General Information of Natural Product (ID: NP0211)
  Natural Product Name
(1S,2S,6S,7R,8R)-1,3-Dimethyl-8-Propan-2-Yltricyclo[4.4.0.02,7]Dec-3-Ene
  Synonyms
alpha-Ylangene; Q22026403
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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/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12+,13-,14-,15+/m1/s1
  InChI Key VLXDPFLIRFYIME-KHMAMNHCSA-N
  Isomeric SMILES CC1=CC[C@H]2[C@@H]3[C@@H]1[C@]2(CC[C@@H]3C(C)C)C
  Canonical SMILES CC1=CCC2C3C1C2(CCC3C(C)C)C
  External Links PubChem ID 101607926

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Arabidopsis thaliana
  Factor Name: T-DNA Knock-Out Treatment [1]
              Species Info Factor Info
               Experiment Detail
In vitro cultivation of Arabidopsis wildtype and mutant plants: Seeds were sterilized according to standard lab routines (EtOH, NaOCl/NaOH) prior to aseptical (in vitro) cultivation in 500 ml screw cap jars on MS medium (4.3 g/l; 50 ml/jar) containing Bacto- and Phytoagar (1:2; 6 g/l) and 30 g/l sucrose. Ten seeds were pipetted into each jar and plants grown for 6 weeks until flowering at a temperature of 20 ℃ under a 16/8 h day/ night regime using fluorescent tubes (Osram Lumilux Plus Eco 36 W). Both Arabidopsis thaliana wildtype plants of ecotype Columbia-0 (Col) and 4 Col-derived T-DNA knock-out mutants (homozygous lines) showing deficiencies in the GLS biosynthesis pathway were used in this study (five parallels for wildtype and mutants): TGG1 (Atg526000; Salk_130469), TGG2 (At5g25980; Salk_038730), Cyp83A1 (At4g13770) and Cyp83B1 (At4g31500; Salk_028573). Greenhouse-cultivation of Arabidopsis ecotypes: The following Arabidopsis ecotypes were used in the study: Columbia (Col), Cape Verde Islands (Cvi), Landsberg erecta (Ler) and Wassilewskija (Ws). Single plants were greenhouse-cultivated on fertilized soil (P-Jord; Emmaljunga Torvmull AB) in plug trays (9 × 6 cells) at a temperature of 20 ℃ (three parallels for each ecotype). Due to the 6-weeks growth period (November/December 2003), the plants were cultivated under a 16/8 h day/night regime using metal halide lamps (Osram HQI-T 400 W) placed 130 cm above the trays. Depending on the ecotypical plant development, whole plants were sampled after 3-4 weeks right before bolting for in vivo studies, while investigations of single plant organs (leaf, stem, inflorescence) were carried out after 5-6 weeks of cultivation.
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               Factor Function
Metabolites from methionine, leucine and phenylalanine-derived glucosinolates were most abundant (4-methylthiobutyl, 4-methylpentyl, 2-phenylethyl). In addition, 24 monoterpenes, 26 sesquiterpenes and 12 aromatic structures, predominantly observed in inflorescenses, are described. Excluding the vast group of straight chain aliphatic structures, a total of 102 volatile compounds were detected, of which 59 are reported in Arabidopsis thaliana for the first time, thus emphasizing the sensitivity and applicability of solid-phase microextraction for volatile profiling of plant secondary metabolites.
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               Factor Part Location NP Content
 
Inflorescences: A. thaliana wildtype detected in vivo
Flowers Norway
NP Content: 0.04 %
 
Stem: A. thaliana wildtype detected in vivo
Stems Norway
NP Content: 0.17 %
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
The plant material was collected in eastern Lithuania (July-August, 2002). Numbers of growing localities of H. arenarium with yellow (Y) and orange (O) flowers were as follows: Svencionys district (Zalavas) and Ukmerge district (Sventupe).
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               Factor Function
The 68 constituents identified comprised 73.8-90.7% of the total oil content. It was found that the principal constituents were: beta-caryophyllene (in three inflorescence and one leaf oil), delta-cadinene (in two leaf oils), octadecane (in one leaf oil) and heneicosane (in one inflorescence sample). Monoterpenes and oxygenated monoterpenes made up 4.0-13.9%, aliphatic hydrocarbons 0.4-35.3%, and sesquiterpenes 24.7-71.2% of the oils.
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               Factor Part Location NP Content
 
Inflorescence: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.6 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.3 %
 
Inflorescence: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.9 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.4 %
 
Leaf: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 1.1 %
 
Leaf: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.6 %
 
Leaf: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.8 %
 
Leaf: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.9 %
      Species Name: Pimpinella tragioides
  Factor Name: Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from Chalous Road (north of Tehran province) both at the flowering stage in June and the seed stage in September 2003. The fresh plants were dried at room temperature. Dried stems/leaves (S/L) (collected during flowering stage), seeds (S) were hydrodistilled for 3 h in a Clevenger-type apparatus to produce the oils.
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               Factor Function
The major constituent in the stem/leaf oil was trans-alpha-bergamotene (77.1%), whereas the major constituent of the seed oil was pregeijerene (87.0%). Nonadecane (8.6%) were the other major constituents in the stem/leaf.
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               Factor Part Location NP Content
 
Seed: seed stage
Seeds Iran
NP Content: 1 %
      Species Name: Rosmarinus officinalis
  Factor Name: Developmental Stage Variation [4]
              Species Info Factor Info
               Experiment Detail
Samples of R. officinalis were collected in April 1998 during the full flowering period (Ro-1a), between June and July 1998 during the fruiting period (Ro-1b) and in December 1998 during the hibernation period (Ro-1c) from Cazorla, Segura y Las Villas Natural Park (province of Jaen, Spain). The plant material consisted of ca. 10 twigs per plant (with blossoming tips or not, depending of the harvesting date) from 5-10 single plants. Ro-1a (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: April 21, 1998, Phenological stage: Flowering); Ro-1b (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: June 19, 1998, Phenological stage: Fruiting); Ro-1c (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: December 30, 1998, Phenological stage: Hibernation).
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               Factor Function
The highest oil yields (161.8%) were recorded during the fruiting period (summer). In general, minimum amounts of camphor and maximum amounts of alpha-pinene were observed in winter. The concentration of 1,8-cineole was almost constant throughout the year, though other oil constituent levels varied randomly with the plant life cycle
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Twigs Las Chozuelas, Southern Spain
NP Content: 0.2 %
 
Whole plant: Fruiting stage
Twigs Las Chozuelas, Southern Spain
NP Content: 0.2 %
 
Hibernation stage
Twigs Las Chozuelas, Southern Spain
NP Content: 0.1 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [5]
              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: Vitis vinifera
  Factor Name: Variety Comparison [6]
              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: 3.48 %
 
Vitis vinifera var. Frappato
Pomaces Italy
NP Content: 0.35 %
 
Vitis vinifera var. Frappato
Stalks Italy
NP Content: 1.23 %
 
Vitis vinifera var. Nerello Mascalese
Stalks Italy
NP Content: 1.86 %
 
Vitis vinifera var. Nero d'Avola
Stalks Italy
NP Content: 0.82 %
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
2 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
3 Essential Oil Composition of Pimpinella tragioides (Boiss.) Benth. et Hook. from Iran
4 Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain
5 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey
6 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.