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MedKoo Cat#: 592853 | Name: Ampelopsin C

Description:

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

Ampelopsin C protects endothelial cells from hyperglycemia-induced oxidative damage by inducing autophagy via the AMPK signaling pathway.

Chemical Structure

Ampelopsin C
Ampelopsin C
CAS#130518-20-6

Theoretical Analysis

MedKoo Cat#: 592853

Name: Ampelopsin C

CAS#: 130518-20-6

Chemical Formula: C42H32O9

Exact Mass: 680.2046

Molecular Weight: 680.71

Elemental Analysis: C, 74.11; H, 4.74; O, 21.15

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
Ampelopsin C
IUPAC/Chemical Name
Benz(5,6)azuleno(7,8,1-cde)benzofuran-2,6,8-triol, 4-(3,5-dihydroxyphenyl)-3,4,4a,5,9b,10-hexahydro-3,5,10-tris(4-hydroxyphenyl)-,(3alpha,4bbeta,4abeta,5alpha,9balpha,10alpha)-(+)-
InChi Key
QDEHKEFWCRAFDN-WTEBWGKASA-N
InChi Code
InChI=1S/C42H32O9/c43-23-7-1-19(2-8-23)33-35(22-13-26(46)15-27(47)14-22)40-34(20-3-9-24(44)10-4-20)36-29(16-28(48)17-30(36)49)37-39-32(18-31(50)38(33)41(39)40)51-42(37)21-5-11-25(45)12-6-21/h1-18,33-35,37,40,42-50H/t33-,34-,35-,37-,40+,42+/m1/s1
SMILES Code
OC1=C([C@H](C2=CC=C(O)C=C2)[C@@H](C3=CC(O)=CC(O)=C3)[C@]4([H])[C@H](C5=CC=C(O)C=C5)C6=C(O)C=C(O)C=C67)C4=C8[C@]7([H])[C@H](C9=CC=C(O)C=C9)OC8=C1
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 680.71 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
1: Chen XM, Xie XB, Zhao Q, Wang F, Bai Y, Yin JQ, Jiang H, Xie XL, Jia Q, Huang G. Ampelopsin induces apoptosis by regulating multiple c-Myc/S-phase kinase-associated protein 2/F-box and WD repeat-containing protein 7/histone deacetylase 2 pathways in human lung adenocarcinoma cells. Mol Med Rep. 2015 Jan;11(1):105-12. doi: 10.3892/mmr.2014.2733. Epub 2014 Oct 21. PubMed PMID: 25333250; PubMed Central PMCID: PMC4237074. 2: Liang X, Zhang T, Shi L, Kang C, Wan J, Zhou Y, Zhu J, Mi M. Ampelopsin protects endothelial cells from hyperglycemia-induced oxidative damage by inducing autophagy via the AMPK signaling pathway. Biofactors. 2015 Nov-Dec;41(6):463-75. doi: 10.1002/biof.1248. Epub 2015 Dec 8. PubMed PMID: 26644014. 3: Qi S, Kou X, Lv J, Qi Z, Yan L. Ampelopsin induces apoptosis in HepG2 human hepatoma cell line through extrinsic and intrinsic pathways: Involvement of P38 and ERK. Environ Toxicol Pharmacol. 2015 Nov;40(3):847-54. doi: 10.1016/j.etap.2015.09.015. Epub 2015 Sep 30. PubMed PMID: 26476886. 4: Kou X, Shen K, An Y, Qi S, Dai WX, Yin Z. Ampelopsin inhibits H₂O₂-induced apoptosis by ERK and Akt signaling pathways and up-regulation of heme oxygenase-1. Phytother Res. 2012 Jul;26(7):988-94. doi: 10.1002/ptr.3671. Epub 2011 Dec 6. PubMed PMID: 22144097. 5: Qi S, Xin Y, Guo Y, Diao Y, Kou X, Luo L, Yin Z. Ampelopsin reduces endotoxic inflammation via repressing ROS-mediated activation of PI3K/Akt/NF-κB signaling pathways. Int Immunopharmacol. 2012 Jan;12(1):278-87. doi: 10.1016/j.intimp.2011.12.001. Epub 2011 Dec 20. PubMed PMID: 22193240. 6: Zhang B, Dong S, Cen X, Wang X, Liu X, Zhang H, Zhao X, Wu Y. Ampelopsin sodium exhibits antitumor effects against bladder carcinoma in orthotopic xenograft models. Anticancer Drugs. 2012 Jul;23(6):590-6. doi: 10.1097/CAD.0b013e32835019f9. PubMed PMID: 22241170. 7: Guerrero RF, Cantos-Villar E, Puertas B, Richard T. Daily Preharvest UV-C Light Maintains the High Stilbenoid Concentration in Grapes. J Agric Food Chem. 2016 Jun 29;64(25):5139-47. doi: 10.1021/acs.jafc.6b01276. Epub 2016 Jun 16. PubMed PMID: 27268503. 8: Zhou J, Zeng P, Tu HH, Wang FQ. Development and application of high-performance liquid chromatography for the study of ampelopsin pharmacokinetics in rat plasma using cloud-point extraction. J Sep Sci. 2011 Jan;34(2):160-8. doi: 10.1002/jssc.201000382. Epub 2010 Dec 20. PubMed PMID: 21246721. 9: Chang H, Peng X, Bai Q, Zhou Y, Yu X, Zhang Q, Zhu J, Mi M. Ampelopsin suppresses breast carcinogenesis by inhibiting the mTOR signalling pathway. Carcinogenesis. 2014 Aug;35(8):1847-54. doi: 10.1093/carcin/bgu118. Epub 2014 May 26. PubMed PMID: 24861637. 10: Zeng S, Liu D, Ye Y, Wang L, Wang W. [Anti-tumor effects of ampelopsin on human lung cancer GLC-82 implanted in nude mice]. Zhong Yao Cai. 2004 Nov;27(11):842-5. Chinese. PubMed PMID: 15810594. 11: Zhou Y, Liang X, Chang H, Shu F, Wu Y, Zhang T, Fu Y, Zhang Q, Zhu JD, Mi M. Ampelopsin-induced autophagy protects breast cancer cells from apoptosis through Akt-mTOR pathway via endoplasmic reticulum stress. Cancer Sci. 2014 Oct;105(10):1279-87. doi: 10.1111/cas.12494. Epub 2014 Sep 18. PubMed PMID: 25088800; PubMed Central PMCID: PMC4462353. 12: Liu DY, Ye JT, Yang WH, Yan J, Zeng CH, Zeng S. Ampelopsin, a small molecule inhibitor of HIV-1 infection targeting HIV entry. Biomed Environ Sci. 2004 Jun;17(2):153-64. PubMed PMID: 15386941. 13: Zhou Y, Wu Y, Qin Y, Liu L, Wan J, Zou L, Zhang Q, Zhu J, Mi M. Ampelopsin Improves Insulin Resistance by Activating PPARγ and Subsequently Up-Regulating FGF21-AMPK Signaling Pathway. PLoS One. 2016 Jul 8;11(7):e0159191. doi: 10.1371/journal.pone.0159191. eCollection 2016. PubMed PMID: 27391974; PubMed Central PMCID: PMC4938387. 14: Lee S, Yoon KD, Lee M, Cho Y, Choi G, Jang H, Kim B, Jung DH, Oh JG, Kim GW, Oh JW, Jeong YJ, Kwon HJ, Bae SK, Min DH, Windisch MP, Heo TH, Lee C. Identification of a resveratrol tetramer as a potent inhibitor of hepatitis C virus helicase. Br J Pharmacol. 2016 Jan;173(1):191-211. doi: 10.1111/bph.13358. Epub 2015 Nov 25. PubMed PMID: 26445091; PubMed Central PMCID: PMC4813382. 15: Pawlus AD, Sahli R, Bisson J, Rivière C, Delaunay JC, Richard T, Gomès E, Bordenave L, Waffo-Téguo P, Mérillon JM. Stilbenoid profiles of canes from Vitis and Muscadinia species. J Agric Food Chem. 2013 Jan 23;61(3):501-11. doi: 10.1021/jf303843z. Epub 2013 Jan 11. PubMed PMID: 23270496. 16: Ahmat N, Wibowo A, Mohamad SA, Low AL, Sufian AS, Yusof MI, Latip J. A new symmetrical tetramer oligostilbenoid containing tetrahydrofuran ring from the stem bark of Dryobalanops lanceolata. J Asian Nat Prod Res. 2014;16(11):1099-107. doi: 10.1080/10286020.2014.938059. Epub 2014 Jul 18. PubMed PMID: 25034352. 17: Hu J, Lin T, Xu J, Ding R, Wang G, Shen R, Zhang YW, Chen H. Polyphenols isolated from leaves of Vitis thunbergii var. taiwaniana regulate APP related pathway. Bioorg Med Chem Lett. 2016 Jan 15;26(2):505-511. doi: 10.1016/j.bmcl.2015.11.085. Epub 2015 Nov 24. PubMed PMID: 26675439. 18: Lin YS, Lu YL, Wang GJ, Chen LG, Wen CL, Hou WC. Ethanolic extracts and isolated compounds from small-leaf grape (Vitis thunbergii var. taiwaniana) with antihypertensive activities. J Agric Food Chem. 2012 Aug 1;60(30):7435-41. doi: 10.1021/jf302445x. Epub 2012 Jul 17. PubMed PMID: 22762395. 19: Huang YL, Liu YW, Huang YJ, Chiou WF. A Special Ingredient (VtR) Containing Oligostilbenes Isolated from Vitis thunbergii Prevents Bone Loss in Ovariectomized Mice: In Vitro and In Vivo Study. Evid Based Complement Alternat Med. 2013;2013:409421. doi: 10.1155/2013/409421. Epub 2013 Apr 11. PubMed PMID: 23662133; PubMed Central PMCID: PMC3638587. 20: Papastamoulis Y, Richard T, Nassra M, Badoc A, Krisa S, Harakat D, Monti JP, Mérillon JM, Waffo-Teguo P. Viniphenol A, a complex resveratrol hexamer from Vitis vinifera stalks: structural elucidation and protective effects against amyloid-β-induced toxicity in PC12 cells. J Nat Prod. 2014 Feb 28;77(2):213-7. doi: 10.1021/np4005294. Epub 2014 Feb 12. PubMed PMID: 24521157.