ATRACTYLENOLIDE-1
Atractylenolide-1
CAS: 73069-13-3
Molecular Formula: C15H18O2
ATRACTYLENOLIDE-1 - Names and Identifiers
| Name | Atractylenolide-1 |
| Synonyms | Atractylenolide Ⅰ ATRACTYLENOLIDE-1 Atractylenolide-1 atractylenolide I 8,9-Dehydroasterolide Eudesma-4(15),7(11),8-trien-12-olide 3,8aβ-Dimethyl-5-methylene-2,4,4aα,5,6,7,8,8a-octahydronaphtho[2,3-b]furan-2-one (4aS,8aS)-4a,5,6,7,8,8a-Hexahydro-3,8a-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one (4aS,8aS)-3,8a-dimethyl-5-methylidene-4a,5,6,7,8,8a-hexahydronaphtho[2,3-b]furan-2(4H)-one Naphtho[2,3-b]furan-2(4H)-one,4a,5,6,7,8,8a-hexahydro-3,8a-dimethyl-5-methylene-, (4aS,8aS)- |
| CAS | 73069-13-3 |
| InChI | InChI=1/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h8,12H,1,4-7H2,2-3H3/t12-,15+/m0/s1 |
| InChIKey | ZTVSGQPHMUYCRS-SWLSCSKDSA-N |
ATRACTYLENOLIDE-1 - Physico-chemical Properties
| Molecular Formula | C15H18O2 |
| Molar Mass | 230.3 |
| Density | 1.12 |
| Melting Point | 121-123 °C(Solv: ligroine (8032-32-4)) |
| Boling Point | 405.0±44.0 °C(Predicted) |
| Specific Rotation(α) | (c, 0.01 in MeOH)+222 |
| Flash Point | 170℃ |
| Solubility | Soluble in methanol, ethanol, DMSO and other organic solvents |
| Vapor Presure | 9.08E-07mmHg at 25°C |
| Appearance | White needle crystal |
| Storage Condition | 2-8°C |
| Refractive Index | 1.554 |
| MDL | MFCD09037395 |
| Physical and Chemical Properties | White-like crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from atractyolodesmacrocephalagoidz.. |
| In vitro study | Atractylenolide I (40, 60, 80, 100, 120, 150 μM) dose- and time-dependently reduces the cell viability in human A375 melanoma cells after treatment for 24, 48 and 72 hours. Atractylenolide I (50 and 100 μM) induces apoptosis of A375 cells in a dose-dependent manner at 48 h of treatment. Atractylenolide I (100 μM) significantly reduces protein levels of phosphorylated JAK2 and STAT3 in A375 cells, without effect on total JAK2 and STAT3. Furthermore, Atractylenolide I inhibits the mRNA expression of STAT3-targeted genes, including Bcl-xL, MMP-2 and MMP-9. Atractylenolide I (up to 100 μM) shows no toxicity in normal cells. Atractylenolide I (25, 50 μM) decreases the Ox-LDL induced TNF-α, IL-6 and NO production in VSMCs. Atractylenolide I (12.5, 25 or 50 μM) significantly reduces the level of MCP-1 and inhibits Ox-LDL-induced VSMCs proliferation and migration. Atractylenolide I (25, 50 μM) inhibits positive staining of foam cells, and also significantly decreases lipid accumulation. Atractylenolide I (50 μM) suppresses p38MAPK and NF-κB p65 expression in VSMCs stimulated by Ox-LDL. Atractylenolide I (1, 10, 100 μM) downregulates paclitaxel-induced expression of VEGF and survivin via MyD88-dependent TLR4 signaling in EOC cells. |
| In vivo study | Atractylenolide I (5, 10 or 20 mg/kg, p.o.) restores the decreased body weight in mice subjected to chronic unpredictable mild stress (CUMS). Atractylenolide I alleviates CUMS-induced depressive-like behavior, attenuates CUMS-induced imbalances in hippocampal neurotransmitter levels and reduces CUMS-induced increases in hippocampal pro-inflammatory cytokine levels and in the NLRP3 inflammasome in the hippocampi of mice. |
ATRACTYLENOLIDE-1 - Risk and Safety
| WGK Germany | 3 |
ATRACTYLENOLIDE-1 - Reference
| Reference Show more | 1. Di Si-rong, Wang Xue, Wang cancan et al. Simultaneous determination of four active components in ganyankang powder by HPLC and its fingerprint [J]. Journal of Shenyang Pharmaceutical University, 2019, 36(04):308-314. 2. Shen Jiantao, Zhang Zhenling. Study on the changes of content of Atractylodes macrocephala lactone Ⅰ, Ⅲ with storage time in processed products of Atractylodes macrocephala [J]. Shi Zhen, National Medicine, 2014, 025(008):1873-1875. 3. Deng song, Wang Aiping, Chen Xi, et al. Huangqi Baizhu decoction down-regulates miR-31-5p/STAT3 loop to inhibit colitis-associated colon cancer process [J]. Chinese pharmacological Bulletin, 2019, v.35(09):134-139. 4. Zhang Dong, Zhouqi. Determination of Atractylodes macrocephala lactone Ⅰ and Atractylodes macrocephala lactone Ⅲ in Atractylodes macrocephala by HPLC [J]. Northern Pharmacy 2017 14(03):1-2. 5. Wang Jianjian. Optimization of extraction process of Atractylodes macrocephala lactone Ⅰ,Ⅱ,Ⅲ from Atractylodes macrocephala [J]. Chinese Journal of Experimental prescriptions, 2015. 6. Li Hongying, long Lan, Cheng Xinhua, Li Yajie, Huang Jianmin, super. Determination of Atractylodes macrocephala lactone Ⅰ and Atractylodes macrocephala lactone Ⅲ in Atractylodes macrocephala [J]. Journal of Hubei University for Nationalities (Natural Science Edition),2013,31(02):142-144. 7. Ouyang Limin, Wang Xinhong, Zhu Simin, etc. Study on the best harvest time of Atractylodes lancea based on AHP-CRITIC method [J]. Chinese traditional medicines, 2020, 042(003):708-713. 8. Li Chunhua, Li Jiajia, Da Jia Ying, etc. Optimization of extraction process of volatile oil from Rhizoma atractylodis macrocephalae and Ramulus cinnamomi by extraction-azeotropic distillation coupling technology [J]. Chinese patent medicine, 2019, 41(05):1132-1135. 9. Ding, Yi, Xue, Xu, Ji-Chang, Wu, Wei, et al. Simultaneous determination of four sesquiterpenes in Atractylodes macrocephala by HPLC [J]. Chinese patent medicine 2020 042(004):927-931. 10. Wenting Chen, Yang Chen, Bo Cui, et al. Feasibility study of gas chromatography "one test and multiple evaluation" for determination of multi-component content in Atractylodes lancea [J]. Chinese Journal of Traditional Chinese Medicine, 2018, 043(003):551-556. 11. Li Qin-yu, Wu Wei-gang, Cui Bo, et al. High performance liquid chromatography combined with multivariate statistical analysis for quality evaluation of Atractylodes lancea [J]. Journal of Pharmaceutical Analysis, 2018, v.38(04):56-66. 12. Wang, Qian, et al. "Content determination of the major constituents of Yinchenzhufu decoction via ultra high-performance liquid chromatography coupled with electrospray ionisation tandem mass spectrometry." Journal of pharmaceutical and biomedical analysis 13. Wang, Qian, et al. "Content determination of the major constituents of Yinchenzhufu decoction via ultra high-performance liquid chromatography coupled with electrospray ionisation tandem mass spectrometry ." Journal of pharmaceutical and biomedical analysis 14. [IF=3.935] Qian Wang et al."Content determination of the major constituents of Yinchenzhufu decoction via ultra high-performance liquid chromatography coupled with electrospray ionisation tandem mass spectrometry."J Pharmaceut Biomed. 2013 Apr;77:88 15. [IF=4.96] Yangyang Guo et al."Inhibition of proliferation-linked signaling cascades with atractylenolide I reduces myofibroblastic phenotype and renal fibrosis."Biochem Pharmacol. 2021 Jan;183:114344 16. [IF=4.36] Xiaoli Zhao et al."Transcriptomic study of the mechanism by which the Kai Yu Zhong Yu recipe improves oocyte quality in a stressed mouse model."J Ethnopharmacol. 2021 Oct;278:114298 17. [IF=4.032] Qiu-yue Xiao et al."A network pharmacology-based study on key pharmacological pathways and targets of Qi Fu Yin acting on Alzheimer's disease."Exp Gerontol. 2021 Jul;149:111336 18. [IF=3.205] Jie Tang et al."Metabolite profiling of Shuganzhi tablets in rats and pharmacokinetics study of four bioactive compounds with liquid chromatography combined with electrospray ionization tandem mass spectrometry."J Chromatogr B. 2021 Aug;1179:122827 19. [IF=4.759] Gao-Yan Tong et al."Analysis of active compounds and geographical origin discrimination of Atractylodes macrocephala Koidz. by using high performance liquid chromatography-diode array detection fingerprints combined with chemometrics."JOURNAL OF CHROMATOGR |
ATRACTYLENOLIDE-1 - Reference Information
| trait | The oil is red-brown oily liquid with unique aroma of Atractylodes macrocephala Koidz. The volatile oil containing 1.4%, the main components of Atractylol (Atractylol), Atractylon (Atractylon), etc., and contains vitamin A. The rhizome contains about 1.4% of volatile oil, and the oil contains atractylodes lancetone (a-tractylone), Atractylodes macrocephala, B (butenolide A,B), and clostenadienone [selina-4(14)], 7(11)-dien-8-one], β-apigenin (β- Se-linene), Eucalyptus terpene (aromaden-drene); Other oxygen-containing coumarines, sugars and resins. |
| Use | Baizhu oil can be used as other APIs. Atractylodes macrocephala lactone Ⅰ has anti-inflammatory, anti-tumor effects, regulating gastrointestinal function and promoting nutrient absorption. for content determination/identification/pharmacological experiments. Pharmacological Efficacy: Atractylodes macrocephala lactone I can promote gastrointestinal digestion and absorption function, is the active ingredient of the spleen atractylodes-. Has anti-inflammatory, anti-tumor effect, the ingredient also has the function of regulating gastrointestinal function and promote the absorption of nutrients. |
| biological activity | Atractylenolide I is a sesquiterpene derived from the root of Atractylodes macrocephala, with neuroprotective, anti-allergic, anti-inflammatory and anti-cancer and other biological activities. Atractylenolide I is an antagonist of TLR4 and reduces the phosphorylation levels of JAK2 and STAT3 in A375 cells. |
| Target | JAK2, STAT3, TLR4 |
Last Update：2024-04-09 21:04:16
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View History
ATRACTYLENOLIDE-1
N-丙基-4-氨基哌啶盐酸盐
(2Z)-2-[(3-氯苯基)亚甲基]-6-羟基-3-苯并呋喃酮
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1-[(叔丁氧羰基)氨基]环丙烷羧基 酸
2-苄基八氢吡咯并[3,4-C]吡啶
TOSLAB 775448
2-羟基-4-甲基嘧啶-5-甲酸 乙酯
5-甲基-3-(三氟甲基)吡啶甲酸
N-丙基-4-氨基哌啶盐酸盐
(2Z)-2-[(3-氯苯基)亚甲基]-6-羟基-3-苯并呋喃酮
TimTec1_008382
2-异丙基-5,5-二甲基噻唑烷-4-羧酸
1-[(叔丁氧羰基)氨基]环丙烷羧基 酸
2-苄基八氢吡咯并[3,4-C]吡啶
TOSLAB 775448
2-羟基-4-甲基嘧啶-5-甲酸 乙酯
5-甲基-3-(三氟甲基)吡啶甲酸