582-46-7
基本信息
土曲霉酮
Terrain
NSC 29130
(+)Terrein
NSC-291308
(+) Terrein, NSC 291308
(4S,5R)-4,5-Dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one
(4S,5R)-4,5-Dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one
2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1E)-1-propen-1-yl-, (4S,5R)-
物理化学性质
| 熔点 | 125-127℃ |
| 沸点 | 327.2±42.0 °C(Predicted) |
| 密度 | 1.449±0.06 g/cm3(Predicted) |
| 储存条件 | ?20°C |
| 溶解度 | H2O：可溶 1-1.10 mg/mL，透明，无色 |
| 酸度系数(pKa) | 11.77±0.60(Predicted) |
| 形态 | 固体 |
| 生物来源 | Aspergillus terreus |
| 水溶解性 | H2O: soluble 1-1.10mg/mL, clear, colorless DMSO: soluble |
| 化妆品成分功效 | SKIN CONDITIONING |
| InChI | 1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+ |
| InChIKey | MHOOPNKRBMHHEC-NSCUHMNNSA-N |
| SMILES | OC1C(C(=O)C=C1\C=C\C)O |
安全数据
| 危险性符号(GHS) |  GHS07 |
| 警示词 | 警告 |
| 危险性描述 | H302-H315-H319-H335 |
| 防范说明 | P261-P305+P351+P338 |
| WGK Germany | 3 |
| 海关编码 | 29419000 |
| 存储类别 | 11 - Combustible Solids |
常见问题列表
Treatment of Mel-Ab cells with Terrein (10-100 µM) for 4 days significantly reduces melanin levels in a dose-dependent manner. Terrein reduces melanin synthesis by reducing tyrosinase production via ERK activation.
Terrein (5-500 µM; 24 and 48 hours) reduces the viability of these cells in concentration- and time-dependent manners.
Terrein (150, 250, 500µM; 24 hours) induces programmed cell death in both invasive and non-invasive breast cancer cell lines. Thus, the optimal non-toxic concentrations of Terrein (25 and 75 µM) were used for subsequent experiments.
Terrein (25 and 75 µM) significantly decrease the mRNA levels of both MMP-2 and MMP-9 in MDA-MB-231 cells. Terrein (75 µM) significantly decrease the mRNA levels of both MMP-2 and MMP-9 in MCF-7 cells.
Terrein (75 µM) inhibits the expression of RhoA, RhoB, p-Rac1 in MCF-7 cells. Terrein (75 µM) inhibits the expression of RhoB, p-Rac1 in MDA-MB-231 cells.
Terrein (10, 30, and 100 μM) inhibits the production of virulence factors such as elastase, pyocyanin, and rhamnolipid, as well as biofilm formation in P. aeruginosa PAO1 and PA14 strains.
Cell Viability Assay
| Cell Line: | MCF-7 and MDA-MB-231 cells |
| Concentration: | 5, 25, 50, 75, 100, 150, 250, 500 µM |
| Incubation Time: | 24 and 48 hours |
| Result: | The IC 50 s for MCF-7 and MDA-MB-231 cells after 24 h of incubation were 2.34 mM and 700 µM, respectively. After 48 h of incubation, the IC 50 s are 244.3 µM for MCF-7 and 244.5 µM for MDA-MB-231 cells. |
Apoptosis Analysis
| Cell Line: | MCF-7 and MDA-MB-231 cells |
| Concentration: | 25, 75, 150, 250, 500 µM |
| Incubation Time: | 24 hours |
| Result: | The percentages of apoptotic cells after 25 and 75 µM treatment were 7.52 and 5.82%, respectively for MCF-7 cells (9.94% for the control), and 15.77 and 15.82%, respectively for MDA-MB-231 cells (8.79% for the control). |
RT-PCR
| Cell Line: | MCF-7 and MDA-MB-231 cells |
| Concentration: | 25, 75 µM |
| Incubation Time: | |
| Result: | Decreased the mRNA levels of both MMP-2 and MMP-9 in a concentration-dependent manner. |
Western Blot Analysis
| Cell Line: | MCF-7 and MDA-MB-231 cells |
| Concentration: | 75 µM |
| Incubation Time: | 6, 12 and 24 hours |
| Result: |
RhoA and RhoB protein levels were significantly decreased after 6 h of 75 µM treatment in MCF-7 cells.
Phosphorylated (p)-Rac1 was also slightly decreased at 12 h. However, RhoC and Cdc42 levels remained unchanged. RhoB protein levels and Rac1 phosphorylation were also decreased in MDA-MB-231 cells at 12 and 24 h, respectively. |