Phaseoloidin
(Synonyms: 榼藤子苷) 目录号 : GC61178
Phaseoloidin, a homogentisic acid glucoside from Nicotiana attenuata trichomes, contributes to the plant's resistance against lepidopteran herbivores. Phaseoloidin has anti-complement effects.
Cas No.:118555-82-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Phaseoloidin, a homogentisic acid glucoside from Nicotiana attenuata trichomes, contributes to the plant's resistance against lepidopteran herbivores. Phaseoloidin has anti-complement effects.
[1] Alexander Weinhold, et al. J Chem Ecol. 2011 Oct;37(10):1091-8. [2] Shihua Xing, et al. J Nat Med. 2015 Apr;69(2):171-7.
| Cas No. | 118555-82-1 | SDF | |
| 别名 | 榼藤子苷 | ||
| Canonical SMILES | O=C(O)CC1=CC(O)=CC=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O | ||
| 分子式 | C14H18O9 | 分子量 | 330.29 |
| 溶解度 | DMSO : 100 mg/mL (302.76 mM; Need ultrasonic) | 储存条件 | Store at -20°C,protect from light |
| 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 | 3.0276 mL | 15.1382 mL | 30.2764 mL |
| 5 mM | 0.6055 mL | 3.0276 mL | 6.0553 mL |
| 10 mM | 0.3028 mL | 1.5138 mL | 3.0276 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。
Phaseoloidin, a homogentisic acid glucoside from Nicotiana attenuata trichomes, contributes to the plant's resistance against lepidopteran herbivores
J Chem Ecol 2011 Oct;37(10):1091-8.PMID:21904938DOI:10.1007/s10886-011-0012-7.
Plant trichomes are known for their capability to produce and store secondary metabolites that protect plants from biotic and abiotic stresses. (1)H NMR studies on intact individual trichomes located on the leaf surface of Nicotiana attenuata revealed the presence of two major secondary metabolites: nicotine, the signature metabolite of the genus, and Phaseoloidin, a homogentisic acid glucoside. This glucoside was reported originally from the seeds of Entada phaseoloides, and this is the first report of its occurrence in a Solanaceous plant. Artificial diet feeding bioassays with Manduca sexta and Spodoptera littoralis larvae, two important herbivores of N. attenuata, revealed that the ingestion of Phaseoloidin negatively influenced caterpillar performance. This effect was more pronounced for the generalist, S. littoralis, than for the specialists, M. sexta.
[Quality standard study on Entadae Semen]
Zhongguo Zhong Yao Za Zhi 2015 May;40(10):1860-4.PMID:26390638doi
Objective: To establish the quality standard of Entadae Semen, and provide scientific basis for its quality control. Method: TLC and HPLC were used for qualitative identification and quantitative analysis of Phaseoloidin and entadamide A-O-β-D-glucopyranoside in Entadae Semen. The test of water content, ash and ethanol-soluble extractives of Entadae Semen was carried out according to the methods recorded in appendix of Chinese Pharmacopeia (2010 edition). Result: The TLC was well separated with clear spots. The linear range of Phaseoloidin was between 0.014 to 2.747 g x L(-1) (r = 0.999 6, n = 9) with an average recovery rate of 101.06% (RSD 0.90%, n = 6); the linear range of entadamide A-O-β-D-glucopyranoside was between 0.002 to 0.452 g x L(-1) (r = 0.999 7, n = 9) withan average recovery rate of 101.52% (RSD 1.09%, n = 6). The content of Phaseoloidin in sample is between 5.12% to 9.24%, entadamide A-O-β-D-glucopyranoside is between 0.55% to 2.17%, alcohol-soluble extracts is between 30.9% to 45.2%, water is between 6.6% to 8.6%, and total ash is between 2.4% to 2.9%. Conclusion: The established standard is acceptable for quality control of Entadae Semen.
Optimization, extraction, and purification of three bioactive compounds from Entada phaseoloides by high-speed countercurrent chromatography
Biomed Chromatogr 2021 Dec;35(12):e5232.PMID:34424556DOI:10.1002/bmc.5232.
The objective of this paper was to develop a preparative method for the separation and purification of Phaseoloidin, entadamide A, and entadamide A-β-D-glucopyranoside from the crude extract of Entada phaseoloides by high-speed countercurrent chromatography (HSCCC) for the first time. Optimized by orthogonal experiments, the extraction conditions were extraction temperature of 65°C, solid-to-liquid ratio of 1:15 (g/mL), ethanol concentration of 40%, and extraction time of 2.5 h. Using n-butanol-acetic acid-water (4:1:5, v/v/v) as the two-phase solvent system, 38.79 mg Phaseoloidin (the purity was 99.3% with a recovery of 98.1%), 34.85 mg entadamide A (the purity was 96.4% with a recovery of 98.5%), and 33.97 mg entadamide A-β-D-glucopyranoside (the purity was 98.6% with a recovery of 97.7%) were obtained from 500 mg crude extract by HSCCC in head-to-tail elution mode. The retention ratio of stationary phase was 51.0%. According to the antioxidant activity assays, Phaseoloidin, entadamide A, and entadamide A-β-D-glucopyranoside had certain scavenging abilities on 1,1-diphenyl-2-picrylhydrazyl free radicals and hydroxyl free radicals.
Intestinal bacterial metabolism and anti-complement activities of three major components of the seeds of Entada phaseoloides
J Nat Med 2015 Apr;69(2):171-7.PMID:25398297DOI:10.1007/s11418-014-0874-4.
The present study aimed to investigate the metabolism of Entadae Semen by human fecal bacteria to clarify the relationship between its pharmacological activities and intestinal metabolism. Three major components (Phaseoloidin, entadamide A-β-D-glucopyranoside and entadamide A) were isolated and identified from Entadae Semen and then incubated with human fecal microflora in vitro to investigate the metabolic processes. The metabolites were analyzed with high-performance liquid chromatography (HPLC). The anti-complement activities of the three components and their metabolites produced by human fecal microflora were evaluated in vitro using a hemolysis assay. Phaseoloidin and entadamide A-β-D-glucopyranoside were metabolized into their respective aglycones during the incubation process, which enhanced their anti-complement effects. These results indicated that the presence of intestinal bacteria likely plays an important role and that the pharmacological effects of Entadae Semen may be dependent on intestinal bacterial metabolism.
Pursaethosides A-E, triterpene saponins from Entada pursaetha
J Nat Prod 2005 Aug;68(8):1185-90.PMID:16124758DOI:10.1021/np0580311.
Five new triterpenoid saponins, pursaethosides A-E (1-5), were isolated from the n-BuOH extract of the seed kernels of Entada pursaetha along with the known Phaseoloidin. The structures of 1-5 were elucidated mainly by spectroscopic data interpretation and chemical degradation. Pursaethosides C-E (3-5) possess as a common structural feature entagenic acid as aglycon, which is rare among triterpene saponins. Compounds 2-4 and phaesolidin were found to be not cytotoxic when tested against HCT 116 and HT-29 human colon cancer cells.