Azadirachtin B
(Synonyms: 印楝素 B) 目录号 : GC46093
An azadirachtin with diverse biological activities
Cas No.:106500-25-8
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
Azadirachtin B is an azadirachtin that has been found in the neem tree, A. indica, and has diverse biological activities, including insecticidal, nematocidal, anticancer, and osteogenic properties.1,2,3,4,5 It has antifeedant activity against P. xylostella third instar larvae when used at a concentration of 3 mg/ml and induces mortality with an LC50 of 1.03 mg/ml.2 It induces mortality in M. incognita second instar larvae with an LD50 value of 125.8 ppm.3 Azadirachtin B (780 nmol in the drinking water) reduces the number of papillomas formed on mouse skin in a model of skin carcinogenesis induced by peroxynitrite and phorbol 12-myristate 13-acetate but is not cytotoxic to HL-60, A549, AZ521, SK-BR-3, or CRL1579 cancer cells (IC50s = >20 μM for all).4,5 It induces osteoblast differentiation and increases the rate of osteoblast proliferation in primary calvarial osteoblast cells when used at concentrations of 100 pM and 10 nM but not 1 pM, 1 μM, or 100 μM.1
| Cas No. | 106500-25-8 | SDF | |
| 别名 | 印楝素 B | ||
| Canonical SMILES | O=C(OC)[C@H]1OC[C@]23[C@@H](O)C[C@@H](OC(/C(C)=C/C)=O)[C@]4(C(OC)=O)[C@]2([H])[C@](OC4)([H])[C@@H](O)[C@@](C)([C@]56[C@@](C)(O6)[C@]7([H])[C@](C=CO8)(O)[C@]8([H])O[C@@]5([H])C7)[C@@]31[H] | ||
| 分子式 | C33H42O14 | 分子量 | 662.7 |
| 溶解度 | DMSO : 50 mg/mL (75.45 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 | 1.509 mL | 7.5449 mL | 15.0898 mL |
| 5 mM | 0.3018 mL | 1.509 mL | 3.018 mL |
| 10 mM | 0.1509 mL | 0.7545 mL | 1.509 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。
Azadirachtin derivatives from seed kernels of Azadirachta excelsa
J Nat Prod 2005 Jul;68(7):1047-50.PMID:16038546DOI:10.1021/np050064t.
Three new azadirachtin derivatives, named azadirachtins O-Q (1-3), along with the known Azadirachtin B (4), azadirachtin L (5), azadirachtin M (6) 11alpha-azadirachtin H (7), 11beta-azadirachtin H (8), and azadirachtol (9) were isolated from seed kernels of Azadirachta excelsa. Their structures were established by spectroscopic techniques, and the structure of 3 was confirmed by X-ray analysis. Compounds 1-7 and 9 exhibited toxicity to the diamondback moth (Plutella xylostella) with an LD50 of 0.75-1.92 microg/g body weight, in 92 h.
Variability in Neem (Azadirachta indica) with respect to azadirachtin content
J Agric Food Chem 2003 Feb 12;51(4):910-5.PMID:12568548DOI:10.1021/jf025994m.
There is a controversy over variations in azadirachtin content in neem (Azadirachta indica) seeds among various provenances and countries. Also, variations in azadirachtins are usually attributed to climatic conditions such as temperature and humidity. The present study was undertaken to evaluate qualitative and quantitative variability in azadirachtins A and B among various neem provenances or individual neem trees. Forty-three provenances of India were examined for intraprovenance variability in azadirachtin A and B content and oil percentage. Twenty-eight individual neem trees from five provenances of different agroclimatic regions were also examined for interprovenance variability. The azadirachtins were quantified using reversed phase analytical HPLC. There were wide variations in oil and azadirachtin contents among different provenances. Azadirachtin A ranged from 556.9 to 3030.8 mg kg(-)(1) of kernels, whereas Azadirachtin B was in the range 43.1-590.6 mg kg(-)(1) of kernel among the provenances investigated. Analysis of variance among various neem provenances showed significant differences in oil content, azadirachtin A, total azadirachtin (A + B), and A:B ratio. There were individuals with high and low azadirachtins within a single provenance, and this trend was observed in all of the provenances selected from five agroclimatic regions of the country. Variations among individual trees of a particular provenance indicated that climatic factors such as rainfall, humidity, or temperature did not influence azadirachtin content in the neem trees. The present study shows that there are individual genetic differences among neem trees. A systematic study for tree improvement with a population of mother trees with desired traits should be undertaken by performing half-sib progeny trials and further selections by clonal propagations. The role of genetic makeup needs further research.
An efficient method for the purification and characterization of nematicidal azadirachtins A, B, and H, using MPLC and ESIMS
J Agric Food Chem 2003 Jul 2;51(14):3966-72.PMID:12822931DOI:10.1021/jf0342167.
Azadirachtin A enriched concentrate containing 60% active ingredient (a.i.) was prepared from the methanolic extract of the de-fatted neem (Azadirachta indica A. Juss) seed kernels. Azadirachtins A, B, and H, the three major bioactive constituents of neem seed kernel, were purified from this methanolic concentrate by employing reverse phase medium-pressure liquid chromatography (MPLC), using methanol-water solvent system as an eluant. The three pure azadirachtin congeners thus obtained were characterized by their unique mass spectral fragmentation, using electrospray probe in positive ion mode (ESI). All three azadirachtins exhibited nematicidal and antifungal activities. Azadirachtin B was the most effective against the reniform nematode Rotylenchulus reniformis (EC(50) 96.6 ppm), followed by Azadirachtin A (119.1 ppm) and H (141.2 ppm). At 200-ppm concentration, the test compounds caused 50-65% mortality of Caenorhabditis elegans nematode. Azadirachtin H showed the highest activity against the phytophagous fungi Rhizoctonia solani (EC(50) 63.7 ppm) and Sclerotium rolfsii (EC(50) 43.9 ppm), followed by B and A. The isolation of pure azadirachtins A, B, and H directly by MPLC purification from its concentrate and their characterization by ESIMS are unique and less time-consuming.
Fate and effects of azadirachtin in aquatic mesocosms--1: fate in water and bottom sediments
Ecotoxicol Environ Saf 2004 Oct;59(2):186-93.PMID:15327874DOI:10.1016/j.ecoenv.2003.09.007.
The fate and effects of azadirachtin were examined using in situ enclosures deployed in a typical forest pond of northern Ontario. A commercial azadirachtin-based insecticide formulation, Neemix 4.5, was applied as the test substance. Fate studies were conducted to determine kinetics and persistence of azadirachtin isomers A and B in the aqueous phase and whether either isomer partitioned significantly to bottom sediments or pore water. Aqueous azadirachtin residues dissipated following slow linear kinetics with time to 50% dissipation of 25, 45, and 30 days for azadirachtin A, Azadirachtin B, and total residues, respectively. Sediment pore water concentrations increased slowly, reaching low-level equilibrium with the overlying water column toward the end of the summer season. No significant sorption to bottom sediments was observed. Results demonstrated that fate and dissipation of azadirachtin residues are consistent from year to year and that biota may be chronically exposed to diminishing levels of azadirachtins A and B in aqueous phase under conditions of a typical forest pond environment.
Soil application of azadirachtin and 3-tigloyl-azadirachtol to control western flower thrips, Frankliniella occidentalis (Thysanoptera: Thripidae): translocation and persistence in bean plants
Pest Manag Sci 2006 Aug;62(8):759-67.PMID:16752388DOI:10.1002/ps.1239.
To study the systemic effects of active neem ingredients, the substrate of bean plants was treated with a 170 g kg(-1) azadirachtin (NeemAzal-U; Trifolio-M GmbH, Lahnau, Germany, registration pending). This product was used at a dose rate of 10 mg AZA (azadirachtin a) and 1.2 mg 3-tigloyl-azadirachtol (Azadirachtin B) per treated bean plant. Afterwards, the translocation and persistence of AZA and 3-tigloyl-azadirachtol and the effects on western flower thrips, Frankliniella occidentalis (Pergande), were studied. Residues of AZA and 3-tigloyl-azadirachtol from substrates with different contents of organic matter [pure culture substrate (CS), CS-sand mixture] and from various plant parts were quantified by high-performance liquid chromatography-mass spectrometry (HPLC-MS). The dissipation trends of AZA and 3-tigloyl-azadirachtol were similar within the same substrates. A slower decline of both active ingredients was measured with CS than with CS-sand mixture. Residue analysis of the bean plants showed that only small proportions of the initial amounts of AZA and 3-tigloyl-azadirachtol applied to the substrate were present in the plant (0.3-8.1%). Variable amounts of residues of the active components in relation to plant parts and time of analysis indicated a different translocation pattern for the two active ingredients. Higher residues of the active ingredients were found in roots and stems after neem application using CS, whereas higher residues were found in leaves after CS-sand mixture treatments. Mortality of F. occidentalis after NeemAzal-U soil applications reached up to 95% on CS-sand mixture, compared with 86% in CS.