Karrikinolide
(Synonyms: 3-甲基2H-呋喃并[2,3-C]吡喃-2-) 目录号 : GC47525
Karrikinolide是从烧焦的植物材料及其烟雾中提取出的化合物，具有打破种子休眠，刺激发芽，促进幼苗活力的作用，可应用于园艺、生态恢复和农业。
Cas No.:857054-02-5
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
本实验来自文献，请根据具体需要进行修改。
1. 将完整的小花和清洁的种子在10至40°C的温度下，在交替的光照或恒定的黑暗下，以及在烟雾衍生的发芽兴奋剂karrikinolide存在或不存在的情况下孵育。
2. 在发芽测试之前，实验中使用的小花和清洁的种子在2%（w/v）次氯酸钙溶液中表面灭菌30分钟，交替真空循环10分钟（例如，在-70kPa下开/关/开），然后用无菌去离子水冲洗。
3. 灭菌后，将25朵小花或清洗后的种子分别置于含有0.7 (w/v)水琼脂（含或不含karrikinolide，karrikinolide浓度为0.67 μM）的90 mm培养皿上。
4. 将培养皿转移到单独的培养箱中，随机排列，设置为交替的12小时光/暗条件和10、15、20、25、30、35或40°C的恒温。为了在恒定的黑暗处理中排除光线，将培养皿包裹在铝箔中，直到实验结束。培养箱中的光为冷白色荧光灯（45μmol m–2s–1） 。
5. 在28天内进行发芽测试，当胚根的出现大于小花或种皮长度的三分之一即可定义为萌发。
参考文献:
[1] Wolfgang Lewandrowski, Todd E Erickson, Emma L Dalziell, Jason C Stevens, Ecological niche and bet-hedging strategies for Triodia (R.Br.) seed germination, Annals of Botany, Volume 121, Issue 2, 23 January 2018, Pages 367–375.
Karrikinolide is a compound extracted from charred plant material and its smoke that breaks seed dormancy, stimulates germination and promotes seedling vigor, with applications in horticulture, ecological restoration, and agriculture[1-3]. Karrikinolide is highly active in promoting seed germination at low concentrations. Karrikinolide (1 nM) reduced the expression levels of genes related to abscisic acid biosynthesis and signal transduction by regulating the relative expression of gibberellin biosynthesis genes, thereby improving the seed germination rate under salt stress. Under salt stress, exogenous addition of Karrikinolide significantly induced antioxidant activity, reduced endogenous hydrogen peroxide (H2O2) and malondialdehyde (MDA) levels, and reduced electrolyte leakage. Karrikinolide maintained K+/Na+ homeostasis and enhanced the tolerance of wheat seedlings to salinity and alkali stress[3].
References:
[1] Burger B V, Pošta M, Light M E, et al. More butenolides from plant-derived smoke with germination inhibitory activity against karrikinolide[J]. South African Journal of Botany, 2018, 115: 256-263.
[2] Aremu AO, et al. Cytokinin profiles in ex vitro acclimatized Eucomis autumnalis plants pre-treated with smoke-derived karrikinolide. Plant Cell Rep. 2016 Jan;35(1):227-38.
[3] Shah F A, Ni J, Tang C, et al. Karrikinolide alleviates salt stress in wheat by regulating the redox and K+/Na+ homeostasis[J]. Plant Physiology and Biochemistry, 2021, 167: 921-933.
Karrikinolide是从烧焦的植物材料及其烟雾中提取出的化合物，具有打破种子休眠，刺激发芽，促进幼苗活力的作用，可应用于园艺、生态恢复和农业[1-3]。低浓度的Karrikinolide在促进种子萌发方面具有高度活性。Karrikinolide（1 nM）通过调控赤霉素生物合成基因的相对表达来降低脱落酸生物合成和信号转导相关基因的表达水平，提高了盐胁迫下的种子萌发率。在盐胁迫下，外源添加Karrikinolide显著诱导抗氧化剂活性，降低内源性过氧化氢（H2O2 ）及丙二醛（MDA）水平，减少电解质泄漏。Karrikinolide保持了K+/Na+稳态，增强了小麦幼苗对盐碱的耐受性[3]。
| Cas No. | 857054-02-5 | SDF | |
| 别名 | 3-甲基2H-呋喃并[2,3-C]吡喃-2- | ||
| Canonical SMILES | O=C1C(C)=C2C=COC=C2O1 | ||
| 分子式 | C8H6O3 | 分子量 | 150.1 |
| 溶解度 | Chloroform: slightly soluble,Methanol: slightly soluble | 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 | 6.6622 mL | 33.3111 mL | 66.6223 mL |
| 5 mM | 1.3324 mL | 6.6622 mL | 13.3245 mL |
| 10 mM | 0.6662 mL | 3.3311 mL | 6.6622 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。
Karrikinolide alleviates salt stress in wheat by regulating the redox and K+/Na+ homeostasis
Plant Physiol Biochem 2021 Oct;167:921-933.PMID:34555666DOI:10.1016/j.plaphy.2021.09.023.
Karrikinolide (KAR1), identified in biochars, has gained research attention because of its significant role in seed germination, seedling development, root development, and abiotic stresses. However, KAR1 regulation of salt stress in wheat is elusive. This study investigated the physiological mechanism involved in KAR1 alleviation of salt stress in wheat. The results showed KAR1 boosted seed germination percentage under salinity stress via stimulating the relative expression of genes regulating gibberellins biosynthesis and decreasing the expression levels of abscisic acid biosynthesis and signaling genes. As seen in seed germination, exogenous supplementation of KAR1 dramatically mitigated the salt stress also in wheat seedling, resulting in increased root and shoot growth as measured in biomass as compared to salt stress alone. Salt stress significantly induced the endogenous hydrogen peroxide and malondialdehyde levels, whereas KAR1 strictly counterbalanced them. Under salt stress, KAR1 supplementation showed significant induction in reduced glutathione (GSH) and reduction in oxidized glutathione (GSSG) content, which improved GSH/GSSG ratio in wheat seedlings. Exogenous supplementation of KAR1 significantly promoted the activities of enzymatic antioxidants in wheat seedlings exposed to salt stress. KAR1 induced the relative expression of genes regulating the biosynthesis of antioxidants in wheat seedlings under salinity. Moreover, KAR1 induced the expression level of K+/Na+ homeostasis genes, reduced Na+ concentration, and induced K+ concentration in wheat seedling under salt stress. The results suggest that KAR1 supplementation maintained the redox and K+/Na+ homeostasis in wheat seedling under salinity, which might be a crucial part of physiological mechanisms in KAR1 induced tolerance to salt stress. In conclusion, we exposed the protective role of KAR1 against salt stress in wheat.
Synthesis of Karrikinolide Using the Aldol-Type Acetal Addition Reaction
J Org Chem 2020 Mar 6;85(5):3936-3941.PMID:31975605DOI:10.1021/acs.joc.9b03195.
A short step total synthesis of Karrikinolide has been achieved. Both α and α' positions of O-acylated acetol were alkylated by the boron-mediated aldol-type acetal addition reaction. The one-pot sequence including the Arbuzov reaction, intramolecular Horner-Wadsworth-Emmons reaction, acidic hydrolysis of acetals, and pyran formation provided Karrikinolide. This procedure was applicable to the gram-scale synthesis of Karrikinolide.
Karrikinolide alleviates BDE-28, heat and Cd stressors in Brassica alboglabra by correlating and modulating biochemical attributes, antioxidative machinery and osmoregulators
Ecotoxicol Environ Saf 2021 Apr 15;213:112047.PMID:33601172DOI:10.1016/j.ecoenv.2021.112047.
In this study, we have evaluated the role of karrikin (KAR1) against the absorption and translocation of a persistent organic pollutant (POP), 2,4,4'-Tribromodiphenyl ether (BDE-28) in plants, in the presence of two other stressors, cadmium (Cd) and high temperature. Furthermore, it correlates the physiological damages of Brassica alboglabra with the three stresssors separately. The results revealed that the post-germination application of KAR1 successfully augmented the growth (200%) and pertinent physiochemical parameters of B. alboglabra. KAR1 hindered air absorption of BDE-28 in plant tissues, and reduced its translocation coefficient (TF). Moreover, BDE-28 was the most negatively correlated (-0.9) stressor with chlorophyll contents, while the maximum mitigation by KAR1 was also achieved agaist BDE-28. The effect of temperature was more severe on soluble sugars (0.51), antioxidative machinery (-0.43), and osmoregulators (0.24). Cd exhibited a stronger inverse interrelation with the enzymatic antioxidant cascade. Application of KAR1 mitigated the deleterious effects of Cd and temperature stress on plant physiological parameters along with reduced aero-concentration factor, TF, and metal tolerance index. The phytohormone reduced lipid peroxidation by decreasing synthesis of ROS and persuading its breakdown. The stability of cellular membranes was perhaps due to the commotion of KAR1 as a growth-promoting phytohormone. In the same way, KAR1 supplementation augmented the membrane stability index, antioxidant defense factors, and removal efficiency of the pollutants. Consequently, the exogenously applied KAR1 can efficiently alleviate Cd stress, heat stress, and POP toxicity.
Metabolomics reveals the influences of smoke-water and Karrikinolide on the biosynthesis of flavonoids and terpenoids in Salvia miltiorrhiza
Funct Plant Biol 2021 Feb;48(3):321-332.PMID:33242388DOI:10.1071/FP20172.
Metabolomics was used to study the influences of smoke-water (SW) and Karrikinolide (KAR1) on the biosynthesis of flavonoids and terpenoids in Salvia miltiorrhiza Bunge. The results showed that a total of 178 and 199 differential metabolites were obtained in SW and KAR1, respectively, compared to the control. The differential metabolites were assigned to the corresponding metabolic pathways. The results indicated that some metabolic pathways in treatments of SW and KAR1 overlapped, suggesting that treatments of SW and KAR1 showed similar effects on the metabolic mechanism of S. miltiorrhiza. To obtain a clear overview of changes in metabolic regulation, TCA cycle, glycolytic pathway, biosynthesis of flavonoids and terpenoids and amino acids metabolism pathway were mapped into a network. We found that treatments with SW and KAR1 could significantly promote the biosynthesis of flavonoids and terpenoids in S. miltiorrhiza. This study could help us better understand the influences of SW and KAR1 on secondary metabolites and their underlying mechanism.
A KARRIKIN INSENSITIVE2 paralog in lettuce mediates highly sensitive germination responses to Karrikinolide
Plant Physiol 2022 Sep 28;190(2):1440-1456.PMID:PMC9516758DOI:10.1093/plphys/kiac328.
Karrikins (KARs) are chemicals in smoke that can enhance germination of many plants. Lettuce (Lactuca sativa) cv. Grand Rapids germinates in response to nanomolar Karrikinolide (KAR1). Lettuce is much less responsive to KAR2 or a mixture of synthetic strigolactone analogs, rac-GR24. We investigated the molecular basis of selective and sensitive KAR1 perception in lettuce. The lettuce genome contains two copies of KARRIKIN INSENSITIVE2 (KAI2), which in Arabidopsis (Arabidopsis thaliana) encodes a receptor that is required for KAR responses. LsKAI2b is more highly expressed than LsKAI2a in dry achenes and during early stages of imbibition. Through cross-species complementation assays in Arabidopsis, we found that an LsKAI2b transgene confers robust responses to KAR1, but LsKAI2a does not. Therefore, LsKAI2b likely mediates KAR1 responses in lettuce. We compared homology models of KAI2 proteins from lettuce and a fire-follower, whispering bells (Emmenanthe penduliflora). This identified pocket residues 96, 124, 139, and 161 as candidates that influence the ligand specificity of KAI2. Further support for the importance of these residues was found through a broader comparison of pocket residues among 281 KAI2 proteins from 184 asterid species. Almost all KAI2 proteins had either Tyr or Phe identity at position 124. Genes encoding Y124-type KAI2 are more broadly distributed in asterids than in F124-type KAI2. Substitutions at residues 96, 124, 139, and 161 in Arabidopsis KAI2 produced a broad array of responses to KAR1, KAR2, and rac-GR24. This suggests that the diverse ligand preferences observed among KAI2 proteins in plants could have evolved through relatively few mutations.