-labdan-8-ol. Cistus oil from site 1 was richer in sesquiterpene alcohols and 2,2,6-trimethylcyclohexanone. The amount of ambrox was the same for both oils. Considering the use of fresh or dry plant, the composition of cistus from site 2 was more affected, decreasing the amount of components of middle to high volatility and increasing the amount of the less volatiles. Drying promoted the doubling of the amount of ocimenone isomers in cistus oil from site 2 and of unknown (compound 21) and sesquiperpene alcohol (compound 29) in cistus from site 1. Again the quantity of ambrox was the same for both oils.
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               Factor Part Location NP Content
 
Fresh plant: (Locality: center-interior of Portugal)
Leaves and branches Portugal
NP Content: 3.8 %
 
Dry plant: (Locality: center-interior of Portugal)
Leaves and branches Portugal
NP Content: 2.1 %
      Species Name: Eucalyptus camaldulensis
  Factor Name: Variety Comparison [6]
              Species Info Factor Info
               Experiment Detail
Fresh leaves of the E. camaldulensis varieties(var. mysore and var. Catharine) were collected from 12 mature trees growing in Agodi Gardens, Ibadan, Nigeria.
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               Factor Function
The quantitatively significant constituents in die leaf oil of the two E. camaldulensis varieties were beta-pinene (9.0-17.5%), 1,8-cineole (32.8-70.4%), (Z)-beta-ocimene (11.6%) and alpha-pinene (8.8%). Monoterpenoids also made up the bulk of the two volatile oils (89.0-95.7%).
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               Factor Part Location NP Content
 
Eucalyptus camaldulensis var. mysore
Leaves Nigeria
NP Content: 0.2 %
      Species Name: Eucalyptus grandis
  Factor Name: Seasonal Variation [7]
              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: 0.5 %
 
Harvesting time: Winter
Whole plant Brazil
NP Content: 1.8 %
      Species Name: Fragaria vesca
  Factor Name: Cultivar Comparison [8]
              Species Info Factor Info
               Experiment Detail
Whole leaves and inflorescences of two wild strawberry cultivars ('Rugia' and 'Baron von Solemacher') harvested in 2008 during the agrotechnical experiment performed by Department of Vegetable and Medicinal Plants, University of Life Sciences in Lublin, were used as a material for determinations. Samples were collected before noon at sunny and dry days at the beginning of wild strawberry's flowering stage. Material was dried up to 35 ℃ in shadow and air just after the harvest.
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               Factor Function
Depending on a cultivar, air-dry inflorescences from wild strawberry contain from 0.21% ('Baron von Solemacher' cv.) to 0.30% ('Rugia' cv.), whereas leaves contains from 0.46% ('Baron von Solemacher' cv.) to 0.62% ('Rugia' cv.) of essential oils. GC/MS analysis of essential oils achieved from studied materials revealed presence of 70 (including 59 identified) compounds in leaves of 'Rugia' cv. and 58 (including 50 identified) compounds in leaves of 'Baron von Solemacher' cv. Essential oils from inflorescences of 'Rugia' cv. contained 52 (including 47 identified), while 'Baron von Solemacher' cv. contained 54 (including 46 identified) compounds. The chromatographic analyses by GC-MS revealed that myrthenol, nonal, linalool and phthalide dibuthyl dominated in essential oils obtained from leaves, while myrthenol, citronelol, linalool and geraniol - from those of inflorescences. There were qualitative differences between oil components at both studied materials and differentiation between both cultivars, as well.
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               Factor Part Location NP Content
 
Inflorescence: Fragaria vesca cv. Baron von Solemacher
Inflorescence Poland
NP Content: <0.05 %
 
Inflorescence: Fragaria vesca cv. Rugia
Inflorescence Poland
NP Content: 1.89 %
 
Leaf: Fragaria vesca cv. Baron von Solemacher
Leaves Poland
NP Content: <0.05 %
 
Leaf: Fragaria vesca cv. Rugia
Leaves Poland
NP Content: <0.05 %
      Species Name: Ichthyothere terminalis
  Factor Name: Locality Variation [9]
              Species Info Factor Info
               Experiment Detail
The leaves and stems of Ichthyothere terminalis were collected at Marapanim, PA (sample A) and Manaus, AM (sample B).
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               Factor Function
The chief constituent found in the leaf oil of sample of, I. terminalis collected at Marapanim (PA) was sabinene (18.0%). The leaf oil of I. terminalis collected at Manaus (AM) was dominated by alpha-pinene (19-8%), sabinene (14.8%) and limonene (35.8%), while the main components identified in the stem oil were alpha-pinene (13.9%) and limonene (20.0%).
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               Factor Part Location NP Content
 
Leaves: Manaus, Brazil
Leaves Brazil
NP Content: 1.9 %
      Species Name: Juniperus thurifera
  Factor Name: Altitude Variation; High Temperature Treatment [10]
              Species Info Factor Info
               Experiment Detail
The plant materials were collected for P1: 2900 m, Ait Akak, Oukaimden, Atlas Mts, Morocco, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 12/12/2003; P2, 2200 m, Plateau of Matat, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 18/03/2003; P3: 2000 m, Foret Islane, Oukaimden, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns,12/12/2003. A portion of the leaves from each of the three trees (per population) were air dried for 16 days at room temperature (ca. 22 &#8451) to produce the dried leaf samples.
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               Factor Function
The oil yields from fresh leaves showed on differences among geographical sources. Air dried leaves appeared to yield more oil at the highest elevation (1.03%, Ait Lkak, 2900 m) than lower sites (0.67%, Plateau of Matat, 2200 m; 0.57%, Foret Islane, 2000 m). The essential oils from each geographic site had very similar composition in fresh versus air dried leaves. The essential oils from provenance Ait Lkak and Plateau of Matat were very similar and characterized by a high sabinene content (21.2, 35.9%), in contrast to 10.% sabinene from the provenance Foret Islane. The oil from Foret Islane had a high delta-cadinene content with 12.7%, whereas Aik Akak and Plateau of Matat contained only 0.6 and 0.8%.
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               Factor Part Location NP Content
 
Fresh leaf: (Locality: Ait Lkak, Tensift Al Haouz-Marrakech, Morocco; Altitude 2900 m)
Fresh leaves Ait Lkak, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
 
Dry leaf: (Locality: Foret Islane, Tensift Al Haouz-Marrakech, Morocco; Altitude 2000 m)
Dry leaves Foret Islane, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
 
Dry leaf: (Locality: Ait Lkak, Tensift Al Haouz-Marrakech, Morocco; Altitude 2900 m)
Dry leaves Ait Lkak, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
      Species Name: Mentha piperita
  Factor Name: Cultivar Comparison [11]
              Species Info Factor Info
               Experiment Detail
Dry leaves of Menlba piperita L. 'Kliment-63' and 'Zefir' of 1997 crop were used.
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               Factor Function
The oil yield from 'Zefir' was 0.97% and that from 'Kliment-63' was 0.54%. The oil from 'Zefir' was found to be rich in menthol (46.2-50.2%) and menthyl acetate (16.8-22.5%). In the oil from 'Kliment-63,' the content of these components was lower, while the menthone content was higher (20.0-23.1%).
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               Factor Part Location NP Content
 
Mentha piperita cv. Kliment-63
Leaves Bulgaria
NP Content: 0.2 %
 
Mentha piperita cv. Zefir
Leaves Bulgaria
NP Content: 0.1 %
      Species Name: Pimenta pseudocaryophyllus
  Factor Name: Developmental Stage Variation [12]
              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: 0.3 %
      Species Name: Salvia aucheri
  Factor Name: Variety Comparison [13]
              Species Info Factor Info
               Experiment Detail
S. aucheri var. aucheri was collected in Karaman: Ermenek to Mutt Road on July 19,1995; Salvia aucheri var. canescens was collected in Karaman: Ermenek, Tekecati Valley on July 19,1995.
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               Factor Function
Eighty components were characterized in the Salvia aucheri var. aucheri oil, with camphor (21.1%), 1, 8-cineole (20.3%), borneol (7.8%), spathulenol (6.3%) and camphene (5.3%) as major constituents. 1, 8-Cineole (25.2%), camphor (17.9%), borneol (10.6%), alpha-pinene (5.4%) and camphene (5.3%) were identified as major constituents among the 88 components characterized in the oil of Salvia aucheri var. canescens.
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               Factor Part Location NP Content
 
Salvia aucheri var. aucheri
Aerial parts Karaman, Turkey
NP Content: 0.1 %
 
Salvia aucheri var. canescens
Aerial parts Karaman, Turkey
NP Content: 0.1 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [14]
              Species Info Factor Info
               Experiment Detail
Aerial parts of both varieties(Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and Salvia euphratica Montbret et Aucher ex Benth. var. leiocalycina) were collected in Malatya, Turkey in June 1999.
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               Factor Function
Ninety-five compounds in var. euphratica and 94 compounds in var. leiocalycina were characterized representing 93% and 95% of the total components detected, respectively, with 1,8-cineole (13.8% and 15.2%) and myrtenyl acetate (15.9% and 13.9%) as main constituents.
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               Factor Part Location NP Content
 
Salvia euphratica var. euphratica
Flowering aerial parts Turkey
NP Content: 1.7 %
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: 2.1 %
      Species Name: Salvia limbata
  Factor Name: Locality Variation [15]
              Species Info Factor Info
               Experiment Detail
Aerial parts were collected in Van and Erzurum in eastern Turkey. A) Van: Van to Ercis road 35th km on June 8, 2001 at an altitude of 1850 m. B) Erzurum: Campus area of Ataturk University on July 30, 2001 at an altitude of 1850 m.
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               Factor Function
Dried aerial parts of S. limbata collected from two localities in Turkey. Oils yielded similar compositions: 70-80% of the oil consisted of monoterpenes and 15-20% of sesquiterpenes. The Erzurum sample contained 3.7% of a diterpene identifi ed as 8,13-epoxy-15,16-dinor-labd-12-ene. Alpha-Pinene or 1,8-cineolerich Salvia oils are used as herbal tea in Turkey.
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               Factor Part Location NP Content
 
Locality: Van, Turkey; Altitude 1850 m
Flowering aerial parts Van, Turkey
NP Content: 0.1 %
 
Locality: Erzurum, Turkey; Altitude 1850 m
Flowering aerial parts Erzurum, Turkey
NP Content: 0.3 %
      Species Name: Sideritis congesta
  Factor Name: Locality Variation [16]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities. A: Antalya: Alanya, Sapadere, Beldibi-Baskoy in July 1991 (ESSE 9562). B: Icel: Anamur, Kas yaylasi in July 1991 (ESSE 9192).
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               Factor Function
Thirty-nine components were characterized in each oil representing 85-90% of the total components detected with beta-pinene (34-35%) and alpha-pinene (24-25%) as major constituents.
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               Factor Part Location NP Content
 
Locality: Beldibi-Baskoy, Sapadere, Alanya, Antalya, Turkey
Inflorescence Turkey
NP Content: 0.5 %
 
Locality: Kas yaylasi, Anamur, Icel, Turkey
Inflorescence Turkey
NP Content: 0.2 %
      Species Name: Sphagneticola trilobata (L.)
  Factor Name: Seasonal Variation [17]
              Species Info Factor Info
               Experiment Detail
Fresh aerial parts of the S. trilobata were collected from CSIR-Central Institute of Medicinal and Aromatic Plants, Research Centre Pantnagar (Uttarakhand) in summer (vegetative stage), rainy (vegetative stage), autumn (flowering stage) and winter (flowering stage) seasons. The experimental site is located between coordinates 29.02° N, 79.31° E and an altitude of 243 m in foothills of northern India.
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               Factor Function
Volatile oil yield varied from 0.18 to 0.25% in different seasons, with the maximum in winter season. Altogether, 43 constituents, representing 96.1-97.3% of the total oil composition were identified. Major constituents of the oils were alpha-pinene (78.6-83.3%), alpha-phellandrene (1.3-4.1%), sabinene (1.4-1.9%), limonene (1.2-1.9%), beta-pinene (1.0-1.6%), camphene (0.7-2.0%), 10-nor-calamenen-10-one (<0.05-1.5%), germacrene D (0.1-1.4%) and gamma-amorphene (<0.05-1.3%). The comparative results showed no big differences in the oil composition of this plant due to season of collection.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Aerial parts India
NP Content: <0.05 %
 
Harvesting time: Autumn
Aerial parts India
NP Content: <0.05 %
 
Harvesting time: Rainy
Aerial parts India
NP Content: <0.05 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [18]
              Species Info Factor Info
               Experiment Detail
Plant material and isolation procedure: Aerial parts of the plant were collected from two regions, from Kazeroon in southern Iran and Shahr-e-kord in western Iran at the time of flowering in June 2002.
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               Factor Function
The main components of the oil of S. pilifera collected from Kazeroon, in southern Iran, were spathulenol (15.8%), cis-chrysanthenol (15.3%), beta-caryophyllene (8.4%) and cis-chrysanthenyl acetate (6.9%), while for the plant collected from Shahr-e-kord, in western Iran, they were cis-chrysanthenyl acetate (21.8%), linalool (18.9%), terpinen-4-ol (11.9%) and cis-chrysanthenol (9.2%).
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               Factor Part Location NP Content
 
Locality: Kazeroon, southern Iran
Aerial parts Iran
NP Content: 0.2 %
      Species Name: Talauma ovata
  Factor Name: Month Variation [19]
              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: 0.1 %
 
Trunk Bark: (Harvesting time: January)
Trunk bark Brazil
NP Content: 0.1 %
 
Trunk Bark: (Harvesting time: February)
Trunk bark Brazil
NP Content: 0.6 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [20]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected during the flowering period in July 2002 from the Dumluca Mountain in the vicinity of Divrigi village of Sivas city at 1900 m altitude and Saksagan Gorge in Saimbeyli village of Adana city at 1900 m altitude.
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               Factor Function
The flower, stem and root oils of T. cadmeum ssp. orientale collected from the Adana location were characterized with alpha-thujone (25%, 5.2%), cis-linalool oxide (6.8%, 12.8%), trans-chrysanthenyl acetate (5.8%, 8.5%) for flower and stem oils, and beta-eudesmol (10.3%, 6.2%, 13.8%); in addition, stem oil contained 1,8-cineole (6.6%) and root oil contained hexadecanoic acid (6.0%), spathulenol (5.8%) and beta-muurolol (5.3%). The flower and stem oils of T. cadmeum ssp. orientale collected from the Sivas location were characterized with camphor (25.9%, 14.8%), borneol (15.4%, 25.8%) and alpha-thujone (7.8%, 5.5%); in addition, stem oil contained 1,8-cineole (7.4%) and root oil contained nonacosane (16.2%), spathulenol (6.8%) and hexadecanoic acid (5.8%).
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               Factor Part Location NP Content
 
Flower: (Locality: Sivas, Turkey)
Flowers Sivas, Turkey
NP Content: 1.3 %
 
Stem: (Locality: Sivas, Turkey)
Stems Sivas, Turkey
NP Content: 0.9 %
      Species Name: Tanacetum larvatum
  Factor Name: Locality Variation [21]
              Species Info Factor Info
               Experiment Detail
Aerial parts of T. larvatum were collected in July and August during a five-year period, starting in 2001, in Montenegro on several locations: Planinica (Sample a), Visitor (Sample b) and Sinjajevina (Sample c).
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               Factor Function
Sixty-four components were identified, representing 83.1%, 96.6% and 89.4% of the total oils content in the Planinica [Sample a], Visitor [Sample b] and Sinjajevina [Sample c], respectively. The major constituent in Samples a and b , was oxygenated monoterpene, trans-sabinyl acetate (38.1% and 55.8% respectively). Monoterpene hydrocarbons, beta-pinene (13.5%) and santolinatriene (30.6%), were found to be the dominant components in Sample c. The toxic trans-sabinyl acetate was present only in traces in this sample. trans-Chrysanthenyl acetate, as one of major components in feverfew essential oil, has not been previously identified in the investigated essential oils.
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               Factor Part Location NP Content
 
Locality: Planinica, Montenegro
Aerial parts Montenegro
NP Content: <0.1 %
 
Locality: Sinjajevina, Montenegro
Aerial parts Montenegro
NP Content: 0.7 %
 
Locality: Visitor, Montenegro
Aerial parts Montenegro
NP Content: 0.4 %
  Factor Name: Altitude Variation [22]
              Species Info Factor Info
               Experiment Detail
Aerial parts of T. larvatum were collected in July 2002, during the period of full flowering from two locations in Montenegro: Mt. Komovi (Sample I) and Mt. Prokletije (Sample II), altitude ca. 1900 m.
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               Factor Function
About 40 compounds were identified, representing ~89% and 96% of the total oil content in the Samples I and II, respectively. trans-Sabinyl acetate was found to be the dominant component (51.2% and 69.7%). Among the rest of compounds beta-pinene (7.7% and 4.3%) and camphor (6.3% and 4.3%) were the most abundant in both samples.
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               Factor Part Location NP Content
 
Locality: Mt.Prokletije, Montenegro, Serbia; Altitude 1900 m
Aerial parts Serbia
NP Content: 0.1 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [23]
              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: 0.1 %
 
Locality: Oristano, Sardinia, Italy
Aerial parts Italy
NP Content: <0.05 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [24]
              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: April; budding stage
Leaves Italy
NP Content: 0.1 %
 
Harvesting time: April; budding stage
Leaves Italy
NP Content: <0.01 %
      Species Name: Thymus carnosus
  Factor Name: Month Variation; Developmental Stage Variation [25]
              Species Info Factor Info
               Experiment Detail
The aerial parts of samples from collective populations of T. carnosus were collected during the vegetative phase (February 2000), at the beginning of the flowering phase (May 2000) and during the flowering phase (July 2000) at Quinta do Lago (Algarve). AQLM: collected in May, beginning of flowering phase; AQLJ: collected in July, flowering stage; AQLF: collected in Feb, vegetative stage.
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               Factor Function
All the oil samples collected in Quinta do Lago (QL) were dominated by borneol (26-31%) and camphene (9-18%), but the third main component varied according to the harvesting period. Bornyl acetate was the third main component (9-13%) in the flower oil and in the aerial parts oils collected in May and July, whereas terpinen-4-ol (8%) was the third main component in oil collected in February from vegetative phase plant material. A fourth main component, alpha-pinene (4-9%), was also present in relative high amounts in the QL oils.
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               Factor Part Location NP Content
 
Harvesting time: Feb, vegetative stage
Aerial parts Quinta do Lago, Portugal
NP Content: 0.4 %
 
Harvesting time: May, beginning of flowering satge
Aerial parts Quinta do Lago, Portugal
NP Content: 0.3 %
 
Harvesting time: July, flowering stage
Aerial parts Quinta do Lago, Portugal
NP Content: 0.3 %
 
Harvesting time: July, flowering stage
Flowers Quinta do Lago, Portugal
NP Content: 0.2 %
      Species Name: Thymus leucostomus
  Factor Name: Altitude Variation [26]
              Species Info Factor Info
               Experiment Detail
Herbal parts were collected from A = Eskisehir: Suluagac village in Turkey, altitude 1100 m, in July 1990 and B = Corum: Osmancik, Berk village in Turkey, altitude 580-600 m, on 22 June 1993.
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               Factor Function
One chemotype (Suluagac village, Eskisehir, Turkey) contained carvacrol (21.59%), p-cymene (17.80%) and thymol (14.10%); and the other chemotype (Berk village, Corum, Turkey) contained alpha-terpinyl acetate (23.80%), borneol (12.85%), linalool (13.67%) and thymol (11.31%) as major constituents.
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               Factor Part Location NP Content
 
Locality: Suluagac village, Eskisehir, Turkey; Altitude 1100 m
Herbal parts Turkey
NP Content: 0.13 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [27]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities in north western Turkey. A = Trabzon: Caykara, Soganli dag on July 28, 1994; B = Bayburt: Caykara, Mohakambo yaylasi on July 25, 1994; C = Trabzon: Koprubasi, Vizara yaylasi on July 20, 1994.
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               Factor Function
One hundred and four compounds were identified representing 97.5-99.5% of the total components detected in thymol/carvacrol (50.14/10.67%), thymol/linalool (23.14/20.24%) and linalool/alpha-terpinyl acetate/geraniol (21.55/16.70/11.17%) rich oils.
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               Factor Part Location NP Content
 
Locality: Soganli dag, Caykara, Trabzon, Eskisehir, Turkey
Aerial parts Eskisehir, Turkey
NP Content: <0.1 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [28]
              Species Info Factor Info
               Experiment Detail
Aerial parts of the plant were collected from four localities: A = Kirklareli: Karadere in May 1991; B = Kirklareli: Karahamza Village in May 1990; C = Kirklareli: Evciler Village on 13 June 1993; D = Kirklareli: Korukoy on 25 May 1994
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               Factor Function
The four oils obtained from plants collected in different localities of the same region gave quite different compositions as follows: A: thymol (10.5%), 1,8-cineole (9.96%), p-cymene (9.48%), carvacrol (5.28%); B: beta-caryophyllene (29.50%), carvacrol(20.59%); C: thymol (34.7%), beta-caryophyllene (12.74%), carvacrol (5.24%); D: beta-caryophyllene (56.48%), germacrene D (11.12%), carvacrol (4.85%). Since the identities of the plant materials were checked repeatedly, any misidentification is ruled out. Except for A and C, all the other materials showed beta-caryophyllene as the major constituent. Carvacrol (20.59%) was present in good amount in the oil of B. In A, however, high percentages of 1,8-cineole (10%) and p-cymene (9.5%) were significant. This oil contained only a trace amount of beta-caryophyllene. Four isomeric caryophyllene alcohols were detected in the oil B. The results clearly indicate that the oil of T. striatus var. interruptus has no consistency and we can safely suggest that there are at least three chemotypes, namely thymol/1,8-cineole/p-cymene-type; thymol/beta-caryophyllene-type; and beta-caryophyllene-type, of this species.
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               Factor Part Location NP Content
 
Locality: Karadere, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.7 %
References
1 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
2 Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
3 Volatile Constituents of the Leaf Oils of Callistemon salignus from Two Provinces in South Africa
4 Study on Roman Chamomile (Chamaemelum nobile L. All.) Oil
5 Characterization of the Portuguese-Grown Cistus ladanifer Essential Oil
6 Essential Oil Composition of Two Varieties of Eucalyptus camaldulensis Dehn. from Nigeria
7 Seasonal Influence on the Essential Oil Compositions of Eucalyptus urophylla S. T. Blake and E. grandis W. Hill ex Maiden from Brazilian Cerrado
8 Contents and chemical composition of essential oils from wild strawberry (Fragaria vesca L.)
9 Volatile Constituents of Ichthyothere terminalis and I. cunabi
10 Effect of the Leaf Drying and Geographic Sources on the Essential Oil Composition of Juniperus thurifera L. var. Africana Maire from the Tensift-Al Haouz, Marrakech Region
11 A Comparative Investigation on the Essential Oil Composition of Two Bulgarian Cultivars of Mentha piperita L.
12 Chemical Differences in the Essential Oil of Pimenta pseudocaryophyllus (Gomes) L. R. Landrum Leaves from Brazil
13 Composition of Essential Oils from Two Varieties of Salvia aucheri Benth. Growing in Turkey
14 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
15 The Essential Oil of Salvia limbata C.A. Meyer Growing in Turkey
16 Composition of the Essential Oil of Sideritis congesta P.H.Davis et Hub.-Mor.
17 Essential oil composition of Sphagneticola trilobata (L.) Pruski from India
18 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
19 Chemical Composition, Seasonal Variation and Evaluation of Antimicrobial Activity of Essential Oils of Talauma ovata A. St. Hil. (Magnoliaceae)
20 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
21 Intraspecific Variation of Tanacetum larvatum Essential Oil
22 Chemical Composition of Tanacetum larvatum Essential Oil
23 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia
24 Seasonal Variations of Teucrium flavum L. Essential Oil
25 Thymus carnosus Boiss.: Effect of Harvesting Period, Collection Site and Type of Plant Material on Essential Oil Composition
26 Essential Oil of Thymus leucostomus Hausskn. et Velen. var. leucostomus
27 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey
28 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey