General Information of Natural Product (ID: NP0147)
  Natural Product Name
Calamenene
  Synonyms
CALAMENENE; cis-Calamenene; UNII-R8O22WBF8L; R8O22WBF8L; Naphthalene, 1,2,3,4-tetrahydro-1,6-dimethyl-4-(1-methylethyl)-, (1S-cis)-; 483-77-2; (-)-Calamenene; 72937-55-4; (1S,4S)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4-tetrahydronaphthalene; (Z)-calamenene; 1-S-cis-Calamenene; Cadina-1,3,5-triene; Calamenene, cis-(+/-)-; (1S,4S)-4-Isopropyl-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene; IT SHOULD BE NOTED THAT cis-calamenene is eluted late vs trans-calamenene; DTXSID40880702; (+/-)-Cadina-1,3,5-triene; (1S,4S)-1,6-dimethyl-4-propan-2-yl-1,2,3,4-tetrahydronaphthalene; ZINC85880350; Q63398612; UNII-5C6W67N6XM component PGTJIOWQJWHTJJ-STQMWFEESA-N; UNII-O38170Y9ES component PGTJIOWQJWHTJJ-STQMWFEESA-N; (1S-cis)-1,6-Dimethyl-4-(1-methylethyl)-1,2,3,4-tetrahydronaphthalene; 1,2,3,4-tetrahydro-1,6-dimethyl-4(1-methylethyl)-(1s-cis)-naphthalene; naphthalene, 1,2,3,4-tetrahydro-1,6-dimethyl-4- (1-methylethyl)-, (1S-cis)-; Naphthalene, 1,2,3,4-tetrahydro-1,6-dimethyl-4-(1-methylethyl)-, (1R,4R)-rel-
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  Formula C15H22
  Weight 202.33
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H22/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5,7,9-10,12-13H,6,8H2,1-4H3/t12-,13-/m0/s1
  InChI Key PGTJIOWQJWHTJJ-STQMWFEESA-N
  Isomeric SMILES C[C@H]1CC[C@H](C2=C1C=CC(=C2)C)C(C)C
  Canonical SMILES CC1CCC(C2=C1C=CC(=C2)C)C(C)C
  External Links PubChem ID 6429077
CAS ID 483-77-2

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [1]
              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: 0.2 %
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: 0.3 %
      Species Name: Mentha rotundifolia
  Factor Name: Altitude Variation [2]
              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: 0.3 %
 
Locality: Miliana, Algeria; Altitude 780 m
Leaves Algeria
NP Content: 0.7 %
      Species Name: Ocimum basilicum
  Factor Name: Drought Stress Treatment [3]
              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: 0.3 %
      Species Name: Ocimum basilicum L
  Factor Name: Cultivar Comparison [4]
              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 %
  Factor Name: Chemotype Comparison [5]
              Species Info Factor Info
               Experiment Detail
The study was conducted in North-Central Anatolia under semi arid conditions. Seeds of 18 basil landraces (O. basilicum L.) were collected from local farms and home gardens in Turkey. To examine essential oil composition of the basil landraces without environmental influences, the plants were grown under identical (same environmental and soil conditions) conditions. Seeds were sown on a medium (1:1:1 washed sand, horse manure and field soil) in greenhouse conditions on March 25, 2003. Seedlings were grown until the 3-5 leaf stage. The seedlings were transplanted into pilots in the Gaziosmanpasxa University Experimental Research Station on May 15, 2003. The plants were harvested at the full blooming stage and dried at 35 ℃ for essential oil isolation.
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               Factor Function
Variation of essential oils in the landraces was subjected to cluster analysis, and seven different chemotypes were identified. They were (1) linalool, (2) methyl cinnamate, (3) methyl cinnamate/linalool, (4) methyl eugenol, (5) citral, (6) methyl chavicol (estragol), and (7) methyl chavicol/citral. Methyl chavicol with high citral contents (methyl chavicol/citral) can be considered as a 'new chemotype' in the Turkish basils.
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               Factor Part Location NP Content
 
Chemotype (linalool-rich type)
Leaves Turkey
NP Content: 0.3 %
 
Chemotype (methyl (E)-cinnamate-rich and linalool-rich type)
Leaves Turkey
NP Content: 0.2 %
 
Chemotype (methyl eugenol-rich type)
Leaves Turkey
NP Content: 0.1 %
      Species Name: Pilocarpus spicatus
  Factor Name: Locality Variation; Harvest Time Variation [6]
              Species Info Factor Info
               Experiment Detail
Five different populations of P. spicatus were collected in different geographical regions of the northeast of Brazil. Populations I: (Locality: Morro do Chapeu,Bahia, harvesting: 02.19.94); Populations II: (Locality: Maranguape,Ceara, harvesting: 06.01.97); Populations III: (Locality: Jacobina,Bahia, harvesting: 02.19.94); Populations IV: (Locality: Cocalzinho,Ceara, harvesting: 02.22.94); Populations V: (Locality: Sitio dos Moreiras,Pernambuco, harvesting: 02.22.94)
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               Factor Function
The aliphatic ketones 2-undecanone, 2-tridecanone and 2-pentadecanone were present in samples of all populations. 2-Tridecanone (1.7-84.7 %) was detected in 30 out of 34 samples analyzed. It was the main component in all samples of root barks, except one where 2-pentadecanone (24.7%) was the major component. 2-Undecanone, beta-eudesmol and sabinene were the major components of leaf oils.
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               Factor Part Location NP Content
 
Root wood: (Locality: Maranguape, Ceara, Northeast of Brazi) + (Harvesting time: 01-June-1997)
Root woods Maranguape, Ceara, Northeast of Brazil
NP Content: 1.5 %
      Species Name: Salvia aucheri
  Factor Name: Variety Comparison [7]
              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. canescens
Aerial parts Karaman, Turkey
NP Content: 0.1 %
      Species Name: Sideritis congesta
  Factor Name: Locality Variation [8]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities. A: Antalya: Alanya, Sapadere, Beldibi-Baskoy in July 1991 (ESSE 9562). B: Icel: Anamur, Kas yaylasi in July 1991 (ESSE 9192).
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               Factor Function
Thirty-nine components were characterized in each oil representing 85-90% of the total components detected with beta-pinene (34-35%) and alpha-pinene (24-25%) as major constituents.
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               Factor Part Location NP Content
 
Locality: Beldibi-Baskoy, Sapadere, Alanya, Antalya, Turkey
Inflorescence Turkey
NP Content: 0.4 %
 
Locality: Kas yaylasi, Anamur, Icel, Turkey
Inflorescence Turkey
NP Content: 0.3 %
      Species Name: Sideritis pusilla
  Factor Name: Variety Comparison; Locality Variation [9]
              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. pusilla var. carthaginensis Font Quer (Locality: Rambla del Hacho)
Aerial parts Rambla del Hacho, Spain
NP Content: 3 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [10]
              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
 
Flower: (Locality: Adana, Turkey)
Flowers Adana, Turkey
NP Content: 0.1 %
 
Stem: (Locality: Adana, Turkey)
Stems Adana, Turkey
NP Content: 0.1 %
 
Root: (Locality: Adana, Turkey)
Roots Adana, Turkey
NP Content: 0.1 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [11]
              Species Info Factor Info
               Experiment Detail
Aerial parts of the plant were collected from four localities: A = Kirklareli: Karadere in May 1991; B = Kirklareli: Karahamza Village in May 1990; C = Kirklareli: Evciler Village on 13 June 1993; D = Kirklareli: Korukoy on 25 May 1994
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               Factor Function
The four oils obtained from plants collected in different localities of the same region gave quite different compositions as follows: A: thymol (10.5%), 1,8-cineole (9.96%), p-cymene (9.48%), carvacrol (5.28%); B: beta-caryophyllene (29.50%), carvacrol(20.59%); C: thymol (34.7%), beta-caryophyllene (12.74%), carvacrol (5.24%); D: beta-caryophyllene (56.48%), germacrene D (11.12%), carvacrol (4.85%). Since the identities of the plant materials were checked repeatedly, any misidentification is ruled out. Except for A and C, all the other materials showed beta-caryophyllene as the major constituent. Carvacrol (20.59%) was present in good amount in the oil of B. In A, however, high percentages of 1,8-cineole (10%) and p-cymene (9.5%) were significant. This oil contained only a trace amount of beta-caryophyllene. Four isomeric caryophyllene alcohols were detected in the oil B. The results clearly indicate that the oil of T. striatus var. interruptus has no consistency and we can safely suggest that there are at least three chemotypes, namely thymol/1,8-cineole/p-cymene-type; thymol/beta-caryophyllene-type; and beta-caryophyllene-type, of this species.
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               Factor Part Location NP Content
 
Locality: Evciler Village, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.1 %
References
1 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
2 Chemical Composition of the Leaf Oil of Mentha rotundifolia (L.) from Algeria
3 Essential oil content and composition of sweet basil (Ocimum basilicum) at different irrigation regimes
4 Biodiversity and selection of European basil (Ocimum basilicum L.) types
5 Variability in essential oil composition of Turkish basils (Ocimum basilicum L.)
6 Volatile Constituents of Different Populations of Pilocarpus spicatus Saint Hill. (Rutaceae) from the Northeast of Brazil
7 Composition of Essential Oils from Two Varieties of Salvia aucheri Benth. Growing in Turkey
8 Composition of the Essential Oil of Sideritis congesta P.H.Davis et Hub.-Mor.
9 Essential Oil Composition of Sideritis pusilla (Lange) Pau ssp.
10 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
11 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey