fukinolic-acid and fukiic-acid

The nucleotide sequence of a BAHD hydroxycinnamoyltransferase was amplified from Actaea racemosa (Ranunculaceae) and expressed in E. coli. The protein catalysed the formation of cimicifugic acids and thus is named hydroxycinnamoyl-CoA:piscidic acid hydroxycinnamoyltransferase (ArHPT1; cimicifugic acid synthase). Actaea racemosa (syn. Cimicifuga racemosa) is known to contain triterpene lactone glycosides and cimicifugic acids. The latter are esters of various hydroxycinnamic or benzoic acids with piscidic or fukiic acid. Amplification of a nucleotide sequence from A. racemosa, that was already known as HCT1 from an EST approach, and its expression in E. coli resulted in a protein that was able to catalyse the formation of several cimicifugic acids. For the characterisation of this hydroxycinnamoyltransferase (hydroxy)cinnamoyl-coenzyme A thioesters were synthesised as donor substrates and piscidic acid isolated as acceptor substrate. The lowest K

Topics: Acyltransferases; Caffeic Acids; Catalysis; Cimicifuga; Escherichia coli; Glycosides; Hydroxybenzoates; Phenylacetates; Phenylpropionates; Plant Proteins; Plant Roots; Succinates; Triterpenes

From the 80% acetone extract of "Cimicifugae Rhizoma" (a mixture of Cimicifuga dahurica and C. heracleifolia used medicinally), seven new fukiic acid derivatives (1-7) and a new phenylethanoid derivative (8) were isolated along with eight known compounds (9-16). Fukinolic acid (9) and cimicifugic acids A-J (10-16, 5-7) showed stronger hyaluronidase inhibitory activities than the positive control, rosmarinic acid.

Topics: Caffeic Acids; Cimicifuga; Cinnamates; Depsides; Hyaluronoglucosaminidase; Japan; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Phenylacetates; Phenylpropionates; Plants, Medicinal; Rhizome; Rosmarinic Acid; Succinates

Fukinolic acid (1) and cimicifugic acid A (2), caffeic acid analogs, as well as rosmarinic acid (3) and caffeic acid (4) showed inhibition on seed germination and seedling growth. The potency of 1 and 2 was comparable with that of 3. Compounds 1 and 2 also showed strong inhibitory activities as well as 3 and 4 on alpha-amylase. The activity of 1 was higher than that of acarbose used as a positive control, and its 50% inhibitory concentration (IC50) was 2.41 x 10(-5) M. Compounds 1 and 2 also showed inhibitory activities strong as 3 and stronger than 4 on carboxypeptidase A. The activities of 1 and 2 were higher than that of 1, 10-phenanthroline used as a positive control.

Topics: alpha-Amylases; Caffeic Acids; Carboxypeptidases; Carboxypeptidases A; Enzyme Inhibitors; Esters; Germination; Phenylacetates; Phenylpropionates; Plant Extracts; Plants, Medicinal; Seeds; Succinates

Vasoactive effects of cimicifugic acids A-E, fukinolic acid and fukiic acid isolated from Cimicifuga plants were investigated using rat aortic strips. Cimicifugic acid D and fukinolic acid at 3x10(-4) M caused a sustained, slowly developing relaxation of aortic strips precontracted with norepinephrine (NE) in preparations with or without endothelium. Cimicifugic acid C inversely caused a weak contraction. Cimicifugic acids A, B and E and fukiic acid showed no vasoactivity at 3x10(-4) M. Cimicifugic acids A-E and fukinolic acid are esters between cinnamic acids and the hydroxyl group of benzyltartaric acids. For the manifestation of vasoactivity in the rat aorta, it is concluded that in the cinnamic acid moiety, a caffeoyl group might be necessary for the relaxation activity, and the p-coumaroyl group causes contraction. Concentration response curves for the Ca2+-induced contracture of depolarized aortic strips with isotonic high K+ were not affected by cimicifugic acid D or fukinolic acid. The Ca2+-induced contraction of aortic strips, preincubated with 10(-6) M NE in the presence of 10(-6) M nicardipine and 0.01 mM EGTA in Ca2+-free solution, were inhibited by cimicifugic acid D and fukinolic acid. These results indicated that the inhibition by cimicifugic acid D and fukinolic acid of the NE-induced contraction of rat aorta are attributable to the suppression of Ca2+ influx from the extracellular space enhanced by NE.

Topics: Animals; Aorta; Caffeic Acids; Calcium; Endothelium, Vascular; Enzyme Inhibitors; In Vitro Techniques; Magnoliopsida; Male; Norepinephrine; Phenylacetates; Phenylpropionates; Rats; Rats, Wistar; Succinates; Vasoconstriction; Vasodilator Agents