Leucocyanidin
(Synonyms: 无色矢车菊素) 目录号 : GC60986
Leucocyanidin是一种活性抗溃疡成分，是从未成熟的车前草香蕉中提取的。Leucocyanidin在大鼠模型中显示出对阿司匹林诱导的侵蚀的显着保护作用。
Cas No.:480-17-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Leucocyanidin is an active anti-ulcerogenic ingredient was extracted from unripe plantain banana. Leucocyanidin demonstrates a significant protective effect against Aspirin-induced erosions in rat models[1].
Leucocyanidin (5 mg/day) exerts great protective effect against aspirin-induced gastric erosions in male Wistar rats of average weight 250 g (220-330 g)[1].
[1]. D A Lewis, et al. A natural flavonoid present in unripe plantain banana pulp (Musa sapientum L. var. paradisiaca) protects the gastric mucosa from aspirin-induced erosions. J Ethnopharmacol. 1999 Jun;65(3):283-8.
| Cas No. | 480-17-1 | SDF | |
| 别名 | 无色矢车菊素 | ||
| Canonical SMILES | O[C@@H]1[C@@H](C2=CC=C(O)C(O)=C2)OC3=CC(O)=CC(O)=C3C1O | ||
| 分子式 | C15H14O7 | 分子量 | 306.27 |
| 溶解度 | DMSO : 100 mg/mL (326.51 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.2651 mL | 16.3255 mL | 32.6509 mL |
| 5 mM | 0.653 mL | 3.2651 mL | 6.5302 mL |
| 10 mM | 0.3265 mL | 1.6325 mL | 3.2651 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Oxidative Transformation of Leucocyanidin by Anthocyanidin Synthase from Vitis vinifera Leads Only to Quercetin
J Agric Food Chem 2019 Apr 3;67(13):3595-3604.PMID:30865451DOI:10.1021/acs.jafc.8b06968.
Anthocyanidin synthase from Vitis vinifera ( VvANS) catalyzes the in vitro transformation of the natural isomer of Leucocyanidin, 2 R,3 S,4 S- cis-leucocyanidin, into 2 R,4 S-flavan-3,3,4-triol ([M + H]+, m/ z 323) and quercetin. The C3-hydroxylation product 2 R,4 S-flavan-3,3,4-triol is first produced and its C3,C4-dehydration product is in tautomeric equilibrium with (+)-dihydroquercetin. The latter undergoes a second VvANS-catalyzed C3-hydroxylation leading to a 4-keto-2 R-flavan-3,3-gem-diol which upon dehydration gives quercetin. The unnatural isomer of Leucocyanidin, 2 R,3 S,4 R- trans-leucocyanidin, is similarly transformed into quercetin upon C3,C4-dehydration, but unlike 3,4- cis-leucocyanidin, it also undergoes some C2,C3-dehydration followed by an acid-catalyzed hydroxyl group extrusion at C4 to give traces of cyanidin. Overall, the C3,C4- trans isomer of Leucocyanidin is transformed into 2 R,4 R-flavan-3,3,4-triol (M + 1, m/ z 323), (+)-DHQ, (-)-epiDHQ, quercetin, and traces of cyanidin. Our data bring the first direct observation of 3,4- cis-leucocyanidin- and 3,4- trans-leucocyanidin-derived 3,3-gem-diols, supporting the idea that the generic function of ANS is to catalyze the C3-hydroxylation of its substrates. No cyanidin is produced with the natural cis isomer of Leucocyanidin, and only traces with the unnatural trans isomer, which suggests that anthocyanidin synthase requires other substrate(s) for the in vivo formation of anthocyanidins.
Synthesis of 3,4-cis-[3H]Leucocyanidin and enzymatic reduction to catechin
Anal Biochem 1993 Mar;209(2):274-7.PMID:8470799DOI:10.1006/abio.1993.1119.
A novel method is presented for the synthesis and purification of (+)-2,3-trans-3,4-cis-[4-3H]Leucocyanidin. Soluble enzyme extracts from developing barley grains and leaves of the forage legume Onobrychis viciifolia (sainfoin) catalyzed the NAD(P)H-dependent reduction of (+)-2,3-trans-3,4-cis-[4-3H]Leucocyanidin to (+)-[4-3H]catechin. NADPH was the preferred substrate. With extracts of barley the rate of reaction with 1 mM NADH was 20% of the rate found with NADPH. With extracts from both tissues there was a broad pH optimum around pH 6.6.
The C-4 stereochemistry of Leucocyanidin substrates for anthocyanidin synthase affects product selectivity
Bioorg Med Chem Lett 2003 Nov 3;13(21):3853-7.PMID:14552794DOI:10.1016/s0960-894x(03)00711-x.
Anthocyanidin synthase (ANS), an iron(II) and 2-oxoglutarate (2OG) dependent oxygenase, catalyses the penultimate step in anthocyanin biosynthesis by oxidation of the 2R,3S,4S-cis-leucoanthocyanidins. It has been believed that in vivo the products of ANS are the anthocyanidins. However, in vitro studies on ANS using optically active cis- and trans-leucocyanidin substrates identified cyanidin as only a minor product; instead both quercetin and dihydroquercetin are products with the distribution being dependent on the C-4 stereochemistry of the Leucocyanidin substrates.
Flavan-3-ol Biosynthesis : The Conversion of (+)-Dihydroquercetin and Flavan-3,4-cis-Diol (Leucocyanidin) to (+)-Catechin by Reductases Extracted from Cell Suspension Cultures of Douglas Fir
Plant Physiol 1984 Sep;76(1):184-6.PMID:16663794DOI:10.1104/pp.76.1.184.
Extracts of cell suspension cultures from Douglas fir (Pseudotsuga menziesii) needles catalyzed the production of (+)-catechin (2,3-trans flavan-3-o1) from the 2,3-trans-flavan,3,4-cis-diol (Leucocyanidin) in a NADPH-dependent reductase reaction at pH 7.4. Catechin was also produced, along with the 3,4-cis-diol, in a double step reduction from (+)-dihydroquercetin. It was necessary to eliminate any thiol such as 2-mercaptoethanol or dithiothreitol from the extract or assay mixture because these thiols apparently formed thioethers with the 3,4-diols.
Antidiabetic effect of a Leucocyanidin derivative isolated from the bark of Ficus bengalensis Linn
Indian J Biochem Biophys 1989 Dec;26(6):400-4.PMID:2632365doi
A dimethoxy derivative of leucocyandin 3-O-beta-D-galactosyl cellobioside isolated from the bark of F. bengalensis Linn demonstrated antidiabetic action. On oral administration, it decreased blood sugar very significantly both in normal and moderately diabetic rats and increased serum insulin significantly in the latter at a dosage of 250 mg/kg for a 2 hr period. During one month treatment of the diabetic rats orally with the active principle, at a dosage of 100 mg/kg, there was a significant decrease in blood and urine sugar, certain lipid components in serum and tissues and glucose-6-phosphatase activity in liver, but significant increase in body weight and the activities of hexokinase and HMGCOA reductase in tissues as compared to diabetic control. The mechanism of action of the principle may be related to its protective/inhibitory action against the insulin degradative processes.