4-deoxyannomontacin and (2,4-cis and trans)-annomontacinone, new bioactive mono-tetrahydrofuran annonaceous acetogenins from Goniothalamus giganteus.
4-Deoxyannomontacin (1) and a mixture of (2,4-cis and trans)-annomontacinone (2), new bioactive mono-tetrahydrofuran (THF) gamma-lactone and keto-lactone acetogenins, respectively, as well as five known mono-THF acetogenins [xylomaticin, longifolicin, longicoricin, (2,4-cis and trans)-gigantetrocinone, and (2,4-cis and trans)-gigantetroneninone], were isolated from the bark of Goniothalamus giganteus (Annonaceae) by activity-directed fractionation using the brine shrimp lethality test (BST). The structures were elucidated based on spectroscopic and chemical methods. The absolute stereochemistries of 1 and 2 were determined by the advanced Mosher ester method and by circular dichroism (CD). Determination of the absolute stereochemistry at C-10 as R for 1 is the first example of the direct determination of the absolute stereochemistry of a carbinol position isolated from other functional groups in the annonaceous acetogenins. 1 and 2 showed selective and potent cytotoxicities to certain human tumor cell lines and were comparable to the activity of rotenone against yellow fever mosquito larvae.
Alali
F
F
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA.
Zeng
L
L
Zhang
Y
Y
Ye
Q
Q
Hopp
D C
DC
Schwedler
J T
JT
McLaughlin
J L
JL
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology; D001156:Artemia; D002942:Circular Dichroism; D009033:Culicidae; D005663:Furans / Q000737:chemistry* / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D014197:Trees / Q000737:chemistry*; D014407:Tumor Cells, Cultured
C107229:4-deoxyannomontacin; D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C073066:annomontacin; D015107:4-Butyrolactone