General Information of Natural Product (ID: NP0214)
  Natural Product Name
Labd-14-Ene, 8,13-Epoxy-, (13S)-
  Synonyms
Manoyl oxide; Labd-14-ene, 8,13-epoxy-, (13S)-; Epimanoyl oxide; 13-Epimanoyl oxide; 13-epi-Manoyl oxide; (13R)-manoyl oxide; 1H-Naphtho[2,1-b]pyran, 3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-, [3S-(3.alpha.,4a.alpha.,6a.beta.,10a.alpha.,10b.beta.)]-; (13R)-8,13-epoxylabd-14-ene; epi-13-Manoyl oxide; Oxyde d'epi-13-manoyle; 3,4a,7,7,10a-Pentamethyl-3-vinyldodecahydro-1H-benzo[f]chromene #; SCHEMBL3967644; ZINC3153996; C21725
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  Formula C20H34O
  Weight 290.5
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
  InChI Key IGGWKHQYMAJOHK-HHUCQEJWSA-N
  Isomeric SMILES C[C@@]1(CC[C@@H]2[C@]3(CCCC([C@@H]3CC[C@]2(O1)C)(C)C)C)C=C
  Canonical SMILES CC1(CCCC2(C1CCC3(C2CCC(O3)(C)C=C)C)C)C
  External Links PubChem ID 6432025
CAS ID 596-84-9

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Cupressus sempervirens
  Factor Name: Month Variation [1]
              Species Info Factor Info
               Experiment Detail
The leaves of C. sempervirens were collected in the region of central Dalmatia (Croatia) within 12 months (1999).
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               Factor Function
The oils produced in the autumn (September and October) were found to contain higher amounts of alpha-pinene (71.0% and 79.2%) than the oils produced from February to May (28.4-32.5%). The smallest amount of alpha-pinene (28.4%) was recorded in February, at the same time as the amount of cedrol, the quantitatively most important oxygenated compound, reached its maximum (12.9%).
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               Factor Part Location NP Content
 
Harvesting time: January
Leaves Dalmatia, Croatia
NP Content: 2.8 %
 
Harvesting time: February
Leaves Dalmatia, Croatia
NP Content: 2.7 %
 
Harvesting time: March
Leaves Dalmatia, Croatia
NP Content: 1.8 %
 
Harvesting time: April
Leaves Dalmatia, Croatia
NP Content: 1.6 %
 
Harvesting time: May
Leaves Dalmatia, Croatia
NP Content: 2 %
 
Harvesting time: June
Leaves Dalmatia, Croatia
NP Content: 2.2 %
 
Harvesting time: July
Leaves Dalmatia, Croatia
NP Content: 1.5 %
 
Harvesting time: August
Leaves Dalmatia, Croatia
NP Content: 1.7 %
 
Harvesting time: September
Leaves Dalmatia, Croatia
NP Content: 1.1 %
 
Harvesting time: October
Leaves Dalmatia, Croatia
NP Content: 0.6 %
 
Harvesting time: December
Leaves Dalmatia, Croatia
NP Content: 1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [2]
              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: Shahr-e-kord, western Iran
Aerial parts Iran
NP Content: <0.05 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [3]
              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. Frappato
Pomaces Italy
NP Content: 0.28 %
 
Vitis vinifera var. Frappato
Stalks Italy
NP Content: 0.57 %
 
Vitis vinifera var. Nerello Mascalese
Pomaces Italy
NP Content: 0.4 %
 
Vitis vinifera var. Nerello Mascalese
Stalks Italy
NP Content: 0.79 %
 
Vitis vinifera var. Nero d'Avola
Pomaces Italy
NP Content: 0.1 %
References
1 Seasonal Variation in Essential Oil Compositions of Cupressus sempervirens L.
2 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
3 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.