General Information of Natural Product (ID: NP0173)
  Natural Product Name
Alpha-Cadinene
  Synonyms
alpha-Cadinene; (+)-alpha-cadinene; UNII-X650G04I0A; X650G04I0A; 11044-40-9; 24406-05-1; (1S,4aR,8aR)-4,7-dimethyl-1-propan-2-yl-1,2,4a,5,6,8a-hexahydronaphthalene; (-)-alpha-Cadinene; alpha-Cadinene, (+)-; Cadinen; a-Cadinene; (-)-a-Cadinene; Cadina-4,9-diene, (-)-; CHEBI:80749; Cadina-4,9-diene, (-)- (8CI); (1S,4aR,8aR)-4,7-dimethyl-1-(propan-2-yl)- 1,2,4a,5,6,8a-hexahydronaphthalene; Naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-(1alpha,4abeta,8aalpha))-; Q27149802; (1S,4aR,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene; 1,2,4a,5,6,8a-Hexahydro-4,7-dimethyl-1-(1-methylethyl)-(1S,4aR,8aR)-Naphthalene
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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(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h6,9-10,13-15H,5,7-8H2,1-4H3/t13-,14-,15-/m0/s1
  InChI Key QMAYBMKBYCGXDH-KKUMJFAQSA-N
  Isomeric SMILES CC1=C[C@@H]2[C@@H](CC1)C(=CC[C@H]2C(C)C)C
  Canonical SMILES CC1=CC2C(CC1)C(=CCC2C(C)C)C
  External Links PubChem ID 12306048
CAS ID 11044-40-9

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Echinacea purpurea
  Factor Name: Plant Pathogen Infection [1]
              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: 0.2 %
 
Infected plants (cucumber mosaic cucumovirus)
Aerial parts Italy
NP Content: 0.2 %
      Species Name: Eucalyptus urophylla
  Factor Name: Seasonal Variation [2]
              Species Info Factor Info
               Experiment Detail
Eucalyptus urophylla and E. grandis were collected in January (summer) and August (winter) 2006 at the mature vegetative state from Goiania city Brazil, and identified by one of the authors (E.P.F.). Leaves from 5-11 randomized individual plants of the same age representing the local population were collected as homogenous samples in each season, dried at room temperature.
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               Factor Function
The results were submitted to Principal Components and Clusters Analysis which enabled four groups of oils to be distinguished with regard to specimens and harvest seasons: clusters I and II with only E. grandis samples collected in the cold and dry winter and the hot and humid summer, which were characterized by a high percentage of isoleptospermone (9.6% and 13.2%), alpha-pinene (12.2% and 24.7%), p-cymene (20.5% and 14.5%), and alpha-terpineol (14.3% and 4.9%), respectively; clusters III and IV only associated with E. urophylla samples collected in summer and winter with 1,8-cineole (36.6% and 44.7%) and alpha-terpinyl acetate (7.0% and 11.7%) rich oils.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Whole plant Brazil
NP Content: 2.3 %
 
Harvesting time: Winter
Whole plant Brazil
NP Content: 1.4 %
      Species Name: Eugenia chlorophylla
  Factor Name: Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Plant material was collected at vegetative stage (stems and leaves,September 2005) and at flowering stage (leaves and flowers,December 2004), inCuritiba,Parana state, Brazil.
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               Factor Function
Thirty-four components were identified, representing more than 80% of total oil. The major components were beta-caryophyllene (flowers-12.8%), caryophyllene oxide (stems-17.2%), globulol (stems-16.5%; leaves-22.5% at vegetative stage and 18.9% at flowering stage), 1-epi-cubenol (stems-10.9%), epi-alpha-muurolol (stems-16.8%) and alpha-cadinol (stems-12.1%; flowers-10.1%).
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               Factor Part Location NP Content
 
Flower: flowering stage
Flowers Brazil
NP Content: 5.2 %
      Species Name: Eugenia dysenterica
  Factor Name: Developmental Stage Variation [4]
              Species Info Factor Info
               Experiment Detail
Unripe, semi-ripe, and ripe fruits of E. dysenterica were collected in rural area of Abadia de Goias city (S 16° 45′ 1″, W 49° 25′ 5″, 850 m), Goias State, Brazil, in October 2002.
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               Factor Function
Limonene (25.8% and 24.6%), (E)-beta-ocimene (20.3% and 21.7%) and beta-pinene (12.0% and 14.2%) were the major compounds in the unripe and semi-ripe stages, respectively, while gamma-muurolene (25.8%), beta-caryophyllene (18.4%) and alpha-humulene (15.4%) became the major compounds in ripe fruits. The concentration of monoterpenes was high in the unripe and semi-ripe stages and decreased afterwards, while sesquiterpenes were intensively synthesized only in the last part of the ripening process.
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               Factor Part Location NP Content
 
Fruit: Ripe fruit stage
Ripe fruits Brazil
NP Content: 0.6 %
      Species Name: Glechoma hederacea
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Samples of Glechoma hederacea were collected at full flowering in seven localities in Vilnius district (Lithuania) at 2005: A - Salininkai, B -Zolyno, C - Mistunai, D -Antakalnis, E - Nemencine, F - Seskine, G -Zujunai.
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               Factor Function
More than half of the oils were rich in sesquiterpene hydrocarbons (56.5-67.9%). The most predominant compound was germacrene D (14.1-20.7%). The other main constituents were gamma-elemene (9.0-16.0%), beta-elemene (8.7-12.9%), phytols (2.8-15.6%), (Z)-beta-ocimene (2.2-8.5%), 1,8-cineole (92.2-5.4%), beta-ylangene (2.7-4.1%) and germacrene B (2.2-3.9%). Forty-three identified compounds made up 89.1-96.2%. Four oils (A, D-G) might be attributed to germacrene / elemene chemotype and three samples (A-C) containing marked amounts of phytols beside above compounds were of germacrene/elemene/phytols chemotype.
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               Factor Part Location NP Content
 
Locality: Salininkai, Lithuania
Aerial parts Lithuania
NP Content: 1.1 %
 
Locality: Zolyno, Lithuania
Aerial parts Lithuania
NP Content: <0.05 %
 
Locality: Mistunai, Lithuania
Aerial parts Lithuania
NP Content: 0.4 %
 
Locality: Antakalnis, Lithuania
Aerial parts Lithuania
NP Content: 0.5 %
 
Locality: Seskine, Lithuania
Aerial parts Lithuania
NP Content: 0.2 %
 
Locality: Zujunai, Lithuania
Aerial parts Lithuania
NP Content: 0.2 %
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [6]
              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: 1.8 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 2.8 %
 
Inflorescence: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 1.5 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 1.1 %
 
Leaf: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.5 %
 
Leaf: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 5.4 %
 
Leaf: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 1.3 %
 
Leaf: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: < 0.05 %
      Species Name: Mentha rotundifolia
  Factor Name: Altitude Variation [7]
              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: < 0.1 %
 
Locality: Miliana, Algeria; Altitude 780 m
Leaves Algeria
NP Content: < 0.1 %
      Species Name: Ocimum basilicum
  Factor Name: Drought Stress Treatment [8]
              Species Info Factor Info
               Experiment Detail
Seeds of Ocimum basilicum cv. keskenylevelu provided from Hungary, were used in this study. Potted seedlings of Ocimum basilicum were subjected to study the effect of different irrigation rigimes on the essential oil content and composition at experimental farm of college of agriculture, Tarbiat Modarres, University, located in Tehran. (1215 m above sea level, latitude 35° 43′ north, altitude 51° 8′ east). The seeds were sown in spring of 2001 in pots. The irrigation regimes to induce of water stress were: 100%, 85%, 70% and 55% of field capacity. This percentage of field capacity kept constant in the soil by daily weighting of pots. The soil was sandy-loam with 22.6% of field capacity. The harvest of whole plants was performed at the beginning of the flowering stage.
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               Factor Function
The essential oil content of herb increased from 1.12 to 1.26% as plant water deficit increased (till 70% of field capacity). The number of component of the oil of Ocimum basilicum increased as water stress increase. Amount of the main constituents of the oil such as linalool, methyl chavicol, 1,8-cineole and trans alpha-bergamotene significantly affected by water stress.
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               Factor Part Location NP Content
 
55% Field Irrigation
Whole plant Mali
NP Content: 0.4 %
      Species Name: Pinus sylvestris
  Factor Name: Locality Variation [9]
              Species Info Factor Info
               Experiment Detail
The branches of pine were collected in July, 1996 in 15 different locations in Lithuania in the following regions: Western part (Silute, Jurbarkas, Kursiu Nerija), Eastern part (Salcininkai, Zarasai, Moletai), Southern part (Varena, Trakai, Radviliskis) and central part (Ukmerge, Jonava, Kaisiadorys). The branches in each location were collected from the trees in approximately 1 km radius.
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               Factor Function
More than 70 constituents were identified (64 positively and 10 tentatively) in the oils. alpha-Pinene (18.5-33.0%) and delta-3-carene (9.1-24.6%) were dominating constituents with the only one exception when the germacrene-4-ol content in one of the samples was 13.2%. The important bornyl acetate content varied from 0.5% to 3.0%. The main sesquiterpenes were beta-caryophyllene, germacrene D, bicyclogermacrene, delta-cadinene, gamma-cadinene, germacrene D-4-ol, cubenol (2.0-5.1%) and alpha-cadinol (1.9-7.7%).
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               Factor Part Location NP Content
 
Locality: Jonava, Lithuania
Branches Jonava, Lithuania
NP Content: 0.3 %
 
Locality: Jurbarkas, Lithuania
Branches Jurbarkas, Lithuania
NP Content: 0.4 %
 
Locality: Kaisiadorys, Lithuania
Branches Kaisiadorys, Lithuania
NP Content: 0.3 %
 
Locality: Moletai, Lithuania
Branches Moletai, Lithuania
NP Content: 0.3 %
 
Locality: Neringa (Smiltyne), Lithuania
Branches Neringa (Smiltyne), Lithuania
NP Content: 0.4 %
 
Locality: Radviliskis, Lithuania
Branches Radviliskis, Lithuania
NP Content: 0.2 %
 
Locality: Salacininkai, Lithuania
Branches Salacininkai, Lithuania
NP Content: 0.3 %
 
Locality: Silute, Lithuania
Branches Silute, Lithuania
NP Content: 0.3 %
 
Locality: Trakai, Lithuania
Branches Trakai, Lithuania
NP Content: 0.3 %
 
Locality: Ukmerge, Lithuania
Branches Ukmerge, Lithuania
NP Content: 0.2 %
 
Locality: Varena, Lithuania
Branches Varena, Lithuania
NP Content: 0.3 %
 
Locality: Vilnius, Lithuania
Branches Vilnius, Lithuania
NP Content: 0.3 %
 
Locality: Zarasai, Lithuania
Branches Zarasai, Lithuania
NP Content: 0.3 %
 
Locality: Zarsai (lmbradas), Lithuania
Branches Zarsai (lmbradas), Lithuania
NP Content: 0.3 %
 
Locality: Zarasai (Sunele), Lithuania
Branches Zarasai (Sunele), Lithuania
NP Content: 0.3 %
      Species Name: Sideritis pusilla
  Factor Name: Variety Comparison; Locality Variation [10]
              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 ssp. almeriensis var. salina Font Quer (Locality: Los Pedregales)
Aerial parts Los Pedregales, Spain
NP Content: 0.2 %
 
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: 0.4 %
 
Sideritis pusilla ssp. flavovirens (Rouy) Malagarriga (Locality: Velez Rubio, Cerro del Huezno)
Aerial parts Velez Rubio, Cerro del Huezno, Spain
NP Content: 0.6 %
 
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: 0.6 %
 
Sideritis pusilla ssp. pusilla var. carthaginensis Font Quer (Locality: Rambla del Hacho)
Aerial parts Rambla del Hacho, Spain
NP Content: 0.2 %
 
Sideritis pusilla ssp. pusilla var. granatensis (Pau) Font Quer (Locality: Gafarillos)
Aerial parts Gafarillos, Spain
NP Content: 0.2 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [11]
              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: 0.03 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [12]
              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
 
Stem: (Locality: Adana, Turkey)
Stems Adana, Turkey
NP Content: 0.1 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [13]
              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: 1.83 %
 
Vitis vinifera var. Nerello Mascalese
Stalks Italy
NP Content: 2.27 %
 
Vitis vinifera var. Nero d'Avola
Stalks Italy
NP Content: 0.72 %
References
1 Characterization of the Essential Oils of Healthy and Virus Infected Echinacea purpurea (L.) Moench Plants
2 Seasonal Influence on the Essential Oil Compositions of Eucalyptus urophylla S. T. Blake and E. grandis W. Hill ex Maiden from Brazilian Cerrado
3 Chemical Composition and Antimicrobial Activity of Essential Oils of Eugenia chlorophylla (Myrtaceae)
4 Changes in Volatile Constituents During Fruit Ripening of Wild Eugenia dysenterica DC.
5 The Essential Oil of Ground Ivy (Glechoma hederacea L) Growing Wild In Eastern Lithuania
6 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
7 Chemical Composition of the Leaf Oil of Mentha rotundifolia (L.) from Algeria
8 Essential oil content and composition of sweet basil (Ocimum basilicum) at different irrigation regimes
9 Composition of Essential Oils of Pinus sylvestris L. from Different Locations of Lithuania
10 Essential Oil Composition of Sideritis pusilla (Lange) Pau ssp.
11 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
12 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
13 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.