Fukinolic acid and cimicifugic acids: a review

Abstract

During the last decades, the research on the biological activities of extracts from Cimicifuga/Actaea species and Petasites japonicus as well as their active ingredients has been intensified. Besides terpenoids as dominant natural product group, hydroxycinnamic acid esters such as fukinolic acid and several cimicifugic acids have been isolated from Actaea and Petasites species and their chemical structures have been elucidated. Investigations on the biological properties of these hydroxycinnamic acid esters are currently undertaken and some compounds might be promising therapeutic tools. In this review, we have gathered information on the genera Actaea and Petasites, the occurrence of cimicifugic and fukinolic acids and some aspects of their biosynthesis. Furthermore, we have summarized the medicinal aspects of fukinolic acid and cimicifugic acids. In connection with the biological activities of these compounds, structural features of the hydroxycinnamic acid derivatives move into the focus. The position of the hydroxyl group at the aromatic rings and the introduction of an electron-donating moiety may be important for anti-inflammatory, antiviral, cytotoxic and vasoactive effects of these compounds.

Chemical Composition of Methanol Extracts from Leaves and Flowers of Anemonopsis macrophylla (Ranunculaceae)

“…Further, in Cimicifuga species, a number of phenolic acids have been registered: cimicifugic acids A-N, cimiracemates A-D, and others, which are exclusive chemical constituents of the genus Cimicifuga [47]. These phenolic compounds are formed via the condensation of piscidic acid or fukiic acid with isoferulic, ferulic, caffeic, 3,4dihydroxybenzoic, or some other acids [48]. Further research is needed to verify whether A. macrophylla synthesizes such acids.…”

“…The flavonols found in A. macrophylla are based on quercetin (40), kaempferol (46), and their derivatives. The following quercetin glycosides were identified in the assayed samples: quercetin-3β-glucoside (45), quercetin-6-O-β-xylopyranosyl-β-glucopyranoside (43), rutin (47), patulitrin (51), narcissin (56), rhamnetin-3-O-xylopyranosyl-glucopyranoside (48), and dihydroquercetin-3-rhamnoside, better known as astilbin (57). Additionally, a flavonoid (40) was found whose aglycone is quercetin that has substituents at positions C-3 and C-7 in the form of hexose sugars, which we were unable to identify.…”