Isoferulic acid

Cimicifuga foetida L. China Ferulic acid, isoferulic acid, cimigenol, khellol, aminol, cimifugenol, cimitin.33 Induce diaphoresis, promote skin eruption. 

N.A. Triterpene glycosides, actein, tannins, cimicifugoside, isoflavones, isoferulic acid, salicylic acid, resin.99-100 103 119-120 Promote menstrual flow, antirheumatic, expectorant, sedative. Treat inflammatory arthritis, high blood pressure, whooping cough, and asthma. 

Isoferulic acid Cimicifuga dahurica, C. foetida, C. heracleifolia, C. racemosa, C. ussuriensis... 

MFM Borges, FMF Roleira, MMM Pinto. Simultaneous isocratic HPLC separation of the dias-tereoisomers of caffeic, ferulic, and isoferulic acids and related coumarins. J Liquid Chromatogr 16 149-160, 1993. 

Chlorogenic acid has been used as a name for 5-O-caffeoylquinic acid by the authors of the reports cited except [Monteiro et al., 2007], 3-, 4-, or 5-CQA, 3-, 4-or 5-O-caffeoylquinic acid BA, benzoic acid CA, caffeic acid CLA, chlorogenic acid or 5-O-caffeoylquinic acid dHCA, dihydrocaffeic acid diCQA, dicaffeoylquinic acid FA, ferulic acid FQA, feruloylquinic acid GA, gallic acid HA, hippuric isoFA, isoferulic acid m-CA, ra-coumaric acid ra-HPPA, m-hydroxyphenylpropionic acid p-CA, p-coumaric acid p-HBA, p-hydroxybenzoic acid PPA, phenylpropionic acid. 

Fig. 15.3. A proposed route to vanillic acid via isoferulic acid (Funk and Brodelius, 1990a,b, 1992).

Isoferulic acid (phenolic acid) Helianthus animus (Asteraceae), Catalpa ovata (Bignoniaceae) [root], Arachis hypogaea (Fabaceae), Triticum aesdvum (Poaceae), Tamarix aphylla (Tamaricaceae) [leaf] Cimidjuga dahurica C. racemosa (Ranunculaceae) [rhizome] HypoGlc (DB rat)... 

Ferulic acid, (I), is obtained from the Korean angelica root by extraction. When administered to mice in the current investigation, a considerable improvement in memory retention was observed. This effect has also been reported by Castillo (3). Isoferulic acid, (II), was ineffective in treating dementia. 

A new type of plant constituent, isoferulic acid choline ester (30), has been isolated. ... 

The fluorescence of an extract of the seeds of this plant proved to be due to the cation of the choline ester of isoferulic acid 228). 

Except perhaps for caffeic acid (H.86), these acids were mainly identified after hydrolysis of extracts, which means after degradation of the chlorogenic acids, CGA (See Section 2.1.4). In commercial roasted coffee, Hughes and Thorpe (1987) identified, by comparison with standard compounds, coumaric acid (without specification, probably p-), isoferulic acid (H.88) but surprisingly not ferulic acid (H.87), caffeic acid (H.86) and its dimethyl ether (H.89) as well as sinapic acid (H.90). They used capillary GC for the separation and identification of these phenolic acids and other carboxylic acids. The cinnamic acids are generally linked to quinic acid, but in robusta coffee caffeic and /j-coumaric (H.84) acids have also been identified as derivatives of tryptophan (see Section 2.1.2) (Morishita et al., 1987 Murata et ah, 1995) and... 

H.88) 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-, 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid, 3-hydroxy-4-methoxycinnamic acid, isoferulic acid (537-73-5] ( )- 125522-33-2] (Z)- (1135-16-6]... 

It is probably biosynthesised from an isoferulic acid derivative [21] and its 1-decarboxy derivative has previously been obtained from the same intermediate as that of salvianolic acid F [22,23], To date, attempts to synthetise it by a more straightforward strategy have failed. In order to obtain the correctly substituted 2-phenylnaphthalene skeleton, 2-bromo-... 

Cimicifuga. Black cohosh black snake root Ac-taea bugbane bug wort. Dried rhizome and roots of Cimici-fuga racemosa (L.) Nutt.. Ranuncuiaceae. Habit. U.S., Canada, Constit. Isoferulic acid. 15-20% cimicifugin, tannin, volatile oil, resin, a sugar. 

In the subterranean parts of V. officinalis, a number of alkaloids (0.05-0.1%) occur actinidine, 8-methoxyactinidine (valerianine) and naphthyridylmethylketone have been found as well as several other, yet unidentified alkaloids. Furthermore, isoferulic acid, y- aminobutyric acid, free fatty acids and short-chain carboxylic acids have been isolated. In the leaves of V officinalis, the presence of four flavonoids has also been demonstrated. From the subterranean parts of V. jatamansi, isomers of lanarin isovalerate and 4-methoxy-8-pentyl-l- naphtholic acid were isolated and characterized [50, 51]. 

Experiments with tritium and C-labelled phenylalanine samples established that this amino-acid was incorporated intact as a Cg unit (with loss of C-1). Support for a pathway proceeding via cinnamic acid and hydroxylated derivatives and benzoylacetic acid derivatives was provided in further experiments with cinnamic acid, ferulic acid/isoferulic acid, and the (easily hydrolysed) ethyl esters of benzoylacetic acid and piperonylacetic acid. As far as they go the results suggest that a mixed pathway is in operation with introduction of hydroxy- and methylenedioxy-groups on more than one intermediate. 

The compound isoferulic acid, isolated from Chinese cimicifuga, has been shown to lower plasma glucose in diabetic rats in a dose-dependent manner with effects on plasma glucose observed at doses of 5 mg/kg (intravenous) and higher (Liu et al. 1999). 

Both ferulic and isoferulic acids occur as side chains in CGAs [24]. In human metabolism, the enzyme catechol-O-methyltransferase produces femlic and isoferulic acid from caffeoyl side chains of the molecules. 

By selecting a fragment ion in MS that corresponds to either ferulic or isoferulic acid as a precursor ion for an MS experiment, the diagnostic fragments in MS of the CGA derivative allow unambiguous structure assignment (Fig. 25) [24]. The differences of fragmentation between the two isomers can be rationalized in terms of stabilization of anionic species by resonance in the gas phase (Fig. 25). 

FIGURE 24 Tandem MS spectra of ferulic acid and isoferulic acid (positive ion mode on the left and negative ion mode on the right). 

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