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MedKoo Cat#: 574473 | Name: Equisetin
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Description:

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

Equisetin is a fungal metabolite that inhibits HIV-1 integrase 3’ end-processing and strand transfer activities. Equisetin inhibits the ATPase activity of rat liver mitochondria and mitoplasts stimulated by 2,4-dinitrophenol (Dnp) in a concentration-dependent manner. It also inhibits ADP-stimulated respiration and the mitochondrial transport of ATP, inorganic phosphate, and succinate.

Chemical Structure

Equisetin
Equisetin
CAS#57749-43-6

Theoretical Analysis

MedKoo Cat#: 574473

Name: Equisetin

CAS#: 57749-43-6

Chemical Formula: C22H31NO4

Exact Mass: 373.2253

Molecular Weight: 373.49

Elemental Analysis: C, 70.75; H, 8.37; N, 3.75; O, 17.13

Price and Availability

Size Price Availability Quantity
1mg USD 385.00 2 Weeks
5mg USD 1,250.00 2 Weeks
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Related CAS #
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Synonym
Equisetin; (-)-Equisetin; N-methyltrichosetin; NSC790850; NSC 790850; NSC-790850
IUPAC/Chemical Name
(3E,5S)-5-(hydroxymethyl)-3-[hydroxy[(1S,2R,4aS,6R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-1,6-dimethyl-2-(1E)-1-propen-1-yl-1-naphthalenyl]methylene]-1-methyl-2,4-pyrrolidinedione
InChi Key
QNQBPPQLRODXET-AIMHRHHOSA-N
InChi Code
InChI=1S/C22H31NO4/c1-5-6-15-9-8-14-11-13(2)7-10-16(14)22(15,3)20(26)18-19(25)17(12-24)23(4)21(18)27/h5-6,8-9,13-17,24,26H,7,10-12H2,1-4H3/b6-5+,20-18+/t13-,14-,15-,16-,17+,22-/m1/s1
SMILES Code
O=C(/C1=C(O)\[C@]2(C)[C@H](/C=C/C)C=C[C@]3([H])C[C@H](C)CC[C@@]23[H])N(C)[C@@H](CO)C1=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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 373.49 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: Zhang Q, Chen S, Liu X, Lin W, Zhu K. Equisetin Restores Colistin Sensitivity against Multi-Drug Resistant Gram-Negative Bacteria. Antibiotics (Basel). 2021 Oct 18;10(10):1263. doi: 10.3390/antibiotics10101263. PMID: 34680843; PMCID: PMC8532683. 2: Tian J, Chen S, Liu F, Zhu Q, Shen J, Lin W, Zhu K. Equisetin Targets Intracellular Staphylococcus aureus through a Host Acting Strategy. Mar Drugs. 2022 Oct 22;20(11):656. doi: 10.3390/md20110656. PMID: 36354979; PMCID: PMC9694014. 3: Xu Z, Liu D, Liu D, Ren X, Liu H, Qi G, Zhou Y, Wu C, Zhu K, Zou Z, Yuan J, Lin W, Guo P. Equisetin is an anti-obesity candidate through targeting 11β-HSD1. Acta Pharm Sin B. 2022 May;12(5):2358-2373. doi: 10.1016/j.apsb.2022.01.006. Epub 2022 Jan 15. PMID: 35646525; PMCID: PMC9136616. 4: Zhang M, Wang M, Zhu X, Yu W, Gong Q. Equisetin as potential quorum sensing inhibitor of Pseudomonas aeruginosa. Biotechnol Lett. 2018 May;40(5):865-870. doi: 10.1007/s10529-018-2527-2. Epub 2018 Mar 3. PMID: 29502217. 5: Li X, Zheng Q, Yin J, Liu W, Gao S. Chemo-enzymatic synthesis of equisetin. Chem Commun (Camb). 2017 Apr 25;53(34):4695-4697. doi: 10.1039/c7cc01929g. PMID: 28401214. 6: Larson EC, Lim AL, Pond CD, Craft M, Čavužić M, Waldrop GL, Schmidt EW, Barrows LR. Pyrrolocin C and equisetin inhibit bacterial acetyl-CoA carboxylase. PLoS One. 2020 May 29;15(5):e0233485. doi: 10.1371/journal.pone.0233485. PMID: 32470050; PMCID: PMC7259786. 7: Zhu J, Liu S, Dai L, Yu F, Zhou T, Chen J, Xu J, Yu B, Tang S, Liu Q, Yang XL, Han XL. Elucidating the interaction between equisetin and human serum albumin: A comprehensive study using spectroscopy, microcalorimetry and molecular docking approaches. Spectrochim Acta A Mol Biomol Spectrosc. 2024 Jan 5;304:123409. doi: 10.1016/j.saa.2023.123409. Epub 2023 Sep 14. PMID: 37729815. 8: Yin J, Kong L, Wang C, Shi Y, Cai S, Gao S. Biomimetic synthesis of equisetin and (+)-fusarisetin A. Chemistry. 2013 Sep 23;19(39):13040-6. doi: 10.1002/chem.201302163. Epub 2013 Aug 12. PMID: 24038394. 9: Sims JW, Fillmore JP, Warner DD, Schmidt EW. Equisetin biosynthesis in Fusarium heterosporum. Chem Commun (Camb). 2005 Jan 14;(2):186-8. doi: 10.1039/b413523g. Epub 2004 Nov 22. PMID: 15724180. 10: Nyrén P, Strid A. The effect of equisetin on energy-linked reactions in Rhodospirillum rubrum chromatophores. Arch Biochem Biophys. 1989 Feb 1;268(2):659-66. doi: 10.1016/0003-9861(89)90334-2. PMID: 2536535. 11: König T, Kapus A, Sarkadi B. Effects of equisetin on rat liver mitochondria: evidence for inhibition of substrate anion carriers of the inner membrane. J Bioenerg Biomembr. 1993 Oct;25(5):537-45. doi: 10.1007/BF01108410. PMID: 8132493. 12: Jeong YC, Moloney MG. Equisetin, reutericyclin and streptolodygin as natural product lead structures for novel antibiotic libraries. Future Med Chem. 2015;7(14):1861-77. doi: 10.4155/fmc.15.97. Epub 2015 Oct 2. PMID: 26431450. 13: Burke LT, Dixon DJ, Ley SV, Rodríguez F. Total synthesis of the Fusarium toxin equisetin. Org Biomol Chem. 2005 Jan 21;3(2):274-80. doi: 10.1039/b411350k. Epub 2004 Dec 7. PMID: 15632969. 14: Vesonder RF, Tjarks LW, Rohwedder WK, Burmeister HR, Laugal JA. Equisetin, an antibiotic from Fusarium equiseti NRRL 5537, identified as a derivative of N-methyl-2,4-pyrollidone. J Antibiot (Tokyo). 1979 Jul;32(7):759-61. doi: 10.7164/antibiotics.32.759. PMID: 541270. 15: Kato N, Nogawa T, Hirota H, Jang JH, Takahashi S, Ahn JS, Osada H. A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis. Biochem Biophys Res Commun. 2015 May 1;460(2):210-5. doi: 10.1016/j.bbrc.2015.03.011. Epub 2015 Mar 11. PMID: 25770422. 16: Chi C, Wang Z, Liu T, Zhang Z, Zhou H, Li A, Jin H, Jia H, Yin F, Yang D, Ma M. Crystal Structures of Fsa2 and Phm7 Catalyzing [4 + 2] Cycloaddition Reactions with Reverse Stereoselectivities in Equisetin and Phomasetin Biosynthesis. ACS Omega. 2021 May 6;6(19):12913-12922. doi: 10.1021/acsomega.1c01593. PMID: 34056443; PMCID: PMC8154222. 17: Burke LT, Dixon DJ, Ley SV, Rodríguez F. A short stereoselective total synthesis of the fusarium toxin equisetin. Org Lett. 2000 Nov 16;2(23):3611-3. doi: 10.1021/ol006493u. PMID: 11073657. 18: Quek NC, Matthews JH, Bloor SJ, Jones DA, Bircham PW, Heathcott RW, Atkinson PH. The novel equisetin-like compound, TA-289, causes aberrant mitochondrial morphology which is independent of the production of reactive oxygen species in Saccharomyces cerevisiae. Mol Biosyst. 2013 Aug;9(8):2125-33. doi: 10.1039/c3mb70056a. Epub 2013 May 28. PMID: 23715404. 19: Chen S, Liu D, Zhang Q, Guo P, Ding S, Shen J, Zhu K, Lin W. A Marine Antibiotic Kills Multidrug-Resistant Bacteria without Detectable High-Level Resistance. ACS Infect Dis. 2021 Apr 9;7(4):884-893. doi: 10.1021/acsinfecdis.0c00913. Epub 2021 Mar 3. PMID: 33653026. 20: Ratnaweera PB, de Silva ED, Williams DE, Andersen RJ. Antimicrobial activities of endophytic fungi obtained from the arid zone invasive plant Opuntia dillenii and the isolation of equisetin, from endophytic Fusarium sp. BMC Complement Altern Med. 2015 Jul 10;15:220. doi: 10.1186/s12906-015-0722-4. PMID: 26160390; PMCID: PMC4496918.