ABSTRACT
From the methanol extract of the stem bark of Ficus exasperata, a new sphingolipid named Ficusamide, (2S,3S,4R,11E)-2-[(2',3'-dihydroxyhexacosanoylamino)]-11-octadecene-1,3,4-triol (1), along with three known furanocoumarins, (S)-(-) oxypeucedanin hydrate (2), (R)-(+) oxypeucedanin hydrate (3), bergapten (5-methoxypsoralen) and six other known compounds, were isolated. Their structures were characterized basing on spectroscopic methods and chemical evidence. Compounds (1-3) were analyzed for their antimicrobial activity. Ficusamide (1) showed wick activity (minimal inhibitory concentration (MIC)=312.5 µg/mL) against Escherichia coli, while the furanocoumarins (2) and (3) showed significant activity (MIC=9.76 µg/mL) against Bacillus cereus, Candida albicans and Microsporum audouinii.
Subject(s)
Ficus/chemistry , Furocoumarins/pharmacology , Sphingolipids/pharmacology , Bacillus cereus/drug effects , Candida albicans/drug effects , Escherichia coli/drug effects , Furocoumarins/chemistry , Furocoumarins/isolation & purification , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Microsporum/drug effects , Molecular Structure , Plant Bark/chemistry , Plant Extracts/pharmacology , Spectrometry, Mass, Electrospray Ionization , Sphingolipids/chemistry , Sphingolipids/isolation & purificationABSTRACT
Two new friedelane-type triterpenes named 12alpha-hydroxyfriedelane-3,15-dione and 3beta-hydroxyfriedelan-25-al, together with six known compounds were isolated from the stems of Drypetes paxii Hutch. (Euphorbiaceae). Their structures were established on the basis of conventional 1 dimensional (1D) NMR methods, 2D shift-correlated NMR experiments and mass spectra. The five friedelane-type triterpene derivatives and one olean-12-ene triterpene saponin were tested for antimicrobial activity against some gram-positive and gram-negative bacteria, and they appeared to be modestly active.
Subject(s)
Anti-Bacterial Agents/chemistry , Triterpenes/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Disk Diffusion Antimicrobial Tests , Euphorbiaceae/chemistry , Magnetic Resonance Spectroscopy , Molecular Conformation , Plant Stems/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacologyABSTRACT
The air-dried stems and ripe fruit of Drypetes inaequalis Hutch. (Euphorbiaceae) were studied. Four triterpene derivatives, characterized as lup-20(29)-en-3beta,6alpha-diol, 3beta-acetoxylup-20(29)-en-6alpha-ol, 3beta-caffeoyloxylup-20(29)-en-6alpha-ol and 28-betad-glucopyranosyl-30-methyl 3beta-hydroxyolean-12-en-28,30-dioate along with 10 known compounds were isolated from the whole stems. One triterpene, characterized as 3alpha-hydroxyfriedelan-25-al along with six known compounds were isolated from the ripe fruit. Their structures were established on the basis of spectroscopic analysis and chemical evidence. The triterpenes were tested for antimicrobial activity against some Gram-positive and Gram-negative bacteria, and two of them appeared to be modestly active.
Subject(s)
Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Magnoliopsida/chemistry , Triterpenes/chemistry , Triterpenes/pharmacology , Anti-Infective Agents/isolation & purification , Fruit/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Stems/chemistry , Triterpenes/isolation & purificationABSTRACT
Condensation of 2-hydroxy-1-naphthalenecarboxylic acid with phloroglucinol afforded 9,11-dihydroxy-12H-benzo[a]xanthen-12-one (6). Construction of an additional dimethylpyran ring onto this skeleton, by alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement, gave access to 6-hydroxy-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (12) and 5-hydroxy-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (13), which were methylated into 6-methoxy-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (14) and 5-methoxy-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (15), respectively. Osmium tetroxide oxidation of 14 and 15 gave the corresponding (+/-)-cis-diols 16 and 17, which afforded the corresponding esters 18-21 upon acylation. Similarly, condensation of 2-hydroxy-1-naphthalenecarboxylic acid with 3,5-dimethoxyaniline gave 11-amino-9-methoxy-12H-benzo[a]xanthen-12-one (23) which was converted into 11-amino-9-hydroxy-12H-benzo[a]xanthen-12-one (24) upon treatment with hydrogen bromide in acetic acid. Alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement afforded 6-amino-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (25) and 5-amino-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (26). The new benzopyranoxanthone derivatives only displayed marginal antiproliferative activity when tested against L1210 and KB-3-1 cell lines. The only compounds found significantly active against L1210 cell line, 16 and 20, belong to the benzo[a]pyrano[3,2-h]xanthen-7-one series, which possess a pyran ring fused angularly onto the xanthone basic core.
Subject(s)
Acronine/analogs & derivatives , Acronine/chemistry , Benzo(a)pyrene/chemistry , Xanthones/chemistry , Xanthones/pharmacology , Acronine/chemical synthesis , Acronine/pharmacology , Animals , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Benzo(a)pyrene/analogs & derivatives , Benzo(a)pyrene/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Drug Screening Assays, Antitumor , Humans , Inhibitory Concentration 50 , Mice , Molecular Structure , Xanthones/chemical synthesisABSTRACT
Various 2,2,5,11-tetramethyl- and 2,2,5,6,11-pentamethyl-2,6-dihydropyrano[3,2-b]carbazole derivatives were synthesized by condensation of 3-methylbut-2-enal or 3-chloro-3-methylbut-1-yne with an appropriate hydroxycarbazole. These compounds associate the tricyclic system responsible for the intercalating properties of ellipticine related drugs, with the dimethylpyran pharmacophore of acronycine derivatives. The study of the biological properties of the new pyrano[3,2-b]carbazole derivatives was carried out in vitro on L1210 murine leukaemia cell line. The three (+/-)-cis-diol diesters 15, 16, and 18 were the most active compounds.
