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Journal ArticleDOI

Occurrence of о-Hydroxycinnamic Acid in Species of Melilotus and Trigonella 1

01 Mar 1964-Crop Science (Crop Science Society of America)-Vol. 4, Iss: 2, pp 193-196

AboutThis article is published in Crop Science.The article was published on 1964-03-01 and is currently open access. It has received 15 citation(s) till now. The article focuses on the topic(s): Trigonella & Hydroxycinnamic acid.

Topics: Trigonella (63%), Hydroxycinnamic acid (61%), Melilotus (59%)

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Citations
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Journal ArticleDOI
01 Mar 1976-Nature
TL;DR: The first successful application of phytoalexin induction as a tool in taxonomic studies to the problems of classification at the generic and species level in the Leguminosae is reported.
Abstract: IT is well established that many higher plants respond to microbial invasion by the de novo production of organic substances called phytoalexins1,2. These compounds are absent from healthy plants and are induced by the attacking microorganisms. Although the role of phytoalexins in disease resistance is not yet entirely clear, considerable evidence suggests that they are of importance in the protection of higher plants from fungal colonisation. Although few surveys have been attempted, there is clearly a taxonomic element in phytoalexin biosynthesis, in that different plant families accumulate chemically different types of compounds3. Thus, the Leguminosae in general produce isoflavonoids, the Solanaceae diterpenes, the Compositae polyacetylenes and so on2; anomalies are rare, for example, the furanoacetylene, wyerone acid, from Vicia faba (Leguminosae)4. As lesser variations also occur within these families, there is the clear possibility of using phytoalexin induction as a tool in taxonomic studies. We report here the first successful application of this technique to the problems of classification at the generic and species level in the Leguminosae.

63 citations


Journal ArticleDOI
TL;DR: All eight lupane triterpenes possess potential allelopathic activity in particular over dicotyledon species and they are likely to be significantly involved in the allelopathy action of Melilotus messanensis.
Abstract: The aerial parts of Melilotus messanenis (sweet clover) afforded, from the medium polar bioactive fractions, in addition to the known lupane triterpenes lupeol, betulin, betulin aldehyde and betulinic acid, the new norlupane messagenin (30-norlupane-3β,28-diol-20-one) which have been tested as allelochemicals. Structures and their stereochemistries were elucidated by spectral methods and chemical transformations. Messagenin has been synthesized from betulinic acid. The effect of a series of aqueous solutions at 10 −4 -10 −9 M of eight natural and synthetic lupane derivatives were tested for their effects on the germination and growth of the dicotyledon species Lactuca sativa and Lepidium sativum and the monocotyledon species Hordeum vulgare and Triticum aestivum . All eight lupane triterpenes possess potential allelopathic activity in particular over dicotyledon species and they are likely to be significantly involved in the allelopathic action of Melilotus messanensis .

61 citations


Journal ArticleDOI
TL;DR: It is concluded that rumen microbial metabolism of dietary phenolic cinnamic acids to 3-phenylpropionic acid followed by its absorption and oxidation in the body tissues is responsible for the greater part of the benzoic and cinnic acids found in ruminant urine.
Abstract: 1. The extent to which phenolic derivatives of benzoic acid (seven); of phenylacetic acid (one); of 3-phenylpropionic acid (one) and of cinnamic acid (six) served as precursors of the urinary benzoic acid excreted by sheep was determined after administration as continuous drips via rumen or abomasal cannulas. 2. Phenolic derivatives of benzoic or of phenylacetic acid were not dehydroxylated to yield aromatic acids following administration via either route. 3. Rumen infusion of phenolic derivatives of both 3-phenylpropionic and cinnamic acids gave enhanced rumen concentrations of 3-phenylpropionic acid with negligible amounts of benzoic acid. Between 63 and 106% of the 2-, 3- or 4-hydroxy acids, of the 3,4-dihydroxy acids or of the 3-methoxy, 4-hydroxy acids infused were excreted in the urine as benzoic acid and a variable proportion, characteristic of the individual animal, of up to 20% of the dose as cinnamic acid. 4. Abomasal infusion of monohydroxy 3-phenylpropionic and cinnamic acids did not yield urinary benzoic acid increments. However, between 11 and 34% of abomasally-infused disubstituted phenolic cinnamic acids infused were excreted in the urine as benzoic acid due, it is postulated, to entero-hepatic circulation and microbial metabolism of the infused acids in the large intestine. 5. It is concluded that rumen microbial metabolism of dietary phenolic cinnamic acids to 3-phenylpropionic acid followed by its absorption and oxidation in the body tissues is responsible for the greater part of the benzoic and cinnamic acids found in ruminant urine.

53 citations


Cites background from "Occurrence of о-Hydroxycinnamic Aci..."

  • ...Negligible amounts of the phenolic cinnamic acids found in plants exist in the tissues as free acids (Gorz & Haskins, 1964; El-Basyouni & Towers, 1964; Durkee & Thivierge, 1977; Salomonsson et al. 1978); they occur in a variety of conjugated forms some of which are soluble and readily isolated and…...

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01 Jan 1969
Abstract: Seed of eighteen species of sweetclover (Melilotus) from various sources in Europe and Asia has been grown at the Research Station, Brandon, Manitoba. Based on material grown, a key to the species has been developed that will be useful to agronomists. Each species is described and comments are made on its agronomic characteristics. Controversial taxa are discussed and their status is clarified.

41 citations


Journal ArticleDOI
TL;DR: Based on material grown, a key to the species has been developed that will be useful to agronomists and comments are made on its agronomic characteristics.
Abstract: Seed of eighteen species of sweetclover (Melilotus) from various sources in Europe and Asia has been grown at the Research Station, Brandon, Manitoba. Based on material grown, a key to the species has been developed that will be useful to agronomists. Each species is described and comments are made on its agronomic characteristics. Controversial taxa are discussed and their status is clarified.

37 citations


References
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18 Mar 2018

8,733 citations




Journal ArticleDOI
TL;DR: The authors concluded that the Cu/cu allelic pair governed presence or absence of coumarin and that the B/b alleles determined the type of cou marin (free or bound) present in Cu individuals.
Abstract: DUNCAN and Dustman (3, 4), Clayton and Larmour (1), and Stevenson and Clayton (13) were among the first investigators to attempt the assay of coumarin in sweetclover (Melilotus spp.). All of these workers apparently believed that the coumarin measured by their assay methods existed in the free form in the plant. Roberts and Link (8, 9) recognized the presence of bound coumarin in sweetclover seeds and green tissues and indicated that provision must be made for the hydrolysis of this form if reliable values for total coumarin content were to be obtained. However, they stated that in succulent, green tissues the free form usually predominated over the bound form (9). Slatensek and Washburn (12) observed that Pioneer sweetclover, a variety described by Stevenson and White (14) as being low in coumarin on the basis of colorimetric analysis of alcoholic extracts, appeared to be high in coumarin when assayed by a fluorometric method which involved heating the plant tissue in alkali. The difference in values obtained by the two methods was attributed to the presence of bound coumarin which was hydrolyzed in the fluorometric procedure but not in the colorimetric assay. Although the fluorometric assay described by Slatensek and Washburn (12) did not permit distinction between free and bound coumarin, it is apparent that these investigators considered coumarin to be in the free form in all coumarincontaining varieties other than Pioneer. In recent years, Goplen et al. (5) have reported on the influence of two pairs of alleles, Cu/cu and B/b, upon the level and form of coumarin in sweetclover. A qualitative colorimetric method was used for the detection of free coumarin in alcoholic extracts; and, for quantitative measurements of total coumarin, a fluorometric assay similar to that described by Slatensek and Washburn (12) was used. The authors concluded that the Cu/cu allelic pair governed presence or absence of coumarin and that the B/b alleles determined the type of coumarin (free or bound) present in Cu individuals. The assay methods did not permit deter-

30 citations