Cynandione A | CAS#168706-29-4

MedKoo Cat#: 333093 | Name: Cynandione A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cynandione A is an acetophenone isolated from Cynanchum Wilfordii Radix. Cynandione A inhibit inflammation through macrophageal α7 nAChR activation and subsequent IL-10 expression. Cynandione A inhibits hepatic de novo lipogenesis by activating the LKB1/AMPK pathway in HepG2 cells. Cynandione A inhibits lipopolysaccharide-induced cell adhesion via suppression of the protein expression of VCAM‑1 in human endothelial cells. Cynandione A attenuates lipopolysaccharide-induced production of inflammatory mediators via MAPK inhibition and NF-κB inactivation in RAW264.7 macrophages and protects mice against endotoxin shock.

Chemical Structure

Cynandione A

CAS#168706-29-4

Theoretical Analysis

MedKoo Cat#: 333093

Name: Cynandione A

CAS#: 168706-29-4

Chemical Formula: C16H14O6

Exact Mass: 302.0790

Molecular Weight: 302.28

Elemental Analysis: C, 63.58; H, 4.67; O, 31.76

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Cynandione A;

IUPAC/Chemical Name

1,1'-(2',3,6,6'-Tetrahydroxy-[1,1'-biphenyl]-2,3'-diyl)diethanone

InChi Key

DYQDHRLBSZIKEM-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H14O6/c1-7(17)9-3-4-12(21)15(16(9)22)14-11(20)6-5-10(19)13(14)8(2)18/h3-6,19-22H,1-2H3

SMILES Code

OC1=C(C2=C(O)C=CC(O)=C2C(C)=O)C(O)=C(C(C)=O)C=C1

Appearance

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 302.28 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.

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

1: Wang L, Cai F, Zhao W, Tian J, Kong D, Sun X, Liu Q, Chen Y, An Y, Wang F, Liu X, Wu Y, Zhou H. Cynanchum auriculatum Royle ex Wight., Cynanchum bungei Decne. and Cynanchum wilfordii (Maxim.) Hemsl.: Current Research and Prospects. Molecules. 2021 Nov 23;26(23):7065. doi: 10.3390/molecules26237065. PMID: 34885647; PMCID: PMC8658831. 2: Sawamoto A, Kanazaki A, Nakanishi M, Amakura Y, Yoshimura M, Uchiyama N, Hakamatsuka T, Okuyama S, Nakajima M. Cynandione A causes a dynamic change in SIRT1 nuclear trafficking via PKA signaling and beige adipocyte differentiation in 3T3-L1 cells. Eur J Pharmacol. 2021 Oct 15;909:174382. doi: 10.1016/j.ejphar.2021.174382. Epub 2021 Jul 28. PMID: 34329615. 3: Han QQ, Deng MY, Liu H, Ali U, Li XY, Wang YX. Cynandione A and PHA-543613 inhibit inflammation and stimulate macrophageal IL-10 expression following α7 nAChR activation. Biochem Pharmacol. 2021 Aug;190:114600. doi: 10.1016/j.bcp.2021.114600. Epub 2021 May 13. PMID: 33992630. 4: Han QQ, Yin M, Wang ZY, Liu H, Ao JP, Wang YX. Cynandione A Alleviates Neuropathic Pain Through α7-nAChR-Dependent IL-10/β-Endorphin Signaling Complexes. Front Pharmacol. 2021 Jan 27;11:614450. doi: 10.3389/fphar.2020.614450. PMID: 33584292; PMCID: PMC7873367. 5: Kim S, Yoon YY, Park YW, Whang WK, Park SY, Hwang KW. Cynandione A from Cynanchum wilfordii inhibits hepatic de novo lipogenesis by activating the LKB1/AMPK pathway in HepG2 cells. J Nat Med. 2020 Jan;74(1):142-152. doi: 10.1007/s11418-019-01356-x. Epub 2019 Aug 28. PMID: 31463669. 6: Chen WH, Zhang ZZ, Ban YF, Rahman K, Ye BZ, Sun XL, Tan HY, Zheng XH, Liu HY, Xu LC, Yan B, Han T. Cynanchum bungei Decne and its two related species for "Baishouwu": A review on traditional uses, phytochemistry, and pharmacological activities. J Ethnopharmacol. 2019 Oct 28;243:112110. doi: 10.1016/j.jep.2019.112110. Epub 2019 Jul 24. PMID: 31351190. 7: Sheng L, Yang Y, Zhang Y, Li N. Chemical constituents of Patrinia heterophylla Bunge and selective cytotoxicity against six human tumor cells. J Ethnopharmacol. 2019 May 23;236:129-135. doi: 10.1016/j.jep.2019.03.005. Epub 2019 Mar 7. PMID: 30853646. 8: Uchikura T, Tanaka H, Sugiwaki H, Yoshimura M, Sato-Masumoto N, Tsujimoto T, Uchiyama N, Hakamatsuka T, Amakura Y. Preliminary Quality Evaluation and Characterization of Phenolic Constituents in Cynanchi Wilfordii Radix. Molecules. 2018 Mar 14;23(3):656. doi: 10.3390/molecules23030656. PMID: 29538318; PMCID: PMC6017071. 9: Jiang HW, Gu SS, Cao L, Jiang SS, Lin J, Chen Y, Wang L, Jiao H, Li JY, Zhao WM, Li JL. Potential hypoglycemic effect of acetophenones from the root bark of Cynanchum wilfordii. Nat Prod Res. 2019 Aug;33(16):2314-2321. doi: 10.1080/14786419.2018.1443100. Epub 2018 Feb 25. PMID: 29480065. 10: Park KH, Kim J, Lee EH, Lee TH. Cynandione A inhibits lipopolysaccharide- induced cell adhesion via suppression of the protein expression of VCAM‑1 in human endothelial cells. Int J Mol Med. 2018 Mar;41(3):1756-1764. doi: 10.3892/ijmm.2018.3376. Epub 2018 Jan 10. PMID: 29328438. 11: Huang Q, Mao XF, Wu HY, Liu H, Sun ML, Wang X, Wang YX. Cynandione A attenuates neuropathic pain through p38β MAPK-mediated spinal microglial expression of β-endorphin. Brain Behav Immun. 2017 May;62:64-77. doi: 10.1016/j.bbi.2017.02.005. Epub 2017 Feb 9. PMID: 28189715. 12: Fang H, Yue R, Ga Y, Zhang Y, Shan L, Zhao J. Analysis of Cynandione A's Anti-Ischemic Stroke Effects from Pathways and Protein-Protein Interactome. PLoS One. 2015 May 8;10(5):e0124632. doi: 10.1371/journal.pone.0124632. PMID: 25955557; PMCID: PMC4425521. 13: Koo HJ, Sohn EH, Pyo S, Woo HG, Park DW, Ham YM, Jang SA, Park SY, Kang SC. An ethanol root extract of Cynanchum wilfordii containing acetophenones suppresses the expression of VCAM-1 and ICAM-1 in TNF-α-stimulated human aortic smooth muscle cells through the NF-κB pathway. Int J Mol Med. 2015 Apr;35(4):915-24. doi: 10.3892/ijmm.2015.2112. Epub 2015 Feb 26. PMID: 25716870; PMCID: PMC4356471. 14: Kim SH, Lee TH, Lee SM, Park JH, Park KH, Jung M, Jung H, Mohamed MA, Baek NI, Chung IS, Kim J. Cynandione A attenuates lipopolysaccharide-induced production of inflammatory mediators via MAPK inhibition and NF-κB inactivation in RAW264.7 macrophages and protects mice against endotoxin shock. Exp Biol Med (Maywood). 2015 Jul;240(7):946-54. doi: 10.1177/1535370214558022. Epub 2014 Oct 30. PMID: 25361770; PMCID: PMC4935409. 15: Yang SB, Lee SM, Park JH, Lee TH, Baek NI, Park HJ, Lee H, Kim J. Cynandione A from Cynanchum wilfordii attenuates the production of inflammatory mediators in LPS-induced BV-2 microglial cells via NF-κB inactivation. Biol Pharm Bull. 2014;37(8):1390-6. doi: 10.1248/bpb.b13-00939. PMID: 25087960. 16: Yue R, Yuan X, Liu X, Zhang J, Jiang P, He C, Shan L, Yu Y, Zhang W. Cynandione A mitigates ischemic injuries in rats with cerebral ischemia. J Neurochem. 2012 May;121(3):451-64. doi: 10.1111/j.1471-4159.2012.07682.x. Epub 2012 Mar 14. PMID: 22309483. 17: Jiang Y, Choi HG, Li Y, Park YM, Lee JH, Kim DH, Lee JH, Son JK, Na M, Lee SH. Chemical constituents of Cynanchum wilfordii and the chemotaxonomy of two species of the family Asclepiadacease, C. wilfordii and C. auriculatum. Arch Pharm Res. 2011 Dec;34(12):2021-7. doi: 10.1007/s12272-011-1203-z. Epub 2011 Dec 31. PMID: 22210026. 18: Zhang X, Shan L, Huang H, Yang X, Liang X, Xing A, Huang H, Liu X, Su J, Zhang W. Rapid identification of acetophenones in two Cynanchum species using liquid chromatography-electrospray ionization tandem mass spectrometry. J Pharm Biomed Anal. 2009 Apr 5;49(3):715-25. doi: 10.1016/j.jpba.2009.01.009. Epub 2009 Jan 19. PMID: 19201126. 19: Zhang Y, Shan L, Xu W, Yang M, Zhang W, Li H. LC-MS/MS method for the determination of cynandione A in rat plasma and tissues. Biomed Chromatogr. 2008 Oct;22(10):1173-9. doi: 10.1002/bmc.1044. PMID: 18651611. 20: Lee MK, Yeo H, Kim J, Kim YC. Protection of rat hepatocytes exposed to CCl4 in-vitro by cynandione A, a biacetophenone from Cynanchum wilfordii. J Pharm Pharmacol. 2000 Mar;52(3):341-5. doi: 10.1211/0022357001773896. PMID: 10757424.