Details of Natural Product (NP)

General Information of Natural Product (ID: NP0546)
  Natural Product Name
Jasmone
  Synonyms
cis-Jasmone; JASMONE; 488-10-8; (Z)-Jasmone; UNII-RC4W0G9YUK; cis-?Jasmone; 3-Methyl-2-pent-2-enylcyclopent-2-enone; (Z)-3-Methyl-2-(pent-2-en-1-yl)cyclopent-2-enone; 3-Methyl-2-(cis-2-penten-1-yl)-2-cyclopenten-1-one; 2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)-; RC4W0G9YUK; cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one; 3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, (Z)-; CHEBI:6084; MFCD00001402; 3-methyl-2-(pent-2Z-enyl)cyclopent-2-enone; 3-Methyl-2-(cis-2-pentenyl)-2-cyclopenten-1-one; 2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-penten-1-yl-; 2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9CI); (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopentenone; 2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8CI); FEMA No. 3196; 3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one; EINECS 207-668-4; BRN 1907713; 3-methyl-2-[(Z)-pent-2-enyl]cyclopent-2-en-1-one; Jasmone (6CI); Jasmone, 90%; cis-3-methyl-2-pent-2-enyl-cyclopent-2-enone; cis-Jasmone, stabilized; Jasmone, analytical standard; DSSTox_CID_27092; DSSTox_RID_82104; DSSTox_GSID_47092; SCHEMBL20385; 4-07-00-00337 (Beilstein Handbook Reference); CHEMBL2251602; DTXSID4047092; HSDB 8273; BCP18948; CMC_7381; HY-N7058; ZINC4467398; Tox21_301825; LMFA02020009; s4960; AKOS024318891; CCG-266315; GS-3251; NCGC00256139-01; CAS-488-10-8; J0003; 3-Methyl-2-n-penten-2'-ylcyclopenten-2-one; C08490; Q418077; (z)-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one; 3-Methyl-2-(2-cis-pentenyl)-2-cyclopenten-1-one; 3-Methyl-2-[(2Z)-2-pentenyl]-2-cyclopenten-1-one; 3-methyl-2-[(Z)-pent-2-enyl]-cyclopent-2-en-1-one; 2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2- pentenyl-; 2-cyclopenten-1-one, 3-methyl-2-[(2Z)-2-pentenyl]-; 3-Methyl-2-[(2Z)-2-pentenyl]-2-cyclopenten-1-one #; 3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
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  Formula C11H16O
  Weight 164.24
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
  InChI Key XMLSXPIVAXONDL-PLNGDYQASA-N
  Isomeric SMILES CC/C=C\\CC1=C(CCC1=O)C
  Canonical SMILES CCC=CCC1=C(CCC1=O)C
  External Links PubChem ID 1549018
CAS ID 488-10-8
NPASS ID NPC100380
HIT ID C1063
CHEMBL ID CHEMBL2251602
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia absinthium
  Factor Name: Chemotype Comparison [1]
              Species Info Factor Info
               Experiment Detail
Ten different plants of wormwood were collected in March 1997 from each one of the following four wild populations in the Spanish Pyrenees: Tallo de Aulet (prov. Huesca) and Pont de Suert, Sort and Farga de Moles (prov. Lleida). In three of the four populations studied, there was another chemotype, with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate. This chemotype, called chemotype B, was less frequent in the Pyrenees than the chemotype A, appearing only in 17% of the samples (two samples in TallO de Aulet and in Pont de Suert and three samples in Farga de Moles).
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               Factor Function
Two chemotypes were detected; a cis-epoxyocimene type (with more than 50% of this compound) which was predominant in all the populations, and a cis-epoxyocimene + chrysanthenyl acetate type (with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate). The distribution of these chemotypes had no relation with the altitude of the samples.
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               Factor Part Location NP Content
 
Chemotype (cis-epoxyocimene type)
 Leaves Spain
NP Content: 0.04 %
 
Chemotype (cis-epoxyocimene + chrysanthenyl acetate type)
 Leaves Spain
NP Content: 0.14 %
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [2]
              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: 0.4 %
 
Artemisia annua cv. Jeevanraksha
 Aerial parts India
NP Content: <0.05 %
      Species Name: Artemisia ferganensis
  Factor Name: Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
The leaves of aerial parts were collected in Heshuo county of Xinjiang province in China in July 2003 (a vegetative stage), June 2003 (a budding stage); and August 2003 (a flowering stage), respectively.
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               Factor Function
Only 23 constituents were present at the budding stage, while 24 and 26 at the flowering and vegetative stages, respectively. p-Cymene and gamma-terpinene were not detected at the vegetative stage of the plant. During the budding stage, butyric, beta-caryophyllene, geranyl acetate and cis-jasmone could not be detected. Benzaldehyde was observed only at the vegetative stage. Variations were also observed in quantity. In all cases the analyzed oils were characterized by the high concentration of alpha-thujone, ranging in amount from 37.0% at the vegetative stage to 54.8% at the budding stage. The concentration of alpha-thujone at the flowering stage (49.0%) was lower than the budding stage, but higher than the vegetative stage. The concentration of cis-chrysanthenyl acetate varied between 23.5% and 7.2%, respectively, at the vegetative and budding stages. At the vegetative stage the concentration of 1,8-cineole was observed to be the lowest. It was highest at the budding stage, representing 10.4%, then decreased gradually to 8.8% at the flowering stage. The concentration of beta-thujone was relatively low at the vegetative stage, representing 8.6%, and then increased to 10.5% at the budding stage. When flowers appeared it was found to vary a little. Finally, the concentration of sabinyl acetate ranged from 10.2% (vegetative stage) to 6.5% (flowering stage).
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               Factor Part Location NP Content
 
Vegetative stage
 Leaves Heshuo, Xinjiang, China
NP Content: 0.1 %
 
Aerial part: Flowering stage
 Leaves Heshuo, Xinjiang, China
NP Content: 0.1 %
      Species Name: Mentha longifolia
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
Plants were collected in the Inner plain, the Sharon plain and the kava valley.
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               Factor Function
The major constituent of all three oils was found to be 1,8-cineole (26.4-34.5%) followed by menthone (10.0-16.7%), pulegone (7.0-7.5%), and isomenthone (4.7-7.8%). Despite some differences in the component proportions, the plants of all three populations clearly belong to the same chemotype.
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               Factor Part Location NP Content
 
Locality: Sharon plain, Israel
 Aerial parts Israel
NP Content: 1.4 %
 
Locality: Arava valley, Israel
 Aerial parts Israel
NP Content: 0.1 %
 
Locality: Inner plain, Israel
 Aerial parts Israel
NP Content: trace %
      Species Name: Mentha rotundifolia
  Factor Name: Altitude Variation [5]
              Species Info Factor Info
               Experiment Detail
Mentha rotundifolia leaves were collected in the second week of November 2004 in two localities of Algeria (Rouina: altitude 250 m, Miliana: altitude 780 m) within the region of Ain-Defla located in northern Algeria.
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               Factor Function
Thirty-nine compounds were identified in leaf oil of sample 1 (Rouina, Algeria), the main one being cis-piperitone oxide. Thirty-nine compounds were identified in leaf oil of sample 2 (Miliana, Algeria). The main one being piperitenone oxide.
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               Factor Part Location NP Content
 
Locality: Rouina, Algeria; Altitude 250 m
 Leaves Algeria
NP Content: 0.4 %
 
Locality: Miliana, Algeria; Altitude 780 m
 Leaves Algeria
NP Content: 0.7 %
      Species Name: Salvia limbata
  Factor Name: Locality Variation [6]
              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: 0.3 %
References
1 Essential Oil of Artemisia absinthium L. from the Spanish Pyrenees
2 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
3 Seasonal Analyses of the Essential Oil of Artemisia ferganensis
4 Volatile Extract of Mentha longifolia Growing in Israel. Aromatic Plants of the Holy Land and the Sinai. Part XIII
5 Chemical Composition of the Leaf Oil of Mentha rotundifolia (L.) from Algeria
6 The Essential Oil of Salvia limbata C.A. Meyer Growing in Turkey