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Bioassay-guided isolation of antimicrobial benzopyrans and phloroglucinol derivatives from Hypericum species.

Recently the crude methanol extracts of six Hypericum species were analysed against a panel of microorganisms and it was found that H. caprifoliatum Cham. & Schlecht., H. myrianthum Cham. & Schlecht. and H. polyanthemum Klotzsch ex Reichardt were the most active. This paper reports the activity of the hexane, chloroform and methanol fractions of these plants as well as the activity of some isolated compounds against Staphylococcus aureus determined by bioautographic procedures.

Anti-Bacterial Agents↗

New prenylated bi- and tricyclic phloroglucinol derivatives from Hypericum papuanum.

Five new prenylated tricyclic and three new bicyclic acylphloroglucinol derivatives have been isolated by bioactivity-guided fractionation of the petroleum ether extract of the dried aerial parts of Hypericum papuanum. The tricyclic compounds (1--5) were named papuaforins A--E. The bicyclic compounds were isolated together with their corresponding tautomers and were named hyperguinones A and B (6/6a,7/7a) and hyperpapuanone (8/8a), respectively. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments, as well as mass spectrometry. Furthermore, the cytotoxicity toward KB nasopharyngeal carcinoma cells and the antibacterial activity of the isolated compounds were determined.

Anti-Bacterial Agents↗

Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).

The ethyl acetate soluble fraction of hops (Humulus lupulus) showed potent inhibitory activity on the production of nitric oxide (NO) induced by a combination of LPS and IFN-gamma. Four known prenylflavonoids (1-4) and a new prenylflavonoid (5), hulupinic acid (6), lupulone (7), and its six new derivatives (8-13) were isolated from the active fraction. The structures were determined on the basis of physiochemical properties and spectroscopic analysis. Their inhibitory activities on the production of NO in macrophage RAW 264.7 cells were examined.

Animals↗

Inhibition of tumor-promoter-enhanced 3H-choline incorporation into cellular phospholipids by phloroglucinol derivatives from Mallotus japonicus.

The MeOH and CHCl3 extracts of the pericarps of Mallotus japonicus showed potential anti-tumor-promoter activity. Seven constituents of the CHCl3 extract and two derivatives from the most abundant constituent, mallotojaponin, markedly inhibited the incorporation of 3H-choline into phospholipids of C3H101/2 cells enhanced by 12-O-tetradecanoylphorbol-13-acetate (TPA), a potent tumor promoter.

Anticarcinogenic Agents↗

Novel detection of formylated phloroglucinol compounds (FPCs) in the wound wood of Eucalyptus globulus and E. nitens.

This study characterized the chemical responses of Eucalyptus globulus and Eucalyptus nitens to artificial inoculation with a basidiomycete decay fungus. Nine-year-old trees responded to mechanical wounding or inoculation with the decay fungus by producing new wound wood characterized by the presence of dark extractives 17 months after wounding. Analysis of crude wound wood extracts by HPLC coupled to negative ion electrospray mass spectrometry revealed the presence of a complex mixture of many unidentified formylated phlorglucinol compounds (FPCs), in addition to a diverse range of other polyphenolic compounds (hydrolyzable tannins, proanthocyanidins, flavanone glycoside, stilbene glycosides). Prior to this study, FPCs have only been reported from leaves and buds of Eucalyptus spp. Unequivocal evidence for the presence of macrocarpal A and B, and sideroxylonal A and B in the crude extracts was obtained, as well as evidence for a wide range of as yet unreported FPCs. Subsequent preliminary in vitro fungal and bacterial bioassays did not support an antimicrobial role for FPCs in host-pathogen interactions in eucalypts.

Basidiomycota↗