480-19-3
基本信息
异鼠李素
3,5,7-TRIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-4-BENZOPYRONE
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4h-1-benzopyran-4-one
3,5,7-trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-on
3'-METHOXY-3,4',5,7-TETRAHYDROXYFLAVONE
3'-METHOXY-3,5,7,4'-TETRAHYDROXYFLAVONE
3-METHYLQUERCETIN
ISOHAMNETIN
ISORHAMNETIN
2-(3-methoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-4h-1-benzopyran-4-on
3,4’,5,7-tetrahydroxy-3’-methoxy-flavon
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4h-1-benzopyran-4-on
3’-methoxy-3,4’,5,7-tetrahydroxy-flavon
3’-methoxyquercetin
c.i.75680
isorhamnetol
ISOHAMNETIN:3'-METHOXY-3,4',5,7-TETRAHYDRO-XY-FLAVONE
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxy-phenyl)chromen-4-one
QUERCETIN-3-METHYLETHER
QUERCETIN-3-ORTHO-METHYLETHER
物理化学性质
| 熔点 | 307°C |
| 沸点 | 599.4±50.0 °C(Predicted) |
| 密度 | 1.634±0.06 g/cm3(Predicted) |
| 储存条件 | 2-8°C |
| 溶解度 | DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml |
| 酸度系数(pKa) | 6.31±0.40(Predicted) |
| 形态 | neat |
| 颜色 | 淡黄色至琥珀色至深绿色 |
| BRN | 44723 |
| 稳定性 | 吸湿性 |
| InChIKey | IZQSVPBOUDKVDZ-UHFFFAOYSA-N |
| LogP | 1.760 (est) |
| CAS 数据库 | 480-19-3(CAS DataBase Reference) |
安全数据
| 危险性符号(GHS) |  GHS08 |
| 警示词 | 警告 |
| 危险性描述 | H351 |
| 防范说明 | P281-P280 |
| 危险品标志 | Xi,Xn |
| 危险类别码 | 36/37/38-40 |
| 安全说明 | S22 |
| WGK Germany | 3 |
| RTECS号 | LK9275450 |
| 海关编码 | 29329990 |
常见问题列表
图1为异鼠李素
1.胡颓子科：植物沙棘Hippophae fhamnoides L.的果实。
2.萝藦科 (Asclepiadaceae)：台湾眼树莲Dischidia formosana maxim.全草。
3.紫葳科 (Bingoniaceae)：黄钟花 Tecoma stans H. B. K.花。
4.卫矛科(Celastraceae)：微缺美登木Maytenus emarginata Willd. 叶。
5.菊科(Compositae)：长叶山金车Arnica longifolia D.C.Eaton花；黄花蒿 Artemisia annua L.叶，茎：茵陈蒿 Artemisia capillaris Thunb.
6.葫芦科 (Cucurbitaceae)：喙果绞股兰 Gynostemma yixingense C. Y. Wu et S. K. Chen地上部分。
7.豆科 (Leguminosae)：槐Sophora?japonica L.花蕾；红车轴草 Trifolium pratense L.花瓣。
8.无患子科(Sapindaceae)：车桑子 Dodonaea viscosa (L.) Jacq.花。
9.柽柳科(Tamaricaceae)：西河柳Tamarix chinensis Lour.枝。
10.红豆杉科(Taxaceae)：短叶红豆杉Taxus brevifolia Nutt.叶。
11.椴树科(Tiliaceae)：布渣叶Microcos paniculata L.
12.香蒲科(Typhaceae)：长苞香蒲Typha angustata Bory et Chaub.；狭叶香蒲 Typha angustifolia L.
13.伞形科(Umbelliferae)：秦岭柴胡Bupleurum longicaule Wall. ex DC. var. giraldii Wolff全植物；水芹Oenanthe javanica.
14.蒺藜科(Zygophyllaceae)：甘青白刺Nitraria tangutorum Bolor种子。
2.抑制血小板聚集。
3.抗止血作用。抑制某些止血成分的作用。
4.抗肝毒成分。对CCl4和GalN诱导的大鼠肝细胞中毒有抑制作用。5.V9Z：调节雄性植物的繁殖能力。
6.降低大鼠血清和肝脏的胆固醇浓度。
7.抗脂质过氧化。降低大鼠肝脏中硫代巴比妥酸反应物质TBARS的量。
8.抗肿瘤作用，异鼠李素主要是抑制肿瘤细胞增殖，诱导细胞凋亡、抑制信号转导等。，异鼠李素具有显著的抗乳腺癌作用，其作用机制与抑制细胞的增殖通路及促进细胞的凋亡有关。
精确秤取1.0 g 左右的沙棘果渣→加入提取液→超声波提取→过滤→滤液定容→异鼠李素
沙棘果渣中异鼠李素的最佳工艺为：在50℃条件下，超声频率40 kHz，用V 乙酸乙酯︰V95%乙醇为4:6 的提取液超声提取2 次，每次1 h，料液比为1:25。以此方法提取所得异鼠李素含量可达5.09 mg·g-1。
化学合成法：以槲皮素（Ⅰ）为起始原料经乙酰化，苄基化和甲基化反应分别获得槲皮素五乙酸酯（Ⅱ）和4’,7-二-O-苄基槲皮素（Ⅲ），4’,7-二-O-苄基槲皮素三乙酸酯（Ⅳ）和4’,7-二-O-苄基-3’-甲基槲皮素（Ⅴ）中间体。化合物（Ⅴ）经苄基化反应则得到异鼠李素（Ⅵ）。
|
PI3-K
|
MEK1
|
Human Endogenous Metabolite
|
Isorhamnetin is a plant flavonoid that occurs in fruits and medicinal herbs. Isorhamnetin binds directly to MEK1 in an ATP-noncompetitive manner and to PI3-K in an ATP-competitive manner. In vitro and ex vivo kinase assay data show that Isorhamnetin inhibits the kinase activity of MAP/ERK kinase (MEK) 1 and PI3-K and the inhibition is due to direct binding with Isorhamnetin. Isorhamnetin inhibits the Akt/mTOR and MEK/ERK signaling pathways, and promotes the activity of the mitochondrial apoptosis signaling pathway. The inhibitory effects of Isorhamnetin on breast cancer cells are determined using the CCK-8 method. Isorhamnetin inhibits the proliferation of numerous breast cancer cells (IC 50 , ~10 µM), including MCF7, T47D, BT474, BT-549, MDA-MB-231 and MDA-MB-468, whereas less inhibitory activity is observed in the MCF10A normal breast epithelial cell line (IC 50 , 38 µM).
Photographic data shows that Isorhamnetin treatment suppresses tumor development in mice. The average volume of tumors in untreated mice increases over time and reaches a volume of 623 mm 3 at 4 weeks post-inoculation; however, at this time, in mice treated with 1 or 5 mg/kg Isorhamnetin, the average tumor volume is only 280 or 198 mm 3 , respectively. At the end of the study, Isorhamnetin treatment (1 or 5 mg/kg) reduces tumor weight compared with the untreated control group.