Chrysomycin A

Names

[ Name ]:
Chrysomycin A

[Synonym ]:
Chrysomycin V
6H-Benzo(d)naphtho(1,2-b)pyran-6-one, 4-(6-deoxy-3-C-methyl-β-gulopyranosyl)-8-ethenyl-1-hydroxy-10,12-dimethoxy-
L-Glucitol, 2,6-anhydro-1-deoxy-6-C-(8-ethenyl-1-hydroxy-10,12-dimethoxy-6-oxo-6H-benzo[d]naphtho[1,2-b]pyran-4-yl)-4-C-methyl-, (6S)-
Virenomycin V
(6S)-2,6-Anhydro-1-deoxy-6-(1-hydroxy-10,12-dimethoxy-6-oxo-8-vinyl-6H-dibenzo[c,h]chromen-4-yl)-4-C-methyl-L-glucitol

Biological Activity

[Description]:

Chrysomycin A (Chr-A), an antibiotic, can be obtained from Streptomyces. Chrysomycin A exhibits antitumor and anti-tuberculous and MRSA activities. As for glioblastoma, Chrysomycin A inhibits the proliferation, migration, and invasion of cancer cells through the Akt/GSK-3β/β-catenin signaling pathway[1].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> GSK-3

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> PI3K/Akt/mTOR >> Akt

Signaling Pathways >> Apoptosis >> c-Myc

Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Chrysomycin A (0.2-1.8 μM; 48 h) 具有抗胶质母细胞瘤作用，抑制 U251 和 U87-MG 人胶质母细胞瘤的细胞活力，以及迁移和侵袭[1]。 Chrysomycin A (0.2-1.8 μM; 48 h) 抑制 U251 和 U87-MG 细胞中 Akt/GSK-3β/β-Catenin 信号通路[1]。 Cell Viability Assay[1] Cell Line: U251 and U87-MG human glioblastoma Concentration: 0.2, 0.4 and 0.8 μM for U251; 0.2, 0.6 and 1.8 μM for U87-MG Incubation Time: 48 hours Result: Inhibited U251 and U87-MG with 0.475 μM and 1.77 μM, respectively. Western Blot Analysis[1] Cell Line: U251 and U87-MG human glioblastoma Concentration: 0.2, 0.4 and 0.8 μM for U251; 0.2, 0.6 and 1.8 μM for U87-MG Incubation Time: 48 hours Result: Significantly downregulated the expression of slug and MMP2. Significantly decreased the protein expression of PI3K-p85, p-PI3K-p85, Akt and p-Akt, as well as c-Myc, cyclin D1.

[References]

[1]. Liu DN, et al. Chrysomycin A Inhibits the Proliferation, Migration and Invasion of U251 and U87-MG Glioblastoma Cells to Exert Its Anti-Cancer Effects. Molecules. 2022 Sep 20;27(19):6148.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
799.7±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₈H₂₈O₉

[ Molecular Weight ]:
508.517

[ Flash Point ]:
269.6±26.4 °C

[ Exact Mass ]:
508.173340

[ PSA ]:
138.82000

[ LogP ]:
5.08

[ Appearance of Characters ]:
solid

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.679

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMF: soluble

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis.

Nat. Prod. Rep. 29(2) , 264-325, (2012)

Covering: 1997 to 2010. The angucycline group is the largest group of type II PKS-engineered natural products, rich in biological activities and chemical scaffolds. This stimulated synthetic creativit...

The chemistry of the antibiotics chrysomycin A and B. Antitumor activity of chrysomycin A.

J. Antibiot. 35(9) , 1194-201, (1982)

The yellow antibiotic chrysomycin, isolated in crystalline form in 1955, is found to consist of two closely related components, a major one, chrysomycin A, and a minor one, chrysomycin B. They differ ...

Antitumor activity of chrysomycins M and V.

J. Antibiot. 42(9) , 1446-8, (1989)