General Information of Natural Product (ID: NP0160)
  Natural Product Name
6-Methyl-5-Hepten-2-One
  Synonyms
6-METHYL-5-HEPTEN-2-ONE; 6-Methylhept-5-en-2-one; 110-93-0; Sulcatone; 5-HEPTEN-2-ONE, 6-METHYL-; 2-Methyl-2-hepten-6-one; METHYL HEPTENONE; 6-Methyl-5-heptene-2-one; Heptenone, methyl-; 2-Methyl-6-oxo-2-heptene; 2-Oxo-6-methylhept-5-ene; NSC 15294; 6-methyl-hept-5-en-2-one; UNII-448353S93V; 6-Methyl hept-5-en-2-one; 6-methylheptan-5-ene-2-one; CHEBI:16310; NSC66569; MFCD00008905; 448353S93V; DSSTox_CID_1629; DSSTox_RID_76244; DSSTox_GSID_21629; CAS-110-93-0; FEMA No. 2707; EINECS 203-816-7; 6-Methyl-5-hepten-2-one (natural); BRN 1741705; prenylacetone; AI3-05639; LAUROYLCOENZYMEA; 2-Methyl-6-heptenone; 6-Methyl-hepten-2-one; 6-methyl-5-hepten-2-on; EC 203-816-7; 2-methylhept-2-en-6-one; 2-methyl-hept-2-en-6-one; 4-01-00-03493 (Beilstein Handbook Reference); CHEMBL46340; SCHEMBL157735; DTXSID5021629; FEMA 2707; HSDB 5565; ZINC896810; 6-Methyl-5-Hepten-2-One Natural; 6-Methyl-5-hepten-2-one, 99%; NSC15294; EINECS 206-990-2; Tox21_201381; Tox21_302899; BBL027733; LMFA12000039; NSC-15294; NSC-66569; STK801685; AKOS006034959; CS-W011151; FS-3837; HY-W010435; MCULE-3832720881; Sulcatone (6-Methylhept-5-en-2-one); NCGC00249039-01; NCGC00256420-01; NCGC00258932-01; DB-040945; FT-0621226; FT-0628888; M0252; X5960; 6-Methyl-5-hepten-2-one, analytical standard; C07287; D77716; 6-Methyl-5-hepten-2-one, >=98%, FCC, FG; 6-Methyl-5-hepten-2-one, natural, >=98%, FCC; Q3209146; W-108682; 6-Methyl-5-hepten-2-one, natural, >=98.0%, FCC; 0VT
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  Formula C8H14O
  Weight 126.2
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3
  InChI Key UHEPJGULSIKKTP-UHFFFAOYSA-N
  Isomeric SMILES CC(=CCCC(=O)C)C
  Canonical SMILES CC(=CCCC(=O)C)C
  External Links PubChem ID 9862
CAS ID 110-93-0
NPASS ID NPC38497
CHEMBL ID CHEMBL46340
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Arabidopsis thaliana
  Factor Name: T-DNA Knock-Out Treatment [1]
              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
 
Inflorescences: A. thaliana wildtype detected in vivo
Flowers Norway
NP Content: 6.57 %
 
Leaves: A. thaliana wildtype detected in vivo
Leaves Norway
NP Content: 8.23 %
 
Stem: A. thaliana wildtype detected in vivo
Stems Norway
NP Content: 6.42 %
 
Whole plant: A. thaliana wildtype detected in situ
Whole plant Norway
NP Content: 0.46 %
 
Arabidopsis thaliana wildtype
Whole plant Norway
NP Content: 0.74 %
 
A. thaliana T-DNA knock-out mutant Cyp83A1: (At4g13770)
Whole plant Norway
NP Content: 0.56 %
 
A. thaliana T-DNA knock-out mutant Cyp83B: (At4g31500; Salk_028573)
Whole plant Norway
NP Content: 0.73 %
 
A. thaliana T-DNA knock-out mutant TGG1: (Atg526000; Salk_130469)
Whole plant Norway
NP Content: 0.79 %
 
A. thaliana T-DNA knock-out mutant TGG2: (At5g25980; Salk_038730)
Whole plant Norway
NP Content: 0.65 %
      Species Name: Artemisia arborescens
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
Fresh plant samples of A. arborescens growing in Sicily were collected from five different sites: Petru (N 37° 59′ 46″, E 13° 38′ 53″, 69 m); Diga (N 37° 57′ 23″, E 13° 39′ 05″, 198 m), Felice (N 37° 56′ 44″, E 13° 36′ 38″, 484 m), Torto (N 37° 57′ 53″, E 13° 46′ 30″, 55 m) and Artese (N 37° 58′ 28″, E 13° 44′ 13″, 10 m) in January 2010.
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               Factor Function
Forty-three compounds, accounting for more than 92% of the oil, were identified. Monoterpene fraction with the exception of Petru population was higher than the sesquiterpene fraction. beta-Thujone (20.5-55.9%), chamazulene (15.2-49.4%), camphor (1.3-10.7%) and germacrene D (2.3-3.4%) were the main compounds.
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               Factor Part Location NP Content
 
Locality: Petru, Sicily
Aerial parts Sicily
NP Content: <0.1 %
 
Locality: Diga, Sicily
Aerial parts Sicily
NP Content: <0.1 %
 
Locality: Felice, Sicily
Aerial parts Sicily
NP Content: <0.1 %
 
Locality: Venti, Sicily
Aerial parts Sicily
NP Content: <0.1 %
 
Locality: Arte, Sicily
Aerial parts Sicily
NP Content: <0.1 %
      Species Name: Artemisia verlotiorum
  Factor Name: Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Plant material of A. verlotiorum was harvested near Marseille (France) in May (before blooming) and November (full flowering) 2000.
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               Factor Function
For the oil from the vegetative plants, 50 compounds, representing 99.8% of the oil were characterized. Fifty-nine compounds, representing 99.6% of the oil were identified in the oil from flowering plants. In both cases, the constituents were mainly oxygenated monoterpenes (74% and 88%). The composition of each oil showed only a few differences, as the main components were alpha-thujone (55% and 44%), 1,8-cineole (5% and 15%), beta-caryophyllene (13% and 7%) and beta-thujone (5% and 11%), in the oils of the vegetative plant and flowering plant, respectively. The proportions of the oxygenated compounds seemed to increase during flowering.
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               Factor Part Location NP Content
 
Aerial part: full flowering stage
Aerial parts Marseille, France
NP Content: 0.1 %
      Species Name: Cymbopogon martinii
  Factor Name: Ethyl methane sulfonate Treatment; Ethyleneimine Treatment; Gamma ray Treatment; Cultivar Comparison [4]
              Species Info Factor Info
               Experiment Detail
The materials (dry palmarosa seeds with 12% moisture content of four cultivars 'Tripta', 'Trishna', 'PRC' and 'MP') and methods of gamma rays (15 Kr, 60CO source with dose rate 0.38 Mrads\h) and chemicals ethyl methane sulfonate (EMS - 0.4%) and ethyleneimine (EI-0.04%) induced mutagenesis. The seed of the four varieties had already been selfed for 4-5 flowering seasons before mutagenesis to maintain genetic homogeneity (or purity) and thereafter all the selected M1 generation suspected mutant plants were individually selfed by bagging to give rise to controlled M2 plant to progeny segregants for further selection. Oil content was estimated on freshly harvested herbage (stems, leaves and inflorescence) using a Clevenger-type apparatus.
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               Factor Function
The oil content was increased in all the 20 mutants as compared to their respective contols. Most M2 generation mutants were found to exhibit a straight relationship between high herbage (stem, leaves and inflorescence) yield, oil content (%) and oil quality in terms of major and trace constituents of the oil. Six mutants specifically were endowed with the desirable rosy note which remained predominant in the samples of Trishna-gamma-5, MP-gamma-13, Tripta-gamma-8, Tripta-Ethyl methane sulfonate (EMS)-19, Tripta-EMS-21 and PRC-Ethyleneimine (EI)-44. The fresh herbage and oil yield and odor criteria, i.e., rosy note were satisified by the three best mutants, viz., Trishna-gamma-5, MP-gamma-13 and Tripta-gamma-19. The results have been interpreted in the sense that induction of mutations brings about gene level changes from dominance to recessive and vice versa in morpho-economic traits having quantitative trait loci (QTL) under polygenic genetic control.
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               Factor Part Location NP Content
 
Cymbopogon martinii cv. MP (Control)
Herbages India
NP Content: 1.32 %
 
Mutant 31: C. martinii cv. MP induced by ethyl methane sulfonate
Herbages India
NP Content: 0.23 %
 
Mutant 31: C. martinii cv. MP induced by ethyl methane sulfonate
Herbages India
NP Content: 0.12 %
 
Mutant 13: C. martinii cv. MP induced by gamma rays
Herbages India
NP Content: 0.15 %
 
Cymbopogon martinii cv. PRC (Control)
Herbages India
NP Content: 2.14 %
 
Mutant 43: C. martinii cv. PRC induced by ethyleneimine
Herbages India
NP Content: 0.25 %
 
Mutant 44: C. martinii cv. PRC induced by ethyleneimine
Herbages India
NP Content: 0.24 %
 
Mutant 45: C. martinii cv. PRC induced by ethyleneimine
Herbages India
NP Content: 1.48 %
 
Mutant 48: C. martinii cv. PRC induced by ethyleneimine
Herbages India
NP Content: 0.24 %
 
Mutant 9: C. martinii cv. PRC induced by gamma rays
Herbages India
NP Content: 0.78 %
 
Mutant 10: C. martinii cv. PRC induced by gamma rays
Herbages India
NP Content: 0.12 %
 
Mutant 12: C. martinii cv. PRC induced by gamma rays
Herbages India
NP Content: 0.33 %
 
Cymbopogon martinii cv. Tripta (Control)
Herbages India
NP Content: 1 %
 
Mutant 18: C. martinii cv. Tripta induced by ethyl methane sulfonate
Herbages India
NP Content: 1.08 %
 
Mutant 19: C. martinii cv. Tripta induced by ethyl methane sulfonate
Herbages India
NP Content: 0.27 %
 
Mutant 20: C. martinii cv. Tripta induced by ethyl methane sulfonate
Herbages India
NP Content: 0.58 %
 
Mutant 21: C. martinii cv. Tripta induced by ethyl methane sulfonate
Herbages India
NP Content: 0.65 %
 
Mutant 1: C. martinii cv. Trishna induced by gamma rays
Herbages India
NP Content: 2.34 %
 
Mutant 2: C. martinii cv. Trishna induced by gamma rays
Herbages India
NP Content: 0.39 %
 
Cymbopogon martinii cv. Trishna (Control)
Herbages India
NP Content: 2.2 %
 
Mutant 41: C. martinii cv. Trishna induced by ethyleneimine
Herbages India
NP Content: 2.01 %
 
Mutant 5: C. martinii cv. Trishna induced by gamma rays
Herbages India
NP Content: 1.31 %
 
Mutant 6: C. martinii cv. Trishna induced by gamma rays
Herbages India
NP Content: 0.3 %
 
Mutant 8: C. martinii cv. Trishna induced by gamma rays
Herbages India
NP Content: 0.05 %
      Species Name: Micromeria biflora
  Factor Name: Seasonal Variation [5]
              Species Info Factor Info
               Experiment Detail
The aerial parts of M. biflora collected during November 1993 and June 1994 were used for the investigation.
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               Factor Function
The major constituents of the oil were neral (25.3-32.2%) and geranial (26.7-41.3%). The oil produced in the winter was found to contain higher amounts of oxygenated monoterpenes than the oil produced in the summer.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Aerial parts South India
NP Content: 1.01 %
 
Harvesting time: Winter
Aerial parts South India
NP Content: 0.75 %
      Species Name: Ocimum basilicum
  Factor Name: Variety Comparison [6]
              Species Info Factor Info
               Experiment Detail
Aerial parts of Ocimum basilicum var. purpurascens Benth, Ocimum basilicum var. dianatnejadii Salimi at flowering stage were collected from plants grown in Experimental Station of Pykan Shahr, near Tehran. Elevation 1215 m above sea level, latitude 35° 42′ North, 51° 8′ East, average humidity 36% and climatic category semi-arid.
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               Factor Function
Methyl chavicol (43.0%) and linalool (28.9%) were identified as the major compounds in the oil of O. basilicum var. purpurascens, while methyl chavicol (37.6%), linalool (33.4%) and alpha-cadinol (5.7%) were the major constituents in the oil of O. basilicum var. dianatnejadii.
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               Factor Part Location NP Content
 
Ocimum basilicum var. dianatnejadii Salimi
Aerial parts Iran
NP Content: 0.5 %
 
Ocimum basilicum var. purpurascens Benth
Aerial parts Iran
NP Content: 0.3 %
      Species Name: Pimenta pseudocaryophyllus
  Factor Name: Developmental Stage Variation [7]
              Species Info Factor Info
               Experiment Detail
Two samples were collected in Sao Goncalo do Abaete, one in July 2000 and the other in November 2005, in periods of post-anthesis and preanthesis, respectively.
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               Factor Function
Thirty compounds were detected in the samples collected in Sao Goncalo do Abaete. Among the identified compounds, 53.8% are sesquiterpenes and 42.3% are monoterpenes. The majority components in the two samples were neral and geranial. The sample in anthesis presented a lower percentage of neral (21.4%) and geranial (36.5%) than the sample in pre-anthesis, whose percentages of neral and geranial were 33.6% and 47.2%, respectively.
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               Factor Part Location NP Content
 
post-anthesis stage
Leaves Sao Goncalo do Abaete, Brazil
NP Content: 0.2 %
      Species Name: Ruta chalepensis
  Factor Name: Developmental Stage Variation [8]
              Species Info Factor Info
               Experiment Detail
Ruta chalepensis seedlings were sown in the field in January 1999. Leaf materials were collected at vegetative stage (25th August 1999, plant height 60 cm, temp. min. 26.4 ℃, max. 35.6 ℃) and at budding stage (25th February 1999, plant height 115 cm, temp. min. 9.6 ℃, ma. 26.2 ℃). At flowering stage (2Sth March 2000, plant height 118 cm, temp. min. 14.3 ℃, max. 29.7 ℃), both leaves and flowers were collected; at fruiting stage (25th April 2000, plant height 119 cm, temp. min. 21.5 ℃, max. 39.1 ℃), leaves and fruits were again collected for oil isolation and analysis.
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               Factor Function
Analysis of the oils from R. chalepensis showed that the major constituents of oils were 2-undecanone, 2-nonanone, 2- nonyl-acetate and 2-dodecanone. 2-Undecanone was found to reach a maximum in the flower oil followed by fruit and leaf oils. The quantity of 2-undecanone was highest in the leaves when the plants were young and in the vegetative stage, and it gradually decreased when the plants started flowering and fruiting. 2-Nonanone, on the other hand, was at its maximum in the Leaf oil followed by flower and fruit oils. The quantity of 2-nonanone in the leaves gradually increased from the vegetative stage to the flowering stage and was highest during fruiting stage. The concentration of 2-nonyl acetate was observed to be highest in the leaves during the vegetative stage, while 2-dodecanone was at its maximum in the fruits. Lina-lool, an important aromatic compound, has been found to be highest in flowers. Gamma-Terpinene and 6-methyl-5-hepten-2-one were observed only in vegetative stage of the plants. During the flowering and fruiting stages they could not be detected. Pregeijerene was observed during flowering only, while geijerene was observed both during flowering and fruiting; however, this compound was found in leaves.
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               Factor Part Location NP Content
 
Leaf: Budding Stage
Leaves Lucknow, India
NP Content: 0.2 %
 
Leaf: Vegetative stage
Leaves Lucknow, India
NP Content: 0.01 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [9]
              Species Info Factor Info
               Experiment Detail
Aerial parts of both varieties(Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and Salvia euphratica Montbret et Aucher ex Benth. var. leiocalycina) were collected in Malatya, Turkey in June 1999.
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               Factor Function
Ninety-five compounds in var. euphratica and 94 compounds in var. leiocalycina were characterized representing 93% and 95% of the total components detected, respectively, with 1,8-cineole (13.8% and 15.2%) and myrtenyl acetate (15.9% and 13.9%) as main constituents.
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               Factor Part Location NP Content
 
Salvia euphratica var. euphratica
Flowering aerial parts Turkey
NP Content: 0.1 %
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: 0.1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [10]
              Species Info Factor Info
               Experiment Detail
Plant material and isolation procedure: Aerial parts of the plant were collected from two regions, from Kazeroon in southern Iran and Shahr-e-kord in western Iran at the time of flowering in June 2002.
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               Factor Function
The main components of the oil of S. pilifera collected from Kazeroon, in southern Iran, were spathulenol (15.8%), cis-chrysanthenol (15.3%), beta-caryophyllene (8.4%) and cis-chrysanthenyl acetate (6.9%), while for the plant collected from Shahr-e-kord, in western Iran, they were cis-chrysanthenyl acetate (21.8%), linalool (18.9%), terpinen-4-ol (11.9%) and cis-chrysanthenol (9.2%).
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               Factor Part Location NP Content
 
Locality: Kazeroon, southern Iran
Aerial parts Iran
NP Content: <0.05 %
 
Locality: Shahr-e-kord, western Iran
Aerial parts Iran
NP Content: <0.05 %
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [11]
              Species Info Factor Info
               Experiment Detail
3-year old single shoot V. vinifera plants (cultivar Pinot noir 18 Gm grafted on Kober 5BB, 51 plants) potted in 3L pots in a sandy loam soil were used. All plants were well watered (200 mL per day) at the beginning of the experiment (04.06.2010; DAY 0; 5 plants) and water was supplied to all control plants once every day (250 mL per day), whereas water supply of stressed plants was stopped. Physiological measurements and sampling of leaves took place on 07.06.2010 (DAY 3; 5 control, 5 stressed plants), 10.06.2010 (DAY 6; 5 control, 5 stressed plants) and 12.06.2010 (DAY 8; 5 control, 10 stressed plants). Due to very hot weather conditions in June 2010 the experiment was stopped after 8 days and 12 available control plants were used to restart the drought treatment with 6 control and 6 stressed plants on 11.06.2010 and all plants were measured on 15.06.2010 (DAY 5). The mean leaf temperatures at midday were: 25 ℃ (04.06.2010; DAY 0), 31.9 ℃ (07.06.2010; DAY 3), 30.8 ℃ (15.06.2010; DAY 5), 35.8 ℃ (10.06.2010; DAY 6) and 35.7 ℃ (12.06.2010; DAY 8). The mean PAR radiation per day (measured from 6:00 am till 7:00 pm) was 144.1 µmol m-2 s-1. Each plant was used only once for physiological measurements and sampling of leaves.On every day of the experiment (day 0, 3, 5, 6, 8) the pot weight and the volumetric soil moisture content (ThetaProbe ML2x and handheld data logger Moisture Meter HH2, Delta-T Devices, Cambridge, United Kingdom) was recorded. The water potential (PWSC Model 3000, Soilmoisture Equipment Corporation, Santa Barbara, USA) was determined for the 6th leaf (representing the insertion level of the shoot from the basis) of every plant and measurement day. Chlorophyll fluorescence and gas exchange parameters of light adapted leaves were determined with the 4th and 5th leaf, whereas dark adaptation was performed only with the 5th leaf. Immediately after these non-invasive measurements, the 5th leaf was harvested, frozen in liquid nitrogen and further used for the measurement of polyphenols, selected primary metabolites and volatiles (VOCs).
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               Factor Function
The content of different groups of primary and secondary metabolites is significantly influenced by severe drought stress in grapevine leaves. The content of the majority of the metabolites (around 60% of primary metabolites, around 85% of polyphenols and about 40% of the detected and identified VOCs) increased upon drought stress treatment. Among these especially the primary metabolites citric acid and glyceric acid were strongly influenced by the short as well as the prolonged drought stress treatment, whereas all polyphenols were only induced upon the prolonged drought stress treatment.
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               Factor Part Location NP Content
 
Normal condition
Leaves Vienna, Austria
NP Content: 2496.6 ± 1091.3 peak areas
 
Dry 3-5 days
Leaves Vienna, Austria
NP Content: 3530.6 ± 1794.3 peak areas
 
Dry 6-8 days
Leaves Vienna, Austria
NP Content: 6888.6 ± 8142.5 peak areas
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
2 Artemisia arborescens L.: essential oil composition and effects of plant growth stage in some genotypes from Sicily
3 Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
4 Induced Mutants in M2 Generation and Selection for Enhanced Essential Oil Yield and Quality in Palmarosa (Cymbopogon martinii, Roxb.) Wats., var. martinii
5 Composition of the Essential Oil of Micromeria biflora
6 Essential oil composition of four Ocimum species and varieties growing in Iran
7 Chemical Differences in the Essential Oil of Pimenta pseudocaryophyllus (Gomes) L. R. Landrum Leaves from Brazil
8 Variations in Essential Oil Constituents at Different Growth Stages of Ruta chalepensis on Cultivation at North Indian Plains
9 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
10 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
11 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)