Details of Natural Product (NP)

General Information of Natural Product (ID: NP0175)
  Natural Product Name
Alpha-Fenchol
  Synonyms
alpha-Fenchol; (-)-endo-Fenchol; 512-13-0; alpha-Fenchyl alcohol; endo-Fenchol; (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol; UNII-UJ108AQX3M; (-)-alpha-Fenchyl alcohol; UJ108AQX3M; FENCHYL ALCOHOL; beta-Fenchol; 2-Fenchanol; (-)-alpha-fenchol; (+/-)-alpha-Fenchol; l-alpha-Fenchyl alcohol; Bicyclo(2.2.1)heptan-2-ol, 1,3,3-trimethyl-, (1S,2S,4R)-; endo-alpha-Fenchol; 14575-74-7; EINECS 208-135-9; BRN 2038083; Fenchyl Alcohol Natural; 1-alpha-Fenchyl alcohol; 4-06-00-00278 (Beilstein Handbook Reference); (1S,2S,4R)-endo-fenchol; alpha-Fenchyl alcohol, (-)-; SCHEMBL1245968; DTXSID7041205; CHEBI:15405; DTXSID101014534; Bicyclo(2.2.1)heptan-2-ol, 1,3,3-trimethyl-, (1S-endo)-; ZINC1081099; STK801828; AKOS005622496; LMPR0102120005; MCULE-6621779699; CS-0238492; (1S,2-endo)-1,3,3-trimethylnorbornan-2-ol; 1,3,3-Trimethyl-2-norbornanol, (1S-endo)-; C02344; 2-Norbornanol, 1,3,3-trimethyl-, (-)-endo-; Q27089421; (1S-endo)-1,3,3-Trimethylbicyclo(2.2.1)heptan-2-ol; alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol; UNII-32Y92U27DU component IAIHUHQCLTYTSF-MRTMQBJTSA-N; UNII-410Q2GK1HF component IAIHUHQCLTYTSF-MRTMQBJTSA-N; rel-(1S,2S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol; (1S,2S,4R)-1,3,3-trimethyl-bicyclo[2.2.1]heptan-2-ol, AldrichCPR
Click to Show/Hide
  Formula C10H18O
  Weight 154.25
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
  InChI Key IAIHUHQCLTYTSF-MRTMQBJTSA-N
  Isomeric SMILES C[C@]12CC[C@H](C1)C([C@H]2O)(C)C
  Canonical SMILES CC1(C2CCC(C2)(C1O)C)C
  External Links PubChem ID 439711
CAS ID 512-13-0

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Callistemon salignus
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
Fresh leaf samples of C. salignus were collected on the campus of University of Zululand, KwaDlangezwa and Empangeni (Both in KwaZulu-Natal Province) , South Africa.
Click to Show/Hide
               Factor Function
1,8-Cineole (63.4%), alpha-pinene (17.8%) and E-(beta)-ocimene (6.7%) were the major constituents identified in the KwaDlangezwa sample (Sample A). The Empangeni sample (Sample B) contained only 1,8-cineole (85.4%) and alpha-pinene (6.2%) as the main compounds present in the oil.
Click to Show/Hide
               Factor Part Location NP Content
 
Locality: Empangeni, KwaZulu-Natal Province, South Africa
 Leaves South Africa
NP Content: <0.05 %
 
Locality: KwaDlangezwa, KwaZulu-Natal Province, South Africa
 Leaves South Africa
NP Content: <0.05 %
      Species Name: Citrus aurantifolia
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Fresh mature lime fruits were harvested from experimental orchards of I.I.H.R., Bangalore at six ripening stages: Peel color; Dark Green, Light Green, Color Turning, 1/2 Yellow, 3/4th Yellow and Full Yellow.
Click to Show/Hide
               Factor Function
The constituents of lime oil mainly belong to two categories: hydrocarbons and oxygenated compounds. The hydrocarbons were 85.4% of the peel oil isolated from full yellow fruits compared to 57.5% in green fruits. The most abundant monoterpene hydrocarbons, limonene and beta-pinene, showed gradual increase during ripening of lime fruit and they together accounted for 70.7% in full yellow fruits. Organoleptically important oxygenated compounds (neral, geranial, linalool and geraniol) were found to be rich in oil isolated from the peel of green fruits (29.7%); however, it decreased to 8.4% when color of the fruit turned to full yellow. Neral and geranial were found to be high in the peel oil of green fruits (7.8%) compared to full yellow fruits (2.5%).
Click to Show/Hide
               Factor Part Location NP Content
 
Fruit: Dark green stage
 Fruits (dark green) Bangalore, India
NP Content: 1 %
 
Fruit: Light green stage
 Fruits (light green) Bangalore, India
NP Content: 1.3 %
 
Fruit: Color turning stage
 Fruits (color turn) Bangalore, India
NP Content: 0.9 %
 
Fruit: Half yellow stage
 Fruits (half yellow) Bangalore, India
NP Content: 0.8 %
 
Fruit: 3/4th yellow stage
 Fruits (3/4th yellow) Bangalore, India
NP Content: 0.6 %
 
Fruit: Full yellow stage
 Fruits (full yellow) Bangalore, India
NP Content: 0.5 %
      Species Name: Echinacea purpurea
  Factor Name: Plant Pathogen Infection [3]
              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.
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Healthy plant
 Aerial parts Italy
NP Content: <0.05 %
 
Infected plants (cucumber mosaic cucumovirus)
 Aerial parts Italy
NP Content: 0.1 %
      Species Name: Eucalyptus camaldulensis
  Factor Name: Variety Comparison [4]
              Species Info Factor Info
               Experiment Detail
Fresh leaves of the E. camaldulensis varieties(var. mysore and var. Catharine) were collected from 12 mature trees growing in Agodi Gardens, Ibadan, Nigeria.
Click to Show/Hide
               Factor Function
The quantitatively significant constituents in die leaf oil of the two E. camaldulensis varieties were beta-pinene (9.0-17.5%), 1,8-cineole (32.8-70.4%), (Z)-beta-ocimene (11.6%) and alpha-pinene (8.8%). Monoterpenoids also made up the bulk of the two volatile oils (89.0-95.7%).
Click to Show/Hide
               Factor Part Location NP Content
 
Eucalyptus camaldulensis var. Catharine
 Leaves Nigeria
NP Content: 0.5 %
      Species Name: Eucalyptus grandis
  Factor Name: Seasonal Variation [5]
              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.
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Harvesting time: Summer
 Whole plant Brazil
NP Content: 0.7 %
 
Harvesting time: Winter
 Whole plant Brazil
NP Content: 0.7 %
      Species Name: Eucalyptus urophylla
  Factor Name: Seasonal Variation [5]
              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.
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Harvesting time: Summer
 Whole plant Brazil
NP Content: 0.2 %
 
Harvesting time: Winter
 Whole plant Brazil
NP Content: 0.1 %
      Species Name: Hyptis pectinata
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
H. pectinutu is an odoriferous plant and occurs as a natural weed on the Fiji Islands and in West Africa as a winter hardy bush. In India, it grows as an erect perrennial shrub in Assam, Bengal and Madras regions. Tlie leaves are ovate and the leaf margins range from crenate to serrate. The flowers are pale purple to yellow in cymose clusters, arranged unilaterally. The nutlets are small, oblong and black.
Click to Show/Hide
               Factor Function
The major compounds present in the Indian oil were sabinene (27.8%), beta-pinene (6.7%), limonene (4.03%), alpha-terpinolene (6.0%), caryopliyllcne (17.2%), alpha-bergamotene (4.1%) and a C20H32-diterpene (5.8%). Other major hydrocarbons present were gamma-terpinene (1.4%), alpha-humulene (1.1%), beta-selinene (1.0%) and gamma-elemene (2.7%). The oil is rather poor in oxygenated terpenoids, the only major oxygen compounds detected were terpinen-4-ol(3.1%), spathulenol(1.1%), an unidentified sesquiterpene alcohol (1.4%) and trans-alpha-bergamotot (2.5%). The total oxygenated compounds constituted about 11% of the oil.
Click to Show/Hide
               Factor Part Location NP Content
 
Locality: India
 Whole plant Kumaon, India
NP Content: 0.7 %
      Species Name: Sideritis pusilla
  Factor Name: Variety Comparison; Locality Variation [7]
              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)
Click to Show/Hide
               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.
Click to Show/Hide
               Factor Part Location NP Content
 
Sideritis pusilla (Lange) Pau ssp. pusilla var. typica (Locality: Los Matarines)
 Aerial parts Los Matarines, Spain
NP Content: 1.3 %
 
Sideritis pusilla ssp. almeriensis var. salina Font Quer (Locality: Los Pedregales)
 Aerial parts Los Pedregales, Spain
NP Content: 0.3 %
 
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: 4.9 %
 
Sideritis pusilla ssp. flavovirens (Rouy) Malagarriga (Locality: Velez Rubio, Cerro del Huezno)
 Aerial parts Velez Rubio, Cerro del Huezno, Spain
NP Content: 2.6 %
 
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: 2.2 %
 
Sideritis pusilla ssp. pusilla var. carthaginensis Font Quer (Locality: Rambla del Hacho)
 Aerial parts Rambla del Hacho, Spain
NP Content: 2.9 %
 
Sideritis pusilla ssp. pusilla var. granatensis (Pau) Font Quer (Locality: Gafarillos)
 Aerial parts Gafarillos, Spain
NP Content: 4 %
References
1 Volatile Constituents of the Leaf Oils of Callistemon salignus from Two Provinces in South Africa
2 Changes in the Peel Oil Composition of Kagzi Lime (Citrus aurantifolia Swingle) during Ripening
3 Characterization of the Essential Oils of Healthy and Virus Infected Echinacea purpurea (L.) Moench Plants
4 Essential Oil Composition of Two Varieties of Eucalyptus camaldulensis Dehn. from Nigeria
5 Seasonal Influence on the Essential Oil Compositions of Eucalyptus urophylla S. T. Blake and E. grandis W. Hill ex Maiden from Brazilian Cerrado
6 Volatile Constituents of Hyptis pectinata Poit. (Lamiaceae)
7 Essential Oil Composition of Sideritis pusilla (Lange) Pau ssp.