Gymnemic Acid I | CAS# 122168-40-5 | Antisweetness Agent

MedKoo Cat#: 581031 | Name: Gymnemic Acid I

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Description:

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

Gymnemic acids have been reported to effect a natural treatment for diabetes. Gymnemic acids inhibit rabbit glyceraldehyde-3-phosphate dehydrogenase and induce a smearing of its electrophoretic band and dephosphorylation. Gymnemic Acid Stimulates In Vitro Splenic Lymphocyte Proliferation.

Chemical Structure

Gymnemic Acid I

CAS#122168-40-5

Theoretical Analysis

MedKoo Cat#: 581031

Name: Gymnemic Acid I

CAS#: 122168-40-5

Chemical Formula: C43H66O14

Exact Mass: 806.4453

Molecular Weight: 806.99

Elemental Analysis: C, 64.00; H, 8.24; O, 27.76

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Synonym

Gymnemic Acid I; (+)-Gymnemic acid I; Gymnemic acid I, (+)-; beta-D-Glucopyranosiduronic acid

IUPAC/Chemical Name

(2S,3S,4S,5R,6R)-6-(((3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetoxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-(((E)-2-methylbut-2-enoyl)oxy)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

InChi Key

VEFSVJGWJQPWFS-ZXKKMYOJSA-N

InChi Code

InChI=1S/C43H66O14/c1-10-21(2)36(53)57-34-33(50)43(20-54-22(3)45)24(17-38(34,4)5)23-11-12-26-39(6)15-14-28(55-37-31(49)29(47)30(48)32(56-37)35(51)52)40(7,19-44)25(39)13-16-41(26,8)42(23,9)18-27(43)46/h10-11,24-34,37,44,46-50H,12-20H2,1-9H3,(H,51,52)/b21-10+/t24-,25+,26+,27-,28-,29-,30-,31+,32-,33-,34-,37+,39-,40-,41+,42+,43-/m0/s1

SMILES Code

CC1(C)[C@@H](OC(/C(C)=C/C)=O)[C@H](O)[C@]2(COC(C)=O)[C@@H](O)C[C@@]3(C)[C@]4(C)CC[C@@]5([H])[C@](C)(CO)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O6)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])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

>2 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 806.99 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: Vaghela M, Sahu N, Kharkar P, Pandita N. In vivo pharmacokinetic interaction by ethanolic extract of Gymnema sylvestre with CYP2C9 (tolbutamide), CYP3A4 (amlodipine) and CYP1A2 (phenacetin) in rats. Chem Biol Interact. 2017 Oct 14. pii: S0009-2797(17)30894-3. doi: 10.1016/j.cbi.2017.10.015. [Epub ahead of print] PubMed PMID: 29042257. 2: Vaghela M, Iyer K, Pandita N. In vitro Inhibitory Effect of Gymnema sylvestre Extracts and Total Gymnemic Acids Fraction on Select Cytochrome P450 Activities in Rat Liver Microsomes. Eur J Drug Metab Pharmacokinet. 2017 Oct 10. doi: 10.1007/s13318-017-0443-9. [Epub ahead of print] PubMed PMID: 29019074. 3: Vellai RD, Chandiran S, Pillai SS. GTF-231, a Mixture of Gymnemic Acid, Trigonelline and Ferulic Acid Significantly Ameliorates Oxidative Stress in Experimental Type 2 Diabetes in Rats. Can J Diabetes. 2017 Jul 17. pii: S1499-2671(16)30841-3. doi: 10.1016/j.jcjd.2017.05.007. [Epub ahead of print] PubMed PMID: 28728928. 4: Chen G, Guo M. Rapid Screening for α-Glucosidase Inhibitors from Gymnema sylvestre by Affinity Ultrafiltration-HPLC-MS. Front Pharmacol. 2017 Apr 27;8:228. doi: 10.3389/fphar.2017.00228. eCollection 2017. PubMed PMID: 28496409; PubMed Central PMCID: PMC5406464. 5: Capolupo A, Esposito R, Zampella A, Festa C, Riccio R, Casapullo A, Tosco A, Monti MC. Determination of Gymnemic Acid I as a Protein Biosynthesis Inhibitor Using Chemical Proteomics. J Nat Prod. 2017 Apr 28;80(4):909-915. doi: 10.1021/acs.jnatprod.6b00793. Epub 2017 Mar 3. PubMed PMID: 28256837. 6: Tiwari P, Ahmad K, Baig MH. Gymnema sylvestre for Diabetes: From Traditional Herb to Future's Therapeutic. Curr Pharm Des. 2017;23(11):1667-1676. doi: 10.2174/1381612823666161108162048. PubMed PMID: 27834124. 7: Verma AK, Dhawan SS, Singh S, Bharati KA, Jyotsana. Genetic and Chemical Profiling of Gymnema sylvestre Accessions from Central India: Its Implication for Quality Control and Therapeutic Potential of Plant. Pharmacogn Mag. 2016 Jul;12(Suppl 4):S407-S413. PubMed PMID: 27761067; PubMed Central PMCID: PMC5068116. 8: Rammohan B, Samit K, Chinmoy D, Arup S, Amit K, Ratul S, Sanmoy K, Dipan A, Tuhinadri S. Human Cytochrome P450 Enzyme Modulation by Gymnema sylvestre: A Predictive Safety Evaluation by LC-MS/MS. Pharmacogn Mag. 2016 Jul;12(Suppl 4):S389-S394. PubMed PMID: 27761064; PubMed Central PMCID: PMC5068113. 9: Kim HJ, Hong SH, Chang SH, Kim S, Lee AY, Jang Y, Davaadamdin O, Yu KN, Kim JE, Cho MH. Effects of feeding a diet containing Gymnema sylvestre extract: Attenuating progression of obesity in C57BL/6J mice. Asian Pac J Trop Med. 2016 May;9(5):437-44. doi: 10.1016/j.apjtm.2016.03.037. Epub 2016 Mar 24. PubMed PMID: 27261851. 10: Rajashekar J, Kumar V, Veerashree V, Poornima DV, Sannabommaji T, Gajula H, Giridhara B. Hairy Root Cultures of Gymnema sylvestre R. Br. to Produce Gymnemic Acid. Methods Mol Biol. 2016;1391:427-43. doi: 10.1007/978-1-4939-3332-7_29. PubMed PMID: 27108334. 11: Nagella P, Dandin VS, Murthy HN. Production of Gymnemic Acid from Cell Suspension Cultures of Gymnema sylvestre. Methods Mol Biol. 2016;1391:229-39. doi: 10.1007/978-1-4939-3332-7_16. PubMed PMID: 27108321. 12: Netala VR, Kotakadi VS, Gaddam SA, Ghosh SB, Tartte V. Elicitation of gymnemic acid production in cell suspension cultures of Gymnema sylvestre R.Br. through endophytic fungi. 3 Biotech. 2016 Dec;6(2):232. doi: 10.1007/s13205-016-0555-y. Epub 2016 Oct 28. PubMed PMID: 28330304; PubMed Central PMCID: PMC5234528. 13: Singh VK, Dwivedi P, Chaudhary BR, Singh R. Gymnemic Acid Stimulates In Vitro Splenic Lymphocyte Proliferation. Phytother Res. 2016 Feb;30(2):341-4. doi: 10.1002/ptr.5514. Epub 2015 Nov 9. PubMed PMID: 26549619. 14: Singh VK, Dwivedi P, Chaudhary BR, Singh R. Immunomodulatory Effect of Gymnema sylvestre (R.Br.) Leaf Extract: An In Vitro Study in Rat Model. PLoS One. 2015 Oct 16;10(10):e0139631. doi: 10.1371/journal.pone.0139631. eCollection 2015. PubMed PMID: 26474420; PubMed Central PMCID: PMC4608767. 15: Tiwari P, Sharma P, Khan F, Sangwan NS, Mishra BN, Sangwan RS. Structure Activity Relationship Studies of Gymnemic Acid Analogues for Antidiabetic Activity Targeting PPARγ. Curr Comput Aided Drug Des. 2015;11(1):57-71. PubMed PMID: 26058590. 16: Renga B, Festa C, De Marino S, Di Micco S, D'Auria MV, Bifulco G, Fiorucci S, Zampella A. Molecular decodification of gymnemic acids from Gymnema sylvestre. Discovery of a new class of liver X receptor antagonists. Steroids. 2015 Apr;96:121-31. doi: 10.1016/j.steroids.2015.01.024. Epub 2015 Feb 7. PubMed PMID: 25668616. 17: Arunachalam KD, Arun LB, Annamalai SK, Arunachalam AM. Potential anticancer properties of bioactive compounds of Gymnema sylvestre and its biofunctionalized silver nanoparticles. Int J Nanomedicine. 2014 Dec 16;10:31-41. doi: 10.2147/IJN.S71182. eCollection 2015. PubMed PMID: 25565802; PubMed Central PMCID: PMC4274148. 18: Ahamad J, Amin S, Mir SR. Simultaneous Quantification of Gymnemic Acid as Gymnemagenin and Charantin as β-Sitosterol Using Validated HPTLC Densitometric Method. J Chromatogr Sci. 2015 Aug;53(7):1203-9. doi: 10.1093/chromsci/bmu166. Epub 2014 Dec 18. PubMed PMID: 25523465. 19: Zarrelli A, Romanucci V, Gravante R, Di Marino C, Di Fabio G. History of gymnemic acid, a molecule that does not exist. . Nat Prod Commun. 2014 Oct;9(10):1429-32. PubMed PMID: 25522530. 20: Sheoran S, Panda BP, Admane PS, Panda AK, Wajid S. Ultrasound-assisted extraction of gymnemic acids from Gymnema sylvestre leaves and its effect on insulin-producing RINm-5 F β cell lines. Phytochem Anal. 2015 Mar-Apr;26(2):97-104. doi: 10.1002/pca.2540. Epub 2014 Dec 3. PubMed PMID: 25469471.