General Information of Natural Product (ID: NP0645)
  Natural Product Name
Bulnesol
  Synonyms
Bulnesol; Guai-1(10)-en-11-ol; Bullnesol; 2-(3,8-dimethyl-1,2,3,3a,4,5,6,7-octahydroazulen-5-yl)propan-2-ol; SCHEMBL6511521; 2-(3,8-Dimethyl-1,2,3,3a,4,5,6,7-octahydro-5-azulenyl)-2-propanol #; DTXSID9052472; 5-Azulenemethanol, 1,2,3,3a,4,5,6,7-octahydro-alpha,alpha,3,8-tetramethyl-, (3S,3aS,5R)-; 5-Azulenemethanol, 1,2,3,3a,4,5,6,7-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, (3S,3aS,5R)-; FT-0777865; Q67879762; 1,2,3,3a,4,5,6,7-Octahydro-3,8,alpha,alpha-tetramethylazulene-5-methanol; 55255-90-8
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  Formula C15H26O
  Weight 222.37
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h11-12,14,16H,5-9H2,1-4H3
  InChI Key LGOFSGDSFQNIAT-UHFFFAOYSA-N
  Isomeric SMILES CC1CCC2=C(CCC(CC12)C(C)(C)O)C
  Canonical SMILES CC1CCC2=C(CCC(CC12)C(C)(C)O)C
  External Links PubChem ID 90785
CAS ID 55255-90-8

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Bupleurum gibraltarium
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
Plant material: Samples of B. gibraltarium were gathered in November 1995 during the fruiting period (F), in May 1996 during the pre-flowering period (PF), in July 1996 during the full flowering period (FF), and in September 1996 during the late flowering period (LF) from El Zumbel area (UTM: 30SVG3278) . Every sample consisted in the whole aerial parts of five single plants growing wild near one to another. Once the plants reached the laboratory, they were airdried for seven to 15 days, and separated by parts, i.e., leaves, stems, umbel rays and, when present, fruits.
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               Factor Function
In the leaf oils, sabinene (12.0-33.9%) and limonene (7.8-23.4%) were the main components, the sabinene level being minimum in full flowering and maximum in fruiting. In stem oils, sabinene (4.7-21.6%) and 2,3,4-trimethylbenzaldehyde (9.3-13.6%) were the main components, the sabinene level being minimum in pre-flowering and maximum in full flowering. In umbel ray oils, sabinene (20.7-43.1%) was the first component in all the phenological periods, followed by alpha-pinene (7.3-28.2%). Both monoterpenes increased their levels in late flowering and reached minimum amounts in fruiting.
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               Factor Part Location NP Content
 
Leaf: full pre-flowering stage
Leaves Spain
NP Content: 1.2 %
 
Stem: full pre-flowering stage
Stems Spain
NP Content: 6.2 %
 
Aerial part: full flowering stage
Aerial parts Spain
NP Content: 2.2 %
 
Umbel: full flowering stage
Umbels Spain
NP Content: 0.8 %
      Species Name: Cassinia laevis
  Factor Name: Locality Variation [2]
              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: 0.4 %
 
Flower: Sample 4 (Locality: Lat. 27º 33′ 08″ S; Long. 152º 15′ 00″ E, Brisbane, Queensland)
Flowers Brisbane, Queensland, Australia
NP Content: 1.1 %
 
Flower: Sample 2 (Locality: roadside verge of the Gatton-Toowoomba, Brisbane, Queensland)
Flowers Brisbane, Queensland, Australia
NP Content: 0.8 %
 
Leaf: Sample 3 (Locality: Lat. 27º 33′ 08″ S; Long. 152º 15′ 00″ E, Brisbane, Queensland)
Leaves Brisbane, Queensland, Australia
NP Content: 0.9 %
 
Leaf: Sample 6 (Locality: Murphy's creek area, Brisbane, Queensland)
Leaves Brisbane, Queensland, Australia
NP Content: 0.2 %
      Species Name: Melaleuca quinquenervia (Cav.) S.T. Blake
  Factor Name: Chemotype Comparison [3]
              Species Info Factor Info
               Experiment Detail
One hundred grams of mature leaves were collected from 2 to 10 widely spaced trees per site and sent to Sydney for analysis as soon as possible after collection. Samples usually arrived in the laboratory within 48 h of collection. The majority of the sampling was done between December 1998 and October 1999. Seasonal trends in oil yields and composition are confounded in the data on geographic variation, but these were considered minor in the context of this study.
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               Factor Function
Chemotype 1 is comprised of E-nerolidol (74-95%) and linalool (14-30%) and is found from Sydney, north along the east coast of Australia to Selection Flat, New South Wales, with an isolated occurrence near Maryborough, Queensland. Two divisions occur in this chemotype which are based on the presence or absence of significant proportions of linalool (14-40%). Chemotype 2 contains 1,8-cineole (10-75%), viridiflorol (13-66%), alpha-terpineol (0.5-14%) and beta-caryophyllene (0.5-28%) in varying proportions and order of dominance in the oils. It is found throughout the distribution of the species, from Sydney to Papua New Guinea and New Caledonia. Within chemotype 2 there appears to be a continuous spread of oil composition without formation of any further discrete divisions as in chemotype 1. Analyses have shown that M. quinquenervia trees that occur at latitudes south of 25d S have high oil yields (1-3% w/w%, fresh leaves) and comprise chemotypes 1 and 2. North of 25d S, however, chemotype 1 does not occur and oil yields amongst the Australian populations are uniformly low (0.1-0.2%).
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               Factor Part Location NP Content
 
Chemotype (E-nerolidol in large concentration type)
Leaves Australia and Papua New Guinea
NP Content: 0.2 %
 
Chemotype (either 1,8-cineole or viridiflorol in highest proportion type)
Leaves Australia and Papua New Guinea
NP Content: 0.2 %
      Species Name: Pilocarpus spicatus
  Factor Name: Locality Variation; Harvest Time Variation [4]
              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
 
Leaf: (Locality: Morro do Chapeu, Bahia, Northeast of Brazi) + (Harvesting time: 19-February-1994)
Leaves Morro do Chapeu, Bahia, Northeast of Brazil
NP Content: 3.8 %
 
Root bark: (Locality: Morro do Chapeu, Bahia, Northeast of Brazi) + (Harvesting time: 19-February-1994)
Root bark Morro do Chapeu, Bahia, Northeast of Brazil
NP Content: 9 %
 
Root bark: (Locality: Jacobina, Bahia, Northeast of Brazi) + (Harvesting time: 19-February-1994)
Root bark Jacobina, Bahia, Northeast of Brazil
NP Content: 16.3 %
 
Root wood: (Locality: Morro do Chapeu, Bahia, Northeast of Brazi) + (Harvesting time: 19-February-1994)
Root woods Morro do Chapeu, Bahia, Northeast of Brazil
NP Content: 14.4 %
 
Root wood: (Locality: Maranguape, Ceara, Northeast of Brazi) + (Harvesting time: 01-June-1997)
Root woods Maranguape, Ceara, Northeast of Brazil
NP Content: 1.3 %
 
Stem bark: (Locality: Morro do Chapeu, Bahia, Northeast of Brazi) + (Harvesting time: 19-February-1994)
Stem bark Morro do Chapeu, Bahia, Northeast of Brazil
NP Content: 17.9 %
 
Stem bark: (Locality: Jacobina, Bahia, Northeast of Brazi) + (Harvesting time: 19-February-1994)
Stem bark Jacobina, Bahia, Northeast of Brazil
NP Content: 3.6 %
 
Stem wood: (Locality: Morro do Chapeu, Bahia, Northeast of Brazi) + (Harvesting time: 19-February-1994)
Stem woods Morro do Chapeu, Bahia, Northeast of Brazil
NP Content: 7.5 %
References
1 Seasonal Variation of Leaf, Stem and Umbel Ray Essential Oils of Bupleurum gibraltarium Lam.
2 Cassinia laevis R. Br. Flower and Leaf Essential Oils
3 Chemical variation in the leaf essential oil of Melaleuca quinquenervia (Cav.) S.T. Blake
4 Volatile Constituents of Different Populations of Pilocarpus spicatus Saint Hill. (Rutaceae) from the Northeast of Brazil