Untargeted GC-MS metabolomics to identify and classify bioactive compounds in Combretum platypetalum subsp. oatesii (Rolfe) Exell (Combretaceae).

INTRODUCTION: Combretum platypetalum is used in traditional African healing practices against different infections. Unfortunately, no scientific knowledge of its phytochemical composition exists, except for the isolation of two compounds from the leaves. Scientific study has been limited to the leaves only, despite the applications of stems and roots in traditional medicine practice and natural product drug discovery programs. OBJECTIVE: Omics was applied to identify and classify different volatile and semivolatile bioactive compounds in the leaf, stem, and root parts of C. platypetalum. The thermal stability of the plant constituents at 60-65°C extraction temperature by Soxhlet and maceration at room temperature on the type, class, and concentration of compounds in the leaf was further investigated. METHOD: A GC-MS untargeted metabolomics approach, automated deconvolution by the Automated Mass Spectral Deconvolution and Identification System (AMDIS) for GC-MS data, preprocessing by Metab R, and multivariate statistical data analysis were employed in this study. RESULTS: A total of 97 phytoconstituents, including 17 bioactive compounds belonging to the terpenoids, flavonoids, long-chain fatty acids, and other unclassified structural arrangements distributed across C. platypetalum, were identified for the first time. A correlation (r = 0.782; P = 0.000) between Soxhlet and maceration extraction methods relative to resolved chromatographic peak areas of metabolites was established. CONCLUSION: Findings corroborate the reported bio-investigation of its leaf extracts, its traditional uses, and previous findings from the Combretum genus. The results substantiate the possible applications of C. platypetalum in natural product drug discovery and provide a guide for future investigations.

A phenanthridin-6(5H)-one derivative and a lanostane-type triterpene with antibacterial properties from Anonidium mannii (Oliv). Engl. & Diels (Annonaceae).

The chemical investigation of Anonidium mannii root extract by column chromatography techniques led to the isolation of eight compounds among which two previously unreported compounds; a lanostane-type triterpene, lanosta-7,9(11),23-triene-3ß,15α-diol 1 and an alkaloid, 9-hydroxy-8-methoxyphenanthridin-6(5H)-one 2 along with six known compounds: lanosta-7,9(11),24-triene-3ß,21-diol 3, oxoanolobine 4, 3, 4-dihydroxybenzoic acid 5, stigmasterol 6, ß-sitosterol 7 and 3-O-ß-D-glucopyranosyl-ß-stigmasterol 8. Their structures were established from spectral data, mainly HR-ESIMS, 1 D and 2 D NMR and by comparison with literature data. The crude root and stem bark extracts (AMR and AMB) and the isolated compounds (1-8) were tested against nine Gram-negative bacteria using rapid p-iodonitrotetrazolium chloride ≥97% (INT) microdilution technique. It was found that AMR, AMB and compound 5 were active against the nine tested bacteria with MIC values ranging from 64 to 1024 µg/mL. Compounds 1-4 had selective antibacterial activities whilst 6-8 were not active.

Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars.

The first heteroatom-based dienophile cycloadditions to cross-conjugated alkenes ([n]dendralenes) are reported. Nitroso-dienophiles undergo smooth single and double Diels-Alder additions to the parent dendralenes with orientational regio- and stereoselectivity and, notably, with reactivity that depends upon the parity of the [n]dendralene. The first crystal structure of a cross-conjugated hexaene is reported. Vasella's nitroso-sugar reagent gives a highly enantiomerically enriched double cycloadduct with [3]dendralene. This bicyclic oxazine is successively dihydroxylated and then ring-opened to form a branched chain diamino tetrol.

Practical synthesis of the dendralene family reveals alternation in behavior.

Back from obscurity: The practical synthesis of the first six members of the fundamental class of acyclic branched oligoalkenes has been achieved. The syntheses allow access to the target compounds on multigram scales in good yields. Members of the family with even numbers of double bonds are significantly more stable than those with odd numbers (see picture), and exhibit different chemical reactivities in Diels-Alder reactions.

Antimicrobial flavonoids from Bolusanthus speciosus.

A new isoflavanone namely 3,5,7,2',4'-pentahydroxy-8,3'-di(gamma,gamma-dimethylallyl)isoflavanone (bolusanthin II) and four new pterocarpans identified as 3-hydroxy-6',6'-dimethylpyrano[2',3':1,2] [6a R,11a R]-8,9-methylenedioxypterocarpan (bolucarpan A), 3-hydroxy-6',6'-dimethyl-4',5'-dihydropyrano[2',3':1,2][6a R,11a R]- 8,9-methylenedioxypterocarpan (bolucarpan B), 3-hydroxy-9-methoxy-6',6'-dimethylpyrano-[2',3':1,2][6a R,11a R]-pterocarpan (bolucarpan C) and 3-hydroxy-9-methoxy-6',6'-dimethyl-4',5'-dihydropyrano[2',3':1,2][6a R,11a R]-pterocarpan (bolucarpan D) and three known isoflavonoids were isolated from the methanolic extracts of the root bark, while eight known isoflavonoids were isolated from the stem bark of Bolusanthus speciosus. These compounds showed antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Saccharomyces cerevisiae and Candida mycoderma using the agar overlay technique.

Erythrinaline alkaloids and antimicrobial flavonoids from Erythrina latissima.

The seed pods of Erythrina latissima yielded erysotrine, erysodine, syringaresinol, vanillic acid, a new erythrina alkaloid, (+)-10,11-dioxoerysotrine, which was lethal to brine shrimp and 2-(5'-hydroxy-3'-methoxy phenyl)-6-hydroxy-5-methoxybenzofuran, which showed strong antimicrobial activity against the yeast spores, Gram-positive and Gram-negative bacteria. The root bark gave four known pterocarpans which showed moderate to strong antifungal activity against the yeast spores and three known flavonoids showed antimicrobial activity against all test microorganisms.