Sanguiin H 6

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

MedKoo CAT#: 461772

CAS#: 82978-00-5

Description: Sanguiin H 6 is a dimeric ellagitannin isolated from Sanguisorba officinalis and is responsible for the antioxidant capacity of raspberries.


Chemical Structure

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Sanguiin H 6
CAS# 82978-00-5

Theoretical Analysis

MedKoo Cat#: 461772
Name: Sanguiin H 6
CAS#: 82978-00-5
Chemical Formula: C82H53O52
Exact Mass: 869.1503
Molecular Weight: 1870.27
Elemental Analysis: C, 52.66; H, 2.86; O, 44.48

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Sanguiin H 6; Sanguiin H-6;

IUPAC/Chemical Name: (E)-3-(5-(((17-(((1,2,3,15,16,17-hexahydroxy-10-(hydroxymethyl)-18-(l3-oxidanylidene)-5,13-dioxo-5,7,8,10,11,13-hexahydro-7,11-methanodibenzo[i,k][1,4,7]trioxacyclotridecin-8-yl)oxy)carbonyl)-1,2,3,15,20,21,22,23,31,32,33-undecahydroxy-5,12,25,29-tetraoxo-5,6a,7,12,25,27,27a,29-octahydrobenzo[k]benzo[5',6'][1,4]dioxino[2',3':4,5]benzo[1,2-m]dibenzo[6,7:8,9][1,4]dioxecino[2,3-f][1,4,9]trioxacyclopentadecin-7-yl)oxy)carbonyl)-2,3-dihydroxyphenoxy)-4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid

InChi Key: NBUYFBLGWAUSQK-OWOJBTEDSA-N

InChi Code: 1S/C82H54O52/c83-14-36-67-64(109)70(132-80(121)23-12-31(90)53(98)59(104)43(23)41-21(78(119)130-67)10-29(88)51(96)57(41)102)82(129-36)134-74(115)17-4-32(91)65-34(6-17)127-66-35(126-65)13-24-44(61(66)106)39-19(8-27(86)49(94)55(39)100)76(117)124-15-37-68(131-79(120)22-11-30(89)52(97)58(103)42(22)40-20(77(118)128-37)9-28(87)50(95)56(40)101)81(123-2-1-122-75(24)116)133-73(114)16-3-25(84)47(92)33(5-16)125-69-46(72(112)113)45(60(105)62(107)63(69)108)38-18(71(110)111)7-26(85)48(93)54(38)99/h1-13,36-37,64,67-68,70,81-109H,14-15H2,(H,110,111)(H,112,113)/b2-1+

SMILES Code: Oc1cc(C(OC2C3c(C(OC(c4c(c5c(O)c(O)c(O)cc5C(O3)=O)c(O)c(O)c(O)c4)=O)C(CO)O2)[oH])=O)cc6c1Oc7c(O6)c(O)c(c8c(O)c(O)c(O)cc8C(OCC9C(OC(c%10c(c%11c(O)c(O)c(O)cc%11C(O9)=O)c(O)c(O)c(O)c%10)=O)C(OC(c%12cc(Oc%13c(O)c(O)c(O)c(c%14c(O)c(O)c(O)cc%14C(O)=O)c%13C(O)=O)c(O)c(O)c%12)=O)O/C=C/OC%15=O)=O)c%15c7

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

Preparing Stock Solutions

The following data is based on the product molecular weight 1870.27 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

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1: Park EH, Park JY, Yoo HS, Yoo JE, Lee HL. Assessment of the anti-metastatic properties of sanguiin H-6 in HUVECs and MDA-MB-231 human breast cancer cells. Bioorg Med Chem Lett. 2016 Jul 15;26(14):3291-3294. doi: 10.1016/j.bmcl.2016.05.050. Epub 2016 May 18. PubMed PMID: 27237777.

2: Lee D, Ko H, Kim YJ, Kim SN, Choi KC, Yamabe N, Kim KH, Kang KS, Kim HY, Shibamoto T. Inhibition of A2780 Human Ovarian Carcinoma Cell Proliferation by a Rubus Component, Sanguiin H-6. J Agric Food Chem. 2016 Feb 3;64(4):801-5. doi: 10.1021/acs.jafc.5b05461. Epub 2016 Jan 19. PubMed PMID: 26725849.

3: Sakai E, Aoki Y, Yoshimatsu M, Nishishita K, Iwatake M, Fukuma Y, Okamoto K, Tanaka T, Tsukuba T. Sanguiin H-6, a constituent of Rubus parvifolius L., inhibits receptor activator of nuclear factor-κB ligand-induced osteoclastogenesis and bone resorption in vitro and prevents tumor necrosis factor-α-induced osteoclast formation in vivo. Phytomedicine. 2016 Jul 15;23(8):828-37. doi: 10.1016/j.phymed.2016.04.002. Epub 2016 Apr 23. PubMed PMID: 27288918.

4: Yokozawa T, Chen CP, Tanaka T, Kitani K. Effects of sanguiin H-6, a component of Sanguisorbae Radix, on lipopolysaccharide-stimulated nitric oxide production. Biochem Pharmacol. 2002 Mar 1;63(5):853-8. PubMed PMID: 11911836.

5: Bastow KF, Bori ID, Fukushima Y, Kashiwada Y, Tanaka T, Nonaka G, Nishioka I, Lee KH. Inhibition of DNA topoisomerases by sanguiin H-6, a cytotoxic dimeric ellagitannin from Sanguisorba officinalis. Planta Med. 1993 Jun;59(3):240-5. PubMed PMID: 8391144.

6: Yokozawa T, Chen CP, Rhyu DY, Tanaka T, Park JC, Kitani K. Potential of sanguiin H-6 against oxidative damage in renal mitochondria and apoptosis mediated by peroxynitrite in vivo. Nephron. 2002 Sep;92(1):133-41. PubMed PMID: 12187096.

7: Lee SJ, Lee HK. Sanguiin H-6 blocks endothelial cell growth through inhibition of VEGF binding to VEGF receptor. Arch Pharm Res. 2005 Nov;28(11):1270-4. PubMed PMID: 16350854.

8: Krauze-Baranowska M, Majdan M, Hałasa R, Głód D, Kula M, Fecka I, Orzeł A. The antimicrobial activity of fruits from some cultivar varieties of Rubus idaeus and Rubus occidentalis. Food Funct. 2014 Oct;5(10):2536-41. doi: 10.1039/c4fo00129j. Epub 2014 Aug 18. PubMed PMID: 25131001.

9: Park EJ, Lee D, Baek SE, Kim KH, Kang KS, Jang TS, Lee HL, Song JH, Yoo JE. Cytotoxic effect of sanguiin H-6 on MCF-7 and MDA-MB-231 human breast carcinoma cells. Bioorg Med Chem Lett. 2017 Sep 15;27(18):4389-4392. doi: 10.1016/j.bmcl.2017.08.019. Epub 2017 Aug 12. PubMed PMID: 28835347.

10: Krauze-Baranowska M, Głód D, Kula M, Majdan M, Hałasa R, Matkowski A, Kozłowska W, Kawiak A. Chemical composition and biological activity of Rubus idaeus shoots--a traditional herbal remedy of Eastern Europe. BMC Complement Altern Med. 2014 Dec 12;14:480. doi: 10.1186/1472-6882-14-480. PubMed PMID: 25496130; PubMed Central PMCID: PMC4295307.

11: Ko H, Jeon H, Lee D, Choi HK, Kang KS, Choi KC. Sanguiin H6 suppresses TGF-β induction of the epithelial-mesenchymal transition and inhibits migration and invasion in A549 lung cancer. Bioorg Med Chem Lett. 2015 Dec 1;25(23):5508-13. doi: 10.1016/j.bmcl.2015.10.067. Epub 2015 Oct 23. PubMed PMID: 26508552.

12: Mullen W, McGinn J, Lean ME, MacLean MR, Gardner P, Duthie GG, Yokota T, Crozier A. Ellagitannins, flavonoids, and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties. J Agric Food Chem. 2002 Aug 28;50(18):5191-6. PubMed PMID: 12188628.

13: Yokozawa T, Chen CP, Tanaka T, Kitani K. A study on the nitric oxide production-suppressing activity of sanguisorbae radix components. Biol Pharm Bull. 2000 Jun;23(6):717-22. PubMed PMID: 10864022.

14: Sójka M, Macierzyński J, Zaweracz W, Buczek M. Transfer and Mass Balance of Ellagitannins, Anthocyanins, Flavan-3-ols, and Flavonols during the Processing of Red Raspberries (Rubus idaeus L.) to Juice. J Agric Food Chem. 2016 Jul 13;64(27):5549-63. doi: 10.1021/acs.jafc.6b01590. Epub 2016 Jun 28. PubMed PMID: 27292440.

15: Jang E, Inn KS, Jang YP, Lee KT, Lee JH. Phytotherapeutic Activities of Sanguisorba officinalis and its Chemical Constituents: A Review. Am J Chin Med. 2018;46(2):299-318. doi: 10.1142/S0192415X18500155. Epub 2018 Feb 12. Review. PubMed PMID: 29433389.