General Information of Natural Product (ID: NP0520)
  Natural Product Name
1,2,3,4,5,6,7,8-Octahydro-1Beta,4Alpha-Dimethyl-7-(1-Methylethylidene)Azulene
  Synonyms
ZINC2169368; 1,2,3,4,5,6,7,8-Octahydro-1beta,4alpha-dimethyl-7-(1-methylethylidene)azulene
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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/h11-12H,5-9H2,1-4H3/t11-,12+/m1/s1
  InChI Key GIBQERSGRNPMEH-NEPJUHHUSA-N
  Isomeric SMILES C[C@@H]1CCC(=C(C)C)CC2=C1CC[C@@H]2C
  Canonical SMILES CC1CCC(=C(C)C)CC2=C1CCC2C
  External Links PubChem ID 91746511

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia campestris
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
The aerial parts (~20 cm, 15-100 g) of A. campestris L. from ten different wild populations of Lithuania were gathered at the full flowering stage. Plant material was dried at room temperature (20-25 ℃). Oils (samples 1-10) obtained from Artemisia campestris plants collected at sampling sites (A-I,Y) characterized by locality, city (c.) or district (d.), soil type (Or, ordo; Sn, sand; Sl, sandy loam; Gr, gravel; Lm, loam) and description of natural habitat (Af, abandoned field; Fe, forest edge; Ct, cutting area; Mw, meadow; Rs, roadside; Rv, river valley): A (1) Birstonas c. (Or, Ct); B (2) Palanga c. (Sn, Fe); C (3) Nociunai, Kedainai d. (Or, Mw); D (4) Alytus c. (Sl, Rs); E (5) Moletai c. (Lm, Af); F (6) Kaltanenai, Sencionys d. (Gr, Fe); G (7) Merkine, Alytus d. (Sl, Ct); H (8) Trakai c. (Gr, Af); I (9) Druskininkai c. (Or, Rv); Y (10) Vilnius c. (Gr, Af).
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               Factor Function
The main chemical profile (ten samples) was characterized by the predominance of germacrene D (9.8-31.2%), while spathulenol, humulene epoxide II and caryophyllene oxide were found as the first major compounds in another three oils. One oil was determined as a mixed chemotype. Some compounds such as gamma-curcumene, alpha-cadinol, (E,E)-alpha-farnesene, beta-ylangene, beta-selinene and humulene epoxide II have been mentioned for the first time among three principal constituents in A. campestris oils. The fifty-six components made up 73.6.1-98.5% of the total content, while the remaining twenty-six volatile compounds were identified in insignificant amounts in the A. campestris essential oils.
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               Factor Part Location NP Content
 
Locality: Birstonas city, Lithuania (soil type: ordo; natural habitat: cutting area)
Aerial parts Lithuania
NP Content: 0.3 %
 
Locality: Nociunai, Kedainai district, Lithuania (soil type: ordo; natural habitat: meadow)
Aerial parts Lithuania
NP Content: 1 %
 
Locality: Moletai city, Lithuania (soil type: loam; natural habitat: abandoned field)
Aerial parts Lithuania
NP Content: 0.8 %
      Species Name: Artemisia nilagirica var. Septentrionalis
  Factor Name: Altitude Variation [2]
              Species Info Factor Info
               Experiment Detail
Leaves from mature plants of Artemisia nilagirica var. septentrionalis, before flowering, were collected from different altitudes in Himachal Pradesh such as Shimla (2210 m), Mandi (1044 m) and Manali (2050 m) in June 2005.
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               Factor Function
The major constituents of the oil show variation with changes in altitude. At lower, middle and higher altitudes, the major constituents of the oil were caryophyllene oxide (28.6%), borneol (35.8%) and camphor (46.9%), respectively. The percentages of alpha-humulene and trans-beta-guaiene also increased, but the percentage of sabinene, trans-sabinene hydrate, 4-terpineol, caryophyllene oxide and humulene epoxide-II decreased with an increase in altitude. The characteristic compounds observed in the plants from lower altitudes were 2-hexene-1-ol, beta-thujone, thujanol, myrtenol and linalyl acetate, while the higher altitude plants were characterized by the presence of alpha-pinene, beta-pinene, limonene, linalool, gamma-gurijunene, germacrene-D and farnesol.
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               Factor Part Location NP Content
 
Locality: Mandi, Himachal Pradesh, India; Altitude 1044 m
Leaves Himachal Pradesh, India
NP Content: 0.6 %
 
Locality: Manali, Himachal Pradesh, India; Altitude 2050 m
Leaves Himachal Pradesh, India
NP Content: 2.1 %
 
Locality: Shimla, Himachal Pradesh, India; Altitude 2210 m
Leaves Himachal Pradesh, India
NP Content: 2.8 %
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [3]
              Species Info Factor Info
               Experiment Detail
Aerial parts of endemic pichana were harvested in December 1996 at different localities of northern Patagonia. Origin: Planicie Banderita, Dept. Confluencia, Province of NeuquCn. Habitat: altitude, 327 m; average temperature in the station, 21.8 ℃; annual precipitation, 125 mm; sandy soils. Aerial parts (5 kg, 2 kg of dried material;humidity, 11%) from four well developed plants at the fullflowering stage (December, 1996). Sample 2 : Origin: RincBn de 10s; Sauces, Dept. of Pehuenclies, Province of Neuqukn. Habitat: altitude, 750 m; average temperature in the station, 20.9 ℃; annual precipitation, 147 mm; sandy and gritty salty soils. Aerial parts (5 kg, 1.85 kg of dried material, humidity, 10%), from two well developed plants at the full flowering stage, and after several days copious rains (December, 1996). Sample 3: Origin: Coronel GBmez, Dept. General Roca, Province of Rio Negro. Habitat: altitude, 242 m; average temperature in the station, 22.5 ℃; annual precipitation, 179 mm; sandy and stony soils. Aerial parts (4.5 kg, 1.3 kg of dried material, humidity, 9%), from 12 young plants at the beginning flowering stage (December, 1996).
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               Factor Function
Fifty-four components, representing approximately 84.6-97.4% of the oil samples, were identified. The samples consisted mainly of hydrocarbons and oxygenated monoterpenes. The major constituents were limonene (28.7-56.7%), 6R-7R-bisabolone (3.2-9.1%), sabinene (0.1-11.0%) and citronellal (2.4-5.2%). Significant differences among the content of the three samples could be the result of changes in the climatic conditions (sample 2: Rincon de los Sauces, Province of Neuquen, after strong rains) or by translocations in different parts of the plant (sample 3: Coronel Gomez, Province of Rio Negro, more leaves and less stems).
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               Factor Part Location NP Content
 
Locality: Planicie Banderita, Province of Neuquen; Altitude 327 m
Aerial parts Patagonia, Argentina
NP Content: 0.4 %
      Species Name: Talauma ovata
  Factor Name: Month Variation [4]
              Species Info Factor Info
               Experiment Detail
Talauma ovata was collected from October 2003 to February 2005. Leaves and trunk bark from the same set of plants were collected in the four seasons: spring (October 15th, 2003), autumn (April 10th, 2004), winter (July 17th, 2004) and summer (February 15th, 2005). In addition, trunk bark was also collected on January 22nd, 2004 (summer). The plant material was harvested from wild-growing population in Santos Dumont City, Minas Gerais State, Brazil, (21° 28′ 03″ S, 43° 39′ 26″ W), at 1000 m of altitude.
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               Factor Function
In each season the composition of trunk bark oils was similar to leaf oils, with mainly quantitative differences. However considerable seasonal variation was observed. Significant levels of monoterpenes were found only in autumn. The content of oxygenated sesquiterpenes was highest in samples of spring (October) and decreased in summer (January and February), reaching the lowest level in autumn (April) and increasing again in winter (July). In trunk bark oils the main constituents were: spathulenol, alpha-eudesmol, linalool, trans-beta-guaiene and caryophyllene oxide. The major component in all samples of trunk bark was spathulenol. Its level was highest in October (46.8%), decreased in January (33.3%), remained stable in April and July (18.0%) and increased again in February of next year (27.7%). Levels of alpha-eudesmol were high in spring (13.0%) and autumn (11.5%). Linalool peaked only in April, while trans-beta-guaiane peaked in July (11.1%). Caryophyllene oxide ranged between 10.7-2.0%. The level was highest in January, decreased regularly until July and increased slightly again in October. In leaf oils the main components were: spathulenol, germacrene B, germacrene D, caryophyllene oxide and viridiflorol. Spathulenol was the major component in sample of spring (34.4%), but decreased gradually until winter, when reached the lowest level (9.4%). Caryophyllene oxide showed a similar pattern, varying from 14.1% (spring) to 2.4% (winter). An inverse effect was observed for viridiflorol, which increased from 0.1% in October to 13.7% in July. Important levels of alpha-eudesmol were observed in October (12.3%) and February (9.5%). The percentage of germacrene D was highest in summer, while germacrene B showed high amounts in autumn and winter. The seasonal changes in oil composition of T. ovata can be associated with cycle of life of plant (flowering, fruiting and vegetative stages) and climatic parameters such as intense raining in the spring and summer.
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               Factor Part Location NP Content
 
Leaf: (Harvesting time: February)
Leaves Brazil
NP Content: 0.5 %
 
Leaf: (Harvesting time: April)
Leaves Brazil
NP Content: 0.1 %
 
Leaf: (Harvesting time: July)
Leaves Brazil
NP Content: 4.9 %
 
Leaf: (Harvesting time: October)
Leaves Brazil
NP Content: 0.5 %
 
Trunk Bark: (Harvesting time: January)
Trunk bark Brazil
NP Content: 0.4 %
 
Trunk Bark: (Harvesting time: February)
Trunk bark Brazil
NP Content: 0.5 %
 
Trunk Bark: (Harvesting time: April)
Trunk bark Brazil
NP Content: 4.3 %
 
Trunk Bark: (Harvesting time: July)
Trunk bark Brazil
NP Content: 11.1 %
 
Trunk Bark: (Harvesting time: October)
Trunk bark Brazil
NP Content: 0.1 %
References
1 Variability of Artemisia campestris L. essential oils from Lithuania
2 Oil Constituents of Artemisia nilagirica var. septentrionalis Growing at Different Altitudes
3 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
4 Chemical Composition, Seasonal Variation and Evaluation of Antimicrobial Activity of Essential Oils of Talauma ovata A. St. Hil. (Magnoliaceae)