Nootkatone

CAS# 4674-50-4

Nootkatone

Catalog No. BCN5517----Order now to get a substantial discount!

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Quality Control of Nootkatone

Number of papers citing our products

Chemical structure

Nootkatone

3D structure

Chemical Properties of Nootkatone

Cas No. 4674-50-4 SDF Download SDF
PubChem ID 20797 Appearance Oil
Formula C15H22O M.Wt 218.3
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility DMSO : ≥ 250 mg/mL (1145.06 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
SMILES CC1CC(=O)C=C2C1(CC(CC2)C(=C)C)C
Standard InChIKey WTOYNNBCKUYIKC-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Nootkatone

The rhizoma of Bupleurum longibrachiatum Turcz.

Biological Activity of Nootkatone

DescriptionNootkatone, a naturally occurring AMPK activator, can stimulate energy metabolism and prevents diet-induced obesity by activating AMPK. (+)-Nootkatone has antiallergic, anti-inflammatory, antiproliferative, and antiplatelet activities. Nootkatone is a strong repellent and toxicant to Formosan subterranean termites, the lowest effective concentration tested is 10 micrograms/g substrate. (+)-Nootkatone has potent inhibitory effect on collagen-, thrombin-, and AA-induced platelet aggregation, it also has a significant inhibitory effect on rat platelet aggregation ex vivo.
TargetsTNF-α | IFN-γ | NF-kB | p38MAPK | IkB | AMPK | Calcium Channel | Antifection | IKK
In vitro

Antiplatelet effects of Cyperus rotundus and its component (+)-nootkatone.[Pubmed: 21354294 ]

J Ethnopharmacol. 2011 Apr 26;135(1):48-54.

Cyperus rotundus, a well-known oriental traditional medicine, has been reported to exhibit wide spectrum activity in biological systems including the circulatory system, however, little information is available on its antiplatelet activity. This study was undertaken to investigate the antiplatelet effects of Cyperus rotundus EtOH extract (CRE) and its constituent compounds.
METHODS AND RESULTS:
The antiplatelet activities of CRE and its eight constituent compounds were evaluated by examining their effects on rat platelet aggregations in vitro and ex vivo, and on mice tail bleeding times. During the in vitro platelet aggregation study, CRE showed significant and concentration-dependent inhibitory effects on collagen-, thrombin-, and/or AA-induced platelet aggregation. Of its eight components, (+)-Nootkatone was found to have the most potent inhibitory effect on collagen-, thrombin-, and AA-induced platelet aggregation. In addition, CRE- and (+)-Nootkatone-treated mice exhibited significantly prolonged bleeding times. Furthermore, (+)-Nootkatone had a significant inhibitory effect on rat platelet aggregation ex vivo.
CONCLUSIONS:
This study demonstrates the antiplatelet effects of CRE and its active component (+)-Nootkatone, and suggests that these agents might be of therapeutic benefit for the prevention of platelet-associated cardiovascular diseases.

Ability of two natural products, nootkatone and carvacrol, to suppress Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in a Lyme disease endemic area of New Jersey.[Pubmed: 20069863]

J Econ Entomol. 2009 Dec;102(6):2316-24.

We evaluated the ability of the natural, plant-derived acaricides Nootkatone and carvacrol to suppress Ixodes scapularis Say and Amblyomma americanum (L.) (Acari: Ixodidae).
METHODS AND RESULTS:
Aqueous formulations of 1 and 5% Nootkatone applied by backpack sprayer to the forest litter layer completely suppressed I. scapularis nymphs through 2 d. Thereafter, the level of reduction gradually declined to < or =50% at 28 d postapplication. Against A. americanum nymphs, 1% Nootkatone was less effective, but at a 5% concentration, the level of control was similar or greater to that observed with I. scapularis through 21 d postapplication. Initial applications of 0.05% carvacrol were ineffective, but a 5% carvacrol formulation completely suppressed nymphs of both species through 2 d and resulted in significant reduction in I. scapularis and A. americanum nymphs through 28 and 14 d postapplication, respectively. Backpack sprayer applications of 5% Nootkatone to the shrub and litter layers resulted in 100% control of I. scapularis adults through 6 d, but the level of reduction declined to 71.5% at 28 d postapplication. By contrast, high-pressure applications of 2% Nootkatone to the litter layer resulted in 96.2-100% suppression of both I. scapularis and A. americanum nymphs through 42 d, whereas much lower control was obtained from the same formulation applied by backpack sprayer. Backpack sprayer application of a 3.1% Nootkatone nanoemulsion resulted in 97.5-98.9 and 99.3-100% reduction in I. scapularis and A. americanum nymphs, respectively, at 1 d postapplication. Between 7 d and 35 d postapplication, the level of control varied between 57.1% and 92.5% for I. scapularis and between 78.5 and 97.1% for A. americanum nymphs.
CONCLUSIONS:
The ability of natural products to quickly suppress and maintain significant control of populations of these medically important ticks at relatively low concentrations may represent a future alternative to the use of conventional synthetic acaricides.

Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus).[Pubmed: 11441443]

J Chem Ecol. 2001 Mar;27(3):523-31.

We examined the behavior of Formosan subterranean termites toward one of the components of vetiver grass oil, the roots of which manufacture insect repellents.
METHODS AND RESULTS:
We found Nootkatone, a sesquiterpene ketone, isolated from vetiver oil is a strong repellent and toxicant to Formosan subterranean termites. The lowest effective concentration tested was 10 micrograms/g substrate.
CONCLUSIONS:
This is the first report of Nootkatone being a repellent to insects.

In vivo

Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK.[Pubmed: 20501876 ]

Am J Physiol Endocrinol Metab. 2010 Aug;299(2):E266-75.

AMP-activated protein kinase (AMPK) is a serine/threonine kinase that is implicated in the control of energy metabolism and is considered to be a molecular target for the suppression of obesity and the treatment of metabolic syndrome.
METHODS AND RESULTS:
Here, we identified and characterized Nootkatone, a constituent of grapefruit, as a naturally occurring AMPK activator. Nootkatone induced an increase in AMPKalpha1 and -alpha2 activity along with an increase in the AMP/ATP ratio and an increase the phosphorylation of AMPKalpha and the downstream target acetyl-CoA carboxylase (ACC), in C(2)C(12) cells. Nootkatone-induced activation of AMPK was possibly mediated both by LKB1 and Ca(2+)/calmodulin-dependent protein kinase kinase. Nootkatone also upregulated PPARgamma coactivator-1alpha in C(2)C(12) cells and C57BL/6J mouse muscle. In addition, administration of Nootkatone (200 mg/kg body wt) significantly enhanced AMPK activity, accompanied by LKB1, AMPK, and ACC phosphorylation in the liver and muscle of mice. Whole body energy expenditure evaluated by indirect calorimetry was also increased by Nootkatone administration. Long-term intake of diets containing 0.1% to 0.3% (wt/wt) Nootkatone significantly reduced high-fat and high-sucrose diet-induced body weight gain, abdominal fat accumulation, and the development of hyperglycemia, hyperinsulinemia, and hyperleptinemia in C57BL/6J mice. Furthermore, endurance capacity, evaluated as swimming time to exhaustion in BALB/c mice, was 21% longer in mice fed 0.2% Nootkatone than in control mice.
CONCLUSIONS:
These findings indicate that long-term intake of Nootkatone is beneficial toward preventing obesity and improving physical performance and that these effects are due, at least in part, to enhanced energy metabolism through AMPK activation in skeletal muscle and liver.

Protocol of Nootkatone

Cell Research

(+)-Nootkatone inhibits tumor necrosis factor α/interferon γ-induced production of chemokines in HaCaT cells.[Pubmed: 24704449]

Biochem Biophys Res Commun. 2014 May 2;447(2):278-84.

Chemokines are important mediators of cell migration, and thymus and activation-regulated chemokine (TARC/CCL17) and macrophage-derived chemokine (MDC/CCL22) are well-known typical inflammatory chemokines involved in atopic dermatitis (AD). (+)-Nootkatone is the major component of Cyperus rotundus. (+)-Nootkatone has antiallergic, anti-inflammatory, and antiplatelet activities. The purpose of this study was to investigate the effect of (+)-Nootkatone on tumor necrosis factor α (TNF-α)/interferon γ (IFN-γ)-induced expression of Th2 chemokines in HaCaT cells.
METHODS AND RESULTS:
We found that (+)-Nootkatone inhibited the TNF-α/IFN-γ-induced expression of TARC/CCL17 and MDC/CCL22 mRNA in HaCaT cells. It also significantly inhibited TNF-α/IFN-γ-induced activation of nuclear factor kappa B (NF-κB), p38 mitogen-activated protein kinase (MAPK), and protein kinase Cζ (PKCζ). Furthermore, we showed that PKCζ and p38 MAPK contributed to the inhibition of TNF-α/IFN-γ-induced TARC/CCL17 and MDC/CCL22 expression by blocking IκBα degradation in HaCaT cells.
CONCLUSIONS:
Taken together, these results suggest that (+)-Nootkatone may suppress TNF-α/IFN-γ-induced TARC/CCL17 and MDC/CCL22 expression in HaCaT cells by inhibiting of PKCζ and p38 MAPK signaling pathways that lead to activation of NF-κB. We propose that (+)-Nootkatone may be a useful therapeutic candidate for inflammatory skin diseases such as AD.

Structure Identification
Bioorg Med Chem. 2011 Apr 1;19(7):2464-9.

Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites.[Pubmed: 21377882 ]


METHODS AND RESULTS:
Six metabolites were obtained as a result of microbial transformation of (+)-Nootkatone (1) by the fungal strains: Botrytis, Didymosphaeria, Aspergillus, Chaetomium and Fusarium. Their structure were established as (+)-(4R,5S,7R,9R)-9α-hydroxyNootkatone (2), (+)-(4R,5S,7R)-13-hydroxyNootkatone (3) and (+)-(4R,5S,7R,9R,11S)-11,12-epoxy-9α-hydroxyNootkatone (4), (+)-(4R,5S,7R,11S)-11,12-epoksyNootkatone (5), (+)-(4R,5S,7R)-11,12-dihydroxyNootkatone (6) and (+)-(4R,5S,7R)-7,11,12-trihydroxyNootkatone (7) on the basis of their spectral data. Two products: (4) and (7) were not previously reported in the literature.
CONCLUSIONS:
The antiproliferative activity of (+)-Nootkatone (1) and isolated metabolites (2-7) of its biotransformation has been evaluated.

Nootkatone Dilution Calculator

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Preparing Stock Solutions of Nootkatone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.5809 mL 22.9043 mL 45.8085 mL 91.617 mL 114.5213 mL
5 mM 0.9162 mL 4.5809 mL 9.1617 mL 18.3234 mL 22.9043 mL
10 mM 0.4581 mL 2.2904 mL 4.5809 mL 9.1617 mL 11.4521 mL
50 mM 0.0916 mL 0.4581 mL 0.9162 mL 1.8323 mL 2.2904 mL
100 mM 0.0458 mL 0.229 mL 0.4581 mL 0.9162 mL 1.1452 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Nootkatone

Antiplatelet effects of Cyperus rotundus and its component (+)-nootkatone.[Pubmed:21354294]

J Ethnopharmacol. 2011 Apr 26;135(1):48-54.

ETHNOPHARMACOLOGICAL RELEVANCE: Cyperus rotundus, a well-known oriental traditional medicine, has been reported to exhibit wide spectrum activity in biological systems including the circulatory system, however, little information is available on its antiplatelet activity. This study was undertaken to investigate the antiplatelet effects of Cyperus rotundus EtOH extract (CRE) and its constituent compounds. MATERIALS AND METHODS: The antiplatelet activities of CRE and its eight constituent compounds were evaluated by examining their effects on rat platelet aggregations in vitro and ex vivo, and on mice tail bleeding times. RESULTS: During the in vitro platelet aggregation study, CRE showed significant and concentration-dependent inhibitory effects on collagen-, thrombin-, and/or AA-induced platelet aggregation. Of its eight components, (+)-Nootkatone was found to have the most potent inhibitory effect on collagen-, thrombin-, and AA-induced platelet aggregation. In addition, CRE- and (+)-Nootkatone-treated mice exhibited significantly prolonged bleeding times. Furthermore, (+)-Nootkatone had a significant inhibitory effect on rat platelet aggregation ex vivo. CONCLUSIONS: This study demonstrates the antiplatelet effects of CRE and its active component (+)-Nootkatone, and suggests that these agents might be of therapeutic benefit for the prevention of platelet-associated cardiovascular diseases.

(+)-Nootkatone inhibits tumor necrosis factor alpha/interferon gamma-induced production of chemokines in HaCaT cells.[Pubmed:24704449]

Biochem Biophys Res Commun. 2014 May 2;447(2):278-84.

Chemokines are important mediators of cell migration, and thymus and activation-regulated chemokine (TARC/CCL17) and macrophage-derived chemokine (MDC/CCL22) are well-known typical inflammatory chemokines involved in atopic dermatitis (AD). (+)-Nootkatone is the major component of Cyperus rotundus. (+)-Nootkatone has antiallergic, anti-inflammatory, and antiplatelet activities. The purpose of this study was to investigate the effect of (+)-Nootkatone on tumor necrosis factor alpha (TNF-alpha)/interferon gamma (IFN-gamma)-induced expression of Th2 chemokines in HaCaT cells. We found that (+)-Nootkatone inhibited the TNF-alpha/IFN-gamma-induced expression of TARC/CCL17 and MDC/CCL22 mRNA in HaCaT cells. It also significantly inhibited TNF-alpha/IFN-gamma-induced activation of nuclear factor kappa B (NF-kappaB), p38 mitogen-activated protein kinase (MAPK), and protein kinase Czeta (PKCzeta). Furthermore, we showed that PKCzeta and p38 MAPK contributed to the inhibition of TNF-alpha/IFN-gamma-induced TARC/CCL17 and MDC/CCL22 expression by blocking IkappaBalpha degradation in HaCaT cells. Taken together, these results suggest that (+)-Nootkatone may suppress TNF-alpha/IFN-gamma-induced TARC/CCL17 and MDC/CCL22 expression in HaCaT cells by inhibiting of PKCzeta and p38 MAPK signaling pathways that lead to activation of NF-kappaB. We propose that (+)-Nootkatone may be a useful therapeutic candidate for inflammatory skin diseases such as AD.

Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus).[Pubmed:11441443]

J Chem Ecol. 2001 Mar;27(3):523-31.

We examined the behavior of Formosan subterranean termites toward one of the components of vetiver grass oil, the roots of which manufacture insect repellents. We found Nootkatone, a sesquiterpene ketone, isolated from vetiver oil is a strong repellent and toxicant to Formosan subterranean termites. The lowest effective concentration tested was 10 micrograms/g substrate. This is the first report of Nootkatone being a repellent to insects.

Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites.[Pubmed:21377882]

Bioorg Med Chem. 2011 Apr 1;19(7):2464-9.

Six metabolites were obtained as a result of microbial transformation of (+)-Nootkatone (1) by the fungal strains: Botrytis, Didymosphaeria, Aspergillus, Chaetomium and Fusarium. Their structure were established as (+)-(4R,5S,7R,9R)-9alpha-hydroxyNootkatone (2), (+)-(4R,5S,7R)-13-hydroxyNootkatone (3) and (+)-(4R,5S,7R,9R,11S)-11,12-epoxy-9alpha-hydroxyNootkatone (4), (+)-(4R,5S,7R,11S)-11,12-epoksyNootkatone (5), (+)-(4R,5S,7R)-11,12-dihydroxyNootkatone (6) and (+)-(4R,5S,7R)-7,11,12-trihydroxyNootkatone (7) on the basis of their spectral data. Two products: (4) and (7) were not previously reported in the literature. The antiproliferative activity of (+)-Nootkatone (1) and isolated metabolites (2-7) of its biotransformation has been evaluated.

Ability of two natural products, nootkatone and carvacrol, to suppress Ixodes scapularis and Amblyomma americanum (Acari: Ixodidae) in a Lyme disease endemic area of New Jersey.[Pubmed:20069863]

J Econ Entomol. 2009 Dec;102(6):2316-24.

We evaluated the ability of the natural, plant-derived acaricides Nootkatone and carvacrol to suppress Ixodes scapularis Say and Amblyomma americanum (L.) (Acari: Ixodidae). Aqueous formulations of 1 and 5% Nootkatone applied by backpack sprayer to the forest litter layer completely suppressed I. scapularis nymphs through 2 d. Thereafter, the level of reduction gradually declined to < or =50% at 28 d postapplication. Against A. americanum nymphs, 1% Nootkatone was less effective, but at a 5% concentration, the level of control was similar or greater to that observed with I. scapularis through 21 d postapplication. Initial applications of 0.05% carvacrol were ineffective, but a 5% carvacrol formulation completely suppressed nymphs of both species through 2 d and resulted in significant reduction in I. scapularis and A. americanum nymphs through 28 and 14 d postapplication, respectively. Backpack sprayer applications of 5% Nootkatone to the shrub and litter layers resulted in 100% control of I. scapularis adults through 6 d, but the level of reduction declined to 71.5% at 28 d postapplication. By contrast, high-pressure applications of 2% Nootkatone to the litter layer resulted in 96.2-100% suppression of both I. scapularis and A. americanum nymphs through 42 d, whereas much lower control was obtained from the same formulation applied by backpack sprayer. Backpack sprayer application of a 3.1% Nootkatone nanoemulsion resulted in 97.5-98.9 and 99.3-100% reduction in I. scapularis and A. americanum nymphs, respectively, at 1 d postapplication. Between 7 d and 35 d postapplication, the level of control varied between 57.1% and 92.5% for I. scapularis and between 78.5 and 97.1% for A. americanum nymphs. The ability of natural products to quickly suppress and maintain significant control of populations of these medically important ticks at relatively low concentrations may represent a future alternative to the use of conventional synthetic acaricides.

Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK.[Pubmed:20501876]

Am J Physiol Endocrinol Metab. 2010 Aug;299(2):E266-75.

AMP-activated protein kinase (AMPK) is a serine/threonine kinase that is implicated in the control of energy metabolism and is considered to be a molecular target for the suppression of obesity and the treatment of metabolic syndrome. Here, we identified and characterized Nootkatone, a constituent of grapefruit, as a naturally occurring AMPK activator. Nootkatone induced an increase in AMPKalpha1 and -alpha2 activity along with an increase in the AMP/ATP ratio and an increase the phosphorylation of AMPKalpha and the downstream target acetyl-CoA carboxylase (ACC), in C(2)C(12) cells. Nootkatone-induced activation of AMPK was possibly mediated both by LKB1 and Ca(2+)/calmodulin-dependent protein kinase kinase. Nootkatone also upregulated PPARgamma coactivator-1alpha in C(2)C(12) cells and C57BL/6J mouse muscle. In addition, administration of Nootkatone (200 mg/kg body wt) significantly enhanced AMPK activity, accompanied by LKB1, AMPK, and ACC phosphorylation in the liver and muscle of mice. Whole body energy expenditure evaluated by indirect calorimetry was also increased by Nootkatone administration. Long-term intake of diets containing 0.1% to 0.3% (wt/wt) Nootkatone significantly reduced high-fat and high-sucrose diet-induced body weight gain, abdominal fat accumulation, and the development of hyperglycemia, hyperinsulinemia, and hyperleptinemia in C57BL/6J mice. Furthermore, endurance capacity, evaluated as swimming time to exhaustion in BALB/c mice, was 21% longer in mice fed 0.2% Nootkatone than in control mice. These findings indicate that long-term intake of Nootkatone is beneficial toward preventing obesity and improving physical performance and that these effects are due, at least in part, to enhanced energy metabolism through AMPK activation in skeletal muscle and liver.

Description

Nootkatone, a neuroprotective agent from Alpiniae Oxyphyllae Fructus, has antioxidant and anti-inflammatory effects. Nootkatone improves cognitive impairment in lipopolysaccharide-induced mouse model of Alzheimer's disease.

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