Yatein

• CAS: 40456-50-6
• Catalog Number: ACMA00045792
• Category: Inhibitors
• Molecular Weight: 400.4
• Molecular Formula: C22H24O7
• Description: Yatein is a lignan isolated from A. chilensis, with antiproliferative activity. Yatein suppresses herpes simplex virus type 1 (HSV-1 ) replication by interruption the immediate-early gene expression.
• Synonyms: (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
• IUPAC Name: (3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• SMILES: COC1=CC(=CC(=C1OC)OC)CC2C(COC2=O)CC3=CC4=C(C=C3)OCO4
• InChI: 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
• InChI Key: GMLDZDDTZKXJLU-JKSUJKDBSA-N
• Boiling Point: 565.0±45.0 °C
• Flash Point: 246.2ºC
• Density: 1.266±0.06 g/ml
• Appearance: Powder
• Storage: 4°C, protect from light*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light).
• Exact Mass: 400.15200
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: PlantsCupressaceaeChamaecyparis obtusa

Case Study

Yatein as a New Apoptosis-Inducing Agent in Non-Small-Cell Lung Cancer Treatment

Ho, Shang-Tse, et al. Journal of Wood Science 65.1 (2019): 59.

In the present case study, the antitumor activity of yatein, a bioactive lignan isolated from the leaves of Calocedrus formosana Florin, was investigated by examining its effect on inducing apoptosis in non-small-cell lung cancer (NSCLC).
Key Findings
· Yatein, extracted from the n-hexane fraction of the leaf extract of C. formosana, showed higher cytotoxicity against the NSCLC cells than A549, which was more sensitive to the compound than CL1-5, and was determined to be the main active constituent of the extract.
· Yatein was confirmed to induce apoptosis via dual activation of the intrinsic/extrinsic pathways in both cell lines, as indicated by the upregulation of the expression of caspase 3,8,9 and PARP proteins and ROS-mediated growth inhibition which were supported by flow cytometry and Western blot data.
· Treatment with yatein resulted in the concentration-dependent initiation of apoptosis in both cell lines, with a significantly higher efficacy in the metastatic CL1-5 cells and simultaneous activation of the mitochondrial and death receptor pathways in them.
· Yatein was found to have significant in vitro anti-NSCLC activity by inducing apoptosis through multiple pathways and can be considered a promising natural lead compound to be studied further for in vivo treatment.

Dual Effects and Mechanisms of Yatein Targeting Cell Cycle and Microtubule Dynamics

Ho, Shang-Tse, et al. Cancers 11.9 (2019): 1384.

This case study examined yatein-a bioactive compound from Calocedrus formosana leaves-for its dual mechanisms in inhibiting lung adenocarcinoma through cell-cycle disruption and microtubule destabilization, validated across in vitro and in vivo models.
Key Findings
· Yatein induced G2/M cell-cycle arrest in A549 and CL1-5 cells, upregulating cyclin B1 expression and Cdc2 phosphorylation-key regulators of mitotic entry-as confirmed by flow cytometry and Western blotting.
· Yatein dose-dependently inhibited tubulin polymerization in both cell lines after 24h treatment, mirroring colchicine's microtubule-depolymerizing effects. Immunofluorescence revealed identical tubulin distribution patterns in yatein- and colchicine-treated cells.
· ATM/ATR pathway activation confirmed yatein-induced DNA damage, establishing a third mechanism synergizing with cell-cycle arrest and cytoskeletal disruption.
· In A549 cell xenografts, tumor growth was significantly delayed relative to controls from Day 21 post-treatment (p<0.05). At the end of the study, tumor photon luminescence was 16.5×10⁵ (yatein) and 24.0×10⁵ (control) photons/s, and no difference in body weight or food consumption between groups suggested good tolerability. Elevated cyclin B1/Cdc2 phosphorylation in tumors aligned with in vitro mechanisms.

Custom Q&A

What is the molecular formula of Yatein?

The molecular formula of Yatein is C22H24O7.

What are the synonyms of Yatein?

The synonyms of Yatein are 40456-50-6, (-)-yatein, Dihydroanhydropodorhizol, (-)-deoxypodorhizone, Deoxypodorhizone, CHEBI:4553, CHEMBL471067, 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-((3,4,5-trimethoxyphenyl)methyl)-, trans-(-), and many more.

What is the IUPAC name of Yatein?

The IUPAC name of Yatein is (3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one.

What is the InChI of Yatein?

The InChI of Yatein is 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.

What is the molecular weight of Yatein?

The molecular weight of Yatein is 400.4g/mol.

What is the XLogP3 value of Yatein?

The XLogP3 value of Yatein is 3.8.

What is the CAS number of Yatein?

The CAS number of Yatein is 40456-50-6.

What is the DSSTox Substance ID of Yatein?

The DSSTox Substance ID of Yatein is DTXSID50193471.

What is the Nikkaji Number of Yatein?

The Nikkaji Number of Yatein is J257.868I.

What is the Wikidata ID of Yatein?

The Wikidata ID of Yatein is Q27106408.