Ungeremine

Ungeremine
Names
Preferred IUPAC name
2-Hydroxy-4,5-dihydro-10H-6λ5-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-6-ylium
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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+1
    Key: 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+1
    Key: DFQOXFIPAAMFAU-IKLDFBCSAD
  • C1C[N+]2=CC3=CC4=C(C=C3C5=CC(=CC1=C52)O)OCO4
Properties
C16H12NO3+1
Molar mass 266.275 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ungeremine is a betaine-type alkaloid isolated from Nerine bowdenii[1] and related plants such as Pancratium maritimum.[2] Pharmacologically, it is of interest as an acetylcholinesterase inhibitor and accordingly as possibly relevant to Alzheimer's disease.[3] It also has been investigated as a bactericide.[2]

References

  1. ^ 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.
  2. ^ a b 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.
  3. ^ 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.
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