Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens
TL;DR: A crude MeOH extract of Syzygium aromaticum (clove) exhibited preferential growth-inhibitory activity against Gram-negative anaerobic periodontal oral pathogens, including Porphyromonas gingivalis and Prevotella intermedia.
Abstract: A crude MeOH extract of Syzygium aromaticum (clove) exhibited preferential growth-inhibitory activity against Gram-negative anaerobic periodontal oral pathogens, including Porphyromonas gingivalis and Prevotella intermedia. By means of bioassay-directed chromatographic fractionation, eight active compounds were isolated from this extract and were identified as 5,7-dihydroxy-2-methylchromone 8-C-beta-D-glucopyranoside, biflorin, kaempferol, rhamnocitrin, myricetin, gallic acid, ellagic acid, and oleanolic acid, based on spectroscopic evidence. The antibacterial activity of these pure compounds was determined against Streptococcus mutans, Actinomyces viscosus, P. gingivalis, and P. intermedia. The flavones, kaempferol and myricetin, demonstrated potent growth-inhibitory activity against the periodontal pathogens P. gingivalis and P. intermedia.
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TL;DR: The volatile oils of black pepper, clove, and thyme exhibited considerable inhibitory effects against all the organisms under test while their major components demonstrated various degrees of growth inhibition.
Abstract: The volatile oils of black pepper [Piper nigrum L. (Piperaceae)], clove [Syzygium aromaticum (L.) Merr. & Perry (Myrtaceae)], geranium [Pelargonium graveolens L'Herit (Geraniaceae)], nutmeg [Myristica fragrans Houtt. (Myristicaceae), oregano [Origanum vulgare ssp. hirtum (Link) Letsw. (Lamiaceae)] and thyme [Thymus vulgaris L. (Lamiaceae)] were assessed for antibacterial activity against 25 different genera of bacteria. These included animal and plant pathogens, food poisoning and spoilage bacteria. The volatile oils exhibited considerable inhibitory effects against all the organisms under test while their major components demonstrated various degrees of growth inhibition.
4,014 citations
Cites background from "Compounds from Syzygium aromaticum ..."
...…with previously reported studies on the volatile oils of P. nigrum (Deans & Ritchie 1987; Ouattara et al. 1997), S. aromaticum (Deans et al. 1995; Cai & Wu 1996; Hao et al. 1998; Smith-Palmer et al. 1998), P. graveolens (Pattnaik et al. 1996), M. fragrans, O. vulgare (Kivanc & Akgül 1986) and…...
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...…in medical procedures and applications in the cosmetic, food (Ueda et al. 1982; Shelef 1983; Jay & Rivers 1984; Gallardo et al. 1987; Baratta et al. 1998a,b; Youdim et al. 1999) and pharmaceutical industries (Janssen et al. 1988; Pélissier et al. 1994; Shapiro et al. 1994; Cai & Wu 1996)....
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TL;DR: A review of phenolic and polyphenolic compounds can be found in this article, which summarizes both the synthetic and natural phenolic antioxidants, emphasizing their mode of action, health effects, degradation products and toxicology.
1,800 citations
TL;DR: Qualitative phytochemical tests, thin layer chromatography and TLC-bioautography of certain active extracts demonstrated the presence of common phytocompounds in the plant extracts including phenols, tannins and flavonoids as major active constituents.
1,247 citations
Cites result from "Compounds from Syzygium aromaticum ..."
...Our phytochemical analyses are in agreement with the reports of other workers (Iyengar, 1985; Chopra et al., 1992; Bruneton, 1995; Harborne and Baxter, 1995; Cai and Wu, 1996)....
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TL;DR: The distribution of ka Kempferol in the plant kingdom and its pharmacological properties are reviewed and the pharmacokinetics and safety of kaempferol are analyzed to help understand the health benefits of kaEMPferol-containing plants and to develop this flavonoid as a possible agent for the prevention and treatment of some diseases.
Abstract: Epidemiological studies have revealed that a diet rich in plant-derived foods has a protective effect on human health. Identifying bioactive dietary constituents is an active area of scientific investigation that may lead to new drug discovery. Kaempferol (3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one) is a flavonoid found in many edible plants (e.g. tea, broccoli, cabbage, kale, beans, endive, leek, tomato, strawberries and grapes) and in plants or botanical products commonly used in traditional medicine (e.g. Ginkgo biloba, Tilia spp, Equisetum spp, Moringa oleifera, Sophora japonica and propolis). Some epidemiological studies have found a positive association between the consumption of foods containing kaempferol and a reduced risk of developing several disorders such as cancer and cardiovascular diseases. Numerous preclinical studies have shown that kaempferol and some glycosides of kaempferol have a wide range of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial, anticancer, cardioprotective, neuroprotective, antidiabetic, anti-osteoporotic, estrogenic/antiestrogenic, anxiolytic, analgesic and antiallergic activities. In this article, the distribution of kaempferol in the plant kingdom and its pharmacological properties are reviewed. The pharmacokinetics (e.g. oral bioavailability, metabolism, plasma levels) and safety of kaempferol are also analyzed. This information may help understand the health benefits of kaempferol-containing plants and may contribute to develop this flavonoid as a possible agent for the prevention and treatment of some diseases.
987 citations
Additional excerpts
...Porphyromonas gingivalis Kaempferol [711]...
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...Syzygium aromaticum Myrtaceae Kaempferol [711]...
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TL;DR: The chemical composition and biological effects of clove essential oil are addressed, and new results from GC/MS analysis and a study of its antimicrobial activity against a large number of multi‐resistant Staphylococcus epidermidis isolated from dialysis biomaterials are included.
Abstract: The essential oil extracted from the dried flower buds of clove, Eugenia caryophyllata L. Merr. & Perry (Myrtaceae), is used as a topical application to relieve pain and to promote healing and also finds use in the fragrance and flavouring industries. The main constituents of the essential oil are phenylpropanoids such as carvacrol, thymol, eugenol and cinnamaldehyde. The biological activity of Eugenia caryophyllata has been investigated on several microorganisms and parasites, including pathogenic bacteria, Herpes simplex and hepatitis C viruses. In addition to its antimicrobial, antioxidant, antifungal and antiviral activity, clove essential oil possesses antiinflammatory, cytotoxic, insect repellent and anaesthetic properties. This short review addresses the chemical composition and biological effects of clove essential oil, and includes new results from GC/MS analysis and a study of its antimicrobial activity against a large number of multi-resistant Staphylococcus epidermidis isolated from dialysis biomaterials.
831 citations
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TL;DR: A new generation of more specific antibacterial agents that interfere with attachment to pellicle can be developed, it is hard to predict, however, that they will affect gingivitis, at least until there is more information on what specific organisms should be targeted.
Abstract: There has been a vigorous search for many years for chemical agents that could supplement or even supplant patient-dependent mechanical plaque control and thus reduce or prevent oral disease. 5 categories of agents or approaches have been considered: (1) broad spectrum antiseptics, (2) antibiotics aimed at specific bacteria, (3) single or combinations of enzymes that could modify plaque structure or activity, (4) non-enzymatic dispersing or modifying agents and (5) agents that could affect bacterial attachment. The success of these approaches can be evaluated clinically by the use of standard scoring methods for measuring plaque and gingivitis and their safety established by soft tissue and microbiologic examination. Antiseptic agents have received the bulk of the attention over the years. At present, only 2 antiseptics, the bis-biguanide, chlorhexidine gluconate (Peridex) and a combination of phenol related essential oils (Listerine), have developed sufficient supporting data in 6-month (or longer) studies to gain the approval of the Council On Dental Therapeutics of the American Dental Association. On the basis of short-term studies, cetylpyridinium chloride, zinc and copper salts, sanguinarine and octenidine warrant continued study as does stannous fluoride at an appropriate concentration. On the basis of current research, a new generation of more specific antibacterial agents that interfere with attachment to pellicle can be developed. It is hard to predict, however, that they will affect gingivitis, at least until there is more information on what specific organisms should be targeted.
322 citations
TL;DR: Extracts of green tea and black tea, and polyphenol mixtures showed appreciable inhibition in the synthesis of insoluble glucan, and theaflavin and its mono- and digallates had potent inhibitory activities at concentrations of 1-10 mM against GTF.
Abstract: In the course of our studies on the development of anti-plaque agents for prevention of dental caries, we investigated effects of some of tea preparations and their individual components on the glucan synthesis catalyzed by glucosyltransferase (GTF) from Streptococcus mutans. Extracts of green tea and black tea, and polyphenol mixtures showed appreciable inhibition in the synthesis of insoluble glucan. Among the components isolated from tea infusions, theaflavin and its mono- and digallates had potent inhibitory activities at concentrations of 1-10 mM against GTF. (+)-Catechin, (-)-epicatechin and their enantiomers had moderate inhibitory activities at these concentrations, while galloyl esters of (-)-epicatechin, (-)-epigallocatechin and (-)-gallocatechin had increased inhibitory activities.
173 citations
TL;DR: Ether extract of this crude drug showed a relatively marked antibacterial activity against Gram-positive bacteria and the structure of one of these was elucidated as 2( S), 2′, 5, 6′, 7-tetrahydroxyflavanone.
Abstract: Ogon, an important Chinese crude drug (the dried roots of SCUTELLARIA BAICALENSIS G EORGI), is listed in ancient Chinese herbals and is used in the treatment of a number of diseases. Ether extract of this crude drug showed a relatively marked antibacterial activity against Gram-positive bacteria. Fractionation of the extract accompanied by the bioassay led to the isolation of active principles. The structure of one of these was elucidated as 2( S), 2′, 5, 6′, 7-tetrahydroxyflavanone.
154 citations
TL;DR: Bioassay-directed fractionation of Glycyrrhiza glabra L. var.
Abstract: Bioassay-directed fractionation of Glycyrrhiza glabra L. var. typica resulted in the isolation and characterization of glabridin (I), glabrol (2), glabrene (3), 3-hydroxyglabrol (4), 4'-O-methylglabridin (5), 3'-methoxyglabridin (6), formononetin (7), phaseollinisoflavan (8), hispaglabridin A (9), hispaglabridin B (13), salicylic acid and O-acetyl salicylic acid. Of these, hispaglabridin A, hispaglabridin B, 4'-O-methylglabridin, glabridin, glabrol and 3-hydroxyglabrol possess significant antimicrobial activity in vitro; hispaglabridin A, hispaglabridin B, 3'-methoxyglabridin, 4'-O-methylglabridin 3-hydroxyglabrol, phaseollinisoflavan, salicylic acid, and O, acetyl salicylic acid are newly found in Glycyrrhiza sp.; and hispaglabridin A, hispaglabridin B, 3'-methoxyglabridin, 4'-O-methylglabridin, and 3-hydroxyglabrol are new to the literature and their structures are proposed herein.
130 citations
TL;DR: The methanolic extract of Swartzia polyphylla DC had antibacterial activity against cariogenic bacteria, the mutans Streptococci, and this effect was not detected on isoflavone derivatives.
Abstract: The methanolic extract of Swartzia polyphylla DC. heartwood had antibacterial activity against cariogenic bacteria, the mutans Streptococci. The chromatographic purification of the extract afforded seven flavonoids. Among them, three known isoflavanones, dihydrobiochanin A, ferreirin and darbergioidin, and one new isoflavanone, 5, 2', 4'-trihydroxy-7-methoxyisoflavanone (dihydrocajanin) had potent antibacterial activity against cariogenic bacteria. This effect was not detected on isoflavone derivatives. A comparative antibacterial study of various flavonoids was further performed, and their structure-activity relationship was discussed.
115 citations