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MedKoo Cat#: 578054 | Name: Negundoside

Description:

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

Negundoside is an irridiod glycoside from leaves of Vitex negundo. Negundoside protects human liver cells against calcium-mediated toxicity induced by carbon tetrachloride. Negundoside exerts a protective effect on CYP2E1-dependent CCl(4) toxicity via inhibition of lipid peroxidation, followed by an improved intracellular calcium homeostasis and inhibition of Ca(2+)-dependent proteases.

Chemical Structure

Negundoside
Negundoside
CAS#82451-20-5

Theoretical Analysis

MedKoo Cat#: 578054

Name: Negundoside

CAS#: 82451-20-5

Chemical Formula: C23H28O12

Exact Mass: 496.1581

Molecular Weight: 496.46

Elemental Analysis: C, 55.64; H, 5.68; O, 38.67

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
Negundoside
IUPAC/Chemical Name
Cyclopenta(C)pyran-4-carboxylic acid, 1,4a,5,6,7,7a-hexahydro-7-hydroxy-1-((2-O-(4-hydroxybenzoyl)-beta-D-glucopyranosyl)oxy)-7-methyl-, (1S,4aS,7S,7aS)-
InChi Key
RFCSGMIUBXUYSE-KLZCBZFCSA-N
InChi Code
InChI=1S/C23H28O12/c1-23(31)7-6-12-13(19(28)29)9-32-21(15(12)23)35-22-18(17(27)16(26)14(8-24)33-22)34-20(30)10-2-4-11(25)5-3-10/h2-5,9,12,14-18,21-22,24-27,31H,6-8H2,1H3,(H,28,29)/t12-,14-,15-,16-,17+,18-,21+,22+,23+/m1/s1
SMILES Code
C[C@]1(O)CC[C@H]2[C@@H]1[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)c4ccc(O)cc4)OC=C2C(=O)O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 496.46 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: Islam Z, Caldeira GI, Caniça M, Islam N, Silva O. Vitex Genus as a Source of Antimicrobial Agents. Plants (Basel). 2024 Jan 29;13(3):401. doi: 10.3390/plants13030401. PMID: 38337934; PMCID: PMC10857077. 2: Sp P, R ASK, Ks J. Insights from the molecular docking analysis of compounds from Vitex negundoi with targets from Klebsiella pneumoniai causing urinary tract infection. Bioinformation. 2022 Nov 30;18(11):1062-1068. doi: 10.6026/973206300181062. PMID: 37693077; PMCID: PMC10484700. 3: Kabilan SJ, Kunjiappan S, Sundar K, Pavadai P, Sathishkumar N, Velayuthaperumal H. Pharmacoinformatics-based screening of active compounds from Vitex negundo against lymphatic filariasis by targeting asparaginyl-tRNA synthetase. J Mol Model. 2023 Mar 6;29(4):87. doi: 10.1007/s00894-023-05488-6. PMID: 36872402. 4: Mehta K, Bhagwat DP, Devraj, Sehgal P, Mittal G, Suchal K. Vitex negundo protects against cerebral ischemia-reperfusion injury in mouse via attenuating behavioral deficits and oxidative damage. Psychopharmacology (Berl). 2022 Feb;239(2):573-587. doi: 10.1007/s00213-021-06050-z. Epub 2022 Jan 24. PMID: 35072759. 5: Meena AK, Rekha P, Perumal A, Ilavarasan R, Singh R, Srikant N, Dhiman KS. Identification and estimation of bioactive constituents Negundoside, Berberine chloride, and Marmelosin by HPLC and HPTLC for development of quality control protocols for Ayurvedic medicated oil formulation. Futur J Pharm Sci. 2021;7(1):171. doi: 10.1186/s43094-021-00322-3. Epub 2021 Aug 26. PMID: 34466412; PMCID: PMC8390083. 6: Sogame M, Naraki Y, Sasaki T, Seki M, Yokota K, Masada S, Hakamatsuka T. Quality Assessment of Medicinal Product and Dietary Supplements Containing Vitex agnus-castus by HPLC Fingerprint and Quantitative Analyses. Chem Pharm Bull (Tokyo). 2019;67(6):527-533. doi: 10.1248/cpb.c18-00725. PMID: 31155557. 7: Zhou ZL, Yin WQ, Yang YM, He CH, Li XN, Zhou CP, Guo H. New Iridoid Glycosides with Antidepressant Activity Isolated from Cyperus rotundus. Chem Pharm Bull (Tokyo). 2016;64(1):73-7. doi: 10.1248/cpb.c15-00686. PMID: 26726748. 8: Singh PP, Bhunia D, Verma YK, Sidiq T, Khajuria A, Guptha A, Pallavi MP, Vamshi SS, Qazi GN, Kumar HM. Synthesis of novel lipidated iridoid glycosides as vaccine adjuvants: 6-O-palmitoyl Agnuside elicit strong Th1 and Th2 response to ovalbumin in mice. Int Immunopharmacol. 2013 Nov;17(3):593-600. doi: 10.1016/j.intimp.2013.07.018. Epub 2013 Aug 14. PMID: 23954198. 9: Tiwari N, Luqman S, Masood N, Gupta MM. Validated high performance thin layer chromatographic method for simultaneous quantification of major iridoids in Vitex trifolia and their antioxidant studies. J Pharm Biomed Anal. 2012 Mar 5;61:207-14. doi: 10.1016/j.jpba.2011.12.007. Epub 2011 Dec 17. PMID: 22226914. 10: Sharma RL, Prabhakar A, Dhar KL, Sachar A. A new iridoid glycoside from Vitex negundo Linn (Verbenacea). Nat Prod Res. 2009;23(13):1201-9. doi: 10.1080/14786410802696494. PMID: 19731139. 11: Najar IA, Sachin BS, Sharma SC, Satti NK, Suri KA, Johri RK. Modulation of P-glycoprotein ATPase activity by some phytoconstituents. Phytother Res. 2010 Mar;24(3):454-8. doi: 10.1002/ptr.2951. PMID: 19653312. 12: Tasduq SA, Kaiser PJ, Gupta BD, Gupta VK, Johri RK. Negundoside, an irridiod glycoside from leaves of Vitex negundo, protects human liver cells against calcium-mediated toxicity induced by carbon tetrachloride. World J Gastroenterol. 2008 Jun 21;14(23):3693-709. doi: 10.3748/wjg.14.3693. PMID: 18595136; PMCID: PMC2719232. 13: Sridhar C, Subbaraju GV, Venkateswarlu Y, Venugopal RT. New acylated iridoid glucosides from Vitex altissima. J Nat Prod. 2004 Dec;67(12):2012-6. doi: 10.1021/np040117r. PMID: 15620243.

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