General Information of Species (ID: SP0087)
  Species Name
Achillea biebersteinii
  Species Genus Achillea
  Species Family Asteraceae
  Studied Organism Achillea biebersteinii
  External Links
Taxonomy ID 282722
CMAUP ID NPO24710
NPASS ID NPO24710

 The Content Variation of Natural Product Induced by Different Factor(s)
      Developmental Stage Variation [1]
              Factor Info Click to show the detail information of this Factor
               Experiment Detail
Fresh aerial parts of A. biebersteinii were collected in May and June 2009 at different developmental stages (vegetative, floral budding, flowering and fruit set)from its natural habitat in the Dizin zone, northwest of Tehran, Iran (Latitude: 36° 4′ 52″N, Longitude: 51° 22′ 46″ E, Altitude: 2325-2425 m).
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               Factor Function
All oil samples from different plant parts and phenological stages were mostly made up of monoterpenoid compounds (88.6 - 99.6%), especially oxygenated ones (52.4 - 82.4%). The oil of the vegetative stage contained high amounts of limonene, 4a-alpha,7-alpha,7a-alpha-nepetalactone, p-cymene and 1,8-cineole. The major constituents in the flower budding stage oil were found to be limonene, 1,8-cineole and 4aalpha-7beta-7aalpha-nepetalactone. In the oil of the fruit set stage, gamma-terpinene, p-cymene and cis-chrysanthenyl acetate were the predominant constituents. On the other hand, the most important compounds from the stem oil were 4a-alpha,7-alpha,7a-alpha-nepetalactone, 1,8-cineole, 4aalpha-7beta-7aalpha-nepetalactone and camphor. 4aalpha-7alpha-7aalpha-nepetalactone, limonene, 1,8-cineole and cis-p-menth-2-en-1-ol were found in high concentration in the oil of leaves, whereas 4aalpha-7alpha-7aalpha-nepetalactone, 4aalpha-7beta-7aalpha-nepetalactone, limonene and p-cymene were present in large amounts in the oil of flowers.
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   Aerial part: Vegetative satge    ( Part: Aerial parts; Location: Tehran, Iran )
               NP Name Link Formula PubChem ID NP Content
 
(E)-2,5,5-Trimethylhepta-3,6-Dien-2-Ol
   NP Info                 C10H18O         5315406  
NP Content: 2.6 %
 
2-Cyclohexen-1-Ol, 1-Methyl-4-(1-Methylethyl)-, Trans-
   NP Info                 C10H18O         122484  
NP Content: 3 %
 
4-Carvomenthenol
   NP Info                 C10H18O         11230  
NP Content: 1.6 %
 
Eucalyptol
   NP Info                 C10H18O         2758  
NP Content: 12.3 %
 
Linalool
   NP Info                 C10H18O         6549  
NP Content: 0.3 %
 
3,3,6-Trimethylhepta-1,5-Dien-4-One
   NP Info                 C10H16O         68346  
NP Content: 0.5 %
 
Camphor
   NP Info                 C10H16O         2537  
NP Content: 4.2 %
 
Alpha-Phellandrene
   NP Info                 C10H16         7460  
NP Content: 0.5 %
 
Alpha-Pinene
   NP Info                 C10H16         6654  
NP Content: 1.5 %
 
Camphene
   NP Info                 C10H16         6616  
NP Content: 1.9 %
 
Limonene
   NP Info                 C10H16         22311  
NP Content: 28.9 %
 
Nepetalactone Cis-Trans-Form
   NP Info                 C10H14O2         161367  
NP Content: 5.7 %
 
Nepetalactone Trans-Cis-Form
   NP Info                 C10H14O2         442430  
NP Content: 1.7 %
 
Chrysanthenone
   NP Info                 C10H14O         442463  
NP Content: 0.6 %
 
P-Cymene
   NP Info                 C10H14         7463  
NP Content: 14.4 %
 
4A-Alpha,7-Beta,7A-Alpha-Nepetalactone
   NP Info                 NA         NA
NP Content: 20 %
   Aerial part: Floral Budding satge    ( Part: Aerial parts; Location: Tehran, Iran )
               NP Name Link Formula PubChem ID NP Content
 
(E)-2,5,5-Trimethylhepta-3,6-Dien-2-Ol
   NP Info                 C10H18O         5315406  
NP Content: 4.1 %
 
2-Cyclohexen-1-Ol, 1-Methyl-4-(1-Methylethyl)-, Trans-
   NP Info                 C10H18O         122484  
NP Content: 1.6 %
 
4-Carvomenthenol
   NP Info                 C10H18O         11230  
NP Content: 1.9 %
 
Alpha-Terpineol
   NP Info                 C10H18O         17100  
NP Content: 1.1 %
 
Eucalyptol
   NP Info                 C10H18O         2758  
NP Content: 25.2 %
 
3,3,6-Trimethylhepta-1,5-Dien-4-One
   NP Info                 C10H16O         68346  
NP Content: 0.5 %
 
Camphor
   NP Info                 C10H16O         2537  
NP Content: 1.6 %
 
Alpha-Phellandrene
   NP Info                 C10H16         7460  
NP Content: 1.1 %
 
Alpha-Pinene
   NP Info                 C10H16         6654  
NP Content: 3.1 %
 
Camphene
   NP Info                 C10H16         6616  
NP Content: 0.9 %
 
Limonene
   NP Info                 C10H16         22311  
NP Content: 35.5 %
 
Nepetalactone Cis-Trans-Form
   NP Info                 C10H14O2         161367  
NP Content: 3.5 %
 
Nepetalactone Trans-Cis-Form
   NP Info                 C10H14O2         442430  
NP Content: 1.9 %
 
Chrysanthenone
   NP Info                 C10H14O         442463  
NP Content: 0.4 %
 
4A-Alpha,7-Beta,7A-Alpha-Nepetalactone
   NP Info                 NA         NA
NP Content: 11.1 %
   Aerial part: Fruit Set satge    ( Part: Aerial parts; Location: Tehran, Iran )
               NP Name Link Formula PubChem ID NP Content
 
Cis-Chrysanthenyl Acetate
   NP Info                 C12H18O2         6431301  
NP Content: 4.4 %
 
(E)-2,5,5-Trimethylhepta-3,6-Dien-2-Ol
   NP Info                 C10H18O         5315406  
NP Content: 2.3 %
 
2-Cyclohexen-1-Ol, 1-Methyl-4-(1-Methylethyl)-, Trans-
   NP Info                 C10H18O         122484  
NP Content: 0.6 %
 
3,3,6-Trimethylhepta-1,5-Dien-4-Ol
   NP Info                 C10H18O         100197  
NP Content: 1.2 %
 
Eucalyptol
   NP Info                 C10H18O         2758  
NP Content: 7.1 %
 
Camphor
   NP Info                 C10H16O         2537  
NP Content: 1.2 %
 
Alpha-Pinene
   NP Info                 C10H16         6654  
NP Content: 0.3 %
 
Alpha-Terpinene
   NP Info                 C10H16         7462  
NP Content: 0.2 %
 
Camphene
   NP Info                 C10H16         6616  
NP Content: 0.1 %
 
Gamma-Terpinene
   NP Info                 C10H16         7461  
NP Content: 63.7 %
 
Nepetalactone Trans-Cis-Form
   NP Info                 C10H14O2         442430  
NP Content: 4.3 %
 
P-Cymene
   NP Info                 C10H14         7463  
NP Content: 13.8 %
   flower: flowering stage    ( Part: Flowers; Location: Tehran, Iran )
               NP Name Link Formula PubChem ID NP Content
 
(E)-2,5,5-Trimethylhepta-3,6-Dien-2-Ol
   NP Info                 C10H18O         5315406  
NP Content: 0.6 %
 
2-Cyclohexen-1-Ol, 1-Methyl-4-(1-Methylethyl)-, Trans-
   NP Info                 C10H18O         122484  
NP Content: 5.5 %
 
4-Carvomenthenol
   NP Info                 C10H18O         11230  
NP Content: 0.6 %
 
Eucalyptol
   NP Info                 C10H18O         2758  
NP Content: 4.2 %
 
Linalool
   NP Info                 C10H18O         6549  
NP Content: 0.2 %
 
Trans-Sabinene Hydrate
   NP Info                 C10H18O         12315151  
NP Content: 0.1 %
 
3,3,6-Trimethylhepta-1,5-Dien-4-One
   NP Info                 C10H16O         68346  
NP Content: 0.2 %
 
Camphor
   NP Info                 C10H16O         2537  
NP Content: 1.8 %
 
Alpha-Phellandrene
   NP Info                 C10H16         7460  
NP Content: 0.3 %
 
Alpha-Pinene
   NP Info                 C10H16         6654  
NP Content: 0.6 %
 
Alpha-Terpinene
   NP Info                 C10H16         7462  
NP Content: 0.3 %
 
Camphene
   NP Info                 C10H16         6616  
NP Content: 0.4 %
 
Limonene
   NP Info                 C10H16         22311  
NP Content: 11 %
 
Nepetalactone Cis-Trans-Form
   NP Info                 C10H14O2         161367  
NP Content: 33.6 %
 
Nepetalactone Trans-Cis-Form
   NP Info                 C10H14O2         442430  
NP Content: 0.5 %
 
Chrysanthenone
   NP Info                 C10H14O         442463  
NP Content: 1.7 %
 
P-Cymene
   NP Info                 C10H14         7463  
NP Content: 8.3 %
 
4A-Alpha,7-Beta,7A-Alpha-Nepetalactone
   NP Info                 NA         NA
NP Content: 29.1 %
   leaf: Flowering stage    ( Part: Leaves; Location: Tehran, Iran )
               NP Name Link Formula PubChem ID NP Content
 
(E)-2,5,5-Trimethylhepta-3,6-Dien-2-Ol
   NP Info                 C10H18O         5315406  
NP Content: 0.6 %
 
2-Cyclohexen-1-Ol, 1-Methyl-4-(1-Methylethyl)-, Trans-
   NP Info                 C10H18O         122484  
NP Content: 7.7 %
 
4-Carvomenthenol
   NP Info                 C10H18O         11230  
NP Content: 1.3 %
 
Eucalyptol
   NP Info                 C10H18O         2758  
NP Content: 15.3 %
 
Linalool
   NP Info                 C10H18O         6549  
NP Content: 0.4 %
 
Camphor
   NP Info                 C10H16O         2537  
NP Content: 5.3 %
 
Alpha-Phellandrene
   NP Info                 C10H16         7460  
NP Content: 1.1 %
 
Alpha-Pinene
   NP Info                 C10H16         6654  
NP Content: 2.5 %
 
Camphene
   NP Info                 C10H16         6616  
NP Content: 1.9 %
 
Limonene
   NP Info                 C10H16         22311  
NP Content: 15.4 %
 
Nepetalactone Cis-Trans-Form
   NP Info                 C10H14O2         161367  
NP Content: 34.1 %
 
Nepetalactone Trans-Cis-Form
   NP Info                 C10H14O2         442430  
NP Content: 1.2 %
 
Chrysanthenone
   NP Info                 C10H14O         442463  
NP Content: 3.6 %
 
4A-Alpha,7-Beta,7A-Alpha-Nepetalactone
   NP Info                 NA         NA
NP Content: 5.9 %
   Stem: flowering stage    ( Part: Stems; Location: Tehran, Iran )
               NP Name Link Formula PubChem ID NP Content
 
(-)-Globulol
   NP Info                 C15H26O         12304985  
NP Content: 3.3 %
 
Caryophyllene Oxide
   NP Info                 C15H24O         1742210  
NP Content: 1.6 %
 
Spathulenol
   NP Info                 C15H24O         92231  
NP Content: 1.9 %
 
(E)-2,5,5-Trimethylhepta-3,6-Dien-2-Ol
   NP Info                 C10H18O         5315406  
NP Content: 1.2 %
 
2-Cyclohexen-1-Ol, 1-Methyl-4-(1-Methylethyl)-, Trans-
   NP Info                 C10H18O         122484  
NP Content: 5.9 %
 
4-Carvomenthenol
   NP Info                 C10H18O         11230  
NP Content: 2.8 %
 
Alpha-Terpineol
   NP Info                 C10H18O         17100  
NP Content: 1 %
 
Eucalyptol
   NP Info                 C10H18O         2758  
NP Content: 18.8 %
 
Linalool
   NP Info                 C10H18O         6549  
NP Content: 0.4 %
 
Camphor
   NP Info                 C10H16O         2537  
NP Content: 7.5 %
 
Alpha-Phellandrene
   NP Info                 C10H16         7460  
NP Content: 0.5 %
 
Alpha-Pinene
   NP Info                 C10H16         6654  
NP Content: 0.6 %
 
Alpha-Terpinene
   NP Info                 C10H16         7462  
NP Content: 0.4 %
 
Camphene
   NP Info                 C10H16         6616  
NP Content: 0.6 %
 
Limonene
   NP Info                 C10H16         22311  
NP Content: 3.6 %
 
Nepetalactone Cis-Trans-Form
   NP Info                 C10H14O2         161367  
NP Content: 32.7 %
 
Nepetalactone Trans-Cis-Form
   NP Info                 C10H14O2         442430  
NP Content: 1.2 %
 
Chrysanthenone
   NP Info                 C10H14O         442463  
NP Content: 2.6 %
 
P-Cymene
   NP Info                 C10H14         7463  
NP Content: 0.6 %
 
4A-Alpha,7-Beta,7A-Alpha-Nepetalactone
   NP Info                 NA         NA
NP Content: 8.4 %
References
1 Essential oil content and composition of Achillea biebersteinii Afan. in different plant parts and phenological stages