Higenamine

Higenamine
IUPAC name

1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Other names

Norcoclaurine
Identifiers
CAS number 5843-65-2
PubChem 114840
ChemSpider 102800 Y
KEGG C06346 Y
MeSH higenamine
ChEBI CHEBI:18418 Y
ChEMBL CHEMBL19344 Y
Jmol-3D images Image 1
Properties
Molecular formula C16H17NO3
Molar mass 271.31 g/mol
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Higenamine is a beta-adrenergic agonist. [1] Higenamine is also known as norcoclaurine.

(S)-norcoclaurine is a precursor in plant benzylisoquinoline alkaloid synthesis. The formation of (S)-norcoclaurine is catalyzed by (S)-norcoclaurine synthase. [2] (-)-1(S)-Norcoclaurine can be found in the leaves of Nelumbo nucifera.[3]

References

  1. ^ Liu W, Sato Y, Hosoda Y, Hirasawa K, Hanai H (November 2000). "Effects of higenamine on regulation of ion transport in guinea pig distal colon" (– Scholar search). Jpn. J. Pharmacol. 84 (3): 244–51. doi:10.1254/jjp.84.244. PMID 11138724. http://joi.jlc.jst.go.jp/JST.JSTAGE/jjp/84.244?from=PubMed. 
  2. ^ Facchini PJ (June 2001). "ALKALOID BIOSYNTHESIS IN PLANTS: Biochemistry, Cell Biology, Molecular Regulation, and Metabolic Engineering Applications". Annu. Rev. Plant Physiol. Plant Mol. Biol. 52 (1): 29–66. doi:10.1146/annurev.arplant.52.1.29. PMID 11337391. 
  3. ^ Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. Kashiwada Y, Aoshima A, Ikeshiro Y, Chen YP, Furukawa H, Itoigawa M, Fujioka T, Mihashi K, Cosentino LM, Morris-Natschke SL and Lee KH, Bioorg Med Chem., 2005 Jan 17, 13(2), pages 443-448, PubMed, doi:10.1016/j.bmc.2004.10.020