Hypaphorine | CAS#487-58-1 | indole alkaloid

MedKoo Cat#: 597362 | Name: Hypaphorine

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Description:

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

Hypaphorine is an indole alkaloid, present in the fungus Pisolithus tinctorius in family Sclerodermataceae, that controls the elongation rate of root hairs.

Chemical Structure

Hypaphorine

CAS#487-58-1

Theoretical Analysis

MedKoo Cat#: 597362

Name: Hypaphorine

CAS#: 487-58-1

Chemical Formula: C14H18N2O2

Exact Mass: 246.1368

Molecular Weight: 246.31

Elemental Analysis: C, 68.27; H, 7.37; N, 11.37; O, 12.99

Price and Availability

Size	Price	Availability
1mg	USD 270.00	2 Weeks
5mg	USD 620.00	2 Weeks
10mg	USD 990.00	2 Weeks

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Related CAS #

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Synonym

Hypaphorine; Hypaforin; L-Hypaphorine; Tryptophan betaine;

IUPAC/Chemical Name

(S)-3-(1H-indol-3-yl)-2-(trimethylammonio)propanoate

InChi Key

AOHCBEAZXHZMOR-ZDUSSCGKSA-N

InChi Code

InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1

SMILES Code

C[N+](C)(C)[C@H](C([O-])=O)CC1=CNC2=C1C=CC=C2

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 246.31 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

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Hypaphorine Attenuates Lipopolysaccharide-Induced Endothelial Inflammation via Regulation of TLR4 and PPAR-γ Dependent on PI3K/Akt/mTOR Signal Pathway. Int J Mol Sci. 2017 Apr 17;18(4). pii: E844. doi: 10.3390/ijms18040844. PubMed PMID: 28420166; PubMed Central PMCID: PMC5412428. 5: Luan G, Tie F, Yuan Z, Li G, He J, Wang Z, Wang H. Hypaphorine, an Indole Alkaloid Isolated from Caragana korshinskii Kom., Inhibites 3T3-L1 Adipocyte Differentiation and Improves Insulin Sensitivity in Vitro. Chem Biodivers. 2017 Jul;14(7). doi: 10.1002/cbdv.201700038. Epub 2017 May 29. PubMed PMID: 28398659. 6: Sun H, Cai W, Wang X, Liu Y, Hou B, Zhu X, Qiu L. Vaccaria hypaphorine alleviates lipopolysaccharide-induced inflammation via inactivation of NFκB and ERK pathways in Raw 264.7 cells. BMC Complement Altern Med. 2017 Feb 20;17(1):120. doi: 10.1186/s12906-017-1635-1. PubMed PMID: 28219355; PubMed Central PMCID: PMC5319035. 7: Panneerselvam C, Murugan K, Roni M, Aziz AT, Suresh U, Rajaganesh R, Madhiyazhagan P, Subramaniam J, Dinesh D, Nicoletti M, Higuchi A, Alarfaj AA, Munusamy MA, Kumar S, Desneux N, Benelli G. Fern-synthesized nanoparticles in the fight against malaria: LC/MS analysis of Pteridium aquilinum leaf extract and biosynthesis of silver nanoparticles with high mosquitocidal and antiplasmodial activity. Parasitol Res. 2016 Mar;115(3):997-1013. doi: 10.1007/s00436-015-4828-x. Epub 2015 Nov 27. PubMed PMID: 26612497. 8: Vit A, Misson L, Blankenfeldt W, Seebeck FP. Ergothioneine biosynthetic methyltransferase EgtD reveals the structural basis of aromatic amino acid betaine biosynthesis. Chembiochem. 2015 Jan 2;16(1):119-25. doi: 10.1002/cbic.201402522. Epub 2014 Nov 17. PubMed PMID: 25404173. 9: Keller BO, Wu BT, Li SS, Monga V, Innis SM. Hypaphorine is present in human milk in association with consumption of legumes. J Agric Food Chem. 2013 Aug 7;61(31):7654-60. doi: 10.1021/jf401758f. Epub 2013 Jul 26. PubMed PMID: 23855762. 10: Rigas S, Ditengou FA, Ljung K, Daras G, Tietz O, Palme K, Hatzopoulos P. Root gravitropism and root hair development constitute coupled developmental responses regulated by auxin homeostasis in the Arabidopsis root apex. New Phytol. 2013 Mar;197(4):1130-41. doi: 10.1111/nph.12092. Epub 2012 Dec 18. PubMed PMID: 23252740. 11: Han DQ, Zhao J, Xu J, Peng HS, Chen XJ, Li SP. Quality evaluation of Polygonum multiflorum in China based on HPLC analysis of hydrophilic bioactive compounds and chemometrics. J Pharm Biomed Anal. 2013 Jan;72:223-30. doi: 10.1016/j.jpba.2012.08.026. Epub 2012 Sep 10. PubMed PMID: 23021005. 12: Mollica A, Locatelli M, Stefanucci A, Pinnen F. Synthesis and bioactivity of secondary metabolites from marine sponges containing dibrominated indolic systems. Molecules. 2012 May 21;17(5):6083-99. doi: 10.3390/molecules17056083. Review. PubMed PMID: 22614862. 13: Iranshahi M, Vu H, Pham N, Zencak D, Forster P, Quinn RJ. Cytotoxic evaluation of alkaloids and isoflavonoids from the Australian tree Erythrina vespertilio. Planta Med. 2012 May;78(7):730-6. doi: 10.1055/s-0031-1298310. Epub 2012 Feb 21. Erratum in: Planta Med. 2012 May;78(7):E20. PubMed PMID: 22354391. 14: Longeon A, Copp BR, Quévrain E, Roué M, Kientz B, Cresteil T, Petek S, Debitus C, Bourguet-Kondracki ML. Bioactive indole derivatives from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp. Mar Drugs. 2011;9(5):879-88. doi: 10.3390/md9050879. Epub 2011 May 24. PubMed PMID: 21673896; PubMed Central PMCID: PMC3111189. 15: Gao HM, Liu JX, Wang ZM, Wang WH. Phytolacacinoside A, a new triterpenoid saponin from Phytolacca acinosa Roxb. J Asian Nat Prod Res. 2009;11(5):433-8. doi: 10.1080/10286020902849266. PubMed PMID: 19504386. 16: Chen G, Luo H, Ye J, Hu C. Determination of hypaphorine and oligomeric stilbenes in the root of Caragana sinica by capillary electrophoresis with electrochemical detection. Talanta. 2001 Jul 6;54(6):1067-76. PubMed PMID: 18968328. 17: Ozawa M, Honda K, Nakai I, Kishida A, Ohsaki A. Hypaphorine, an indole alkaloid from Erythrina velutina, induced sleep on normal mice. Bioorg Med Chem Lett. 2008 Jul 15;18(14):3992-4. doi: 10.1016/j.bmcl.2008.06.002. Epub 2008 Jun 6. PubMed PMID: 18571406. 18: Bel-Kassaoui H, Lamnaouer D, Jossang A, Abdennebi el H, Charrouf Z, Bodo B. Role of hypaphorine in the toxicity of Astragalus lusitanicus. Nat Prod Res. 2008 Mar 20;22(5):453-7. doi: 10.1080/14786410701591986. PubMed PMID: 18404567. 19: Dauphin A, Gérard J, Lapeyrie F, Legué V. Fungal hypaphorine reduces growth and induces cytosolic calcium increase in root hairs of Eucalyptus globulus. Protoplasma. 2007;231(1-2):83-8. Epub 2007 Mar 20. PubMed PMID: 17370110. 20: Dauphin A, De Ruijter NC, Emons AM, Legué V. Actin organization during eucalyptus root hair development and its response to fungal hypaphorine. Plant Biol (Stuttg). 2006 Mar;8(2):204-11. PubMed PMID: 16547865.