ChemicalBook Product Catalog Natural Products Lignans (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

Product Name(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
CAS40456-50-6
MFC22H24O7
MW400.42
EINECS
MOL File40456-50-6.mol

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
InChI	1S/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3/t15-,16+/m0/s1
InChIKey	GMLDZDDTZKXJLU-JKSUJKDBSA-N
SMILES	O1C[C@@H]([C@H](C1=O)Cc4cc(c(c(c4)OC)OC)OC)Cc2cc3c(cc2)OCO3

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

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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