General Information of Natural Product (ID: NP0010)
  Natural Product Name
Alpha-Guaiene
  Synonyms
alpha-Guaiene; Guaia-1(5),11-diene; 3691-12-1; (1S,4S,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene; (1S,4S,7R)-1,4-dimethyl-7-prop-1-en-2-yl-1,2,3,4,5,6,7,8-octahydroazulene; .alpha.-Guaiene; Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, [1S-(1.alpha.,4.alpha.,7.alpha.)]-; CHEBI:63443; 7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydroazulene-, [1S-(1.alpha.,4.alpha.,7.alpha.)]-; ZINC70454368; C20161; Q5613309
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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)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+/m0/s1
  InChI Key ADIDQIZBYUABQK-RWMBFGLXSA-N
  Isomeric SMILES C[C@H]1CC[C@H](CC2=C1CC[C@@H]2C)C(=C)C
  Canonical SMILES CC1CCC(CC2=C1CCC2C)C(=C)C
  External Links PubChem ID 5317844
CAS ID 3691-12-01

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Cassinia laevis
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
Six samples of Cassinia laevis R. Br. (coughbush, wild rosemary) were gathered from Lowood, 45 km west of Brisbane to Murphy's Creek area 100 km west of Brisbane, Australia from 1994 to 1998. Samples were identified by a LAEV prefix. LAEV 1 and LAEV 4 were collected from the roadside verge of the Gatton-Toowoomba bypass road (Lat. 27° 32′ 21″ S; Long. 152° 14′ 28″ E). LAEV 2 and LAEV 5 were collected from a different location in the same area (Lat. 27° 33′ 08″ S; Long. 152° 15′ 00″ E). LAEV 7 were collected from the Murphy's creek area (Lat. 27° 31′ 05″ S; Long. 152° 04′ 15″ E), growing on the roadside and in an adjacent paddock. Sample LAEV 9, was collected from the roadside area of the Warrego Highway (Lat. 27° 32′ 10″ S; Long. 152° 27′ 12″ E). The collected leaf and flower samples had aromas of trampled grass with a slight hint of curry.
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               Factor Function
Spathulenol was the major compound in flower oils (8-12%) compared to leaf oils (0.3-4.0%) which had ledol(37.5-53.6%) as the major compound.
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               Factor Part Location NP Content
 
Flower: Sample 1 (Locality: roadside verge of the Gatton-Toowoomba, Brisbane, Queensland)
Flowers Brisbane, Queensland, Australia
NP Content: 0.3 %
 
Flower: Sample 4 (Locality: Lat. 27º 33′ 08″ S; Long. 152º 15′ 00″ E, Brisbane, Queensland)
Flowers Brisbane, Queensland, Australia
NP Content: 0.3 %
 
Flower: Sample 2 (Locality: roadside verge of the Gatton-Toowoomba, Brisbane, Queensland)
Flowers Brisbane, Queensland, Australia
NP Content: 4.2 %
 
Leaf: Sample 3 (Locality: Lat. 27º 33′ 08″ S; Long. 152º 15′ 00″ E, Brisbane, Queensland)
Leaves Brisbane, Queensland, Australia
NP Content: 0.5 %
 
Leaf: Sample 6 (Locality: Murphy's creek area, Brisbane, Queensland)
Leaves Brisbane, Queensland, Australia
NP Content: 0.2 %
      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: Bekka, Lebanon; Altitude 877 m
Leaves and flowers Lebanon
NP Content: 0.2 %
      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: 1.2 %
 
Leaf: flowering stage
Leaves Brazil
NP Content: 1.1 %
 
Leaf: vegetative stage
Leaves Brazil
NP Content: 1.1 %
 
Stem: vegetative stage
Stems Brazil
NP Content: 0.1 %
      Species Name: Fragaria vesca
  Factor Name: Cultivar Comparison [4]
              Species Info Factor Info
               Experiment Detail
Whole leaves and inflorescences of two wild strawberry cultivars ('Rugia' and 'Baron von Solemacher') harvested in 2008 during the agrotechnical experiment performed by Department of Vegetable and Medicinal Plants, University of Life Sciences in Lublin, were used as a material for determinations. Samples were collected before noon at sunny and dry days at the beginning of wild strawberry's flowering stage. Material was dried up to 35 ℃ in shadow and air just after the harvest.
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               Factor Function
Depending on a cultivar, air-dry inflorescences from wild strawberry contain from 0.21% ('Baron von Solemacher' cv.) to 0.30% ('Rugia' cv.), whereas leaves contains from 0.46% ('Baron von Solemacher' cv.) to 0.62% ('Rugia' cv.) of essential oils. GC/MS analysis of essential oils achieved from studied materials revealed presence of 70 (including 59 identified) compounds in leaves of 'Rugia' cv. and 58 (including 50 identified) compounds in leaves of 'Baron von Solemacher' cv. Essential oils from inflorescences of 'Rugia' cv. contained 52 (including 47 identified), while 'Baron von Solemacher' cv. contained 54 (including 46 identified) compounds. The chromatographic analyses by GC-MS revealed that myrthenol, nonal, linalool and phthalide dibuthyl dominated in essential oils obtained from leaves, while myrthenol, citronelol, linalool and geraniol - from those of inflorescences. There were qualitative differences between oil components at both studied materials and differentiation between both cultivars, as well.
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               Factor Part Location NP Content
 
Leaf: Fragaria vesca cv. Rugia
Leaves Poland
NP Content: <0.05 %
      Species Name: Ocimum basilicum
  Factor Name: Variety Comparison [5]
              Species Info Factor Info
               Experiment Detail
Aerial parts of Ocimum basilicum var. purpurascens Benth, Ocimum basilicum var. dianatnejadii Salimi at flowering stage were collected from plants grown in Experimental Station of Pykan Shahr, near Tehran. Elevation 1215 m above sea level, latitude 35° 42′ North, 51° 8′ East, average humidity 36% and climatic category semi-arid.
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               Factor Function
Methyl chavicol (43.0%) and linalool (28.9%) were identified as the major compounds in the oil of O. basilicum var. purpurascens, while methyl chavicol (37.6%), linalool (33.4%) and alpha-cadinol (5.7%) were the major constituents in the oil of O. basilicum var. dianatnejadii.
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               Factor Part Location NP Content
 
Ocimum basilicum var. dianatnejadii Salimi
Aerial parts Iran
NP Content: 1.8 %
 
Ocimum basilicum var. purpurascens Benth
Aerial parts Iran
NP Content: 2.1 %
      Species Name: Ocimum basilicum L
  Factor Name: Cultivar Comparison [6]
              Species Info Factor Info
               Experiment Detail
The 36 'Genovese' and 24 'Foglia di Lattuga' samples preliminarily analysed were grown in Tavazzano (MI), and harvested at flowering, from 5th to 10th August 1998. The breeding program started in 1999, by crossing several selected lines of 'Genovese' with 'Foglia di Lattuga' and 'Compatto'. Selected F1 plants were selfpollinated in 2000. Plants of the F2 (2001), F3 (2002) and F4 (2003) generations were selected on the basis of agronomic and morphologic traits, and self-pollinated. Only the seeds from self pollinated plants with satisfactory essential oil content and composition were used to obtain the next generation. In 2004, some F4 plants were replanted in order to evaluate their stability in relation to environmental variations. All leaf harvests were carried out at flowering.
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               Factor Function
Genovese' showed higher essential oil and linalool content, with almost total absence of methyl chavicol, very abundant in 'Foglia di Lattuga'.
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               Factor Part Location NP Content
 
Ocimum basilicumcv. Foglia Lattuga
Leaves Italy
NP Content: 0.1 %
 
Ocimum basilicumcv. Genovese
Leaves Italy
NP Content: 0.1 %
      Species Name: Persea americana
  Factor Name: Variety Comparison; Locality Variation [7]
              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. 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: 0.2 %
      Species Name: Piper nigrum
  Factor Name: Cultivar Comparison; Harvest Time Variation [8]
              Species Info Factor Info
               Experiment Detail
The cultivars selected for this study are Sreekara, Vellanamban and one Indonesian cultivar Kutching grown in Kerala. These cultivars are commonly cultivated in the northern parts of Kerala. The fresh berries of the authenticated cultivars were collected from Indian Institute of Spices Research, Calicut and were dried in a cross flow drier at 45 ℃ and taken for the analysis.
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               Factor Function
The main components of vellanamban oil were sabinene (3.9-18.8%), beta-pinene (3.9-10.9%), limonene (8.3-19.8%) and beta-caryophyllene (28.4- 32.9%). Sreekara oil contained as major compounds beta-pinene (0-11.2%), limonene (20.1-22.1%) and beta-caryophyllene (16.8-23.1 %). Kutching oil contained alpha-pinene(2.3-5.4%), sabinene (6.7-13.3%), limonene (14.5-17.5%) and beta-caryophyllene (20.8-39.1%).
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               Factor Part Location NP Content
 
Piper nigrum cv. Kuching: (Harvesting time: 1990)
Berries India
NP Content: 1 %
 
Piper nigrum cv. Kuching: (Harvesting time: 1991)
Berries India
NP Content: <0.1 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1990)
Berries India
NP Content: 2.5 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1991)
Berries India
NP Content: 1.7 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1992)
Berries India
NP Content: 0.3 %
 
Piper nigrum cv. Vellanamban: (Harvesting time: 1991)
Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Vellanamban: (Harvesting time: 1992)
Berries India
NP Content: <0.1 %
      Species Name: Rosa damascena
  Factor Name: Variety Comparison [9]
              Species Info Factor Info
               Experiment Detail
Experimental site: The present study was conducted at the experimental farm of the CSIR-Institute of Himalayan Bioresource Technology, Palampur (1325 m amsl, 32° 06′ 05″ N, 76° 34′10″ E), India, in 2011. Minimum temperature ranges from 3.5 ℃ to 19.8 ℃, maximum temperature ranges from 15.2 ℃ to 31.4 ℃, relative humidity varies between 62.2% and 94.1% in the morning and 45.0% and 87.2% in the evening, and bright sunshine hour ranges from 2.9 to 8.9 hours. Plant material: A population of approximately 50,000 plants raised from mixed stem cuttings collected from perennial rose plantations at the University of Agriculture, Udaipur, Rajasthan, India, and maintained in the field of the CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh, India, were utilized as an original gene pool of R. damascena. Two varieties, Jwala and Himroz were diversified through selections of desirable traits (morphological/oil content) across 25,000 plants. The five elites, three of R. damascena var. Jwala, (Indica, Super jwala and Jwala) and two of R. damascena var. Himroz (Hot himroz and Himroz) were developed through field selections and maintained at the Natural Plant Products Division Experimental Farm of the Institute. Rosa bourboniana plants were collected from the Fragrance and Flavour Development Centre, Kannauj, UP, India, during 1992 and maintained at the Natural Plant Products Division Experimental Farm of the Institute.
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               Factor Function
The essential oil content of the varieties of R. damascena varied from 0.037% to 0.051% and that of R. bourboniana was 0.017%. Super jwala recorded the highest oil content (0.051%). A total of 32 components were identified in the different varieties of rose oil. These components constituted 78.1-93.5% of the total rose oil species. The main components of rose oil were citronellol + nerol (16.3-30.1%), geraniol (15.8-29.3%), linalool (0.7-1.9%), rose oxide (0.9-2.6%), phenyl ethyl alcohol (0.1-0.4%), eugenol (0.3-2.2%), nonadecane (7.3-14.7%). The content of citronellol + nerol (30.1%) and geraniol (29.3%) was the highest in Himroz compared with other varieties.
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               Factor Part Location NP Content
 
Rosa damascena var. Himroz
Flowers India
NP Content: 0.4 %
 
Rosa damascena var. Hot Himroz
Flowers India
NP Content: 0.3 %
 
Rosa damascena var. Indica
Flowers India
NP Content: 0.4 %
 
Rosa damascena var. Jwala
Flowers India
NP Content: 0.4 %
 
Rosa damascena var. Super Jwala
Flowers India
NP Content: 0.6 %
      Species Name: Rosmarinus officinalis
  Factor Name: Developmental Stage Variation [10]
              Species Info Factor Info
               Experiment Detail
Samples of R. officinalis were collected in April 1998 during the full flowering period (Ro-1a), between June and July 1998 during the fruiting period (Ro-1b) and in December 1998 during the hibernation period (Ro-1c) from Cazorla, Segura y Las Villas Natural Park (province of Jaen, Spain). The plant material consisted of ca. 10 twigs per plant (with blossoming tips or not, depending of the harvesting date) from 5-10 single plants. Ro-1a (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: April 21, 1998, Phenological stage: Flowering); Ro-1b (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: June 19, 1998, Phenological stage: Fruiting); Ro-1c (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: December 30, 1998, Phenological stage: Hibernation).
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               Factor Function
The highest oil yields (161.8%) were recorded during the fruiting period (summer). In general, minimum amounts of camphor and maximum amounts of alpha-pinene were observed in winter. The concentration of 1,8-cineole was almost constant throughout the year, though other oil constituent levels varied randomly with the plant life cycle
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Twigs Las Chozuelas, Southern Spain
NP Content: 0.1 %
 
Whole plant: Fruiting stage
Twigs Las Chozuelas, Southern Spain
NP Content: <0.1 %
 
Hibernation stage
Twigs Las Chozuelas, Southern Spain
NP Content: <0.1 %
References
1 Cassinia laevis R. Br. Flower and Leaf Essential Oils
2 Chemical Profle of the Dittrichia graveolens (Desf.) Greuter Essential Oil of Lebanese Origin
3 Chemical Composition and Antimicrobial Activity of Essential Oils of Eugenia chlorophylla (Myrtaceae)
4 Contents and chemical composition of essential oils from wild strawberry (Fragaria vesca L.)
5 Essential oil composition of four Ocimum species and varieties growing in Iran
6 Biodiversity and selection of European basil (Ocimum basilicum L.) types
7 Essential Oils of Persea subgenus Persea (Lauraceae)
8 Studies on Essential Oil Composition of Cultivars of Black Pepper (Piper nigrum L.)-V
9 Evaluation of several Rosa damascena varieties and Rosa bourboniana accession for essential oil content and composition in western Himalayas
10 Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain