Kauniolide
目录号 : GC36386
Kauniolide(81066-45-7)是天然产物。
Cas No.:81066-45-7
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
Kauniolide(81066-45-7) is a natural compound.
| Cas No. | 81066-45-7 | SDF | |
| Canonical SMILES | CC([C@]1([H])[C@](OC2=O)([H])[C@](CC3)([H])C2=C)=CCC1=C3C | ||
| 分子式 | C15H18O2 | 分子量 | 230.3 |
| 溶解度 | Soluble in DMSO | 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 | 4.3422 mL | 21.7108 mL | 43.4216 mL |
| 5 mM | 0.8684 mL | 4.3422 mL | 8.6843 mL |
| 10 mM | 0.4342 mL | 2.1711 mL | 4.3422 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。
Kauniolide synthase is a P450 with unusual hydroxylation and cyclization-elimination activity
Nat Commun 2018 Nov 7;9(1):4657.PMID:30405138DOI:10.1038/s41467-018-06565-8.
Guaianolides are an important class of sesquiterpene lactones with unique biological and pharmaceutical properties. They have been postulated to be derived from germacranolides, but for years no progress has been made in the elucidation of their biosynthesis that requires an unknown cyclization mechanism. Here we demonstrate the isolation and characterization of a cytochrome P450 from feverfew (Tanacetum parthenium), Kauniolide synthase. Kauniolide synthase catalyses the formation of the guaianolide Kauniolide from the germacranolide substrate costunolide. Unlike most cytochrome P450s, Kauniolide synthase combines stereoselective hydroxylation of costunolide at the C3 position, with water elimination, cyclization and regioselective deprotonation. This unique mechanism of action is supported by in silico modelling and docking experiments. The full Kauniolide biosynthesis pathway is reconstructed in the heterologous hosts Nicotiana benthamiana and yeast, paving the way for biotechnological production of guaianolide-type sesquiterpene lactones.
CRISPR/Cas9 targeted inactivation of the Kauniolide synthase in chicory results in accumulation of costunolide and its conjugates in taproots
Front Plant Sci 2022 Aug 29;13:940003.PMID:36105709DOI:10.3389/fpls.2022.940003.
Chicory taproots accumulate sesquiterpene lactones lactucin, lactucopicrin, and 8-deoxylactucin, predominantly in their oxalated forms. The biosynthetic pathway for chicory sesquiterpene lactones has only partly been elucidated; the enzymes that convert farnesyl pyrophosphate to costunolide have been described. The next biosynthetic step of the conversion of costunolide to the tricyclic structure, guaianolide Kauniolide, has so far not been elucidated in chicory. In this work three putative Kauniolide synthase genes were identified in chicory named CiKLS1, CiKLS2, and CiKLS3. Their activity to convert costunolide to Kauniolide was demonstrated in vitro using yeast microsome assays. Next, introduction of CRISPR/Cas9 reagents into chicory protoplasts was used to inactivate multiple chicory KLS genes and several chicory lines were successfully regenerated. The inactivation of the Kauniolide synthase genes in chicory by the CRISPR/Cas9 approach resulted in interruption of the sesquiterpene lactone biosynthesis in chicory leaves and taproots. In chicory taproots, but not in leaves, accumulation of costunolide and its conjugates was observed to high levels, namely 1.5 mg/g FW. These results confirmed that all three genes contribute to STL accumulation, albeit to different extent. These observations demonstrate that three genes oriented in tandem on the chicory genome encode Kauniolide synthases that initiate the conversion of costunolide toward the sesquiterpene lactones in chicory.
Essential Oil and Non-Volatile Metabolites from Kaunia longipetiolata (Sch.Bip. ex Rusby) R. M. King and H. Rob., an Andean Plant Native to Southern Ecuador
Plants (Basel) 2022 Nov 3;11(21):2972.PMID:36365423DOI:10.3390/plants11212972.
Kaunia longipetiolata (Sch.Bip. ex Rusby) R. M. King and H. Rob. (Asteraceae) is a plant native to southern Ecuador. The dry leaves afforded, by steam distillation, an essential oil that was qualitatively and quantitatively analyzed by GC-MS and GC-FID, respectively, on two orthogonal columns of different polarity. Sesquiterpenes predominated in the volatile fraction, among which α-zingiberene (19.7-19.1%), ar-curcumene (17.3-18.1%), caryophyllene oxide (5.1-5.3%), (Z)-β-caryophyllene (3.0-3.1%), (2Z,6Z)-farnesal (2.6-3.6%), and spathulenol (2.0-2.1%) were the major components. In addition to the identified compounds, two main unidentified constituents (possibly oxygenated sesquiterpenes) with probable molecular masses of 292 and 230, respectively, were detected. They constituted about 5% and 8% (w/w), respectively, of the whole essential oil. The oil chemical composition was complemented with the enantioselective analysis of ten chiral components. Four scalemic mixtures and six enantiomerically pure terpenes were identified. An enantiomeric excess (ee) was determined for (1R,5R)-(+)-β-pinene (65.0%), (R)-(-)-α-phellandrene (94.6%), (S)-(+)-linalool (15.0%), and (R)-(-)-terpinen-4-ol (33.8%). On the other hand, (1R,5R)-(+)-α-pinene, (1R,5R)-(+)-sabinene, (S)-(-)-limonene, (S)-(+)-β-phellandrene, (1R,2S,6S,7S,8S)-(-)-α-copaene, and (R)-(+)-germacrene D were enantiomerically pure. Finally, the non-volatile fraction obtained by extraction of the leaves with MeOH was investigated. Eight known compounds were isolated by liquid column chromatographic separations. Their structures were determined by NMR spectroscopy as dehydroleucodine, Kauniolide, (3S,3aR,4aR,6aS,9aS,9bR)-3-hydroxy-1,4a-dimethyl-7-methylene-5,6,6a,7,9a,9b-hexahydro-3H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one, novanin, bisabola-1,10-diene-3,4-trans-diol, (R)-2-(2-(acetoxymethyl)oxiran-2-yl)-5-methylphenyl isobutyrate, eupalitin-3-O-glucoside, and 3,5-di-O-caffeoylquinic acid. Literature data about the identified metabolites indicate that K. longipetiolata is a rich source of biologically active natural products.
The yeast platform engineered for synthetic gRNA-landing pads enables multiple gene integrations by a single gRNA/Cas9 system
Metab Eng 2021 Mar;64:111-121.PMID:33549837DOI:10.1016/j.ymben.2021.01.011.
Saccharomyces cerevisiae is a versatile microbial platform to build synthetic metabolic pathways for production of diverse chemicals. To expedite the construction of complex metabolic pathways by multiplex CRISPR-Cas9 genome-edit, eight desirable intergenic loci, located adjacent to highly expressed genes selected from top 100 expressers, were identified and fully characterized for three criteria after integrating green fluorescent protein (GFP) gene - CRISPR-mediated GFP integration efficiency, expression competency assessed by levels of GFP fluorescence, and assessing growth rates of GFP integrated strains. Five best performing intergenic loci were selected to build a multiplex CRISPR platform, and a synthetic 23-bp DNA comprised of 20-bp synthetic DNA with a protospacer adjacent motif (PAM) was integrated into the five loci using CRISPR-Cas9 in a sequential manner. This process resulted in five different yeast strains harbouring 1-5 synthetic gRNA-binding sites in their genomes. Using these pre-engineered yeast strains, simultaneous integrations of 2-, 3-, 4-, or 5-genes to the targeted loci were demonstrated with efficiencies from 85% to 98% using beet pigment betalain (3-gene pathway), hygromycin and geneticin resistance markers. Integrations of the multiple, foreign genes in the targeted loci with 100% precision were validated by genotyping. Finally, we further developed the strain to have 6th synthetic gRNA-binding site, and the resulting yeast strain was used to generate a yeast strain producing a sesquiterpene lactone, Kauniolide by simultaneous 6-gene integrations. This study demonstrates the effectiveness of a single gRNA-mediated CRISPR platform to build complex metabolic pathways in yeast.