ABSTRACT
Betulinic acid (1), isolated from the crude extract of the leaves of Pentalinon andrieuxii (Apocynaceae), together with betulinic acid acetate (2), betulonic acid (3), betulinic acid methyl ester (4), and betulin (5) were evaluated for their antiprotozoal activity. The results showed that modifying the C-3 position increases leishmanicidal activity while modification of the C-3 and C-28 positions decreases trypanocidal activity.
Subject(s)
Antiprotozoal Agents/pharmacology , Apocynaceae/chemistry , Leishmania/drug effects , Plant Extracts/pharmacology , Plasmodium falciparum/drug effects , Triterpenes/pharmacology , Trypanosoma/drug effects , Antiprotozoal Agents/chemical synthesis , Antiprotozoal Agents/isolation & purification , Molecular Structure , Parasitic Sensitivity Tests , Pentacyclic Triterpenes , Plant Extracts/chemistry , Plant Leaves , Triterpenes/chemistry , Triterpenes/isolation & purification , Betulinic AcidABSTRACT
Two new phytotoxic polyketides, tagetolone (1) and tagetenolone (2), in addition to tyrosol and p-hydroxybenzoic acid, have been isolated from the organic crude extract of culture filtrates from the fungal pathogen Alternaria tagetica. Complete characterization of all structures was carried out following a careful analysis of their spectroscopic data (IR, MS, (1)H and (13)C NMR, and 2D NMR experiments).
Subject(s)
Alternaria/chemistry , Mycotoxins/chemistry , Parabens/chemistry , Phenylethyl Alcohol/analogs & derivatives , Alternaria/growth & development , Alternaria/pathogenicity , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Mycotoxins/isolation & purification , Parabens/isolation & purification , Parabens/pharmacology , Phenylethyl Alcohol/isolation & purification , Plants/microbiology , Xylenes/chemistryABSTRACT
Two novel polyketides, bis-7-O-8' '.8-O-7' '- and bis-7-O-7' '. 8-O-8' '-zinniol (2 and 3, respectively) were isolated from the organic crude extract of culture filtrates from Alternaria tagetica. Both structures were determined on the basis of their spectroscopic data (IR, MS, (1)H NMR, (13)C NMR, and 2D NMR experiments) and confirmed by chemical synthesis. Zinniol (1) was isolated as a major component, and its (13)C NMR data was correctly assigned after careful analysis of data from its 2D NMR experiments (HMQC and HMBC).
