General Information of Natural Product (ID: NP0356)
  Natural Product Name
Pentadecanal
  Synonyms
PENTADECANAL; 2765-11-9; 1-pentadecanal; n-pentadecanal; Pentadecanal-; Pentadecanaldehyde; Pentadecyl Aldehyde; UNII-PXR39QX5Q7; PXR39QX5Q7; pentadecan-15-one; SCHEMBL120108; QSPL 086; DTXSID5062633; CHEBI:17302; CAA76511; STR09264; ZINC8217469; EINECS 220-435-1; LMFA06000083; MFCD12911660; AKOS013844767; CS-W004304; AM20120587; FT-0652310; P1869; C01948; 765P119; A819146; Q27102309
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  Formula C15H30O
  Weight 226.4
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16/h15H,2-14H2,1H3
  InChI Key XGQJZNCFDLXSIJ-UHFFFAOYSA-N
  Isomeric SMILES CCCCCCCCCCCCCCC=O
  Canonical SMILES CCCCCCCCCCCCCCC=O
  External Links PubChem ID 17697
CAS ID 2765-11-09

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Aquilaria agallocha
  Factor Name: Plant Pathogen Infection [1]
              Species Info Factor Info
               Experiment Detail
Artificial inoculation of fungal isolates: The most frequently isolated fungi from infected agarwood (e.g. Chaetomium globosum and Fusarium oxysporum) were inoculated to the healthy plants by artifi cial boring on to the plants. Inoculation was made with two different fungi alone and in their combination. Observations were made at an interval of 30 days after inoculation.
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               Factor Function
This investigation showed a marked difference in the oil compositions among the treatments with regards to their quality. Valerianol (3.0%) and tetradec-anioc acid (7.1%) contents were recorded higher in the oils of naturally infected plants than in that of healthy ones (0.1% and 6.9%, respectively). Pentadecenoic acid was totally absent in the oils of healthy, whereas it was found in a greater amount (6.8%) in the oil of naturally infected plants. In contrast, dodecanoic acid (3.1%), pentadecanoic acid (6.2%), hexadecanoic acid (31.5%) and octadecanoic acid (4.1%) were found in a higher amount in the oils of healthy plants, while the oils obtained from naturally infected plants contained lower amounts of these components (2.5%, 4.8%, 20.0% and 1.0%, respectively). The oils obtained from the inoculated plants showed almost similar distribution of the components with healthy plants.
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               Factor Part Location NP Content
 
Healthy plants
Wood chips India
NP Content: 0.2 %
 
Artificial inoculation plants (Chaetomium globosum)
Wood chips India
NP Content: 0.2 %
 
Artificial inoculation plants (Fusarium oxysporum)
Wood chips India
NP Content: 0.3 %
 
Artificial inoculation plants (C. globosum and F. oxysporum)
Wood chips India
NP Content: 0.2 %
      Species Name: Arabidopsis thaliana
  Factor Name: T-DNA Knock-Out Treatment [2]
              Species Info Factor Info
               Experiment Detail
In vitro cultivation of Arabidopsis wildtype and mutant plants: Seeds were sterilized according to standard lab routines (EtOH, NaOCl/NaOH) prior to aseptical (in vitro) cultivation in 500 ml screw cap jars on MS medium (4.3 g/l; 50 ml/jar) containing Bacto- and Phytoagar (1:2; 6 g/l) and 30 g/l sucrose. Ten seeds were pipetted into each jar and plants grown for 6 weeks until flowering at a temperature of 20 ℃ under a 16/8 h day/ night regime using fluorescent tubes (Osram Lumilux Plus Eco 36 W). Both Arabidopsis thaliana wildtype plants of ecotype Columbia-0 (Col) and 4 Col-derived T-DNA knock-out mutants (homozygous lines) showing deficiencies in the GLS biosynthesis pathway were used in this study (five parallels for wildtype and mutants): TGG1 (Atg526000; Salk_130469), TGG2 (At5g25980; Salk_038730), Cyp83A1 (At4g13770) and Cyp83B1 (At4g31500; Salk_028573). Greenhouse-cultivation of Arabidopsis ecotypes: The following Arabidopsis ecotypes were used in the study: Columbia (Col), Cape Verde Islands (Cvi), Landsberg erecta (Ler) and Wassilewskija (Ws). Single plants were greenhouse-cultivated on fertilized soil (P-Jord; Emmaljunga Torvmull AB) in plug trays (9 × 6 cells) at a temperature of 20 ℃ (three parallels for each ecotype). Due to the 6-weeks growth period (November/December 2003), the plants were cultivated under a 16/8 h day/night regime using metal halide lamps (Osram HQI-T 400 W) placed 130 cm above the trays. Depending on the ecotypical plant development, whole plants were sampled after 3-4 weeks right before bolting for in vivo studies, while investigations of single plant organs (leaf, stem, inflorescence) were carried out after 5-6 weeks of cultivation.
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               Factor Function
Metabolites from methionine, leucine and phenylalanine-derived glucosinolates were most abundant (4-methylthiobutyl, 4-methylpentyl, 2-phenylethyl). In addition, 24 monoterpenes, 26 sesquiterpenes and 12 aromatic structures, predominantly observed in inflorescenses, are described. Excluding the vast group of straight chain aliphatic structures, a total of 102 volatile compounds were detected, of which 59 are reported in Arabidopsis thaliana for the first time, thus emphasizing the sensitivity and applicability of solid-phase microextraction for volatile profiling of plant secondary metabolites.
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               Factor Part Location NP Content
 
Whole plant: A. thaliana wildtype detected in situ
Whole plant Norway
NP Content: 0.65 %
 
Arabidopsis thaliana wildtype
Whole plant Norway
NP Content: 0.32 %
 
A. thaliana T-DNA knock-out mutant Cyp83A1: (At4g13770)
Whole plant Norway
NP Content: 0.21 %
 
A. thaliana T-DNA knock-out mutant Cyp83B: (At4g31500; Salk_028573)
Whole plant Norway
NP Content: 0.47 %
 
A. thaliana T-DNA knock-out mutant TGG1: (Atg526000; Salk_130469)
Whole plant Norway
NP Content: 0.48 %
 
A. thaliana T-DNA knock-out mutant TGG2: (At5g25980; Salk_038730)
Whole plant Norway
NP Content: 0.17 %
      Species Name: Fragaria vesca
  Factor Name: Cultivar Comparison [3]
              Species Info Factor Info
               Experiment Detail
Whole leaves and inflorescences of two wild strawberry cultivars ('Rugia' and 'Baron von Solemacher') harvested in 2008 during the agrotechnical experiment performed by Department of Vegetable and Medicinal Plants, University of Life Sciences in Lublin, were used as a material for determinations. Samples were collected before noon at sunny and dry days at the beginning of wild strawberry's flowering stage. Material was dried up to 35 ℃ in shadow and air just after the harvest.
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               Factor Function
Depending on a cultivar, air-dry inflorescences from wild strawberry contain from 0.21% ('Baron von Solemacher' cv.) to 0.30% ('Rugia' cv.), whereas leaves contains from 0.46% ('Baron von Solemacher' cv.) to 0.62% ('Rugia' cv.) of essential oils. GC/MS analysis of essential oils achieved from studied materials revealed presence of 70 (including 59 identified) compounds in leaves of 'Rugia' cv. and 58 (including 50 identified) compounds in leaves of 'Baron von Solemacher' cv. Essential oils from inflorescences of 'Rugia' cv. contained 52 (including 47 identified), while 'Baron von Solemacher' cv. contained 54 (including 46 identified) compounds. The chromatographic analyses by GC-MS revealed that myrthenol, nonal, linalool and phthalide dibuthyl dominated in essential oils obtained from leaves, while myrthenol, citronelol, linalool and geraniol - from those of inflorescences. There were qualitative differences between oil components at both studied materials and differentiation between both cultivars, as well.
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               Factor Part Location NP Content
 
Inflorescence: Fragaria vesca cv. Rugia
Inflorescence Poland
NP Content: <0.05 %
 
Leaf: Fragaria vesca cv. Baron von Solemacher
Leaves Poland
NP Content: <0.05 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [4]
              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: Sivas, Turkey)
Flowers Sivas, Turkey
NP Content: <0.1 %
 
Root: (Locality: Sivas, Turkey)
Roots Sivas, Turkey
NP Content: 0.5 %
      Species Name: Tanacetum dolichophyllum
  Factor Name: Altitude Variation [5]
              Species Info Factor Info
               Experiment Detail
Wild growing Tanacetum dolichophyllum samples were collected during the period of full flowering, between September-October 2009 from high alpine meadows of Western Himalaya (Uttarakhand, India): Sample I (Dayara, altitude 3200 m) and Sample II (Tungnath, altitude 3800 m).
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               Factor Function
Plant collected from Dayara meadow (Sample I) afforded cis-lanceol (11.8%), beta-pinene (10.7%), (E)- beta-farnesene (7.4%), alpha-bisabolol (7.2%), beta-eudesmol (5.2%) and terpinen-4-ol (5.1%) as the major constituents, whereas in the sample collected from Tungnath (Sample II) beta-eudesmol (31.4%), alpha-bisabolol (10.7%) were the most abundant components followed by neryl acetate (5.8%) and (E)-beta-farnesene (5.7%). The composition was dominated by sesquiterpene hydrocarbons and oxygen containing sesquiterpenes (49.2-71.1%). The oils are clearly different from those of all other previously reported T. dolichophyllum oils.
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               Factor Part Location NP Content
 
Locality: Dayara; Altitude 3200m
Aerial parts Himalyas, Uttarakhand, India
NP Content: 0.8 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities in north western Turkey. A = Trabzon: Caykara, Soganli dag on July 28, 1994; B = Bayburt: Caykara, Mohakambo yaylasi on July 25, 1994; C = Trabzon: Koprubasi, Vizara yaylasi on July 20, 1994.
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               Factor Function
One hundred and four compounds were identified representing 97.5-99.5% of the total components detected in thymol/carvacrol (50.14/10.67%), thymol/linalool (23.14/20.24%) and linalool/alpha-terpinyl acetate/geraniol (21.55/16.70/11.17%) rich oils.
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               Factor Part Location NP Content
 
Locality: Soganli dag, Caykara, Trabzon, Eskisehir, Turkey
Aerial parts Eskisehir, Turkey
NP Content: 0.1 %
References
1 Essential Oil of Eaglewood Tree: a Product of Pathogenesis
2 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
3 Contents and chemical composition of essential oils from wild strawberry (Fragaria vesca L.)
4 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
5 Variation in the Constituents of Tanacetum dolichophyllum (Kitam.) Kitam. from Different Locations of Uttarakhand Himalaya (India)
6 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey