Toussaintines A–E: Antimicrobial indolidinoids, a cinnamoylhydrobenzofuranoid and a cinnamoylcyclohexenoid from Toussaintia orientalis leaves

• Published in: Phytochemistry (Oxford) Vol. 72; no. 14; pp. 1826 - 1832
• Main Authors: Samwel, Stephen, Odalo, Josiah O., Nkunya, Mayunga H.H., Joseph, Cosam C., Koorbanally, Neil A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.10.2011; Elsevier
• Subjects: Annonaceae; Annonaceae - chemistry; Anti-Infective Agents - pharmacology; Antimicrobial; Benzofurans - pharmacology; Biochemistry & Molecular Biology; Biological and medical sciences; Candida albicans - drug effects; Chemical constitution; Cinnamates - pharmacology; Cyclohexanones - pharmacology; Disaccharides - pharmacology; Escherichia coli - drug effects; Fundamental and applied biological sciences. Psychology; Hydrobenzofuranoid; Indoles - pharmacology; Indolidinoids; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Extracts - chemistry; Plant Leaves - chemistry; Plant physiology and development; Plant Sciences; Science & Technology; Staphylococcus aureus - drug effects; Toussaintia orientalis; Toussaintines; Antimicrobial; Toussaintia orientalis; Annonaceae; Toussaintines; Hydrobenzofuranoid; Indolidinoids; VIRUS; BARK; MONODORA; GENUS; PRENYLINDOLES; UVARIA; SPONGE; BIOACTIVE CONSTITUENTS; Chemical structure; Plant leaf; Antimicrobial agent; Dicotyledones; Angiospermae; Plant origin; Spermatophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2011.05.010

The indolidinoids 1– 3, the cinnamoyl hydrobenzofuranoid 4 and the cyclohexenoid 5 have been isolated as antibacterial and antifungal constituents of Toussaintia orientalis (Annonaceae) leaves and the structures established on analysis of spectroscopic data. [Display omitted] ► Metabolites of unprecedented indolidinoid, benzofuranoid and cyclohexanoid systems. ► Metabolites derived from leaves of near extinct Toussaintia orientalis (Annonaceae). ► Metabolites formed through mixed biosynthesis of N-cinnamoyl and tetraketide units. ► Metabolites with antibacterial (MIC 20–5 μg/mL) and antifungal activity at 40 μg/mL. Toussaintine A ( N-cinnamoyl-5,6-dehydro-4-hydroxyindolidin-2,7-dione), toussaintine B ( N-cinnamoyl-5,6-dehydro-4,7-dihydroxyindolidin-2-one), toussaintine C ( N-cinnamoyl-5,6-dehydro-4-hydroxyindolidin-7-one), toussaintine D ( N-cinnamoyl-2-amino-4-hydroxy-7-oxo-2,3,8,9-tetrahydrobenzofuran) and toussaintine E ( N-cinnamoyl-1-acetoxymethyl-2-amino-1-hydroxycyclox-5-en-4-one) were isolated as antibacterial and antifungal constituents of the leaves of Toussaintia orientalis Verdc. (Annonaceae) and their structures established from analysis of spectroscopic data . The compounds belong to a series of variously cyclized aminocinnamoyl tetraketide derivatives, showing the importance of rarely occurring Annonaceae species as sources of structurally diverse natural products.