Ancistrocladus korupensis

The dimeric stereoisomer alkaloids michellamines A, B and C (38) were obtained From the liane Ancistrocladus korupensis (Ancistrocladaceae). On the basis of their structural similarity to other PKC inhibitors, they have been studied for this activity. Michellamines inhibited rat brain PKC, with IC50 values in the 15-35 pM range. Michellamine B was a non-competitive PKC inhibitor with respect to ATP, whereas mixed-type inhibition was observed when the peptide concentration varied. The results indicate that the dimeric alkaloids bind to the PKC kinase domain and not to its regulatory domain. All three michellamines blocked both the ATP and the... 

Naphthyltetrahydroisoquinoline alkaloids Ancistrocladus korupensis CHCls-MeOH 0.5% HBr (5 5 3) CPC... 

Catharanthus roseus Schisandra chinensis fruits Magnolia officinalis Blood plasma Ancistrocladus korupensis leaves... 

Ashraf-Khorassani M, Taylor LT. Supercritical fluid extraction of michella-mines A and B from Ancistrocladus korupensis leaves. Anal Chim Acta 1997 347 305-311. 

Source Ancistrocladus korupensis Molecular formula C46 H48 N2 Og. Biological activity Anti HIV. 

G., and Boyd, M. R. (1997) Michellamines D-F, new HlV-inhibitory dimeric naphthylisoquinoline alkaloids, and korupensamine E, a new antimalarial monomer, from Ancistrocladus korupensis. J Nat Prod. 60, 677-683. 

Hoye and co-workers (ref. 92) later reported the total synthesis of ancistrobrevine B (228), isolated from Ancistrocladus abbreviatus (ref. 93) and korupensamine C (229), isolated from Ancistrocladus korupensis. The approach to these natural products also utilised a benzyne cycloaddition to construct the naphthalene moiety. Thus, treatment of the amide 222 and bromide 230 with lithium cyclohexylisopropylamide furnished naphthalene 231 in low yield (Scheme 30). 

Structure-activity relationships indicate that the presence of a secondary amine function, and the absence of an oxygen substituent at C-6 and R-configuration at C-3 are important. Recently, a novel dimeric antiplasmodial naphthylisoquinoline alkaloid heterodimer, korundamine A (98), has been isolated from another species, Ancistrocladus korupensis belonging to the family Ancistrocladaceae that is biogenetically related to Dioncophyllaceae. Korundamide A is one of the most potent naturally occuring naphthylisoquinoline dimers... 

NaphthvlisoQuinoline Michellamines A, B (33), C Ancistrocladus korupensis HIV HIV-induced cell killing HIV-RT [35. 36]... 

MkheNamines. Atropisomeric dimeric naphthyl-(tetrahydro)isoquinoline alkaloids from the tropical lianas Ancistrocladus korupensis and A. abbreviatus. C46H48N2O8, Mr 756.89. 

Boyd MR, HaUock YF, Manfredi KP, Blunt JW, McMahtm JB, Buckheit RW, et al. Anti-HIV michellamines from Ancistrocladus Korupensis. J Med Chem 1994 37 (12) 1740 5. 

Michellamine B (19), from Ancistrocladus korupensis (formerly considered to be /4. abbreviatus) has been shown to possess potent activity against HIV-1 and HIV-2 (Manfredi et al., 1991 Thomas and Gereau, 1993). 

Thomas, D. W. and R. E. Gereau, Ancistrocladus korupensis (An-cistrocladaceae) A new species of liana from Cameroon, Novon, 7, 242-245 (1993). 

Alkaloid from leaves and twigs of Ancistrocladus korupensis (Ancistrocladaceae). Shows antimalarial activity. Light brown solid. [a]p — 75.5 (c, 1.84 in MeOH). 

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