Flavonoids from Brickellia glutinosa

Goodwin, Robert S.; Rosler, Karl-Heinz A.; Mabry, Tom J.; Varma, Shambhu D.

doi:10.1021/np50034a026

Cited by 12 publications

(2 citation statements)

References 9 publications

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“…Many flavonoids are recognized as aldose reductase inhibitors; this enzyme converts D‐glycose and D‐galactose into sorbitol and is of great importance in the diabetic and galactosemic cataract . Few studies can be found concerning sulfated flavonoids.…”

Section: Emerging Bioactive Sulfated Phenolic Small Moleculesmentioning

confidence: 99%

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

2013

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Nature uses sulfation of endogenous and exogenous molecules mainly to avoid potential toxicity. The growing importance of natural sulfated molecules, as modulators of a number of physiological and pathological processes, has inspired the synthesis of non-natural sulfated scaffolds. Until the 1990s, the synthesis of sulfated small molecules was almost restricted to derivatives of flavonoids and aimed mainly at structure elucidation and plant biosynthesis studies. Currently, the synthesis of this type of compounds concerns structurally diverse scaffolds and is aimed at the development of potential drugs and/or exploitation of the biological effects of sulfated metabolites. Some important hit compounds are emerging from sulfated flavonoids and other polyphenols mainly as anticoagulant and antiviral agents. When compared with polymeric macromolecules such as heparins, sulfated small molecules could be of value in therapeutics due to their hydrophobic nature that can contribute to improve the bioavailability. This review highlights the synthetic approaches that were applied to obtain monosulfated or polysulfated phenolic small molecules and compiles the diverse biological activities already reported for this type of derivatives. Toxicity and pharmacokinetic parameters of this emerging class of derivatives will also be considered, emphasizing their value for therapeutic applications.

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Section: Emerging Bioactive Sulfated Phenolic Small Moleculesmentioning

confidence: 99%

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

2013

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“…Inhibition of aldose reductase has been shown to reverse these biochemical changes and has proven effective in delaying and even preventing several diabetic complications (Yabe-Nishimura 1998). During the last three decades, a variety of structurally diverse compounds have been reported to have aldose reductase inhibitory activity in-vitro against rat or bovine lens aldose reductases; these include¯avonoids (Varma 1986), hydantoin derivatives (Varma & Kinoshita 1976), oxazoline-1-acetic acid derivatives (Inagaki et al 1982), pyrimidine acetic acid derivatives (DeRuiter et al 1986), quinazoline acetic acid derivatives (Ellingboe et al 1990) and extracts of natural products (Goodwin et al 1984;Terashima et al 1990;Malamas & Miller 1991). Table 1 lists some aldose reductase inhibitors (ARIs) that have been tested in clinical trials; none is being marketed either because of side-effects (Spielberg et al 1991) or because of the lack of appreciable clinical effect (Engerman & Kern 1993).…”

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Rabbit Corneal and Conjunctival Permeability of the Novel Aldose Reductase Inhibitors: N-{[4-(Benzoylamino)phenyl] sulphonyl}glycines and N-Benzoyl-N-phenylglycines

Kompella

Sunkara

Thomas

et al. 1999

Journal of Pharmacy and Pharmacology

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Corneal and conjunctival permeability has been investigated for novel aldose reductase inhibitors (ARIs) of the N{[4-(benzoylamino)phenyl]sulphonyl}glycine (benzoylaminophenylsulphonylglycine) and N-benzoyl-N-phenylglycine (benzoylphenylglycine) series, compounds developed for prevention of cataract formation in diabetic subjects. Six benzoylaminophenylsulphonylglycines were synthesized with modifications either of the phenyl group or of the glycine structure and three benzoylphenylglycines were synthesized with modification in the phenyl group of the benzoyl moiety. Transport of ARIs in the mucosal to serosal direction was evaluated across rabbit cornea and conjunctiva bathed in glutathione-bicarbonate Ringer's solution maintained at pH 7.4 and 37 degrees C. The permeability coefficients of the novel ARIs across cornea and conjunctiva ranged from 1.87 to 8.95 x 10(-6) cm s(-1) and from 4.6 to 19.15 x 10(-6) cm s(-1), respectively. The ratio of corneal to conjunctival permeability ranged from 0.12 to 0.79. The calculated log partition coefficient (log P) values for the ARIs were in the range 0.84 to 2.78. The log distribution coefficients (log D) were in the range -2.87 to -0.89. There was no apparent relationship between log P or log D and the permeability coefficients of the ARIs for either tissue. Cornea was more resistant to ARI transport than was conjunctiva. Substitution of a phenyl group for hydrogen in the glycine methylene group reduced the permeability coefficient. Permeability coefficients were different for different stereoisomers. Compared with the permeability coefficient of benzoylaminophenylsulphonylglycine, that of 4-fluorobenzoylaminophenylsulphonylglycine was lower in the cornea but similar in the conjunctiva. In both tissues, the permeability coefficient of 2-nitrobenzoylaminophenylsulphonylglycine was less than that of 4-nitrobenzoylaminophenylsulphonylglycine. There was no significant difference between the permeability coefficients of 3-nitro- and 4-nitrobenzoylphenylglycines through either tissue and the permeability coefficients of these compounds were greater than that of the more lipophilic 4-methylbenzoylphenylglycine. The lack of dependence of the permeability coefficients on log P or log D and the different permeabilities of stereoisomers imply the existence of specialized transport processes for the ARIs tested in this study.

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Flavones and flavonols

Wollenweber¹,

Jay²

1988

The Flavonoids

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Flavonoids from Brickellia glutinosa

Abstract: In a continuation of a phytochemical investigation of the genus Brickellia (Tribe Eupatorieae, Subtribe Alomiinae, Family Compositae) (1-6), we now report the isolation and characterization

Cited by 12 publications

References 9 publications

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

Rabbit Corneal and Conjunctival Permeability of the Novel Aldose Reductase Inhibitors: N-{[4-(Benzoylamino)phenyl] sulphonyl}glycines and N-Benzoyl-N-phenylglycines

Flavones and flavonols

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