Sanggenone C | CAS#80651-76-9 | prenylated flavonoid

MedKoo Cat#: 461771 | Name: Sanggenone C

Description:

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

Sanggenone C is a natural prenylated flavonoid that inhibits tumor cellular proteasomal activity and cell viability.

Chemical Structure

Sanggenone C

CAS#80651-76-9

Theoretical Analysis

MedKoo Cat#: 461771

Name: Sanggenone C

CAS#: 80651-76-9

Chemical Formula: C40H36O12

Exact Mass: 708.2207

Molecular Weight: 708.71

Elemental Analysis: C, 67.79; H, 5.12; O, 27.09

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

Sanggenone C; Sanggenon C;

IUPAC/Chemical Name

2-((1S,2R,3S)-2-(2,4-dihydroxybenzoyl)-2',4'-dihydroxy-5-methyl-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-yl)-1,3,8,10a-tetrahydroxy-5a-(3-methylbut-2-en-1-yl)-5a,10a-dihydro-11H-benzofuro[3,2-b]chromen-11-one

InChi Key

XETHJOZXBVWLLM-QAHMVTMMSA-N

InChi Code

InChI=1S/C40H36O12/c1-18(2)10-11-39-27-9-6-22(43)16-31(27)52-40(39,50)38(49)35-32(51-39)17-30(46)34(37(35)48)26-13-19(3)12-25(23-7-4-20(41)14-28(23)44)33(26)36(47)24-8-5-21(42)15-29(24)45/h4-10,13-17,25-26,33,41-46,48,50H,11-12H2,1-3H3/t25-,26+,33-,39?,40?/m1/s1

SMILES Code

O=C1C(OC2=CC(O)=CC=C23)(O)C3(C/C=C(C)\C)OC4=C1C(O)=C([C@@H]5[C@H](C(C6=CC=C(O)C=C6O)=O)[C@@H](C7=CC=C(O)C=C7O)CC(C)=C5)C(O)=C4

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 708.71 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.

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: Huang H, Liu N, Zhao K, Zhu C, Lu X, Li S, Lian W, Zhou P, Dong X, Zhao C, Guo H, Zhang C, Yang C, Wen G, Lu L, Li X, Guan L, Liu C, Wang X, Dou QP, Liu J. Sanggenon C decreases tumor cell viability associated with proteasome inhibition. Front Biosci (Elite Ed). 2011 Jun 1;3:1315-25. PubMed PMID: 21622138; PubMed Central PMCID: PMC3303154. 2: Dat NT, Binh PT, Quynh le TP, Huong HT, Minh CV. Sanggenon C and O inhibit NO production, iNOS expression and NF-κB activation in LPS-induced RAW264.7 cells. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):84-8. doi: 10.3109/08923973.2011.580755. Epub 2011 May 26. PubMed PMID: 21612567. 3: Qi C, Xiong Y, Eschenbrenner-Lux V, Cong H, Porco JA Jr. Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O. J Am Chem Soc. 2016 Jan 27;138(3):798-801. doi: 10.1021/jacs.5b12778. Epub 2016 Jan 19. PubMed PMID: 26735066; PubMed Central PMCID: PMC4863937. 4: Baburajeev CP, Dhananjaya Mohan C, Ananda H, Rangappa S, Fuchs JE, Jagadish S, Sivaraman Siveen K, Chinnathambi A, Ali Alharbi S, Zayed ME, Zhang J, Li F, Sethi G, Girish KS, Bender A, Basappa, Rangappa KS. Development of Novel Triazolo-Thiadiazoles from Heterogeneous "Green" Catalysis as Protein Tyrosine Phosphatase 1B Inhibitors. Sci Rep. 2015 Sep 21;5:14195. doi: 10.1038/srep14195. PubMed PMID: 26388336; PubMed Central PMCID: PMC4585680. 5: Liu YJ, Li SY, Hou J, Liu YF, Wang DD, Jiang YS, Ge GB, Liang XM, Yang L. Identification and characterization of naturally occurring inhibitors against human carboxylesterase 2 in White Mulberry Root-bark. Fitoterapia. 2016 Dec;115:57-63. doi: 10.1016/j.fitote.2016.09.022. Epub 2016 Oct 1. PubMed PMID: 27702666. 6: Li LC, Shen F, Hou Q, Cheng GF. Inhibitory effect and mechanism of action of sanggenon C on human polymorphonuclear leukocyte adhesion to human synovial cells. Acta Pharmacol Sin. 2002 Feb;23(2):138-42. PubMed PMID: 11866874. 7: Kim HJ, Baburin I, Zaugg J, Ebrahimi SN, Hering S, Hamburger M. HPLC-based activity profiling--discovery of sanggenons as GABAA receptor modulators in the traditional Chinese drug Sang bai pi (Morus alba root bark). Planta Med. 2012 Mar;78(5):440-7. doi: 10.1055/s-0031-1298229. Epub 2012 Jan 31. PubMed PMID: 22294264. 8: Zhang QJ, Ni G, Wang YH, Chen RY, Yu DQ. Three new Diels-Alder type adducts from the stem bark of Morus cathayana. J Asian Nat Prod Res. 2009;11(3):267-73. doi: 10.1080/10286020902767690. PubMed PMID: 19408152. 9: Xiao L, Gu Y, Gao L, Shangguan J, Chen Y, Zhang Y, Li L. Sanggenon C protects against pressure overload induced cardiac hypertrophy via the calcineurin/NFAT2 pathway. Mol Med Rep. 2017 Oct;16(4):5338-5346. doi: 10.3892/mmr.2017.7288. Epub 2017 Aug 18. PubMed PMID: 28849031; PubMed Central PMCID: PMC5647066. 10: Dai SJ, Lu ZM, Chen RY, Yu DQ. [Structure and spectral characteristics of Diels-Alder type adducts from Morus]. Yao Xue Xue Bao. 2005 Oct;40(10):876-81. Review. Chinese. PubMed PMID: 16408801. 11: Hou XD, Ge GB, Weng ZM, Dai ZR, Leng YH, Ding LL, Jin LL, Yu Y, Cao YF, Hou J. Natural constituents from Cortex Mori Radicis as new pancreatic lipase inhibitors. Bioorg Chem. 2018 Jul 17;80:577-584. doi: 10.1016/j.bioorg.2018.07.011. [Epub ahead of print] PubMed PMID: 30032067. 12: Chen LD, Liu ZH, Zhang LF, Yao JN, Wang CF. Sanggenon C induces apoptosis of colon cancer cells via inhibition of NO production, iNOS expression and ROS activation of the mitochondrial pathway. Oncol Rep. 2017 Oct;38(4):2123-2131. doi: 10.3892/or.2017.5912. Epub 2017 Aug 22. PubMed PMID: 28849234; PubMed Central PMCID: PMC5652955. 13: Gu Y, Gao L, Chen Y, Xu Z, Yu K, Zhang D, Zhang G, Zhang X. Sanggenon C protects against cardiomyocyte hypoxia injury by increasing autophagy. Mol Med Rep. 2017 Dec;16(6):8130-8136. doi: 10.3892/mmr.2017.7646. Epub 2017 Sep 27. PubMed PMID: 28983604; PubMed Central PMCID: PMC5779897.