α-Cyperone
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MedKoo CAT#: 464937

CAS#: 473-08-5

Description: α-Cyperone is a sesquiterpenoid that has been found in C. rotundus rhizomes and has diverse biological activities. It inhibits LPS-induced nuclear translocation of the NF-κB subunit p65, as well as LPS-induced production of prostaglandin E2 (PGE2) and IL-6, in RAW 264.7 cells. α-Cyperone (15 and 30 µM) reduces hydrogen peroxide-induced production of reactive oxygen species (ROS) and apoptosis in SH-SY5Y cells. It reduces the production of the hepatitis B surface antigen (HBsAG) in infected HepG2 2.2.15 cells (IC50 = 274.7 µM).

Chemical Structure

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α-Cyperone
CAS# 473-08-5
Instruction

Theoretical Analysis

MedKoo Cat#: 464937
Name: α-Cyperone
CAS#: 473-08-5
Chemical Formula: C15H22O
Exact Mass: 218.17
Molecular Weight: 218.340
Elemental Analysis: C, 82.52; H, 10.16; O, 7.33

Price and Availability

Size Price Availability Quantity
10mg USD 280 2 Weeks
25mg USD 490 2 Weeks
50mg USD 820 2 Weeks
100mg USD 1340 2 Weeks
Bulk inquiry

Synonym: α-Cyperone; α Cyperone; (+)-α-Cyperone; (+)-α Cyperone; (+) α-Cyperone; (+) α Cyperone;

IUPAC/Chemical Name: (4aS,7R)-1,4a-dimethyl-7-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one

InChi Key: KUFXJZXMWHNCEH-DOMZBBRYSA-N

InChi Code: InChI=1S/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3/t12-,15+/m1/s1

SMILES Code: C[C@]12C(C[C@H](C(C)=C)CC1)=C(C)C(CC2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 137.40
DMSO 30.0 137.40
Ethanol 30.0 137.40

Preparing Stock Solutions

The following data is based on the product molecular weight 218.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zhang H, Li S, Lu J, Jin J, Zhu G, Wang L, Yan Y, He L, Wang B, Wang X, Yu H. α-Cyperone (CYP) down-regulates NF-κB and MAPKs signaling, attenuating inflammation and extracellular matrix degradation in chondrocytes, to ameliorate osteoarthritis in mice. Aging (Albany NY). 2021 Jul 8;13(undefined). doi: 10.18632/aging.203259. Epub ahead of print. PMID: 34237707.

2: Qin ZM, Li YH, Tan YF, Li HL. Determination of nootkatone in rat plasma by LC-MS/MS and its application in a pharmacokinetic study. Biomed Chromatogr. 2021 Jun 23:e5197. doi: 10.1002/bmc.5197. Epub ahead of print. PMID: 34162012.

3: Horn C, Vediyappan G. Anticapsular and Antifungal Activity of α-Cyperone. Antibiotics (Basel). 2021 Jan 6;10(1):51. doi: 10.3390/antibiotics10010051. PMID: 33419126; PMCID: PMC7825567.

4: Xia B, Tong Y, Xia C, Chen C, Shan X. α-Cyperone Confers Antidepressant-Like Effects in Mice via Neuroplasticity Enhancement by SIRT3/ROS Mediated NLRP3 Inflammasome Deactivation. Front Pharmacol. 2020 Oct 8;11:577062. doi: 10.3389/fphar.2020.577062. PMID: 33132912; PMCID: PMC7579414.

5: Gao P, Ding N, Lv J, Ramzan MN, Wen Q. α-Cyperone inhibitory effects on tumor-derived DNA trigger microglia by STING pathway. J Ethnopharmacol. 2021 Jan 10;264:113246. doi: 10.1016/j.jep.2020.113246. Epub 2020 Aug 8. PMID: 32781257.

6: Pei XD, Yao HL, Shen LQ, Yang Y, Lu L, Xiao JS, Wang XY, He ZL, Jiang LH. α-Cyperone inhibits the proliferation of human cervical cancer HeLa cells via ROS-mediated PI3K/Akt/mTOR signaling pathway. Eur J Pharmacol. 2020 Sep 15;883:173355. doi: 10.1016/j.ejphar.2020.173355. Epub 2020 Jul 17. PMID: 32687921.

7: Huang B, Liu J, Fu S, Zhang Y, Li Y, He D, Ran X, Yan X, Du J, Meng T, Gao X, Liu D. α-Cyperone Attenuates H2O2-Induced Oxidative Stress and Apoptosis in SH-SY5Y Cells via Activation of Nrf2. Front Pharmacol. 2020 Apr 8;11:281. doi: 10.3389/fphar.2020.00281. PMID: 32322198; PMCID: PMC7156596.

8: Brillatz T, Jacmin M, Queiroz EF, Marcourt L, Slacanin I, Petit C, Carrupt PA, Bum EN, Herrling P, Crawford AD, Wolfender JL. Zebrafish bioassay-guided isolation of antiseizure compounds from the Cameroonian medicinal plant Cyperus articulatus L. Phytomedicine. 2020 Jan 23;70:153175. doi: 10.1016/j.phymed.2020.153175. Epub ahead of print. PMID: 32302934.

9: Muria-Gonzalez MJ, Yeng Y, Breen S, Mead O, Wang C, Chooi YH, Barrow RA, Solomon PS. Volatile Molecules Secreted by the Wheat Pathogen Parastagonospora nodorum Are Involved in Development and Phytotoxicity. Front Microbiol. 2020 Mar 25;11:466. doi: 10.3389/fmicb.2020.00466. PMID: 32269554; PMCID: PMC7111460.

10: Liu X, Jin X, Yu D, Liu G. Suppression of NLRP3 and NF-κB signaling pathways by α-Cyperone via activating SIRT1 contributes to attenuation of LPS-induced acute lung injury in mice. Int Immunopharmacol. 2019 Nov;76:105886. doi: 10.1016/j.intimp.2019.105886. Epub 2019 Sep 11. PMID: 31520990.

11: Guo L, Gong M, Wu S, Qiu F, Ma L. Identification and quantification of the quality markers and anti-migraine active components in Chuanxiong Rhizoma and Cyperi Rhizoma herbal pair based on chemometric analysis between chemical constituents and pharmacological effects. J Ethnopharmacol. 2020 Jan 10;246:112228. doi: 10.1016/j.jep.2019.112228. Epub 2019 Sep 9. PMID: 31513838.

12: Wu S, Guo L, Qiu F, Gong M. Anti-Migraine Effect of the Herbal Combination of Chuanxiong Rhizoma and Cyperi Rhizoma and UPLC-MS/MS Method for the Simultaneous Quantification of the Active Constituents in Rat Serum and Cerebral Cortex. Molecules. 2019 Jun 14;24(12):2230. doi: 10.3390/molecules24122230. PMID: 31207980; PMCID: PMC6630925.

13: Park YJ, Zheng H, Kwak JH, Chung KH. Sesquiterpenes from Cyperus rotundus and 4α,5α-oxidoeudesm-11-en-3-one as a potential selective estrogen receptor modulator. Biomed Pharmacother. 2019 Jan;109:1313-1318. doi: 10.1016/j.biopha.2018.10.186. Epub 2018 Nov 9. PMID: 30551381.

14: Attiq A, Jalil J, Husain K, Ahmad W. Raging the War Against Inflammation With Natural Products. Front Pharmacol. 2018 Sep 7;9:976. doi: 10.3389/fphar.2018.00976. PMID: 30245627; PMCID: PMC6137277.

15: Liu P, Shang EX, Zhu Y, Qian DW, Duan JA. Volatile component interaction effects on compatibility of Cyperi Rhizoma and Angelicae Sinensis Radix or Chuanxiong Rhizoma by UPLC-MS/MS and response surface analysis. J Pharm Biomed Anal. 2018 Oct 25;160:135-143. doi: 10.1016/j.jpba.2018.07.060. Epub 2018 Jul 31. PMID: 30086506.

16: Huang B , He D , Chen G , Ran X , Guo W , Kan X , Wang W , Liu D , Fu S , Liu J . α-Cyperone inhibits LPS-induced inflammation in BV-2 cells through activation of Akt/Nrf2/HO-1 and suppression of the NF-κB pathway. Food Funct. 2018 May 23;9(5):2735-2743. doi: 10.1039/c8fo00057c. PMID: 29667667.

17: Ma Y, Zhao Y, Zhang R, Liang X, Yin Z, Geng Y, Shu G, Song X, Zou Y, Li L, Yin L, Yue G, Li Y, Ye G, He C. α-Cyperone Inhibits PMA-Induced EPCR Shedding through PKC Pathway. Biol Pharm Bull. 2017 Oct 1;40(10):1678-1685. doi: 10.1248/bpb.b17-00183. Epub 2017 Aug 11. PMID: 28804104.

18: Hu QP, Cao XM, Hao DL, Zhang LL. Chemical Composition, Antioxidant, DNA Damage Protective, Cytotoxic and Antibacterial Activities of Cyperus rotundus Rhizomes Essential Oil against Foodborne Pathogens. Sci Rep. 2017 Mar 24;7:45231. doi: 10.1038/srep45231. PMID: 28338066; PMCID: PMC5364420.

19: Zhang HY, Gao Y, Lai PX. Chemical Composition, Antioxidant, Antimicrobial and Cytotoxic Activities of Essential Oil from Premna microphylla Turczaninow. Molecules. 2017 Feb 28;22(3):381. doi: 10.3390/molecules22030381. PMID: 28264507; PMCID: PMC6155397.

20: Azimi A, Ghaffari SM, Riazi GH, Arab SS, Tavakol MM, Pooyan S. α-Cyperone of Cyperus rotundus is an effective candidate for reduction of inflammation by destabilization of microtubule fibers in brain. J Ethnopharmacol. 2016 Dec 24;194:219-227. doi: 10.1016/j.jep.2016.06.058. Epub 2016 Jun 25. PMID: 27353867.