General Information of Natural Product (ID: NP0319)
  Natural Product Name
Verbenone
  Synonyms
VERBENONE; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one; 2-Pinen-4-one; 80-57-9; d-Verbenone; dl-Verbenone; NSC6832; ST069322; Verbinone; Verbenone, (d)-; Verbenone, (L)-; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R)-; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S)-; 5480-12-6; NSC 6831; (-)-cis-verbenone; NSC 36846; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-; Verbenone, (+)-; 2-Pinen-4-one, (1R,5R)-(+)-; (1R-cis)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-ene-2-one; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R,5R)-; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R-cis)-; NSC36846; S-Verbenone; 2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one; Verbenone (D,L-); VERBENONE,(DL); SCHEMBL118161; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-; DTXSID2048115; CHEBI:78315; (1s)-(-)-pin-2-en-4-one; NSC-6832; BBL033979; STK801995; AKOS024283493; MCULE-1142475318; 2-Pinen-4-one, (1S,5S)-(-)-; VS-12358; DB-061581; DB-075693; CS-0280756; FT-0604532; FT-0604550; FT-0617225; C09913; Q421151; (-)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1S,5S)-
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  Formula C10H14O
  Weight 150.22
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3
  InChI Key DCSCXTJOXBUFGB-UHFFFAOYSA-N
  Isomeric SMILES CC1=CC(=O)C2CC1C2(C)C
  Canonical SMILES CC1=CC(=O)C2CC1C2(C)C
  External Links PubChem ID 29025
CAS ID 80-57-9

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [1]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
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               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
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               Factor Part Location NP Content
 
Artemisia annua accessions Suraksha
Aerial parts India
NP Content: <0.05 %
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: 0.4 %
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [2]
              Species Info Factor Info
               Experiment Detail
Aerial parts of endemic pichana were harvested in December 1996 at different localities of northern Patagonia. Origin: Planicie Banderita, Dept. Confluencia, Province of NeuquCn. Habitat: altitude, 327 m; average temperature in the station, 21.8 ℃; annual precipitation, 125 mm; sandy soils. Aerial parts (5 kg, 2 kg of dried material;humidity, 11%) from four well developed plants at the fullflowering stage (December, 1996). Sample 2 : Origin: RincBn de 10s; Sauces, Dept. of Pehuenclies, Province of Neuqukn. Habitat: altitude, 750 m; average temperature in the station, 20.9 ℃; annual precipitation, 147 mm; sandy and gritty salty soils. Aerial parts (5 kg, 1.85 kg of dried material, humidity, 10%), from two well developed plants at the full flowering stage, and after several days copious rains (December, 1996). Sample 3: Origin: Coronel GBmez, Dept. General Roca, Province of Rio Negro. Habitat: altitude, 242 m; average temperature in the station, 22.5 ℃; annual precipitation, 179 mm; sandy and stony soils. Aerial parts (4.5 kg, 1.3 kg of dried material, humidity, 9%), from 12 young plants at the beginning flowering stage (December, 1996).
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               Factor Function
Fifty-four components, representing approximately 84.6-97.4% of the oil samples, were identified. The samples consisted mainly of hydrocarbons and oxygenated monoterpenes. The major constituents were limonene (28.7-56.7%), 6R-7R-bisabolone (3.2-9.1%), sabinene (0.1-11.0%) and citronellal (2.4-5.2%). Significant differences among the content of the three samples could be the result of changes in the climatic conditions (sample 2: Rincon de los Sauces, Province of Neuquen, after strong rains) or by translocations in different parts of the plant (sample 3: Coronel Gomez, Province of Rio Negro, more leaves and less stems).
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               Factor Part Location NP Content
 
Locality: Planicie Banderita, Province of Neuquen; Altitude 327 m
Aerial parts Patagonia, Argentina
NP Content: 0.1 %
 
Locality: Rincon de los Sauces, Province of Neuquen; Altitude 750 m
Aerial parts Patagonia, Argentina
NP Content: 0.1 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
Aerial parts Patagonia, Argentina
NP Content: 0.2 %
      Species Name: Ichthyothere terminalis
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
The leaves and stems of Ichthyothere terminalis were collected at Marapanim, PA (sample A) and Manaus, AM (sample B).
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               Factor Function
The chief constituent found in the leaf oil of sample of, I. terminalis collected at Marapanim (PA) was sabinene (18.0%). The leaf oil of I. terminalis collected at Manaus (AM) was dominated by alpha-pinene (19-8%), sabinene (14.8%) and limonene (35.8%), while the main components identified in the stem oil were alpha-pinene (13.9%) and limonene (20.0%).
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               Factor Part Location NP Content
 
Leaves: Manaus, Brazil
Leaves Brazil
NP Content: 0.8 %
 
Leaves: Marapanim, Brazil
Leaves Brazil
NP Content: 0.5 %
      Species Name: Lavandula latifolia
  Factor Name: Developmental Stage Variation [4]
              Species Info Factor Info
               Experiment Detail
Plant material: Samples of L. latifolia were collected in August 1998 during the full flowering period (L/La) and in October 1998 during the fruiting period (L/Lb) from three different spike lavender populations located into the Cazorla, Segura y Las Villas Natural Park (Jaen province, Spain). The plant material from each population consisted of the twigs of several single plants. L/La (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: August 14, 1998, Phenological stage: Flowering); L/Lb (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: October 15, 1998, Phenological stage: Fruiting).
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               Factor Function
The small amounts of linalool needed to match the standard can be reached in a natural way (from full flowering to fruiting) which means it is important to choose the most convenient time of harvest in the studied area.
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Whole plant Spain
NP Content: 0.1 %
 
Whole plant:Fruiting stage
Whole plant Spain
NP Content: 0.1 %
      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: 0.08 %
 
Harvesting time: Winter
Aerial parts South India
NP Content: 0.09 %
      Species Name: Rosmarinus eriocalyx
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
The leaves of R. eriocalyx were harvested at random from two localities of the forest in the North and South ranges of Boutaleb in Algeria at different altitudes during the full flowering stage. Sample N3(Locality: Northern slope; Altitude (m): 850; Collection date: Mar 20,1993); Sample S3(Locality: Southern slope; Altitude (m): 850; Collection date: Mar 20,1993).
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               Factor Function
Concerning the alcohols, the highest amount of 1,8-cineole (11.4%) coincided with a very low amount of terpinen-4-ol(1.0%) in sample N3 as well as with a generally low concentration of hydrocarbons (apart from camphene and pinene) in all samples of R. eriocalyx.
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               Factor Part Location NP Content
 
Locality: Northern slope, Boutaleb range, Algeria; Altitude 850 m + Harvesting time: 20-Mar-1993
Leaves Algeria
NP Content: 0.1 %
      Species Name: Rosmarinus officinalis
  Factor Name: Developmental Stage Variation [7]
              Species Info Factor Info
               Experiment Detail
Samples of R. officinalis were collected in April 1998 during the full flowering period (Ro-1a), between June and July 1998 during the fruiting period (Ro-1b) and in December 1998 during the hibernation period (Ro-1c) from Cazorla, Segura y Las Villas Natural Park (province of Jaen, Spain). The plant material consisted of ca. 10 twigs per plant (with blossoming tips or not, depending of the harvesting date) from 5-10 single plants. Ro-1a (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: April 21, 1998, Phenological stage: Flowering); Ro-1b (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: June 19, 1998, Phenological stage: Fruiting); Ro-1c (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: December 30, 1998, Phenological stage: Hibernation).
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               Factor Function
The highest oil yields (161.8%) were recorded during the fruiting period (summer). In general, minimum amounts of camphor and maximum amounts of alpha-pinene were observed in winter. The concentration of 1,8-cineole was almost constant throughout the year, though other oil constituent levels varied randomly with the plant life cycle
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Twigs Las Chozuelas, Southern Spain
NP Content: 4.3 %
 
Whole plant: Fruiting stage
Twigs Las Chozuelas, Southern Spain
NP Content: 3.6 %
 
Hibernation stage
Twigs Las Chozuelas, Southern Spain
NP Content: 4 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [8]
              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: 1.9 %
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: 1.9 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [9]
              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: 1.1 %
      Species Name: Talauma ovata
  Factor Name: Month Variation [10]
              Species Info Factor Info
               Experiment Detail
Talauma ovata was collected from October 2003 to February 2005. Leaves and trunk bark from the same set of plants were collected in the four seasons: spring (October 15th, 2003), autumn (April 10th, 2004), winter (July 17th, 2004) and summer (February 15th, 2005). In addition, trunk bark was also collected on January 22nd, 2004 (summer). The plant material was harvested from wild-growing population in Santos Dumont City, Minas Gerais State, Brazil, (21° 28′ 03″ S, 43° 39′ 26″ W), at 1000 m of altitude.
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               Factor Function
In each season the composition of trunk bark oils was similar to leaf oils, with mainly quantitative differences. However considerable seasonal variation was observed. Significant levels of monoterpenes were found only in autumn. The content of oxygenated sesquiterpenes was highest in samples of spring (October) and decreased in summer (January and February), reaching the lowest level in autumn (April) and increasing again in winter (July). In trunk bark oils the main constituents were: spathulenol, alpha-eudesmol, linalool, trans-beta-guaiene and caryophyllene oxide. The major component in all samples of trunk bark was spathulenol. Its level was highest in October (46.8%), decreased in January (33.3%), remained stable in April and July (18.0%) and increased again in February of next year (27.7%). Levels of alpha-eudesmol were high in spring (13.0%) and autumn (11.5%). Linalool peaked only in April, while trans-beta-guaiane peaked in July (11.1%). Caryophyllene oxide ranged between 10.7-2.0%. The level was highest in January, decreased regularly until July and increased slightly again in October. In leaf oils the main components were: spathulenol, germacrene B, germacrene D, caryophyllene oxide and viridiflorol. Spathulenol was the major component in sample of spring (34.4%), but decreased gradually until winter, when reached the lowest level (9.4%). Caryophyllene oxide showed a similar pattern, varying from 14.1% (spring) to 2.4% (winter). An inverse effect was observed for viridiflorol, which increased from 0.1% in October to 13.7% in July. Important levels of alpha-eudesmol were observed in October (12.3%) and February (9.5%). The percentage of germacrene D was highest in summer, while germacrene B showed high amounts in autumn and winter. The seasonal changes in oil composition of T. ovata can be associated with cycle of life of plant (flowering, fruiting and vegetative stages) and climatic parameters such as intense raining in the spring and summer.
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               Factor Part Location NP Content
 
Trunk Bark: (Harvesting time: April)
Trunk bark Brazil
NP Content: 2.4 %
 
Trunk Bark: (Harvesting time: July)
Trunk bark Brazil
NP Content: 0.1 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [11]
              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: Adana, Turkey)
Flowers Adana, Turkey
NP Content: 0.1 %
      Species Name: Thymus carnosus
  Factor Name: Month Variation; Developmental Stage Variation [12]
              Species Info Factor Info
               Experiment Detail
The aerial parts of samples from collective populations of T. carnosus were collected during the vegetative phase (February 2000), at the beginning of the flowering phase (May 2000) and during the flowering phase (July 2000) at Quinta do Lago (Algarve). AQLM: collected in May, beginning of flowering phase; AQLJ: collected in July, flowering stage; AQLF: collected in Feb, vegetative stage.
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               Factor Function
All the oil samples collected in Quinta do Lago (QL) were dominated by borneol (26-31%) and camphene (9-18%), but the third main component varied according to the harvesting period. Bornyl acetate was the third main component (9-13%) in the flower oil and in the aerial parts oils collected in May and July, whereas terpinen-4-ol (8%) was the third main component in oil collected in February from vegetative phase plant material. A fourth main component, alpha-pinene (4-9%), was also present in relative high amounts in the QL oils.
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               Factor Part Location NP Content
 
Harvesting time: Feb, vegetative stage
Aerial parts Quinta do Lago, Portugal
NP Content: 0.1 %
 
Harvesting time: May, beginning of flowering satge
Aerial parts Quinta do Lago, Portugal
NP Content: 0.3 %
 
Harvesting time: July, flowering stage
Aerial parts Quinta do Lago, Portugal
NP Content: 0.2 %
 
Harvesting time: July, flowering stage
Flowers Quinta do Lago, Portugal
NP Content: 0.3 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [13]
              Species Info Factor Info
               Experiment Detail
Aerial parts of the plant were collected from four localities: A = Kirklareli: Karadere in May 1991; B = Kirklareli: Karahamza Village in May 1990; C = Kirklareli: Evciler Village on 13 June 1993; D = Kirklareli: Korukoy on 25 May 1994
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               Factor Function
The four oils obtained from plants collected in different localities of the same region gave quite different compositions as follows: A: thymol (10.5%), 1,8-cineole (9.96%), p-cymene (9.48%), carvacrol (5.28%); B: beta-caryophyllene (29.50%), carvacrol(20.59%); C: thymol (34.7%), beta-caryophyllene (12.74%), carvacrol (5.24%); D: beta-caryophyllene (56.48%), germacrene D (11.12%), carvacrol (4.85%). Since the identities of the plant materials were checked repeatedly, any misidentification is ruled out. Except for A and C, all the other materials showed beta-caryophyllene as the major constituent. Carvacrol (20.59%) was present in good amount in the oil of B. In A, however, high percentages of 1,8-cineole (10%) and p-cymene (9.5%) were significant. This oil contained only a trace amount of beta-caryophyllene. Four isomeric caryophyllene alcohols were detected in the oil B. The results clearly indicate that the oil of T. striatus var. interruptus has no consistency and we can safely suggest that there are at least three chemotypes, namely thymol/1,8-cineole/p-cymene-type; thymol/beta-caryophyllene-type; and beta-caryophyllene-type, of this species.
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               Factor Part Location NP Content
 
Locality: Karadere, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.1 %
References
1 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
2 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
3 Volatile Constituents of Ichthyothere terminalis and I. cunabi
4 Chemical Composition and Seasonal Variations of Spike Lavender Oil from Southern Spain
5 Composition of the Essential Oil of Micromeria biflora
6 Comparative Study of the Essential Oils from Rosmarinus eriocalyx Jordan & Fourr. from Algeria and R. officinalis L. from Other Countries
7 Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain
8 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
9 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
10 Chemical Composition, Seasonal Variation and Evaluation of Antimicrobial Activity of Essential Oils of Talauma ovata A. St. Hil. (Magnoliaceae)
11 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
12 Thymus carnosus Boiss.: Effect of Harvesting Period, Collection Site and Type of Plant Material on Essential Oil Composition
13 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey