Details of Natural Product (NP)

General Information of Natural Product (ID: NP0059)
  Natural Product Name
Valencene
  Synonyms
Valencene; (+)-Valencene; 4630-07-3; Valencene (natural); Valencen; UNII-96H21P91IG; (3R,4aS,5R)-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene; CHEBI:61700; 96H21P91IG; ent-7betaH-eremophila-10(1),11-diene; (1R-(1alpha,7beta,8alpha))-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthalene; (3R,4aS,5R)-4a,5-Dimethyl-3-isopropenyl-1,2,3,4,4a,5,6,7-octahydronaphthalene; (A+/-)-valencene; DSSTox_CID_27052; DSSTox_RID_82070; DSSTox_GSID_47052; Valencene, natural, >=65%; FEMA No. 3443; CHEMBL3186909; DTXSID8047052; (+)-Valencene, analytical standard; HY-N6636; Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1R,7R,8aS)-; ZINC1734352; EINECS 225-047-6; Tox21_302397; MFCD00075884; (+)-Valencene, technical, >=70%; NSC 148969; NCGC00256249-01; CAS-4630-07-3; 4Betah,5alpha-eremophila-1(10),11-diene; CS-0044199; (+)-Valencene 1000 microg/mL in Isopropanol; C17277; Q289496; 4betaH,5alpha-Eremophila-1(10),11-diene (8CI); 4alpha,10alpha-Dimethyl-6beta-isopropyl-delta1,9-octalin; 4alpha,10alpha-Dimethyl-6beta-isopropyl-.DELTA.1,9-octalin; (3R,4aS,5R)-4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene; 1,2,3,5,6,7,8,8a-Octahydro-1,8A-dimethyl-7-(1-methylethenyl)naphthalene, (1R-(1alpha,7beta,8aalpha))-; Naphthalene, 1,2,3,5,6,7,8,8A-octahydro-1,8A-dimethyl-7-(1-methylethenyl)-, (1R-(1alpha,7beta,8aalpha))-
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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)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3/t12-,13-,15+/m1/s1
  InChI Key QEBNYNLSCGVZOH-NFAWXSAZSA-N
  Isomeric SMILES C[C@@H]1CCC=C2[C@]1(C[C@@H](CC2)C(=C)C)C
  Canonical SMILES CC1CCC=C2C1(CC(CC2)C(=C)C)C
  External Links PubChem ID 9855795
CAS ID 4630-07-03
NPASS ID NPC86683
CHEMBL ID CHEMBL3186909
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Citrus sinensis (Hongjiang)
  Factor Name: Variety Comparison [1]
              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. Hongjiang
 Fruits China
NP Content: > 0.005; < 0.05 %
 
Citrus sinensis var. Sihui
 Fruits China
NP Content: < 0.005 %
      Species Name: Dittrichia graveolens
  Factor Name: Altitude Variation [2]
              Species Info Factor Info
               Experiment Detail
Wild growing D. graveolens samples were collected from Bekaa-877′ (4 samples) and Sannine-1842′ (3 samples) during the flowering period, between September and November of 2003.
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               Factor Function
The major differences in oil composition between the two populations are the variation in the concentrations of T-cadinol and borneol. The differences can also be ascribed to the distinct climatic pattern of the two samples: Sannine is located in the Mount Lebanon chain of mountains and characterized by heavy precipitations and snow, while the Bekaa valley is shielded by this same chain of mountains, resulting in dry summers and cold winters with less humidity and precipitations.
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               Factor Part Location NP Content
 
Locality: Sannine, Lebanon; Altitude 1842 m
 Leaves and flowers Lebanon
NP Content: 0.04 %
      Species Name: Echinacea purpurea
  Factor Name: Plant Pathogen Infection [3]
              Species Info Factor Info
               Experiment Detail
Plant selection and virological tests: Before effecting the collection procedure, heathy and infected plants of E. purpurea grown in the open field at the Herb Garden of Casola Valsenio were selected and labelled by visual inspection of their aerial parts. The infection by CMV was associated with symptoms on both leaves and flowers. The most characteristic symptoms are yellow mosaic, ring and line-patterns on crinkled and deformed leaves that drop prematurely. The flowers, which may be smaller than normal, show color breaking with white or pale stripes on red petals. Shortening of the internodes is also very common, giving the plant a bushy appearance known as stunting. In Italian environmental conditions, these symptoms are best visible in the summer. On the other hand, plants appeared symptom-free were collected as healthy material. Plant collection: About 3-4 Kg fresh aerial part materials (70% stems, 10% leaves and 20% flowers) of healthy E. purpurea plants were collected in June 2000 at almost the end of flowering. An equivalent quantity of CMV-infected plants (evaluated by DAS-ELISA) was also collected; the percentage of leaves in the infected infected was about 6.0% as due to CMV presence that caused the premature leaf drop.
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               Factor Function
The oil from healthy material was rich in germacrene D (57.8%) and was more abundant. The infected materials afforded a lower oil content and significant quantitative variations in the oil composition. In particular, the observed percentage of germacrene D (52.6%) was reduced as were other sesquiterpene hydrocarbons. These variations, tested to be significant for all the compound-class fractions and individual major components, were ascribed to the cucumber mosaic cucumovirus (CMV) infection, the only fixed-effect variable that might affect the oil composition.
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               Factor Part Location NP Content
 
Healthy plant
 Aerial parts Italy
NP Content: 3 %
 
Infected plants (cucumber mosaic cucumovirus)
 Aerial parts Italy
NP Content: 1.9 %
      Species Name: Hyptis pectinata
  Factor Name: Locality Variation [4]
              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: 0.1 %
      Species Name: Persea americana
  Factor Name: Variety Comparison; Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Experimental: Two hundred grams of healthy mature intact leaves were harvested from each of the taxa growing on their own rootstocks at the UC South Coast Research and Extension Center. flocc = P. americana var. floccosa from Mexico D-7; stey = P. americana var. steyermarkii from Mexico El Salvador 3-22-16; nubi = P. americana var. nubigena from Guatemala 45-C-1; mex = P. americena var. drymfolia from Tasco, Mexico; guat = P. americana var. guatemalensis cult. Nimlioh from Florida; bwl = P. ameticana var. americana cult. Trapp from Florida.
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               Factor Function
Analysis of oils showed the presence of over 90 components, of which 76 were identified. P. schiedeana oil was found to contain alpha-pinene (23.7%), beta-pinene (23.2%) and beta-caryophyllene as major components. The major constituents of P. americana var. floccosa and P. americana var. steyermarkii were alpha-pinene (10.9%, 7.6%), beta-pinene (20.6%, 10.4%), alpha-terpineol (9.6%, 7.9%), beta-caryophyllene (12.6%, 8.4%), viridiflorene (0.1%, 10.3%) and globulol (0.1%, 9.2%), respectively. The oils of P. americana var. nubigena and P. americana var. drymifolia contained alpha-terpineol (18.4%, 393%) and methylchavicol (12.4%, 40.2%), as major components, respectively. P. americana var. guatemalensis was found to be rich in beta-caryophyllene (38.3%), while the oils of P. americana var. americana and P. primatogena contained alpha-pinene (27.5%) and beta-pinene (40.9%), and alpha-pinene (24.6%), beta-caryophyllene (20.7%) and germacene D (10.1%).
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               Factor Part Location NP Content
 
Persea americana var. americana cv. Trapp (Locality: Florida)
 Leaves Florida, USA
NP Content: 0.1 %
 
Persea americana var. drymfolia (Locality: Tasco)
 Leaves Tasco, Mexico
NP Content: 0.2 %
 
Persea americana var. floccosa (Locality: Mexico)
 Leaves Mexico
NP Content: 0.1 %
 
Persea americana var. guatemalensis cv. Nimlioh (Locality: Florida)
 Leaves Florida, USA
NP Content: 0.2 %
 
Persea americana var. nubigena (Locality: Guatemala)
 Leaves Guatemala
NP Content: 0.01 %
 
Persea americana var. steyermarkii (Locality: Mexico El Salvador)
 Leaves Mexico El Salvador
NP Content: 3.8 %
      Species Name: Salvia aucheri
  Factor Name: Variety Comparison [6]
              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: <0.01 %
 
Salvia aucheri var. canescens
 Aerial parts Karaman, Turkey
NP Content: 0.1 %
      Species Name: Salvia sclarea
  Factor Name: Locality Variation [7]
              Species Info Factor Info
               Experiment Detail
200 g of fresh flowering spikes were collected randomly at full bloom stage (browning of lower floret stage) from the 2006-2007 crops of clary sage cultivar CIM-Chandni cultivated at CIMAP Lucknow and resource center Purara, Uttarakhand. The oil of Kashmir origin was collected from the Chemistry division of IIIM Jammu.
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               Factor Function
Linalool (23.6%), alpha-terpineol (3.8%), linalyl acetate (51.2%), beta-caryophyllene (3.2%), germacrene D (1.3%) and sclareol (1.3%) were recorded in the oil S. sclarea cultivated in Lucknow UP while the Kashmir oil sample possessed the highest percentage of linalyl acetate (60.8%) and lowest linalool (14.5%) along with alpha-terpineol (1.8%), geranyl acetate (2.2%), beta-caryophyllene (1.9%), germacrene D (2.6%) and sclareol (1.3%) as the other minor constituents. In contrast, the oil of S. sclarea from Purara in Uttarakhand showed highest percentage of linalool (29.8%), alpha-terpineol (5.3%) and sclareol (2.3%) and the lowest linalyl acetate (45.7%) among all the three samples.
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               Factor Part Location NP Content
 
Locality: Lucknow UP, India
 Spikes India
NP Content: 0.3 %
 
Locality: Jammu and Kashmir, India
 Spikes India
NP Content: 0.1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [8]
              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: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [9]
              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
 
Root: (Locality: Sivas, Turkey)
 Roots Sivas, Turkey
NP Content: 0.2 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [10]
              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
 
Fruit oil
 Fruits Italy
NP Content: 0.1 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [11]
              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: 0.2 %
References
1 Volatile Constituents of the Peel Oils of Several Sweet Oranges in China
2 Chemical Profle of the Dittrichia graveolens (Desf.) Greuter Essential Oil of Lebanese Origin
3 Characterization of the Essential Oils of Healthy and Virus Infected Echinacea purpurea (L.) Moench Plants
4 Volatile Constituents of Hyptis pectinata Poit. (Lamiaceae)
5 Essential Oils of Persea subgenus Persea (Lauraceae)
6 Composition of Essential Oils from Two Varieties of Salvia aucheri Benth. Growing in Turkey
7 Terpenoid Compositions and Enantio-differentiation of Linalool and Sclareol in Salvia sclarea L. from Three Different Climatic Regions in India
8 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
9 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
10 Seasonal Variations of Teucrium flavum L. Essential Oil
11 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey