(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one Basic information
- Product Name:
- (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
- Synonyms:
-
- (-)-Deoxypodorhizone
- (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
- (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-[(1,3-benzodioxole-5-yl)methyl]-4,5-dihydrofuran-2(3H)-one
- (3R,4R)-3-(3,4,5-Trimethoxybenzyl)-4-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
- (3R,4R)-3-(3,4,5-Trimethoxybenzyl)-4-[(1,3-benzodioxol-5-yl)methyl]dihydrofuran-2(3H)-one
- Yatein
- (+)-Deoxypodorhizon
- (3S)-3β-(3,4,5-Trimethoxybenzyl)-4α-[(1,3-benzodioxole-5-yl)methyl]-4,5-dihydrofuran-2(3H)-one
- CAS:
- 40456-50-6
- MF:
- C22H24O7
- MW:
- 400.42
- Mol File:
- 40456-50-6.mol
(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one Chemical Properties
- Boiling point:
- 564.9±45.0 °C(Predicted)
- Density
- 1.266±0.06 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- Soluble in DMSO
- form
- A solid
- color
- Colorless to light yellow
(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one Usage And Synthesis
Description
Yatein is a lignan that has been found in C. formosana and has diverse biological activities. It inhibits the cytochrome P450 (CYP) isoform CYP3A4 (IC50 = 1 μM). Yatein inhibits herpes simplex virus 1 (HSV-1) replication in a plaque reduction assay (IC50 = 30.6 μM). It induces apoptosis and production of reactive oxygen species (ROS) in, and is cytotoxic to, A549 and CL1-5 non-small cell lung cancer (NSCLC) cells (IC50s = 3.5 and 1.9 μM, respectively). Yatein inhibits aggregation of rabbit platelets induced by platelet-activating factor (PAF), collagen, or arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in a concentration-dependent manner.
Uses
Yatein is a lignan isolated from A. chilensis, with antiproliferative activity[1]. Yatein suppresses herpes simplex virus type 1 (HSV-1 ) replication by interruption the immediate-early gene expression[2].
Definition
ChEBI: A member of the class of butan-4-olides carrying 3,4,5-trimethoxybenzyl and (1,3-benzodioxol-5-yl)methyl substituents at positions 3 and 4 respectively.
in vivo
Yatein (20 mg/kg; i.p.; five times per week; for 42 days) exhibits in vivo antitumor effects in a human lung adenocarcinoma xenograft mouse model[3].
| Animal Model: | Male NOD/SCID mice (6-8 weeks), with A549 cells xenograft[3] |
| Dosage: | 20 mg/kg |
| Administration: | Intraperitoneal injection, five times per week, for 42 days |
| Result: | Significantly slowed tumor growth and moderately increased both cyclin B1 expression and Cdc2 phosphorylation. |
IC 50
HSV-1
References
[1] Donoso-Fierro C, et al. Antiproliferative activity of yatein isolated from Austrocedrus chilensis against murine myeloma cells: cytological studies and chemical investigations. Pharm Biol. 2015 Mar;53(3):378-85. DOI:10.3109/13880209.2014.922588
[2] Kuo YC, et al. Yatein from Chamaecyparis obtusa suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. Antiviral Res. 2006 Jul;70(3):112-20. DOI:10.1016/j.antiviral.2006.01.011
[3] Shang-Tse Ho, et al. Molecular Mechanisms Underlying Yatein-Induced Cell-Cycle Arrest and Microtubule Destabilization in Human Lung Adenocarcinoma Cells. Cancers (Basel). 2019 Sep; 11(9): 1384. DOI:10.3390/cancers11091384
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