Guaijaverin | CAS#22255-13-6 | Antioxidant phenol

MedKoo Cat#: 463170 | Name: Guaijaverin

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Description:

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

Quercetin 3-O-α-L-arabinopyranoside (Guaijaverin) is a phenol that has been found in Byrsonima crassa and has antioxidant activity. It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals in a cell-free assay. Quercetin 3-O-α-L-arabinopyranoside inhibits H. pylori-induced oxidative burst of isolated rat polymorphonuclear (PMN) neutrophils. It reduces N-retinylidene-N-retinylethanolamine- and blue light-induced death of ARPE-19 retinal epithelial cells in a concentration-dependent manner. In vivo, quercetin 3-O-α-L-arabinopyranoside prevents blue light-induced retinal degeneration in a mouse model of macular degeneration.

Chemical Structure

Guaijaverin

CAS#22255-13-6

Theoretical Analysis

MedKoo Cat#: 463170

Name: Guaijaverin

CAS#: 22255-13-6

Chemical Formula: C20H18O11

Exact Mass: 434.0849

Molecular Weight: 434.35

Elemental Analysis: C, 55.31; H, 4.18; O, 40.52

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 850.00	2 Weeks
250g	USD 1,650.00	2 Weeks

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Synonym

Guaijaverin; Guajavarin; Guajaverin; Quercetin 3-O-α-L-arabinopyranoside;

IUPAC/Chemical Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key

PZZRDJXEMZMZFD-IEGSVRCHSA-N

InChi Code

InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20-/m0/s1

SMILES Code

OC1=C2C(OC(C3=CC=C(C(O)=C3)O)=C(C2=O)O[C@H]4[C@@H]([C@H]([C@H](CO4)O)O)O)=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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Guaijaverin is a urease inhibitor with an IC50 of 120 μM.

In vitro activity:

Quercetin and two quercetin glycosides, avicularin and guaijaverin, were isolated from Psidium guajava as urease inhibitors with respective IC(50) values of 80 microM-, 140 microM-, and 120 microM-. Reference: Biosci Biotechnol Biochem. 2010;74(4):878-80. https://pubmed.ncbi.nlm.nih.gov/20378972/

In vivo activity:

As shown in Fig. 1, the purified compound, guaijaverin demonstrated anti-Strep. mutans activity, with MIC values of 4 and 2 mg ml−1 for MTCC 1943 and CLSM 001 strain of Strep. mutans, respectively. Reference: J Appl Microbiol. 2006 Aug;101(2):487-95. https://pubmed.ncbi.nlm.nih.gov/16882158/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	230.23

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 434.35 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

Formulation protocol:

1. Shabana S, Kawai A, Kai K, Akiyama K, Hayashi H. Inhibitory activity against urease of quercetin glycosides isolated from Allium cepa and Psidium guajava. Biosci Biotechnol Biochem. 2010;74(4):878-80. doi: 10.1271/bbb.90895. Epub 2010 Apr 7. PMID: 20378972. 2. Prabu GR, Gnanamani A, Sadulla S. Guaijaverin -- a plant flavonoid as potential antiplaque agent against Streptococcus mutans. J Appl Microbiol. 2006 Aug;101(2):487-95. doi: 10.1111/j.1365-2672.2006.02912.x. PMID: 16882158.

In vitro protocol:

In vivo protocol:

1. Prabu GR, Gnanamani A, Sadulla S. Guaijaverin -- a plant flavonoid as potential antiplaque agent against Streptococcus mutans. J Appl Microbiol. 2006 Aug;101(2):487-95. doi: 10.1111/j.1365-2672.2006.02912.x. PMID: 16882158.

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PMID: 30371987. 4: Özbilgin S, Acıkara ÖB, Akkol EK, Süntar I, Keleş H, İşcan GS. In vivo wound- healing activity of Euphorbia characias subsp. wulfenii: Isolation and quantification of quercetin glycosides as bioactive compounds. J Ethnopharmacol. 2018 Oct 5;224:400-408. doi: 10.1016/j.jep.2018.06.015. Epub 2018 Jun 18. PMID: 29920357. 5: Booker A, Agapouda A, Frommenwiler DA, Scotti F, Reich E, Heinrich M. St John's wort (Hypericum perforatum) products - an assessment of their authenticity and quality. Phytomedicine. 2018 Feb 1;40:158-164. doi: 10.1016/j.phymed.2017.12.012. Epub 2017 Dec 28. PMID: 29496168. 6: Liu YL, Lin LC, Tung YT, Ho ST, Chen YL, Lin CC, Wu JH. Rhododendron oldhamii leaf extract improves fatty liver syndrome by increasing lipid oxidation and decreasing the lipogenesis pathway in mice. Int J Med Sci. 2017 Jul 19;14(9):862-870. doi: 10.7150/ijms.19553. 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Zhongguo Zhong Yao Za Zhi. 2015 Dec;40(24):4868-72. Chinese. PMID: 27245036. 11: Houël E, Nardella F, Jullian V, Valentin A, Vonthron-Sénécheau C, Villa P, Obrecht A, Kaiser M, Bourreau E, Odonne G, Fleury M, Bourdy G, Eparvier V, Deharo E, Stien D. Wayanin and guaijaverin, two active metabolites found in a Psidium acutangulum Mart. ex DC (syn. P. persoonii McVaugh) (Myrtaceae) antimalarial decoction from the Wayana Amerindians. J Ethnopharmacol. 2016 Jul 1;187:241-8. doi: 10.1016/j.jep.2016.04.053. Epub 2016 Apr 28. PMID: 27132714. 12: Giovannini P, Howes MJ, Edwards SE. Medicinal plants used in the traditional management of diabetes and its sequelae in Central America: A review. J Ethnopharmacol. 2016 May 26;184:58-71. doi: 10.1016/j.jep.2016.02.034. Epub 2016 Feb 27. PMID: 26924564. 13: Tung YT, Lin LC, Liu YL, Ho ST, Lin CY, Chuang HL, Chiu CC, Huang CC, Wu JH. Antioxidative phytochemicals from Rhododendron oldhamii Maxim. leaf extracts reduce serum uric acid levels in potassium oxonate-induced hyperuricemic mice. BMC Complement Altern Med. 2015 Dec 1;15:423. doi: 10.1186/s12906-015-0950-7. PMID: 26627882; PMCID: PMC4665888. 14: Araki Y, Koshiishi I. Simultaneous evaluation of one-electron reducing systems and radical reactions in cells by nitroxyl biradical as probe. Biomed Chromatogr. 2016 Jul;30(7):1131-1137. doi: 10.1002/bmc.3661. Epub 2015 Dec 22. PMID: 26613564. 15: Li Z, Meng F, Zhang Y, Sun L, Yu L, Zhang Z, Peng S, Guo J. Simultaneous quantification of hyperin, reynoutrin and guaijaverin in mice plasma by LC- MS/MS: application to a pharmacokinetic study. Biomed Chromatogr. 2016 Jul;30(7):1124-1130. doi: 10.1002/bmc.3660. Epub 2016 Jan 3. PMID: 26588877. 16: Kim MH, Kim JN, Han SN, Kim HK. Ursolic acid isolated from guava leaves inhibits inflammatory mediators and reactive oxygen species in LPS-stimulated macrophages. Immunopharmacol Immunotoxicol. 2015 Jun;37(3):228-35. doi: 10.3109/08923973.2015.1021355. Epub 2015 Mar 10. PMID: 25753845. 17: Wang L, Yu MM, Chi YQ, Ouyang WB, Zang Z, Zhao Y. [Chemical constituents of Euphorbia dracunculoides]. Zhongguo Zhong Yao Za Zhi. 2014 Oct;39(20):3969-73. Chinese. PMID: 25751948. 18: Ukwueze SE, Osadebe PO, Okoye FB. A new antibacterial benzophenone glycoside from Psidium guajava (Linn.) leaves. Nat Prod Res. 2015;29(18):1728-34. doi: 10.1080/14786419.2014.1003188. Epub 2015 Jan 29. PMID: 25631395. 19: Samy MN, Sugimoto S, Matsunami K, Otsuka H, Kamel MS. Taxiphyllin 6'-O-gallate, actinidioionoside 6'-O-gallate and myricetrin 2″-O-sulfate from the leaves of Syzygium samarangense and their biological activities. Chem Pharm Bull (Tokyo). 2014;62(10):1013-8. doi: 10.1248/cpb.c14-00352. Erratum in: Chem Pharm Bull (Tokyo). 2014;62(11):1151. Mamdouh, Nabil Samy [corrected to Samy, Mamdouh Nabil]. PMID: 25273060. 20: Ravi K, Divyashree P. Psidium guajava: A review on its potential as an adjunct in treating periodontal disease. Pharmacogn Rev. 2014 Jul;8(16):96-100. doi: 10.4103/0973-7847.134233. PMID: 25125881; PMCID: PMC4127827.