中文名 | R-紫草素 |
英文名 | Shikonin |
别名 | 紫草素 紫草红 紫朱草素 R-紫草素 紫草红,紫朱草素 SHIKONIN 紫草素 紫草素,左旋紫草素(标准品) 5,8-二羟基-2-[(1R)-1-羟基-4-甲基戊-3-烯基]萘-1,4-二酮 |
英文别名 | Shikonin Shikonine Tokyo Violet SHIKONIN(AS) (-)-ShikoninChina Shikonin, froM Arnebia sp. 5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)-1,4-naphthoquinone 5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione 5,8-Dihydroxy-2-[(R)-1-hydroxy-4-methyl-3-pentenyl]-1,4-naphthalenedione 1,4-naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-penten-1-yl)- 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione 5,8-Dihydroxy-2-[(1R)-1-Hydroxy-4-Methyl-Pent-3-Enyl]Naphthalene-1,4-Dione (R)-5,8-Dihydroxy-2-(1-hydroxy-4-Methylpent-3-en-1-yl)naphthalene-1,4-dione 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]naphthalene-1,4-dione Shikonin 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione |
CAS | 517-89-5 |
化学式 | C16H16O5 |
分子量 | 288.3 |
InChI | InChI=1/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1 |
密度 | 1.373±0.06 g/cm3(Predicted) |
熔点 | 148℃ |
沸点 | 567.4±50.0 °C(Predicted) |
闪点 | 311°C |
蒸汽压 | 1.04E-13mmHg at 25°C |
溶解度 | 不溶于水,溶于乙醇、有机溶剂和植物油。易溶于碱水,遇酸又沉淀析出。 |
折射率 | 1.642 |
酸度系数 | 7.34±0.20(Predicted) |
存储条件 | -20°C |
外观 | 红色结晶固体。 |
物化性质 | 紫褐色针状结晶,熔点147℃,旋光度αD20=+135°(苯)。溶于苯乙醚、丙酮、氯仿、甲醇、乙醇、甘油、动植物油和碱性水溶液,不溶于水。色调随Ph值变化,Ph值4~6呈红色,Ph值8呈紫色,Ph值10~12则蓝色。耐光、耐热、耐氧化性好,对还原剂量不稳定,遇铁离子呈深紫色。有一定的抗菌作用。 |
MDL号 | MFCD00075680 |
风险术语 | R20/21/22 - 吸入、皮肤接触及吞食有害。 R50/53 - 对水生生物有极高毒性,可能对水体环境产生长期不良影响。 R20 - 吸入有害。 |
安全术语 | S26 - 不慎与眼睛接触后,请立即用大量清水冲洗并征求医生意见。 S36/37/39 - 穿戴适当的防护服、手套和护目镜或面具。 S61 - 避免释放至环境中。参考特别说明/安全数据说明书。 |
危险品运输编号 | 3077 |
海关编号 | 29146990 |
上游原料 | 丙二醇 大豆油 |
参考资料 展开查看 | 1. 顾依 周琴 刘馨 刁和芳 陈志鹏 陈瑞 朱辰奇.丹参聚多巴胺纳米递药系统的构建及对H_2O_2诱导心肌细胞氧化损伤的保护作用研究[J].中草药 2020 51(14):3655-3662. 2. 李发凯, 张芳, 陆远,等. 紫草素促进肺癌A549细胞凋亡[J]. 现代生物医学进展, 2018, 018(009):1611-1615,1673. 3. 周海, 伍春莲, 徐佳,等. 紫草素对人结肠癌细胞Lovo增殖与凋亡的影响[J]. 西华师范大学学报(自然科学版), 2014, 35(002):135-139. 4. 赵莎, 潘敏, 陈菲菲,等. 紫草素对银屑病样动物模型Th17细胞相关因子的影响[J]. 临床皮肤科杂志, 2016, 045(005):323-327. 5. 魏玉, 康冰亚, 张明昊,等. 紫草素纳米乳的制备及其稳定性考察[J]. 时珍国医国药, 2018, 29(12):2932-2935. 6. 王媛, 刘莉, 陆远,等. 紫草素逆转埃克替尼对肺癌EGFR-TKI耐药及其机制的研究[J]. 现代生物医学进展, 2016, 16(016):3044-3047. 7. 路京, 陈子龙, 闵朕,等. 紫草素逆转由肝细胞生长因子诱导的肺癌吉非替尼耐药[J]. 中国病理生理杂志, 2019, 35(01):68-73. 8. 徐翊雯, 袁瑞娟, 董洁,等. 紫草素锌配合物的合成及其对人宫颈癌HeLa细胞的抑制作用[J]. 中医学报, 2016(3):316-318. 9. 孙健文 温宪春 蔡德富 等. RP-HPLC法同时测定新疆紫草中紫草素、乙酰紫草素、β β-二甲基丙烯酰紫草素的含量[J]. 中国药房 2018 v.29;No.622(04):455-457. 10. 牛敏 刘红燕 刘谦 等. 4个栽培年限丹参颜色与9种活性成分含量的相关性[J]. 中成药 2017(1):131-135. 11. 崔伟亮. 丹参酒炙前后HPLC指纹图谱色谱峰归属比较[J]. 辽宁中医杂志, v.46;No.507(08):1707-1709. 12. Chao Yang, Pei Liu, Shuang Wang, Gan Zhao, Tao Zhang, Shuai Guo, KangFeng Jiang, HaiChong Wu, Ganzhen Deng, Shikonin exerts anti-inflammatory effects in LPS-induced mastitis by inhibiting NF-κB signaling pathway, Biochemical and Biophysical Research Commun 13. Heyong Wang, Chunlian Wu, Shengbang Wan, Huijun Zhang, Songwen Zhou, Gentao Liu, Shikonin attenuates lung cancer cell adhesion to extracellular matrix and metastasis by inhibiting integrin β1 expression and the ERK1/2 signaling pathway, Toxicology, Volume 14. Wen, Xianchun, et al. "Anticancer efficacy of targeted shikonin liposomes modified with RGD in breast cancer cells." Molecules 23.2 (2018): 268.https://doi.org/10.3390/molecules23020268 15. Han Y, Shen M, Tang LY, Tan G, Yang QC, Ye L, Ye LH, Jiang N, Gao GP, Shao Y, Shao Y, et al: Antiangiogenic effects of catalpol on rat corneal neovascularization. Mol Med Rep 17: 2187-2194, 2018 16. Chunfang Liu, Lianhua He, Jingxia Wang, Qianqian Wang, Congcong Sun, Yiqun Li, Kexin Jia, Jinxia Wang, Tengteng Xu, Ruirui Ming, Qingwen Wang, Na Lin,Anti-angiogenic effect of Shikonin in rheumatoid arthritis by downregulating PI3K/AKT and MAPKs signaling 17. [IF=3.547] Heyong Wang et al."Shikonin attenuates lung cancer cell adhesion to extracellular matrix and metastasis by inhibiting integrin β1 expression and the ERK1/2 signaling pathway."Toxicology. 2013 Jun;308:104 18. [IF=3.06] Xianchun Wen et al."Anticancer Efficacy of Targeted Shikonin Liposomes Modified with RGD in Breast Cancer Cells."Molecules. 2018 Feb;23(2):268 19. [IF=2.985] Chao Yang et al."Shikonin exerts anti-inflammatory effects in LPS-induced mastitis by inhibiting NF-κB signaling pathway."Biochem Bioph Res Co. 2018 Oct;505:1 20. [IF=2.896] Lu Wang et al."Rapid assay for testing superoxide anion radical scavenging activities to natural pigments by ultra-high performance liquid chromatography-diode-array detection method."Anal Methods-Uk. 2015 Feb;7(4):1535-1542 21. [IF=1.312] Qi Zhang et al."Rapid and sensitive determination of shikonin and its derivatives in the roots of Arnebia euchroma (Royle) Johnst using matrix solid-phase dispersion extraction and ultrahigh-performance liquid chromatography with photodiode array detecto 22. [IF=5.81] Liu Yun-zi et al."Pyruvate Kinase M2 Mediates Glycolysis Contributes to Psoriasis by Promoting Keratinocyte Proliferation."Front Pharmacol. 2021 Oct;0:2888 23. [IF=5.455] He Lianhua et al."Shikonin attenuates rheumatoid arthritis by targeting SOCS1/JAK/STAT signaling pathway of fibroblast like synoviocytes."Chin Med-Uk. 2021 Dec;16(1):1-15 24. [IF=5.279] Wenqin Li et al."Discovery of Natural Products as Multitarget Inhibitors of Insect Chitinolytic Enzymes through High-Throughput Screening."J Agr Food Chem. 2021;69(37):10830–10837 25. [IF=4.545] Kai Chen et al."Shikonin mitigates ovariectomy-induced bone loss and RANKL-induced osteoclastogenesis via TRAF6-mediated signaling pathways."Biomed Pharmacother. 2020 Jun;126:110067 26. [IF=3.69] Chunfang Liu et al."Anti-angiogenic effect of Shikonin in rheumatoid arthritis by downregulating PI3K/AKT and MAPKs signaling pathways."J Ethnopharmacol. 2020 Oct;260:113039 27. [IF=2.952] Liying Sha et al."Shikonin inhibits the Warburg effect, cell proliferation, invasion and migration by downregulating PFKFB2 expression in lung cancer."Mol Med Rep. 2021 Aug;24(2):1-10 28. [IF=1.785] Fang Zhang et al."Non‑cytotoxic doses of shikonin inhibit lipopolysaccharide‑induced TNF‑α expression via activation of the AMP‑activated protein kinase signaling pathway."Exp Ther Med. 2020 Nov;20(5):1-1 29. [IF=1.312] Xu Wang et al."Microwave-assisted ionic liquid microextraction combined with high performance liquid chromatography for the determination of naphthoquinones from Arnebia euchroma (Royle) Johnst."Journal Of Liquid Chromatography & Related Technologies. 20 30. [IF=5.81] Jieli Pan et al.Up-Regulation of p53/miR-628-3p Pathway, a Novel Mechanism of Shikonin on Inhibiting Proliferation and Inducing Apoptosis of A549 and PC-9 Non-Small Cell Lung Cancer Cell Lines.Front Pharmacol. 2021 Nov 16;12:766165 31. [IF=7.848] Mingyue Zhou et al."Oriented Layered Graphene Oxide Pad Favoring High Loading Capacity and Stability for High-Throughput Chemical Screening."Advanced Materials Technologies. 2022 Mar 11 32. [IF=3.981] Luhua Meng et al."Hyaluronic acid-coated shikonin liposomes for the treatment of triple-negative breast cancer via targeting tumor cells and amplification of oxidative stress."J Drug Deliv Sci Tec. 2022 Apr;70:103193 33. [IF=4.35] Yangli Wan et al."Control of Foodborne Staphylococcus aureus by Shikonin, a Natural Extract."Foods. 2021 Dec;10(12):2954 34. [IF=5.811] |
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