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MedKoo Cat#: 592854 | Name: Ampelopsin A

Description:

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

Ampelopsin reduces the migration and invasion of ovarian cancer cells via inhibition of epithelial-to-mesenchymal transition.

Chemical Structure

Ampelopsin A
Ampelopsin A
CAS#130608-11-6

Theoretical Analysis

MedKoo Cat#: 592854

Name: Ampelopsin A

CAS#: 130608-11-6

Chemical Formula: C28H22O7

Exact Mass: 470.1366

Molecular Weight: 470.48

Elemental Analysis: C, 71.48; H, 4.71; O, 23.80

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 #
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Synonym
Ampelopsin A
IUPAC/Chemical Name
Benzo(6,7)cyclohepta(1,2,3-cd)benzofuran-4,6,8,10-tetrol, 1,6,7,11b-tetrahydro-1,7-bis(4-hydroxyphenyl)-, (1alpha,6beta,7alpha,11balpha)-(+)-
InChi Key
LHUHHURKGTUZHU-QWMXJGQVSA-N
InChi Code
InChI=1S/C28H22O7/c29-15-5-1-13(2-6-15)23-24-19(9-17(31)11-21(24)33)26-25-20(27(23)34)10-18(32)12-22(25)35-28(26)14-3-7-16(30)8-4-14/h1-12,23,26-34H/t23-,26-,27-,28+/m0/s1
SMILES Code
Oc1c2c([C@@H]3[C@@H](c4ccc(O)cc4)Oc5cc(O)cc([C@H](O)[C@H]2c6ccc(O)cc6)c35)cc(O)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 470.48 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: Liu T, Liu P, Ding F, Yu N, Li S, Wang S, Zhang X, Sun X, Chen Y, Wang F, Zhao Y, Li B. Ampelopsin reduces the migration and invasion of ovarian cancer cells via inhibition of epithelial-to-mesenchymal transition. Oncol Rep. 2015 Feb;33(2):861-7. doi: 10.3892/or.2014.3672. Epub 2014 Dec 12. PubMed PMID: 25502786. 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: 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. 4: Lv H, Zhou W, Wang X, Wang Z, Suo Y, Wang H. Extraction and Separation of Vitisin D, Ampelopsin B and cis-Vitisin A from Iris lactea Pall. var. chinensis (Fisch.) Koidz by Alkaline Extraction-Acid Precipitation and High-Speed Counter-Current Chromatography. J Chromatogr Sci. 2016 May-Jun;54(5):744-51. doi: 10.1093/chromsci/bmv249. Epub 2016 Feb 3. PubMed PMID: 26847919; PubMed Central PMCID: PMC4890446. 5: 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. 6: 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. 7: Woo HJ, Kang HK, Nguyen TT, Kim GE, Kim YM, Park JS, Kim D, Cha J, Moon YH, Nam SH, Xia YM, Kimura A, Kim D. Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: glucosylation enhancing physicochemical properties. Enzyme Microb Technol. 2012 Dec 10;51(6-7):311-8. doi: 10.1016/j.enzmictec.2012.07.014. Epub 2012 Jul 31. PubMed PMID: 23040385. 8: Cai T, Cai Y. cis-Ampelopsin E, a stilbene isolated from the seeds of Paeonia suffruticosa, inhibits lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages via blockade of nuclear factor-kappa B signaling pathway. Biol Pharm Bull. 2011;34(9):1501-7. PubMed PMID: 21881241. 9: Zhou Y, Shu F, Liang X, Chang H, Shi L, Peng X, Zhu J, Mi M. Ampelopsin induces cell growth inhibition and apoptosis in breast cancer cells through ROS generation and endoplasmic reticulum stress pathway. PLoS One. 2014 Feb 13;9(2):e89021. doi: 10.1371/journal.pone.0089021. eCollection 2014. PubMed PMID: 24551210; PubMed Central PMCID: PMC3923868. 10: Wang Y, Fu L, Wang L, Xu L, Yang B. [Electrophysiological study on the antiarrhythmic mechanism of ampelopsin in rats]. Zhonghua Xin Xue Guan Bing Za Zhi. 2014 Aug;42(8):675-9. Chinese. PubMed PMID: 25388342. 11: Ni F, Gong Y, Li L, Abdolmaleky HM, Zhou JR. Flavonoid ampelopsin inhibits the growth and metastasis of prostate cancer in vitro and in mice. PLoS One. 2012;7(6):e38802. doi: 10.1371/journal.pone.0038802. Epub 2012 Jun 5. PubMed PMID: 22693649; PubMed Central PMCID: PMC3367907. 12: Lu M, Huang W, Bao N, Zhou G, Zhao J. The flavonoid ampelopsin inhibited cell growth and induced apoptosis and G0/G1 arrest in human osteosarcoma MG-63 cells in vitro. Pharmazie. 2015 Jun;70(6):388-93. PubMed PMID: 26189300. 13: Liu C, Zhao P, Yang Y, Xu X, Wang L, Li B. Ampelopsin suppresses TNF-α-induced migration and invasion of U2OS osteosarcoma cells. Mol Med Rep. 2016 Jun;13(6):4729-36. doi: 10.3892/mmr.2016.5124. Epub 2016 Apr 13. PubMed PMID: 27082056. 14: 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. 15: 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. 16: Solanki SS, Sarkar B, Dhanwani RK. Microemulsion drug delivery system: for bioavailability enhancement of ampelopsin. ISRN Pharm. 2012;2012:108164. doi: 10.5402/2012/108164. Epub 2012 Jul 8. PubMed PMID: 22830055; PubMed Central PMCID: PMC3399350. 17: 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. 18: Huang RJ, Yan XL, Chen HB. [Preparation and in vitro evaluation of ampelopsin-loaded nanomicelles]. Zhongguo Zhong Yao Za Zhi. 2016 Mar;41(6):1054-1058. doi: 10.4268/cjcmm20160613. Chinese. PubMed PMID: 28875669. 19: 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. 20: Rahman NA, Yazan LS, Wibowo A, Ahmat N, Foo JB, Tor YS, Yeap SK, Razali ZA, Ong YS, Fakurazi S. Induction of apoptosis and G2/M arrest by ampelopsin E from Dryobalanops towards triple negative breast cancer cells, MDA-MB-231. BMC Complement Altern Med. 2016 Sep 8;16:354. doi: 10.1186/s12906-016-1328-1. PubMed PMID: 27609190; PubMed Central PMCID: PMC5017001. H