General Information of Natural Product (ID: NP0174)
  Natural Product Name
Cedr-8-Ene
  Synonyms
(-)-alpha-cedrene; Cedr-8-ene; ALPHA-CEDRENE; Cedrene; 469-61-4; (-)-cedrene; UNII-50D4A81G8T; 50D4A81G8T; 1H-3a,7-Methanoazulene, 2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-,(3R,3aS,7S,8aS)-; [3R-(3alpha,3abeta,7beta,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene; 11028-42-5; (1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0(1,5)]undec-8-ene; Levo-alpha-cedrene; Laevo-alpha-cedrene; .alpha.-Cedrene; (3R-(3alpha,3Abeta,7beta,8aalpha))-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene; 1H-3a,7-Methanoazulene, 2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-, [3R-(3.alpha.,3a.beta.,7.beta.,8a.alpha.)]-; EINECS 207-418-4; BRN 3196861; (-)-.alpha.-Cedrene; 3-05-00-01095 (Beilstein Handbook Reference); DTXSID0047032; CHEBI:10216; (3R,3aS,7S,8aS)-3,6,8,8-Tetramethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulene; ZINC8234283; MFCD00063003; a-Cedrene 100 microg/mL in Methanol; AKOS030503768; LMPR0103690006; BS-42448; Q013; HY-135190; CS-0109773; 469C614; W-108691; Q27108601; (-)-alpha-Cedrene, >=95.0% (sum of enantiomers, GC); UNII-1M4BF4O9SA component IRAQOCYXUMOFCW-OSFYFWSMSA-N; [3R-(3?,3a?,7?,8a?)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene; 22567-43-7
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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/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1
  InChI Key IRAQOCYXUMOFCW-OSFYFWSMSA-N
  Isomeric SMILES C[C@@H]1CC[C@@H]2[C@]13CC=C([C@H](C3)C2(C)C)C
  Canonical SMILES CC1CCC2C13CC=C(C(C3)C2(C)C)C
  External Links PubChem ID 6431015
CAS ID 469-61-4

 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 %
 
Whole plant: A. thaliana wildtype detected in situ
Whole plant Norway
NP Content: 0.12 %
      Species Name: Citrus sinensis (Hongjiang)
  Factor Name: Variety Comparison [2]
              Species Info Factor Info
               Experiment Detail
Four kinds of fresh sweet oranges were obtained in the same season, November 2000, in Guangzhou. Citrus sinensis var. Hongjiang (called 'hong jiang chen' in Chinese) and C. sinensis Osbeck var. Anliu (called 'luo gang chen') were obtained at an orchard in Luo gang in Guangzhou (25 km from the center of Guangzhou). Citrus sinensis var. Sihui (called 'sihui ju') was harvested at the Shigou Experimental Farm in Sihui City in Guangdong Province (75 km far away from Guangzhou). Citrus sinensis var. Washington navel (called 'qi chen') which was produced in Jiangxi Province (200 km from Guangzhou; bordering Guangdong Province), was purchased at the wholesale market in Guangzhou. All oranges were kept in a cold room until prepared a few days later.
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               Factor Function
The peel oil compositions of four kinds of sweet oranges in China, Citrus sinensis Osbeck var. Hongjian, C. sinensis Osbeck var. Anliu, C. sinensis Osbeck var. Sihui and C. sinensis Osbeck var. Washington navel, were investigated by GC and GC/MS. The essential oils were extracted by cold-pressing method. Forty-two to 53 compounds were quantitatively determined for each variety. Their percentages, respectively, were: > 97.3%, > 98.4%, > 97.5% and > 98.0% in hydrocarbons; > 1.5%, > 0.7%, > 0.8% and > 0.9% in total aldehydes; 0.8%, 0.5%, 0.5% and 0.5% in alcohols. Either cis-or trans-limonene oxide was detected in small amounts in each of the four samples, with Hongjiang containing both limonene oxides. delta-3-Carene was commonly quantified at a level of 0.1% in all the samples. The content of aliphatic aldehydes, including octanal, nonanal, decanal and dodecanal, exceeded that of terpene aldehydes, such as neral and geranial in Hongjiang (0.9%) and Washington navel (0.6%), whereas the aliphatic aldehydes in Anliu and Sihui were present to a lesser degree than the terpene aldehydes. Either alpha- or beta-sinensal was detected in trace amounts in each of the four samples. Linalool was the major alcohol in all the samples. Nootkatone was not detected.
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               Factor Part Location NP Content
 
Citrus sinensis var. Washington navel
Fruits China
NP Content: > 0.005; < 0.05 %
      Species Name: Sideritis pusilla
  Factor Name: Variety Comparison; Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
The aerial parts (~35 cm) of each taxa growing wild in eight localities of Almeria province were collected in May 1996. All samples were collected at full flowering. Sideritis pusilla (Lange) Pau ssp. pusilla var. typica, Population/location (UTM): Los Matarines (30SWF7992); Sideritis pusilla ssp. pusilla var. carthaginensis Font Quer, Population/location (UTM): Rambla del Hacho (30SWF7178); Sideritis pusilla ssp. pusilla var. granatensis (Pau) Font Quer, Population/location (UTM): Gafarillos (30SWG8702); Sideritis pusilla ssp. almeriensis (Pau) Malagarriga var. typica, Population/location (UTM): Sierra de Gador, Cerro de los Lobos (30SWF3575); Sideritis pusilla ssp. almeriensis var. littoralis Font Quer, Population/location (UTM): Los Morales (30SWF6775); Sideritis pusilla ssp. almeriensis var. salina Font Quer, Population/location (UTM): Los Pedregales (30SWG7835); Sideritis pusilla ssp. flavovirens (Rouy) Malagarriga, Population/location (UTM): Velez Rubio, Cerro del Huezno (30SWG8965); Sideritis pusilla ssp. osteoxylla (Pau) Pallares, Population/location (UTM): Cabo de Gata, Cerro de S. Miguel (30SWF7165)
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               Factor Function
Monoterpene hydrocarbons, alcohols, sesquiterpenes and diterpenes were the main constituents in all samples. Among these, alpha-pinene (7.1-25.4%), sabinene (5.9-20.4%), fenchone (0.9-19.3%), limonene (1.2-7.4%) and 1,8-cineole (1.8-15.6%) were the major compounds. The results confirm that there are differences between varieties and subspecies, while cluster analysis revealed that the oil composition potentially has chemotaxonomical significance for this taxon.
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               Factor Part Location NP Content
 
Sideritis pusilla (Lange) Pau ssp. pusilla var. typica (Locality: Los Matarines)
Aerial parts Los Matarines, Spain
NP Content: 1.8 %
 
Sideritis pusilla ssp. almeriensis var. salina Font Quer (Locality: Los Pedregales)
Aerial parts Los Pedregales, Spain
NP Content: 1 %
 
Sideritis pusilla ssp. almeriensis (Pau) Malagarriga var. typica (Locality: Sierra de Gador, Cerro de los Lobos)
Aerial parts Sierra de Gador, Cerro de los Lobos, Spain
NP Content: 0.8 %
 
Sideritis pusilla ssp. flavovirens (Rouy) Malagarriga (Locality: Velez Rubio, Cerro del Huezno)
Aerial parts Velez Rubio, Cerro del Huezno, Spain
NP Content: 1.1 %
 
Sideritis pusilla ssp. osteoxylla (Pau) Pallares (Locality: Cabo de Gata, Cerro de S. Migue)
Aerial parts Cabo de Gata, Cerro de S. Migue, Spain
NP Content: 0.7 %
 
Sideritis pusilla ssp. pusilla var. carthaginensis Font Quer (Locality: Rambla del Hacho)
Aerial parts Rambla del Hacho, Spain
NP Content: 1.2 %
 
Sideritis pusilla ssp. pusilla var. granatensis (Pau) Font Quer (Locality: Gafarillos)
Aerial parts Gafarillos, Spain
NP Content: 1.9 %
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
2 Volatile Constituents of the Peel Oils of Several Sweet Oranges in China
3 Essential Oil Composition of Sideritis pusilla (Lange) Pau ssp.