General Information of Natural Product (ID: NP0289)
  Natural Product Name
Chrysanthenone
  Synonyms
Chrysanthenone; (+)-Chrysanthenone; 2-Pinen-7-one; 473-06-3; Bicyclo[3.1.1]hept-2-en-6-one, 2,7,7-trimethyl-; AC1L9CVQ; 38301-80-3; CHEBI:19; 2,7,7-Trimethylbicyclo[3.1.1]hept-2-en-6-one; CHEBI:3681; SCHEMBL2384039; DTXSID80894868; C09843; Q5114549; 2,7,7-Trimethylbicyclo[3.1.1]hept-2-en-6-one #
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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/c1-6-4-5-7-9(11)8(6)10(7,2)3/h4,7-8H,5H2,1-3H3
  InChI Key IECBDTGWSQNQID-UHFFFAOYSA-N
  Isomeric SMILES CC1=CCC2C(=O)C1C2(C)C
  Canonical SMILES CC1=CCC2C(=O)C1C2(C)C
  External Links PubChem ID 442463
CAS ID 473-06-3

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Achillea biebersteinii
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               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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               Factor Part Location NP Content
 
Aerial part: Vegetative satge
Aerial parts Tehran, Iran
NP Content: 0.6 %
 
Aerial part: Floral Budding satge
Aerial parts Tehran, Iran
NP Content: 0.4 %
 
flower: flowering stage
Flowers Tehran, Iran
NP Content: 1.7 %
 
leaf: Flowering stage
Leaves Tehran, Iran
NP Content: 3.6 %
 
Stem: flowering stage
Stems Tehran, Iran
NP Content: 2.6 %
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [2]
              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: 0.3 %
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: 0.3 %
      Species Name: Artemisia nilagirica var. Septentrionalis
  Factor Name: Altitude Variation [3]
              Species Info Factor Info
               Experiment Detail
Leaves from mature plants of Artemisia nilagirica var. septentrionalis, before flowering, were collected from different altitudes in Himachal Pradesh such as Shimla (2210 m), Mandi (1044 m) and Manali (2050 m) in June 2005.
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               Factor Function
The major constituents of the oil show variation with changes in altitude. At lower, middle and higher altitudes, the major constituents of the oil were caryophyllene oxide (28.6%), borneol (35.8%) and camphor (46.9%), respectively. The percentages of alpha-humulene and trans-beta-guaiene also increased, but the percentage of sabinene, trans-sabinene hydrate, 4-terpineol, caryophyllene oxide and humulene epoxide-II decreased with an increase in altitude. The characteristic compounds observed in the plants from lower altitudes were 2-hexene-1-ol, beta-thujone, thujanol, myrtenol and linalyl acetate, while the higher altitude plants were characterized by the presence of alpha-pinene, beta-pinene, limonene, linalool, gamma-gurijunene, germacrene-D and farnesol.
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               Factor Part Location NP Content
 
Locality: Mandi, Himachal Pradesh, India; Altitude 1044 m
Leaves Himachal Pradesh, India
NP Content: 0.9 %
 
Locality: Shimla, Himachal Pradesh, India; Altitude 2210 m
Leaves Himachal Pradesh, India
NP Content: 0.7 %
      Species Name: Blumea balsamifera (L.) DC.
  Factor Name: Month Variation; Developmental Stage Variation [4]
              Species Info Factor Info
               Experiment Detail
The experiments were performed in the experimental field of the Tropical Crops Genetic Resources Institute, Chinese Academy of Tropical Agricultural Sciences (Danzhou, Hainan, China; localization 19.52° N, 109.50° E; altitude 118 m; annual average precipitation 1815 mm; annual average temperature 23.5 ℃ ;the soil characteristics are : "Organic matter (g/kg) 11.37;pH 4.94;N (g/kg) 0.51;P (mg/kg) 25.33;K (mg/kg) 33.89). The experimental B. balsamifera plants were one-year old, and were propagated by the seeds collected from B. balsamifera planted in the experimental field of the Tropical Crops Genetic Resources Institute, Chinese Academy of Tropical Agricultural Sciences. They were planted with a planting spacing of 80 cm × 80 cm. On the 20th day of each month (from September 2014 to December 2014, which is the traditional harvest time), 30 one-year old B. balsamifera plants were randomly collected. Their young leaves (leaves on young shoots), mature leaves (leaves which are mature but without yellow spots), senescent leaves (leaves with yellow spots and those with dark brown leaf tips), dead leaves (leaves that have turned dark brown), young shoots (stems from buds to 10-20 cm part without woody parts), and young stems (green stems and not completely woody) were collected. These samples were divided into three parts (replicates), dried under shade, and ground to a fine powder (20-mesh sieve), packed in zip-lock bags, and stored in the refrigerator (4 ℃ ) for oil extraction.
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               Factor Function
Time of growth and type of B. balsamifera plant organs influence the production of oil, its composition, and antioxidant activity. The essential oil level in the young leaves was the highest, followed by mature leaves and senescent leaves, and the oil content was higher in October. A total of 44 compounds were identified. In the essential oils of leaves, the main ingredient is l-borneol, and the content was the highest in senescent leaves and in December. Variations in oil yields did not show the same pattern as the percentages of l-borneol in the essential oil. In the essential oils of young shoots and young stems, the main composition was dimethoxydurene. Therefore, the time of harvest and type of plant organs should be distinguished based on the different harvesting purposes. To extract the volatile oil, the aboveground parts except stems in October should be chosen for harvest. To get a high content of l-borneol in volatile oil, it is more appropriate to select the leaves in December. The antioxidant activity was evaluated using DPPH and BCB assays in this study, and the results proved that the essential oils of B. balsamifera showed a certain antioxidant activity, and the beta-carotene bleaching activity is far stronger than the DPPH radical-scavenging capacity. The young leaves and young shoots showed stronger antioxidant activity due to the high content of dimethoxydurene, beta-caryophyllene, and alpha-caryophyllene.
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               Factor Part Location NP Content
 
Young Leaves (mean value for four months)
Young leaves Danzhou, Hainan, China
NP Content: 0.39 %
 
Mature Leaves (mean value for four months)
Mature leaves Danzhou, Hainan, China
NP Content: 0.35 %
 
Senescent Leaves (mean value for four months)
Senescent Leaves Danzhou, Hainan, China
NP Content: 0.3 %
 
Dead Leaves (mean value for four months)
Dead Leaves Danzhou, Hainan, China
NP Content: 0.22 %
 
September (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.42 %
 
October (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.32 %
 
November (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.28 %
 
December (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.27 %
      Species Name: Rosmarinus officinalis
  Factor Name: Developmental Stage Variation [5]
              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: 0.5 %
 
Whole plant: Fruiting stage
Twigs Las Chozuelas, Southern Spain
NP Content: 0.3 %
 
Hibernation stage
Twigs Las Chozuelas, Southern Spain
NP Content: 0.4 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [6]
              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: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [7]
              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 %
 
Flower: (Locality: Sivas, Turkey)
Flowers Sivas, Turkey
NP Content: 0.1 %
 
Stem: (Locality: Sivas, Turkey)
Stems Sivas, Turkey
NP Content: 0.1 %
      Species Name: Tanacetum larvatum
  Factor Name: Altitude Variation [8]
              Species Info Factor Info
               Experiment Detail
Aerial parts of T. larvatum were collected in July 2002, during the period of full flowering from two locations in Montenegro: Mt. Komovi (Sample I) and Mt. Prokletije (Sample II), altitude ca. 1900 m.
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               Factor Function
About 40 compounds were identified, representing ~89% and 96% of the total oil content in the Samples I and II, respectively. trans-Sabinyl acetate was found to be the dominant component (51.2% and 69.7%). Among the rest of compounds beta-pinene (7.7% and 4.3%) and camphor (6.3% and 4.3%) were the most abundant in both samples.
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               Factor Part Location NP Content
 
Locality: Mt. Komovi, Montenegro, Serbia; Altitude 1900 m
Aerial parts Serbia
NP Content: <0.1 %
References
1 Essential oil content and composition of Achillea biebersteinii Afan. in different plant parts and phenological stages
2 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
3 Oil Constituents of Artemisia nilagirica var. septentrionalis Growing at Different Altitudes
4 Variations in Essential Oil Yield, Composition, and Antioxidant Activity of Different Plant Organs from Blumea balsamifera (L.) DC. at Different Growth Times
5 Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain
6 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
7 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
8 Chemical Composition of Tanacetum larvatum Essential Oil