General Information of Natural Product (ID: NP0227)
  Natural Product Name
Alpha-Bergamotene
  Synonyms
alpha-Bergamotene; 17699-05-7; 2,6-Dimethyl-6-(4-methyl-3-pentenyl)bicyclo[3.1.1]hept-2-ene; alpha-trans-Bergamotene; Bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)-; 2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene; 2-Norpinene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)-; 2,6-dimethyl-6-(4-methylpent-3-enyl)bicyclo[3.1.1]hept-2-ene; Bicyclo(3.1.1)hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)-; 2,6-Dimethyl-6-(4-methyl-3-pentenyl)bicyclo(3.1.1)hept-2-ene; EINECS 241-702-9; .alpha.-Bergamotene; 2-Norpinene, 2,6-dimethyl-6-(4-methyl-3-pentenyl); ALPHA-BERGAM0TENE; .alpha.-trans-Bergamotene; CHEBI:62755; DTXSID90864411; FT-0622209; C17088; Q27132146; 2,6-Dimethyl-6-(4-methyl-3-pentenyl)bicyclo[3.1.1]hept-2-ene #; (E)-2,6-Dimethyl-6-[4-methyl-3-pentenyl]bicyclo[3.1.1]hepta-2-ene; (Z)-2,6-Dimethyl-6-[4-methyl-3-pentenyl]bicyclo[3.1.1]hepta-2-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(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3
  InChI Key YMBFCQPIMVLNIU-UHFFFAOYSA-N
  Isomeric SMILES CC1=CCC2CC1C2(C)CCC=C(C)C
  Canonical SMILES CC1=CCC2CC1C2(C)CCC=C(C)C
  External Links PubChem ID 86608
CAS ID 17699-05-7

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [1]
              Species Info Factor Info
               Experiment Detail
Aerial parts of endemic pichana were harvested in December 1996 at different localities of northern Patagonia. Origin: Planicie Banderita, Dept. Confluencia, Province of NeuquCn. Habitat: altitude, 327 m; average temperature in the station, 21.8 ℃; annual precipitation, 125 mm; sandy soils. Aerial parts (5 kg, 2 kg of dried material;humidity, 11%) from four well developed plants at the fullflowering stage (December, 1996). Sample 2 : Origin: RincBn de 10s; Sauces, Dept. of Pehuenclies, Province of Neuqukn. Habitat: altitude, 750 m; average temperature in the station, 20.9 ℃; annual precipitation, 147 mm; sandy and gritty salty soils. Aerial parts (5 kg, 1.85 kg of dried material, humidity, 10%), from two well developed plants at the full flowering stage, and after several days copious rains (December, 1996). Sample 3: Origin: Coronel GBmez, Dept. General Roca, Province of Rio Negro. Habitat: altitude, 242 m; average temperature in the station, 22.5 ℃; annual precipitation, 179 mm; sandy and stony soils. Aerial parts (4.5 kg, 1.3 kg of dried material, humidity, 9%), from 12 young plants at the beginning flowering stage (December, 1996).
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               Factor Function
Fifty-four components, representing approximately 84.6-97.4% of the oil samples, were identified. The samples consisted mainly of hydrocarbons and oxygenated monoterpenes. The major constituents were limonene (28.7-56.7%), 6R-7R-bisabolone (3.2-9.1%), sabinene (0.1-11.0%) and citronellal (2.4-5.2%). Significant differences among the content of the three samples could be the result of changes in the climatic conditions (sample 2: Rincon de los Sauces, Province of Neuquen, after strong rains) or by translocations in different parts of the plant (sample 3: Coronel Gomez, Province of Rio Negro, more leaves and less stems).
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               Factor Part Location NP Content
 
Locality: Planicie Banderita, Province of Neuquen; Altitude 327 m
Aerial parts Patagonia, Argentina
NP Content: 0.1 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
Aerial parts Patagonia, Argentina
NP Content: 0.1 %
      Species Name: Bocageopsis multiflora
  Factor Name: Seasonal Variation [2]
              Species Info Factor Info
               Experiment Detail
Bocageopsis multiflora leaves were collected in the Adolpho Ducke reserve, Km 26 Manaus - Itacoatiara highway, in the State of Amazonas, Brazil. This species was collected in the rainy (April 2010) and dry seasons (September 2010).
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               Factor Function
The main constituent of the oil collected in the rainy season was bisabolene (13.2%), while the main constituent in the dry season was spathulenol (16.2%). The highest yield (0.3%) was obtained for the oil collected in the rainy season.
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               Factor Part Location NP Content
 
Harvesting time: Rainy season
Leaves Brazil
NP Content: 9 %
 
Harvesting time: Dry season
Leaves Brazil
NP Content: 9.3 %
      Species Name: Hyptis pectinata
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
H. pectinutu is an odoriferous plant and occurs as a natural weed on the Fiji Islands and in West Africa as a winter hardy bush. In India, it grows as an erect perrennial shrub in Assam, Bengal and Madras regions. Tlie leaves are ovate and the leaf margins range from crenate to serrate. The flowers are pale purple to yellow in cymose clusters, arranged unilaterally. The nutlets are small, oblong and black.
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               Factor Function
The major compounds present in the Indian oil were sabinene (27.8%), beta-pinene (6.7%), limonene (4.03%), alpha-terpinolene (6.0%), caryopliyllcne (17.2%), alpha-bergamotene (4.1%) and a C20H32-diterpene (5.8%). Other major hydrocarbons present were gamma-terpinene (1.4%), alpha-humulene (1.1%), beta-selinene (1.0%) and gamma-elemene (2.7%). The oil is rather poor in oxygenated terpenoids, the only major oxygen compounds detected were terpinen-4-ol(3.1%), spathulenol(1.1%), an unidentified sesquiterpene alcohol (1.4%) and trans-alpha-bergamotot (2.5%). The total oxygenated compounds constituted about 11% of the oil.
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               Factor Part Location NP Content
 
Locality: India
Whole plant Kumaon, India
NP Content: 4.1 %
      Species Name: Ocimum basilicum 'Fino Verde'
  Factor Name: Harvest Time Variation; High Temperature Treatment [4]
              Species Info Factor Info
               Experiment Detail
MATERIAL AND METHODS: The study was separated in two experiments performed in our research station Campus Rural of The Federal University of Sergipe (UFS), Sao Cristovao city, Sergipe State, from December 03, 2002 to April 28, 2003. First harvesting: The first harvesting (Experiment 1) was performed 40 days after seedlings transplantation during full bloom on 03/06/2003. Harvesting was performed cutting plants at 20 cm height from the soil. The collected material consisted on separating leaves and inflorescences from the stalk. In the first experiment only used leaves in the analysis. Randomized block design in a 3x4 factorial scheme with three replications was used. Each plot was composed of five plants. Treatments were: three harvesting periods (8:00; 12:00, and 16:00 h) combined with three drying temperatures (40, 50, and 60 ℃) and fresh leaves. Second harvesting: To perform the second harvesting (Experiment 2) we collected the regrowth of plants used in Experiment 1. Plants were harvested fifty three days after the first harvesting (on 04/28/2003) at 8:00 h using the same procedures as the first one; however both leaves and infl orescences were used in the analysis. Randomized block design with three replications was used. Treatments were drying periods of 0, 1, 2, 3, 4, 5, 6, 7, 9, 11, 13, and 16 days for leaves and infl orescences in ovens with air renewal and circulation (Marconi model MA-037/5) at 40 ℃.
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               Factor Function
Harvesting performed at 8:00 h and 12:00 h provided higher essential oil yield. After five days drying, the concentration of linalool raised from 45.18% to 86.80%. O. basilicum should be harvested during morning and the biomass dried at 40 ℃ for five days to obtain linalool rich essential oil.
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               Factor Part Location NP Content
 
Fresh Leaf: (Harvesting time: 8:00 h)
Leaves Brazil
NP Content: 2.59 %
 
Fresh Leaf: (Harvesting time: 12:00 h)
Leaves Brazil
NP Content: 4.33 %
 
Fresh Leaf: (Harvesting time: 16:00 h)
Leaves Brazil
NP Content: 3.88 %
 
Dry Leaf: (Harvesting time: 8:00 h) + (Drying temperature: 40 ℃)
Leaves Brazil
NP Content: 4.8 %
 
Dry Leaf: (Harvesting time: 12:00 h) + (Drying temperature: 40 ℃)
Leaves Brazil
NP Content: 4.7 %
 
Dry Leaf: (Harvesting time: 16:00 h) + (Drying temperature: 40 ℃)
Leaves Brazil
NP Content: 7.75 %
 
Dry Leaf: (Harvesting time: 8:00 h) + (Drying temperature: 50 ℃)
Leaves Brazil
NP Content: 6.33 %
 
Dry Leaf: (Harvesting time: 12:00 h) + (Drying temperature: 50 ℃)
Leaves Brazil
NP Content: 6.31 %
 
Dry Leaf: (Harvesting time: 16:00 h) + (Drying temperature: 50 ℃)
Leaves Brazil
NP Content: 6.36 %
 
Dry Leaf: (Harvesting time: 8:00 h) + (Drying temperature: 60 ℃)
Leaves Brazil
NP Content: 6.66 %
 
Dry Leaf: (Harvesting time: 12:00 h) + (Drying temperature: 60 ℃)
Leaves Brazil
NP Content: 6.59 %
 
Dry Leaf: (Harvesting time: 16:00 h) + (Drying temperature: 60 ℃)
Leaves Brazil
NP Content: 11.16 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [5]
              Species Info Factor Info
               Experiment Detail
Grape pomaces and stalks of Nero d'Avola and Frappato were donated by the ''Valle dell'Acate'' wine firm, Acate, RG, Italy - those from Nerello Mascalese and Cabernet Sauvignon were given by the ''Emanuele Scammacca Barone del Murgo'' wine firm, Santa Venerina, CT, Italy. The winemaking procedures were similar for all samples, namely grape clusters were crushed and destemmed using a destemmer-crusher. The crushed grapes were treated with sulphur dioxide (0.2-0.5% total mash) and with selected strains of Saccharomyces cerevisiae to start up the fermentation. After 6-8 days of maceration, when alcoholic fermentation was finished, the mash was pressed. Stalks coming from destemming procedure and grape pomace coming from the maceration procedure were subjected to the distillation procedures within 24 h of their collection. All materials were collected during the 2004 vintage.
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               Factor Function
On the whole, 38 components have been characterized in the samples of grape pomaces, with Frappato cv. showing the richest composition; instead, 88 components have been detected in the stalks of Frappato, Nero d'Avola, Nerello Mascalese and Cabernet Sauvignon varieties.
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               Factor Part Location NP Content
 
Vitis vinifera var. Cabernet Sauvignon
Stalks Italy
NP Content: < 0.05 %
 
Vitis vinifera var. Nerello Mascalese
Stalks Italy
NP Content: 0.49 %
References
1 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
2 Chemical composition and biological activities of Bocageopsis multiflora essential oil
3 Volatile Constituents of Hyptis pectinata Poit. (Lamiaceae)
4 Influence of the harvesting time, temperature and drying period on basil (Ocimum basilicum L.) essential oil
5 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.