Natural alkaloid glycoside

Two studies were conducted to investigate the effects of feeding raw and water-soaked vetch seeds to male broiler chicks on performance, organ weights, and blood parameters. Intact and ground vetch seeds were soaked in water (1:5) at room temperature for 24 hours (study 1), and (1:10) at 40 degrees C for 24, 48, and 72 hours, with water change every 12 hours (study 2). In study 1, untreated vetch contained, on dry matter basis, 0.530%, 0.731%, and 0.081% total beta-cyanoalanine (BCA), vicine, and convicine, respectively. Toxins were not appreciably reduced in soaked intact and ground vetch. Diets containing untreated, soaked intact, and soaked ground vetch, each at 0%, 20%, 40%, and 60%, were fed to 7-day-old male broilers until onset of neurotoxicity symptoms. Survival time was not only decreased by BCA level but also by those of vicine and convicine (p <.05). In study 2, 60% of untreated or treated vetch seeds were incorporated in chick diets. Although untreated vetch used in this study contained 32% less BCA but 8% and 81% more vicine and convicine, respectively, yet, the chicks on 60% untreated vetch showed toxicity symptoms earlier than those of study 1. Soaking ground vetch for 48 hours or more reduced BCA and totally removed vicine and convicine. Consequently, birds on 60% ground vetch soaked for 48 and 72 hours survived through the starter period and had mean corpuscular hemoglobin concentration and organ weights comparable to those of control at 4 days post trial. The results indicated that "high levels" of vicine or convicine or both might have shortened the birds' survival time by enhancing the neurotoxicity induced by "lower levels" of BCA[1].

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Vicine, along with convicine, was found to enhance the neurotoxicity induced by β-cyanoalanine (BCA) in male broiler chicks. Diets containing untreated vetch seeds (which contained vicine, convicine, and BCA) led to reduced survival time and increased mortality in a dose-dependent manner. [1]
The toxicity was not solely dependent on BCA levels. High levels of Vicine and convicine, even in the presence of relatively lower BCA levels, were associated with earlier onset of neurotoxic symptoms (e.g., muscle inc coordination, respiratory difficulty, convulsions) and higher mortality. [1]
Removal of Vicine and convicine from vetch seeds by extended soaking (grinding seeds and soaking in water at 40°C for 48 or 72 hours with water changes) significantly reduced toxicity, allowing chicks to survive the feeding period with performance comparable to controls, despite the presence of residual BCA. [1]

Experiment 1: One-week-old male broiler chicks were fed experimental diets from day 7. Diets contained 0%, 20%, 40%, or 60% of untreated vetch seeds, or vetch seeds that had been soaked intact or ground before soaking (water, room temperature, 1:5 w/v, 24h). Diets were formulated to be isonitrogenous and isocaloric. Birds were housed in pens (8 birds/pen) with ad libitum access to feed and water. They were monitored until the onset of neurotoxicity symptoms. Performance data (weight gain, feed intake) were recorded. [1]
Experiment 2: One-week-old male broiler chicks were fed diets containing 60% of untreated vetch seeds, or vetch seeds treated by soaking (intact or ground) in warm water (40°C, 1:10 w/v) for 24, 48, or 72 hours with water change every 12 hours. Diets were isocaloric and isonitrogenous. On day 4 post-feeding, blood samples were collected from half of the birds for hematological analysis. Birds were then sacrificed for organ (liver, kidney, gall bladder) weight measurement. Birds from control and selected treatment groups (ground vetch soaked for 48/72h) were continued on feed until day 21 for performance evaluation. [1]
Compound/Diet Preparation: Vicine was not administered as a purified compound. It was present as a natural constituent in common vetch (Vicia sativa) seeds. The seeds were incorporated into complete poultry diets at specified percentages. Detoxification treatments involved soaking the intact or ground seeds in water under specified conditions (temperature, time, seed-to-water ratio). [1]

Vicin is a toxin found in common pea seeds. Ingestion of this toxin by feeding pea seeds can cause poisoning in male broilers. [1] In Experiment 1, feeding pea seeds with 60% untreated pea seeds (containing 0.388% vicin, 0.043% convitin and 0.281% BCA) resulted in a 97.5% mortality rate and a mean survival time of 7.8 days. Feed with 40% untreated pea seeds (0.258% vicin) resulted in a 40% mortality rate. Feed with 20% pea seeds (0.129-0.148% vicin) did not result in mortality. [1] Vicin and convitin appear to synergistically enhance the neurotoxicity of BCA. Feeds with similar BCA content but lower vicinity/convitin content resulted in lower mortality rates. For example, the mortality rate (40%) of birds fed a diet consisting of 40% untreated vetch (higher vetchin content) was significantly higher than that of birds fed a diet consisting of 40% soaked whole vetch (lower vetchin content) (17.5%), despite similar BCA levels in both diets. [1]
Compared to the control group, birds fed a diet high in toxins (e.g., 60% untreated vetch) showed a significant increase in liver weight as a percentage of body weight. [1]
Birds fed vetch seeds containing high vetchin/vetchin content (untreated or whole seeds soaked for 24/48 hours) showed significantly lower mean corpuscular hemoglobin (MCH) and mean corpuscular hemoglobin concentration (MCHC) values in blood analysis 4 days after feeding, indicating impaired hemoglobin synthesis or increased degradation. [1]
This study suggests that, based on its role in human favism, divicine may be involved in inducing hemolysis. [1]

[1]. Vicine and convicine in common vetch (Vicia sativa) seeds enhance beta-cyanoalanine toxicity in male broiler chicks. Int J Toxicol. 2002 May-Jun;21(3):201-9.

Vicia is a glycoside. It has been reported that it is found in broad bean (Vicia faba), narbonensis and bitter melon (Momordica charantia), and there is relevant data. Vicia is a water-soluble pyrimidine glycoside that has been shown to be an anti-nutritional factor in legumes such as broad bean (Vicia sativa) and fava bean. [1] In this study, the main significance of vicia lies in its contribution to the overall toxicity of raw pea seeds fed to poultry, especially its synergistic effect with β-cyanoalanine (BCA). [1] The study showed that to effectively remove toxins from pea seeds for use as animal feed, it is necessary not only to remove BCA, but also to remove vicia and convitin. After grinding the seeds, soaking them in warm water for a long time and changing the water frequently can completely remove detectable vicia and convitin. [1]
The content of vitamin in seeds varies depending on growing conditions and crop maturity. [1]

C10H16N4O7

304.2566

304.101

C, 39.48; H, 5.30; N, 18.41; O, 36.81

152-93-2

135413566

White to off-white solid powder

2.2±0.1 g/cm3

627.4±65.0 °C at 760 mmHg

242-244℃

333.2±34.3 °C

0.0±4.2 mmHg at 25°C

1.820

-2.55

7

9

3

21

494

5

O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1C(N([H])C(N([H])[H])=NC=1N([H])[H])=O

KGNGTSCIQCLKEH-SYCVNHKBSA-N

InChI=1S/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1

2,4-diamino-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-pyrimidin-6-one

Vicine; 152-93-2; Vicioside; 2,6-Diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one; NSC-95092; COL14PJW3X; C08437; CID 91446;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~50 mg/mL (~164.33 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.22 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (8.22 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.22 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)