Sulphated Flavonoids: Biosynthesis, Structures, and Biological Activities

Abstract

The great diversity of enzymatic reactions in plant secondary metabolism allows the continuous discovery of new natural compounds and derivatives. Flavonoids, for example, can be found as aglycone or as several sorts of glycosylated, acetylated, methylated, and sulphated derivatives. This review focuses on sulphated flavonoids, an uncommon group of flavonoid derivatives found in some plant families. This work presents a compilation of sulphated flavonoids and their natural sources reported in the literature. Biosynthetic aspects and biological activities have also been reviewed, showing that these particular kinds of natural compounds play an interesting role in plant metabolism, as well as being potential candidates for the development of new drugs.

Structural characterization of bioactive compounds in Cotula cinerea extracts by ultra‐high‐performance liquid chromatography with photodiode array and high‐resolution time‐of‐flight mass spectrometry detectors

“…From a taxonomic point of view, the presence of sulfated flavonoids in Cotula cinerea is in agreement with the fact that sulfated flavonoids are less common flavonoid derivatives found in some specific plant families such as Asteraceae to which Cotula cinereal belongs . Our findings are also in agreement with the fact that flavonoid sulfates were also reported to occur in species occurring in arid habitats such as the Moroccan Sahara region from which the studied Cotula cinerea sample was collected.…”

“…While the occurrence of phenolic acid derivatives and flavonoids has been previously reported, to the best of our knowledge, this is the first report of sulfated flavonoids in Cotula cinerea extracts. Given the various biological activities attributed to such compounds in the last decade, including anticoagulant, antiplatelet, antiviral, anti‐inflammatory, immunomodulatory and antitumor properties, their presence in this plant will obviously play an important positive role in its biological activities and will make this plant an open research area for further investigations. The biological activities observed for flavonoid sulfates have indeed amplified interest in investigation of sulfated bioactive polyphenols and particularly in the synthesis of sulfated molecules and the exploration of new sources of such interesting compounds.…”

Protocatechuic acid from chicory is bioavailable and undergoes partial glucuronidation and sulfation in healthy humans

“…Because glucuronidation and sulfation significantly impact the physiological properties of polyphenols such as the solubility, intestinal absorption, tissue distribution, and excretion, the health‐promoting activities of polyphenols in vivo might be partially related to their glucuronide and sulfate conjugates. Supporting this possibility, several glucuronide and sulfate conjugates of polyphenols have been documented to exert biological activities (Polycarpou et al, ; Teles, Souza, & Souza, ; Williamson, Kay, & Crozier, ). Our current study showed that protocatechuic acid undergoes partial glucuronidation and sulfation evidenced by their presence in the blood circulation, urine, and feces in humans after chicory consumption.…”

Evaluation of Cypholophus macrocephalus sap as a treatment for infected cutaneous ulcers in Papua New Guinea

“…Sulphated flavonoids have been previously identified from certain plant families, such as Arecaceae, Asteraceae, Bixaceae, Dilleniaceae, Frankeniaceae, Gramineae, Guttiferae, Juncaceae, Malvaceae, Tamaricaceae, Umbelliferae and Verbenaceae (Teles et al, 2018). Quercetin-O-sulphates (including single and multi-sulphate esters) have been frequently observed in the Asteraceae (Harborne and Baxter, 1999 (Prescott et al, 2012;Prescott et al, 2017).…”