Cyasterone

Cyasterone, a natural EGFR inhibitor, mainly isolated from Ajuga decumbens Thunb (Labiatae). Cyasterone manifests anti-proliferation effect by induced apoptosis and cell cycle arrests. Cyasterone may serves as a therapeutic anti-tumor agent against human tumors.

Product information

CAS Number: 17086-76-9

Molecular Weight: 520.65

Formula: C29H44O8

Chemical Name: (3S, 4S, 5R)-4-[(2R, 3R)-3-[(1S, 3aS, 5aR, 7R, 8S, 9aR, 9bR, 11aR)-3a, 7, 8-trihydroxy-9a, 11a-dimethyl-5-oxo-1H, 2H, 3H, 3aH, 5H, 5aH, 6H, 7H, 8H, 9H, 9aH, 9bH, 10H, 11H, 11aH-cyclopenta[a]phenanthren-1-yl]-2, 3-dihydroxybutyl]-3, 5-dimethyloxolan-2-one

Smiles: C[C@@](O)([C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@@]21C)[C@H](O)C[C@H]1[C@H](C)C(=O)O[C@@H]1C

InChiKey: NEFYSBQJYCICOG-YSEUJXISSA-N

InChi: InChI=1S/C29H44O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 100 mg/mL(192.06 mM).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Cyasterone exerts cytotoxicity on multiple cell lines: HeLa (IC50=77.24 μg/ml); HepG-2 (IC50=52.03 μg/ml); MCF-7 (IC50=82.07 μg/ml) and MCF-7 (IC50=82.07 μg/ml). And It has none cytotoxicity (IC50>400 μg/ml) on 3 types of carcinoma (HT-29, Caco-2, T47D) and 1 type of normal (NIH 3T3) cell lines. Cyasterone (0-60 μg/ml; 48 hours) causes a significantly decreasing of the cell proliferation. It inhibits cell growth as a dose-dependent manner, exhibits IC50 values of 38.50 μg/ml and 32.96 μg/ml, respectively. Cyasterone (0-60 μg/ml; 24 hours) decreases p-EGFR, p-MEK, and p-mTOR as a dose-dependent manner in A549 cells, it affects the MAPK signaling pathway activities.

In Vivo:

Cyasterone (intraperitoneal injection; 5 mg/kg, 10 mg/kg and 15 mg/kg; 21 days) has anti-proliferation effect in vivo and inhibits MGC823 cells xenografted tumor growth in vivo with few changes in body weights.

References:

1. Lu X, Qiu H, Yang L, Zhang J, Ma S, Zhen L. Anti-proliferation effects, efficacy of cyasterone in vitro and in vivo and its mechanism. Biomed Pharmacother. 2016 Dec;84:330-339. doi: 10.1016/j.biopha.2016.09.041. Epub 2016 Sep 23. PubMed PMID: 27668532.
2. Okuzumi K, Hara N, Uekusa H, Fujimoto Y. Structure elucidation of cyasterone stereoisomers isolated from Cyathula officinalis. Org Biomol Chem. 2005 Apr 7;3(7):1227-32. Epub 2005 Feb 24. PubMed PMID: 15785811.
3. Hirayama Y, Okuzumi K, Masubuti H, Uekusa H, Girault JP, Fujimoto Y. Stereochemical assignment of C-24 and C-25 of amarasterone A, a putative biosynthetic intermediate of cyasterone. J Org Chem. 2014 Jun 20;79(12):5471-7. doi: 10.1021/jo5005108. Epub 2014 Jun 4. PubMed PMID: 24824008.

Products are for research use only. Not for human use.