Identification of the blue-fluorescent compounds in boron-deficient plants

Perkins, Harold J.; Aronoff, S.

doi:10.1016/0003-9861(56)90293-4

Cited by 42 publications

(12 citation statements)

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“…The (10,18) and glucaric acid (3). To date two mechanisms for the formation of such esters have been described (1); one involving the hydroxycinnamoyl-CoA thioester and the other one the l-O-(hydroxycinnamic acid)-acyl glucoside.…”

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confidence: 99%

“…Tomato plants accumulate various caffeic acid (3,4-dihydroxycinnamic acid) depsides, positional isomers ofcaffeic acid esters of quinic acid (10,18) and glucaric acid (3). To date two mechanisms for the formation of such esters have been described (1); one involving the hydroxycinnamoyl-CoA thioester and the other one the l-O-(hydroxycinnamic acid)-acyl glucoside.…”

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confidence: 99%

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Enzymic Synthesis of Caffeoylglucaric Acid from Chlorogenic Acid and Glucaric Acid by a Protein Preparation from Tomato Cotyledons

Strack¹,

Gross²,

Wray³

et al. 1987

Plant Physiol.

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The phenylpropane metabolism of tomato (Lycopersicon escukntm Mill) cotyledons was investigated. The (10,18) and glucaric acid (3). To date two mechanisms for the formation of such esters have been described (1); one involving the hydroxycinnamoyl-CoA thioester and the other one the l-O-(hydroxycinnamic acid)-acyl glucoside. The former mechanism was first shown to operate in the formation of chlorogenic acid (12), the 5-0-caffeoylquinic acid (6), in Nicotiana cell-suspension cultures and the latter one in the formation ofthe sinapic acid (4-hydroxy-3,5-dimethoxycinnamic acid) ester of malate (17) in Raphanus cotyledons. Both pathways can even lead to the same product, depending on the source of enzyme used, since recently it was shown that Ipomoea root tissue catalyzes the formation of chlorogenic acid from 1-0-caffeoylglucose ( 19,20).We studied the metabolism of hydroxycinnamic acid conjugates in tomato expecting one of the two described biosynthetic mechanisms to be operative in the formation of caffeoylglucaric acid. Earlier work ( 11) had shown that chlorogenic acid in tomato was formed via the caffeoyl-CoA thioester. However, all attempts to find an analogous reaction for the formation of caffeoylglucaric-acid, as well as experiments using 1 -O-caffeoylglucose as possible acyl donor, failed. The latter mechanism was considered possible for the formation of caffeoylglucaric acid in Cestrum 'Supported by the Deutsche Forschungsgemeinschaft. leaves which contain metabolically active l-O-caffeoylglucose (9).Since the accumulation patterns of chlorogenic and caffeoylglucaric acids indicated a precursor-product relationship, we considered chlorogenic acid as the possible acyl donor as was found in the biosynthesis of isochlorogenic acid (3,5-di-O-caffeoylquinic acid) in Ipomoea root tissue (8). Our results show that the enzymic formation of caffeoylglucaric acid in tomato cotyledons proceeds exclusively with chlorogenic acid as the acyl donor.MATERIALS AND METHODS Plant Material. Tomato seeds (Lycopersicon esculentum Mill cv Moneymaker Spezialzucht) were obtained from Waltz, Stuttgart, FRG; seedlings were grown for 3 weeks in a growth chamber with a 14-h day at 24°C and 70% RH in a defined soil as described (15). Adult plants were grown in a greenhouse.Substrates. CoA (free acid), caffeic and chlorogenic acids (5-O-caffeoylquinic acid; IUPAC nomenclature [6]) were purchased from Fluka (Neu-Ulm, FRG), and quinic, glucaric, galactaric and gluconic acids from Merck (Darmstadt, FRG). CaffeoylCoA was synthesized chemically and identified according to Zenk and coworkers (4, 13) and purified by a modification (D Strack, H Keller, G Weissenbock, unpublished data) of a described method (7) involving the hydroxycinnamoyl-N-hydroxysuccinimide ester and subsequent transesterification of the hydroxycinnamoyl moiety onto CoA. Purification was achieved on a polyamide column (details not documented) by stepwise elution with water, methanol and increasing concentrations of aqueous NH40H in methanol (0.01%, 0.05%, 0.1%...

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confidence: 99%

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confidence: 99%

Enzymic Synthesis of Caffeoylglucaric Acid from Chlorogenic Acid and Glucaric Acid by a Protein Preparation from Tomato Cotyledons

Strack¹,

Gross²,

Wray³

et al. 1987

Plant Physiol.

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“…He contends that the primary role of boron is in lignin biosynthesis and, in conjunction with auxin (indole-3-acetic acid, IAA), in xylem differentiation. This hypothesis is based on (1) the many reports in the literature that phenols accumulate under conditions of boron deficiency (Spurr, 1952;Perkins and Aronoff, 1956;Watanabe et al, 1961;Watanabe et al, 1964;Troitskaya et al, 1970); (2) the suggestion in the literature that there is a concomitant decrease in lignin biosynthesis in boron-deficient tissue (Skok, 1958); (3) the fact that hyperauxiny is a frequent symptom of boron deficiency (Odhnoff, 1957;Neales, 1960;Jaweed and Scott, 1967;Coke and Whittington, 1968;Bohnsack and Albert, 1977); and (4) the fact that monocots, which have a much lower requirement for boron, possess an additional lignin biosynthetic pathway not possessed by dicots.…”

Section: Plant Evolution and An Essential Role For Boronmentioning

confidence: 99%

Boron

Lovatt

Dugger

1984

Biochemistry of the Essential Ultratrace Elements

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Boron is the only nonmetal in a family otherwise comprised of active metals, Group IlIA of the periodic table. As expected, boron exhibits bonding and structural characteristics intermediate to both. Like carbon (atomic number 6), boron (atomic number 5) has a tendency to form double bonds and macromolecules. In addition, there are several features that are more or less unique to boron and this group of elements. These include electron-deficient molecules (such as boron trifluoride) and bridge bonds (such as those in diborane, B2H6)' These tendencies have formed the basis for the many hypotheses attempting to predict the mode of action of boron as a nutrient essential to the metabolism of vascular plants (Section 17.2.1), as a toxicant to animals (Section 17.1.5), and for achieving boron accumulation in cancer cells (Section 17.1.8).In this chapter the biochemistry of boron is reviewed predominantly in vascular plants. The discussion is organized around those metabolic processes that boron nutrition repeatedly has been shown to influence: carbohydrate metabolism, hormone action, membrane structure and function, and nucleic acid biosynthesis.17.1.

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“…In the stinflower. the filuorescenlce has l)een shown to restilt primarilv from CA2 and CG.\ acids (2). The latter were estimatedl to l)e as high a-s I () times niorimial valuies in the greeni areas contigtnotus With the necrotic.…”

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confidence: 93%

Relative Kinetics of Chlorogenic and Caffeic Acids During the Onset of Boron Deficiency in Sunflower

Dear¹,

Aronoff²

1965

Plant Physiol.

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-\ characteristic lesion, indicative of )oron dleficiencv in plants, is the appearance of necrotic areas in wvhich a blue-white finiorescenice may oftenl be note (d (3). In the stinflower. the filuorescenlce has l)een shown to restilt primarilv from CA2 and CG.\ acids (2). The latter were estimatedl to l)e as high a-s I () times niorimial valuies in the greeni areas contigtnotus With the necrotic. As it is conceival)le that the necrosis itself restilts fromil excess phenolic acids. we have (leterilinled the overall changes (i.e., withouit regard to turnover) inl plalnts made boron--leficienit in the growinig leaves and(I the growing p)oint. 2) for young, expanding leaves and(l for the growilng points were dleterminie(l fromil the dlata of tables) 1 and 2, respectively. E'achi vadtle rel)resents thle average Of a replication of 2 plants grown in the same p)ot. All )lansL were fromi lalpopation germlinate(l and miade horon-deficient (where al)l)lical)le) siminiltaneoislv. 'I'lhC ratios shoxx n in the figures have an exl)erimelltal ei-ror of + 9 %.

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Identification of the blue-fluorescent compounds in boron-deficient plants

Cited by 42 publications

References 2 publications

Enzymic Synthesis of Caffeoylglucaric Acid from Chlorogenic Acid and Glucaric Acid by a Protein Preparation from Tomato Cotyledons

Enzymic Synthesis of Caffeoylglucaric Acid from Chlorogenic Acid and Glucaric Acid by a Protein Preparation from Tomato Cotyledons

Boron

Relative Kinetics of Chlorogenic and Caffeic Acids During the Onset of Boron Deficiency in Sunflower

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