Ungeremine - Misplaced Pages

Ungeremine
Names

Preferred IUPAC name 2-Hydroxy-4,5-dihydro-10H-6λ-dioxolopyrrolophenanthridin-6-ylium
Identifiers
CAS Number	2121-12-2
3D model (JSmol)	Interactive image
ChemSpider	140368
PubChem CID	159646
UNII	9EVC5B2RPS
CompTox Dashboard (EPA)	DTXSID50175439
InChI InChI=1S/C16H11NO3/c18-11-3-9-1-2-17-7-10-4-14-15(20-8-19-14)6-12(10)13(5-11)16(9)17/h3-7H,1-2,8H2/p+1Key: DFQOXFIPAAMFAU-UHFFFAOYSA-O InChI=1/C16H11NO3/c18-11-3-9-1-2-17-7-10-4-14-15(20-8-19-14)6-12(10)13(5-11)16(9)17/h3-7H,1-2,8H2/p+1Key: DFQOXFIPAAMFAU-IKLDFBCSAD
SMILES C1C2=CC3=CC4=C(C=C3C5=CC(=CC1=C52)O)OCO4
Properties
Chemical formula	C₁₆H₁₂NO₃
Molar mass	266.275 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Ungeremine is a betaine-type alkaloid isolated from Nerine bowdenii and related plants such as Pancratium maritimum. Pharmacologically, it is of interest as an acetylcholinesterase inhibitor and accordingly as possibly relevant to Alzheimer's disease. It also has been investigated as a bactericide.

References

Rhee, I. K.; Appels, N; Hofte, B; Karabatak, B; Erkelens, C; Stark, L. M.; Flippin, L. A.; Verpoorte, R (2004). "Isolation of the acetylcholinesterase inhibitor ungeremine from Nerine bowdenii by preparative HPLC coupled on-line to a flow assay system". Biological & Pharmaceutical Bulletin. 27 (11): 1804–9. doi:10.1248/bpb.27.1804. PMID 15516727.
^ Schrader, Kevin K.; Avolio, Fabiana; Andolfi, Anna; Cimmino, Alessio; Evidente, Antonio (2013). "Ungeremine and Its Hemisynthesized Analogues as Bactericides against Flavobacterium columnare". Journal of Agricultural and Food Chemistry. 61 (6): 1179–83. doi:10.1021/jf304586j. PMID 23331165.
Murray, Ana; Faraoni, Maria; Castro, María; Alza, Natalia; Cavallaro, Valeria (2013). "Natural AChE Inhibitors from Plants and their Contribution to Alzheimer's Disease Therapy". Current Neuropharmacology. 11 (4): 388–413. doi:10.2174/1570159X11311040004. PMC 3744903. PMID 24381530.