Flavonoid sulphates in the Umbelliferae

Harborne, Jeffrey B.; King, L. Carroll

doi:10.1016/0305-1978(76)90021-1

Cited by 34 publications

(17 citation statements)

References 8 publications

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“…One of the first sulfation procedures was reported by Harborne's group who used sulfamic acid in pyridine (Py), in reflux, to sulfate several flavonoids with 3′‐hydroxyl (for example, quercetin, diosmetin, luteolin) (Section in Table ) . This method allowed the introduction of a sulfate group through a pyridinium sulfamate intermediate, in the least acidic position, the 3′‐position, as exemplified in Figure for sulfation of quercetin to quercetin 3′‐sulfate ( 1 ).…”

Section: Sulfation Methodsmentioning

confidence: 99%

“…This method allowed the introduction of a sulfate group through a pyridinium sulfamate intermediate, in the least acidic position, the 3′‐position, as exemplified in Figure for sulfation of quercetin to quercetin 3′‐sulfate ( 1 ). However, 3′‐monosulfated flavonoids with small amounts of other monosulfates and disulfates were obtained, leading to a complex mixture that was very difficult to purify . This method had little utility in the synthesis of plant metabolites since the most frequently found positions of the sulfate group in natural compounds are the 3‐ and/or 7‐positions…”

Section: Sulfation Methodsmentioning

confidence: 99%

“…More than 150 naturally occurring sulfated flavonoids were reported so far, mostly within the flavonol and flavone subclasses. Given the great amount of distribution of sulfated flavonoids in plants that grow in aquatic habitats, the sulfation of flavonoids seems to represent an ecological adaptation . On the other hand, sulfated flavonoids seem to have an important role in copigmentation; due to their increased water solubility, they form stable molecular complexes with polyphenolic pigments, such as anthocyanins, thus contributing to a strong intensification of the natural coloration .…”

Section: Introduction: Nature As An Inspirationmentioning

confidence: 99%

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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: Sulfation Methodsmentioning

confidence: 99%

Section: Sulfation Methodsmentioning

confidence: 99%

Section: Introduction: Nature As An Inspirationmentioning

confidence: 99%

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

2013

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“…Conjugation of natural products (including flavonoids) and xenobiotics as either sulfates or glucuronides is a welldocumented metabolic pathway in mammalian species (11,12). Furthermore, sulfation of flavonoids has been shown to occur in plant systems (13,14). However, while glycosylation by microorganisms is not a common pathway (8), sulfation by microbial systems is extremely rare.…”

Section: Resultsmentioning

confidence: 99%

Aromatic hydroxylation and sulfation of 5-hydroxyflavone by Streptomyces fulvissimus

Ibrahim

Abul-Hajj

1989

Appl Environ Microbiol

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The conversion of 5-hydroxyflavone by various microorganisms was studied. Among them, Streptomyces fulvissimus was the sole microbe which produced a new polar metabolite from 5-hydroxyflavone in addition to 5,4'-dihydroxyand 5,3',4'-trihydroxyflavone. The structure of this polar metabolite was determined to be 5,4'-dihydroxyflavone-4'-sulfate on the basis of mass, infrared, and nuclear magnetic resonance spectroscopies. These results demonstrate that S. fulvissimus catalyzes sulfation at the 4' position of 5,4'-dihydroxyflavone.

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“…20 defatted gm were ground in a blender containing ETOH, another the 20 gm of defatted extract were ground at high speed in a blender and extracted with 85% MEOH at room temperature overnight. Determination of flavonoid by ethanolic extract (F 1) according to (Boham and Kocipai, 1974), for estimation by the methanolic extract (F 2) according to Harbone and King (1976) and Singab (1995). The preliminary analysis of the flavonoid extracts employed two-dimensional TLC (Thin layer chromatography).…”

Section: Estimation Of Flavonoidmentioning

confidence: 99%

Flavonoids and isoenzymes as chemotaxonomic markers in Cleome L.(Cleomaceae Bercht. & J.Presl)

Kasem¹,

Fatahy²

2016

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These studies were conducted on the twoflavonoid compounds of quercetin and kaempferol in addition electrophoretic studies of esterase and peroxidase isoenzymes by SDS-polyacrylamide gel electrophoresisfor five CleomeL. species. Extraction of these flavonoids was carried out using 90% ethanol and 85% methanol. Identification and quantification of quercetin and kaempferol was done using thin Layer chromatography (TLC) and further augmented using high performance liquid chromatography (HPLC) and then isolated,purified and identified using melting point (M.P.) and infrared spectroscopy (IR).eightquercetinand seven kaempferol compounds are isolated and identified with different percentages. Electrophoretic patterns of two isoenzymes ofesterases (Est) and peroxidases (Prx) considered a good taxonomicmarker techniques. A total 45 esterase and peroxidase bands obtained scanning the gels. The highest combined esterase and peroxidase bands (13 bands) are found in C.scaposa DCwhereasthe lowest seven bands are recorded in C. paradoxa B.BR.35 obtained data of two flavonoid compounds and two isoenzymeswere subjected to numerical analysis which separated the studied species into two groups, the first has C.gynandra. and C. viscosa L., the second group included three species of C. scaposa DC, C. brachycarpa . and C. paradoxa.

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Flavonoid sulphates in the Umbelliferae

Cited by 34 publications

References 8 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

Aromatic hydroxylation and sulfation of 5-hydroxyflavone by Streptomyces fulvissimus

Flavonoids and isoenzymes as chemotaxonomic markers in Cleome L.(Cleomaceae Bercht. & J.Presl)

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