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PubMed1990

Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.).

Incubation of linoleic acid with the 105,000g particle fraction of the homogenate of the broad bean (Vicia faba L.) led to the formation of the following products: 13(S)-hydroxy-9(Z),11(E)-octadecadienoic acid, 9,10-epoxy-12(Z)-octadecenoic acid (9(R),10(S)/9(S)/10(R), 80/20), 12,13-epoxy-9(Z)-octadecenoic acid (12(S),13(R)/12(R)/13(S), 64/36), and 9,10-epoxy-13(S)-hydroxy-11(E)-octadecenoic acid (9(S),10(R)/9(R),10(S), 91/9). Oleic acid incubated with the enzyme preparation in the presence of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid or cumene hydroperoxide was converted into 9,10-epoxyoctadecanoic acid (9(R),10(S)/9(S),10(R), 79/21). Two enzyme activities were involved in the formation of the products, an omega 6-lipoxygenase and a hydroperoxide-dependent epoxygenase. The lipoxygenase, but not the epoxygenase, was inhibited by low concentrations of 5,8,11,14-eicosatetraynoic acid and nordihydroguaiaretic acid. In contrast, the epoxygenase, but not the lipoxygenase, was readily inactivated in the presence of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid. Studies with 18O2-labeled 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid showed that the epoxide oxygens of 9,10-epoxyoctadecanoic acid and of 9,10-epoxy-13(S)-hydroxy-11(E)-octadecenoic acid were derived from hydroperoxide and not from molecular oxygen.

5,8,11,14-Eicosatetraynoic Acid↗
PubMed1993

Broad bean (Vicia faba) consumption and Parkinson's disease.

In 1913, Guggenheim identified L-DOPA in the seedlings, pods, and beans of the broad bean, Vicia faba (VF). Since then, anecdotal cases of symptomatic improvement after VF consumption have been described in patients with PD. In the present study, five healthy volunteers and six PD patients (mean age, 63.5 years; mean disease duration, 13 years; stage III, Hoehn-Yahr scale) ate 250 g cooked VF after 12 hours off medication. Blood samples for L-DOPA measurements (by HPLC-ED) were obtained before eating VF and every 30 minutes, for 4 hours. During this period, a substantial clinical improvement was noted and three patients also showed severe dyskinesias. High plasma L-DOPA values were also measured (Cmax 0.66 to 1.20 micrograms/ml; AUC 1.82 to 4.12 micrograms/ml/H). In addition, their clinical performance and plasma L-DOPA levels were compared to those found after 125 mg L-DOPA + 12.5 mg carbidopa ingested on another day. These data show that VF ingestion produces a substantial increase in L-DOPA plasma levels, which correlates with a substantial improvement in motor performance. Our findings may have implications for the treatment of PD, especially in patients with mild symptoms.

Carbidopa↗
PubMed1994

Acetylene Reduction by Symbiosomes and Free Bacteroids from Broad Bean (Vicia faba L.) Nodules (Role of Oxalate).

We report the presence of oxalate in the organic acid fraction of broad bean (Vicia faba L.) nodule cytosol. Using both high-performance liquid chromatography and enzymic assays, high levels of oxalate were detected (70.4 [plus or minus] 2.4 mM). To study the potential role of oxalate as an energy-yielding substrate for nitrogenase activity, free bacteroids were isolated from nodules and found to oxidize oxalate in support of C2H2 reduction under O2 tensions that were lower than those required to oxidize succinate, another dicarboxylate commonly detected in legume nodules. Symbiosomes of broad bean, isolated for the first time from amide-producing nodules, were provided with [14C]oxalate and found to have uptake kinetics with a lower affinity [Km(oxalate) = 330 [mu]M] than that for free bacteroids [Km(oxalate) = 130 [mu]M]. In anaerobic preparations of symbiosomes supplied with purified oxyleghemoglobin, O2 consumption was stimulated by oxalate from 20.2 [plus or minus] 0.8 nmol O2 min-1mg-1 protein to 24.5 [plus or minus] 1.1 nmol O2 min-1 mg-1 protein but always remained lower than the rate of O2 consumption in free bacteroids (32.2 [plus or minus] 1.4 nmol O2 min-1 mg-1 protein). Under these conditions, C2H2 reduction activity was 9.7 [plus or minus] 0.8 and 15.1 [plus or minus] 0.9 nmol C2H4 min-1 mg-1 protein for symbiosomes and bacteroids, respectively. These data support the suggestion that oxalate may play a role as a carbon substrate in support of N2 fixation in broad bean nodules.

Journal Article↗
PubMed1984

Signal recognition particle triggers the translocation of storage globulin polypeptides from field beans (Vicia faba L.) across mammalian endoplasmic reticulum membrane.

Hybridization-selected mRNAs coding for individual storage globulin polypeptides of field beans (Vicia faba L.) were translated in a cell-free system. Added mammalian signal recognition particle (SRP) recognizes cleavable signal peptides of the major vicilin and both legumin polypeptide precursors and induces translational arrest. The latter can be released by potassium-washed membranes (K-RM) leading to shortened polypeptides protected against proteases. Thus, SRP and K-RM function in a similar way with plant polypeptides as described for mammalian secretory proteins [(1981) J. Cell Biol. 91, 557-561]. Obviously, the initial steps in the biosynthesis and processing of plant storage globulin polypeptides are principally identical to those of animal secretory proteins.

Animals↗
PubMed1979

Nutritional effects of field bean (Vicia faba L.) proteinase inhibitors fed to rats.

1. Weanling rats were fed on purified-casein diets containing active and inactive (autoclaved) field bean (Vicia faba L.) proteinase inhibitors (PI) at levels of 1.25, 2.5, 5.0 and 10 g/kg. Diets containing raw- and autoclaved-field-bean meal (FBM) were also given. The body-weight gain, protein efficiency ratio (PER); i.e. the ratio of the live weight gain in g/g of protein consumed and apparent nitrogen digestibility were determined 7, 14 and 21 d after the start of the trial. 2. Significant growth depression (P less than 0.001) was observed in rats given diets containing 2.5 g/kg PI (27--35%). In rats fed on raw FBM growth depression was severe after 7 d (57%). 3. Food intake was depressed at PI inclusion levels of 5 g/kg and higher between 14 and 21 d. 4. PER was depressed significanlty (33-44%) in rats given diets containing the active PI at all levels after 7 d. The protein utilization of all casein diets was higher than that of the FBM diets. 5. Apparent N digestibility was depressed in rats fed on diets containing 10 g/kg PI by 9 and 7% at 14 and 21 d respectively. The N digestibility of both raw and heated FBM was similar at approximately 84%. 6. It was concluded that the PI are not the main factors responsible for the growth depression observed when raw FBM is fed to rats.

Animals↗
PubMed1993

Oxygenation of (3Z)-nonenal to (2E)-4-hydroxy-2-nonenal in the broad bean (Vicia faba L.).

Incubation of (3Z)-nonenal (NON) with the 269,000-g particle fraction of seed homogenate of the broad bean (Vicia faba L.) afforded (2E)-4-hydroxy-2-nonenal (HNE) as the principal product. One pathway of HNE formation consisted of initial oxygenation of NON into (2E)-4-hydroperoxy-2-nonenal (HPNE) by a novel (3Z)-alkenal oxygenase activity, followed by conversion of HPNE into HNE by a previously recognized hydroperoxide-dependent epoxygenase. The hydroperoxide intermediate was detected in coincubations of NON and oleic acid, in which experiments the HPNE generated from NON supported epoxygenase-catalyzed epoxidation of oleic acid into 9,10-epoxystearic acid. Furthermore, by using an enzyme preparation in which the epoxygenase had been inactivated by pretreatment with hydrogen peroxide it was possible to isolate and characterize racemic (4R,4S) HPNE following incubation of NON. Although the (3Z)-alkenal oxygenase resembled a lipoxygenase in its action, it was not inhibited by the lipoxygenase inhibitors, 5,8,11,14-eicosatetraynoic acid and nordihydroguaiaretic acid. In a second pathway, HNE was produced by rearrangement of 3,4-epoxynonenal, which was in turn formed from NON by a reaction catalyzed by hydroperoxide-dependent epoxygenase. Support for this pathway came from experiments in which 18O-labeled HNE was isolated following coincubation of NON and 13-18O-labeled linoleic acid 13-hydroperoxide. The existence of 3,4-epoxynonenal as a transient intermediate in HNE biosynthesis was further demonstrated by the isolation of 3,4-epoxynonenal (61% (4R)-configuration) as a trapping product in short time incubations interrupted by addition of sodium borohydride. The two pathways established for biosynthesis of HNE involved the hydroperoxide-reducing and the olefin-epoxidizing activities of hydroperoxide-dependent epoxygenase. In the absence of extraneous olefins and hydroperoxides the two pathways would be tightly coupled and follow the stoichiometry: 2NON + 1O2-->2HNE. It was also shown that the V. faba particle fraction catalyzed oxygenation of (3Z)-hexenal into (2E)-4-hydroxy-2-hexenal.

Aldehydes↗
PubMed1982

[Determination of the digestibility of crude nutrients and amino acids of 2 horse bean (Vicia faba L.) varieties in colostomized laying hens].

The apparent digestibility of crude nutrients and the amino acids in the varieties Fribo and Erfordia of horse bean (Vicia faba L.) was determined in a digestibility and N-balance experiment with 32 colostomised laying hen hybrids. For this purpose 4 rations each with a rising quota of horse beans (10%, 20%, 40%, 50%) were tested with 4 hens each in a 6-day collecting period; the digestibility values were determined according to the regressive method. The average apparent digestibility is (formula; see text) The values of the apparent digestibility of the 17 amino acids vary for the variety Fribo between 68.6% (methionine) and 90.6% (arginine) and for the variety Erfordia between 47.7% (cystine) and 89.5% (arginine).

Amino Acids↗
PubMed1979

Protein quality in cereals and pulses. 2. Influence of polyethyleneglycol on the nutritional availability of methionine in sorghum (Sorghum vulgar Pers.), field beans (Vicia faba L.) and barley.

1. Polyethyleneglycol (PEG 4000) was examined for its influence on relative nutritional value (RNV) and available methionine in sorghum (Sorghum vulgare Pers.), field beans (Vicia faba L.) and barley, as measured microbiologically with Streptococcus zymogenes. The results were assessed in relation to the content of tannins in the test samples. 2. In grain of hybrid sorghum the RNV averaged 87 (range 79--92) for six low-tannin varieties and 41 (30--53) for eleven high-tannin varieties. The corresponding available methionine values averaged 17.0 (15.7--18.9) and 8.9 (6.7--11.0) g/kg protein. Addition of PEG 4000 to the test samples increased the average RNV of the high-tannin varieties from 41 to 78, and the average available methionine content from 8.9 to 16.2 g/kg protein. 3. With seed of ten coloured flowered varieties of field beans, treatment with PEG gave a small but consistent increase in the available methionine content, which resulted from the inactivation of tannins in the testa. 4. In twenty-three samples of barley grain, treatment with PEG had no effect on the values obtained for available methionine. 5. Treatment of high-tannin sorghum grain with ammonia has been reported to inactivate the tannins and increase the nutritional value for rats and chicks. This finding was confirmed. The present study showed that ammonia and PEG 4000 were equally effective in enhancing the nutritional quality as measured in the microbiological tests.

Dietary Proteins↗
PubMed1979

RNA metabolism and membrane-bound polysomes in relation to globulin biosynthesis in cotyledons of developing field beans (Vicia faba L.).

In cotyledon cells of developing field beans the RNA content per cell does not change in the second half of developmental period 2, whereas globulin biosynthesis continues. The constant RNA content per cell results from an equilibrium between RNA synthesis and degradation. All types of RNA are synthesized until the end of globulin biosynthesis, but poly(A)-containing RNA was preferentially labelled during maximum globulin formation. During stage 2 of seed development of poly(A)-containing RNA fraction represents a discrete peak in the 12--18-S region on agarose gels and corresponds to the peak of poly(A)-containing RNA isolated from polysomes. alpha-Amanitin inhibits selectively the labelling of poly(A)-containing RNA and concomitantly globulin formation. Translation of total poly(A)-containing RNA, free and membrane-bound polysomes in a cell-free wheat germs demonstrates that the globulins are preferentially produced on membrane-bound polysomes and that poly(A)-containing RNA includes the mRNA for both vicilin and legumin.

Amanitins↗
PubMed1991

The inhibitory effects of hull polysaccharides and tannins of field beans (Vicia faba L.) on the digestion of amino acids, starch and lipid and on digestive enzyme activities in young chicks.

The effects of polysaccharides and tannins present in the hulls of field beans (Vicia faba L.) on the digestion of amino acids, starch and lipid were studied in poultry. A control diet without hulls and the same diet substituted with 400 g hulls/kg diet from three different varieties of beans were fed to 3-week-old chicks for 4 d. Digestibility coefficients for amino acids, starch and lipid were calculated from measurements made of these nutrients in the diets and the freeze-dried excreta with the aid of titanium dioxide as a marker. Activities of trypsin (EC 3.4.21.4), alpha-amylase (EC 3.2.1.1), and lipase (EC 3.1.1.3) in digesta removed from the upper jejunum, sucrase (EC 3.2.1.48) in the gut mucosa from the upper jejunum, and alpha-amylase and lipase in the pancreas were measured. The hulls were analysed for their polysaccharide and tannin contents. Results showed that the hulls were mostly carbohydrate in composition, with cellulose the predominant polysaccharide. Tannins present in the hulls of two coloured-flowering varieties (Brunette and Minica) were of the condensed type. The diet with tannin-free hulls (white-flowering variety Medes) lowered slightly the digestion of amino acids, starch and lipid compared with the control diet. This effect was believed to be due to inhibition of digestive enzymes, possibly through their adsorption onto the hulls. Diets with tannin-rich hulls (varieties Brunette and Minica) caused a large reduction in the digestion of amino acids, starch and lipid compared with the control diet mainly due to inactivation of digestive enzymes by the formation of tannin-enzyme complexes in the digestive tract. Enzyme activities could be partially restored by the addition of polyvinylpyrrolidone to the digesta. Tannins inactivated trypsin the most, alpha-amylase to a lesser extent and lipase the least and as a consequence lowered the digestion of amino acids the most, starch to a lesser extent and lipid the least. Tannins did not induce an increased pancreatic production of digestive enzymes, nor did they affect activity of jejunum mucosal sucrase. Condensed tannins from Brunette and Minica hulls were partially extractable in methanol alone, but required acidic methanol for fuller extraction. The vanillin:anthocyanidin ratio suggested that tannins were polymerized to the same degree in the Brunette and Minica varieties, both in the methanol and acidic methanol extracts. Hulls from the variety Minica contained a greater amount of methanol-extractable tannins, the quantity of remaining tannins that required acidic methanol for extraction being the same for both varieties.

Amino Acids↗
PubMed1981

Anabolic action of dianabol (17 alpha-methyl-17beta-hydroxyandrosta-1, 4-dien-3-one) on the nitrogen balance and skeletal muscle composition of rats fed on field bean (Vicia faba L.).

The addition of Dianabol (17alpha-methyl-17beta-hydroxyandrosta-1,4-dien-3-one) (1 mg/100 g of diet) to a diet containing raw field bean (Vicia faba L.) as the sole source of protein has been studied in young male rats, fed for two weeks on the legume diet, as compared to casein-fed animals. A significant improvement (p less than 0.02) in the biological value and net protein utilization was found in the rats fed the legume diet with Dianabol added. Furthermore, a significant reduction (p less than 0.02) in the non-protein nitrogenous fraction of the skeletal musculature, together with a significant rise (p less than 0.02) in the sarcoplasmic and myofibrillar nitrogenous fractions of this musculature, was found in the rats fed the raw legume diet with Dianabol added. Serum insulin levels, significantly reduced (p less than 0.02) in the legume-fed rats, reached the values of the control group by the addition of Dianabol to the legume diet. The possible nature of these effects is discussed.

Animals↗
PubMed1992

[Effect of bean (Vicia faba) extrusion on nitrogen and starch intestinal flux in lactating cows].

Four mature lactating Holstein cows fitted with permanent ruminal, duodenal and ileal cannulae were used to study the effect of extrusion at 195 degrees C of beans (Vicia faba cv Castel) on organic matter (OM), nitrogen (N) and starch degradation in the rumen and their flow to and absorption from the small intestine. The test protein sources, raw beans (RB) and extruded beans (EB), provided about 45% of the dietary protein. The diets were composed of 23.1% beans, 56.2% corn silage, 10.1% corn grain and 10.7% Italian rye-grass hay on a DM basis; the diets were isocaloric (4.5 Mcal/kg of DM) and isonitrogenous (14% of DM). Cr-EDTA, YbCl3 and purines were used as liquid, particulate and bacterial markers respectively. Extruding the beans did not influence intraruminal pH (6.6), ammonia-N (99 mg/l) and volatile fatty acids (97 mM/l) concentrations. Apparent digestibility in total tract of energy, OM, N and starch were not affected with inclusion of EB instead of RB, the corresponding mean values were: 66, 68, 64 and 95% of intake. Apparent ruminal digestion of OM, starch and N in the forestomach were 39, 58 and 52% for diets containing RB and 38, 72 and 45% for EB diets; efficiency of bacterial protein synthesis (gN/kg organic matter truly digested in the stomach) was higher for EN diets compared with RN diets (25 vs 22). Eating diets including EB increased non-ammonia-N, bacterial-N and dietary-N flows (g/d) to the duodenum compared with diets containing RB: 409 vs 366, 216 vs 194 and 193 vs 172 respectively; while starch flow was reduced (1.5 vs 2.2 kg/d) and OM flow was unchanged (9.8 kg/d). Apparent digestion from the small intestine (g/d) of nonammonia-N, bacterial-N and dietary-N were higher for EB diets: 268 vs 229, 181 vs 160 and 87 vs 69 respectively; meanwhile, starch digestion decreased (975 vs 1,612). The PDIA, PDIN and PDIE contents (g/kg of DM) of the RB were 33, 175 and 127 respectively; the corresponding values after extrusion were: 58, 147 and 178.

Animal Feed↗
PubMed2003

[cDNA cloning and sequence analysis of leginsulin gene in broad bean (Vicia faba)].

In order to elucidate the relationship between the structural features of leginsulin gene in legume plants and their phylogenetic significance, we have cloned the cDNA sequence of leginsulin gene from radicles of broad bean (Vicia faba) via RT-PCR techniques according to the leginsulin gene sequence we previously obtained from soybean (Glycine max). The cloned cDNA encoded for a precursor protein consisting of the signal peptide, mature leginsulin and an additional 45 amino acids of another polypeptide. A sequence search for homology comparison revealed the cloned leginsulin cDNA fragment shares 62.5% and 58.7% similarity to soybean and pea, respectively. The results also shown that leginsulin cDNA from broad bean presents 44.2% and 43.6% amino acid sequence homology with soybean and pea (Pisum sativum), respectively, and that there exists highly conserved cysteine sites among the leginsulin cDNAs, which may play a crucial role in maintaining the three-dimensional structure and the physiological functions of leginsulin.

English Abstract↗
PubMed1979

Protein quality in cereals and pulses. 1. Application of microbiological and other in vitro methods in the evaluation of rice (Oryza sativa L.), sorghum (Sorghum vulgare Pers.), barley and field beans (Vicia faba L.).

1. The Streptococcus zymogenes assay procedure was modified and used in the estimation of available methionine and relative nutritional value in rice (Oryza sativa L.), sorghum (Sorghum vulgare Pers.), barley and field beans (Vicia faba L.). The results were assessed in relation to the content of tannins and 'dye-binding lysine', and to published information on the nutritional quality of some of the test samples. 2. In grain of ten varieties of sorghum, for which other workers had reported a correlation (r -0.82; P less than 0.01) between tannin content and amino acid digestibility in chicks, the available methionine content ranged from 6.3 to 17.7 g/kg protein (nitrogen x 6.25) and was highly correlated with tannin content (r -0.97; P less than 0.001). The content of total methionine and dye-binding lysine varied little between varieties and was not related to tannin content. 3. In nine samples of rice the availability of methionine was uniformly high, in accordance with literature values for true digestibility of the N. 4. In field beans the presence of tammins in the seed coat was associated with a significant (P less than 0.001) reduction in the availability of methionine. In eleven tannin-free varieties the coefficient of availability averaged 0.791, compared with 0.685 in eleven tannin-containing varieties. The standard deviation associated with both values was 0.04. There was no such difference between the corresponding dye-binding lysine values. 5. Thirty-three samples of barley were examined, representing fourteen varieties, four of which had been grown at several widely different latitudes in England and Sweden. There was little difference in methionine content between samples. The average availability coefficient for eighteen samples grown in England was 0.995+/-0.044, and for fifteen varieties grown in Sweden it was 0.851+/-0.042. The difference was not associated with any difference in tannin content, which was uniformly low. The findings contradict published evidence for marked increase in tannin content with increase in geographical latitude of cultivation, associated with decrease in digestibility of N.

Biological Assay↗
PubMed1981

Guanidinoacetate methyltransferase activity in growing male rats fed on a raw field bean (Vicia faba L.) diet.

A significant reduction (p less than 0.01) in both the rate of growth and liver protein was found in growing male rats fed ad libitum over a 5-week period on a diet containing raw field bean (Vicia faba L.) as the sole source of protein, as compared to casein-fed rats. The activity of the hepatic enzyme guanidinoacetate methyltransferase (EC 2.1.1.2) as well as the urinary output of total nitrogen and creatinine were also significantly increased (p less than 0.01) in the legume-fed rats. The addition of methionine to the legume diet did not improve the antinutritive effect caused by the raw field bean. The possible nature of these effects is discussed.

Animals↗
PubMed1979

Protein quality in cereals and pulses. 3. Bioassays with rats and chickens on sorghum (Sorghum vulgare Pers.), barley and field beans (Vicia faba L.). Influence of polyethylene glycol on digestibility on the protein in high-tannin grain.

1. Two preceding papers in this series describe the application of microbiological and other in vitro tests in the evaluation of sorghum (Sorghum vulgare Pers.), field beans (Vicia faba L.) and barley, and in assessing the influence of polyethylene glycol (PEG 4000) on the nutritional availability of the methionine. The present paper gives for comparison the results of bioassays on some of the same test samples. Net protein utilization (NPU) in rats was measured by the nitrogen balance method, and N digestibility in chickens by the ileal analysis procedure. 2. In rat tests on sorghum, N in grain of high-tannin varieties was poorly digested. Supplementation of the test diets with 0.1 g PEG 4000/g protein gave a large improvemnet, which was partly offset by an apparent decrease in biological value (BV). With chickens N digestibility was even lower, and was similarly improved with PEG 4000. Treatment of high-tannin grain with ammonia solution was also effective in improving N digestibility. 3. With low-tannin sorghum the amino acid digestibilities were uniformly high and were not affected by addition of PEG to the test diet. With high-tannin sorghums they were low and less uniform, and were much improved by PEG 4000. 4. With field beans, the influence of the seed-coat tannin on protein utilization was much less pronounced than with sorghum. In chickens there was a significant effect (P less than 0.05) of PEG 4000 on N idgestibility in a high-tannin variety. With rats the effect was smaller and not significant. 5. In four samples of barley. N digestibility was high (0.87--0.96) and was not further improved by PEG 4000. The BV of a high-lysine cultivar proved marginally inferior to that of a normal variety. Possible reasons for this are discussed. 6. Over all, the results were closely consistent with those from microbiological tests with Streptococcus zymogenes.

Animals↗
PubMed1987

Liver and muscle proteolytic activity in male growing rats fed a field bean (Vicia faba L.) diet.

Total liver cathepsin A and D and gastrocnemius acid proteolytic activities have been evaluated in male growing rats fed ad libitum over periods of 15 and 30 days on 20%-protein diets containing either casein or raw field bean (Vicia faba L.) as protein sources. It has been found that, compared to the control casein-fed rats, those fed the legume diet exhibited a marked reduction (p less than 0.05) in the rate of growth and protein efficiency rate; liver proteolytic activity increased with ageing in the two dietary treatments and was found to be significantly higher (p less than 0.05) in the legume-fed rats. However, muscle proteolytic activity decreased with ageing and proved significantly increased (p less than 0.05) in the legume-fed rats.

Animals↗
PubMed2005

N-(jasmonoyl)tyrosine-derived compounds from flowers of broad beans (Vicia faba).

Two new amide-linked conjugates of jasmonic acid, N-[(3R,7R)-(-)-jasmonoyl]-(S)-dopa (3) and N-[(3R,7R)-(-)-jasmonoyl]-dopamine (5), were isolated in addition to the known compound N-[(3R,7R)-(-)-jasmonoyl]-(S)-tyrosine (2) from the methanolic extract of flowers of broad bean (Vicia faba). Their structures were proposed on the basis of spectroscopic data (LC-MS/MS) and chromatographic properties on reversed and chiral phases and confirmed by partial syntheses. Furthermore, tyrosine conjugates of two cucurbic acid isomers (7, 8) were detected and characterized by LC-MS. Crude enzyme preparations from flowers of V. faba hydroxylated both (+/-)-2 and N-[(3R,7R/3S,7S)-(-)-jasmonoyl]tyramine [(+/-)-4] to (+/-)-3 and (+/-)-5, respectively, suggesting a possible biosynthetic relationship. In addition, a commercial tyrosinase (mushroom) and a tyrosinase-containing extract from hairy roots of red beet exhibited the same catalytic properties, but with different substrate specificities. The conjugates (+/-)-2, (+/-)-3, (+/-)-4, and (+/-)-5 exhibited in a bioassay low activity to elicit alkaloid formation in comparison to free (+/-)-jasmonic acid [(+/-)-1].

Agaricales↗