Hydroxybenzoic Acids and the Enigma of Gallic Acid

Haslam, Edwin

doi:10.1007/978-1-4684-8056-6_7

Cited by 11 publications

(15 citation statements)

References 51 publications

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“…This could be due in part to the high concentration of secondary metabolites such as condensed tannins in these plants. Condensed tannins are polyphenols with the ability to bind and precipitate proteins, carbohydrates and other molecules,1 thereby making these nutrients less available for productive purposes in the ruminant animal.…”

Section: Introductionmentioning

confidence: 99%

In vitro degradability of mature and immature leaves of tropical forage legumes differing in condensed tannin and non‐starch polysaccharide content and composition

et al. 2003

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Barahona, R., Lascano, C. E., Narvaez, N., Owen, E., Morris, P., Theodorou, M. K. (2003). In vitro degradability of mature and immature leaves of tropical forage legumes differing in condensed tannin and non-starch polysaccharide content and composition. ? Journal of the Science of Food and Agriculture, 83, (12), 1256-1266. Sponsorship: DFID Livestock ProgrammeA study was designed to examine the relationships between protein, condensed tannin and cell wall carbohydrate content and composition and the nutritional quality of seven tropical legumes (Desmodium ovalifolium, Flemingia macrophylla, Leucaena leucocephala, L pallida, L macrophylla, Calliandra calothyrsus and Clitoria fairchildiana). Among the legume species studied, D ovalifolium showed the lowest concentration of nitrogen, while L leucocephala showed the highest. Fibre (NDF) content was lowest in C calothyrsus, L Leucocephala and L pallida and highest in L macrophylla, which had no measurable condensed tannins. The highest tannin concentration was found in C calothyrsus. Total non-structural polysaccharides (NSP) varied among legumes species (lowest in C calothyrsus and highest in D ovalifolium), and glucose and uronic acids were the most abundant carbohydrate constituents in all legumes. Total NSP losses were lowest in F macrophylla and highest in L leucocephala and L pallida. Gas accumulation and acetate and propionate levels were 50% less with F macrophylla and D ovalifolium as compared with L leucocephala. The highest levels of branched-chain fatty acids were observed with non-tanniniferous legumes, and negative concentrations were observed with some of the legumes with high tannin content (D ovalifolium and F macrophylla). Linear regression analysis showed that the presence of condensed tannins was more related to a reduction of the initial rate of gas production (0-48 h) than to the final amount of gas produced or the extent (144 h) of dry matter degradation, which could be due to differences in tannin chemistry. Consequently, more attention should be given in the future to elucidating the impact of tannin structure on the nutritional quality of tropical forage legumes. Copyright ? 2003 Society of Chemical IndustryPeer reviewe

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Section: Introductionmentioning

confidence: 99%

In vitro degradability of mature and immature leaves of tropical forage legumes differing in condensed tannin and non‐starch polysaccharide content and composition

et al. 2003

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“…It is documented that glyphosate treatment decreases levels of cinnamate derivatives in higher plants (Duke and Hoagland, 1985;Duke, 1988). Data indicate that hydroxybenzoic acids can be derived from shikimic acid either directly or indirectly via cinnamates (Haslam, 1986). A shikimate-inducible form of 3-dehydroquinate hydrolase (DHQase 2, EC 4.2.1.10), which is associated with conversion of quínate to protocatechuate, has been isolated from higher plants (Boudet et al, 1986).…”

mentioning

confidence: 99%

Glyphosate induction of elevated levels of hydroxybenzoic acids in higher plants

Lydon¹,

Duke²

1988

J. Agric. Food Chem.

108

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“…The biological origin of this hydroxyl could be (i) H,O, where we would have a 1,5 displacement of water or (ii) molecular oxygen or (iii) intramolecular transfer of a hydroxyl. The first mechanism (i) involving a sigmatropic shift had been first proposed by Haslam (Haslam 1974 of chorismate with isochorismate synthetase in H,'*o gave isochorismate with ''0 as evidenced from the mass spectral data (Fig. 2).…”

Section: Resultsmentioning

confidence: 96%

“…Early research to phenylalanine, tyrosine, and tryptophan. lts total synthesis On isochorismate has been extensively reviewed a an em 1978; has been accomplished simultaneously by two research groups Weiss and Edwards 1980;Haslam 1986;). The ( M~G~~~~ and ~~~~h~~l d 1982; G~~~~ 1982).…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of isochorismate in Klebsiella pneumoniae: origin of O-2

Zamir¹,

Devor²,

Jensen³

et al. 1991

Can. J. Microbiol.

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The shikimate metabolites are key precursors to a large number of natural products, including aromatic amino acids. Chorismic acid is an important branch point in the biosynthetic pathway to aromatic amino acids. Chorismic acid is also unique among natural products since it is the only compound known to undergo an enzymatic Claisen rearrangement. A metabolite of chorismic acid, isochorismic acid, first observed in Aerobacter aerogenes differs in its chemical structure by the location of the hydroxyl group and the double bonds. Isochorismic acid is a precursor to a growing number of shikimate-derived metabolites. Isochorismic acid has also been postulated to be an intermediate of m-carboxyaromatic amino acids, implying another enzymatic Claisen rearrangement. In this publication, we have isolated isochorismate synthase and found that on lyophilization the enzyme is stable for at least 6 months at -20 degrees C. Incubation of chorismate with this preparation in water enriched with 18O led to incorporation of one atom of 18O as proven from the fast atom bombardment mass spectra of the HPLC purified derived isochorismate.

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Hydroxybenzoic Acids and the Enigma of Gallic Acid

Cited by 11 publications

References 51 publications

In vitro degradability of mature and immature leaves of tropical forage legumes differing in condensed tannin and non‐starch polysaccharide content and composition

In vitro degradability of mature and immature leaves of tropical forage legumes differing in condensed tannin and non‐starch polysaccharide content and composition

Glyphosate induction of elevated levels of hydroxybenzoic acids in higher plants

Biosynthesis of isochorismate in Klebsiella pneumoniae: origin of O-2

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