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514-67-0

514-67-0 structure
514-67-0 structure
  • Name: Rubropunctatin
  • Chemical Name: (9aR)-3-hexanoyl-9a-methyl-6-[(E)-prop-1-enyl]furo[3,2-g]isochromene-2,9-dione
  • CAS Number: 514-67-0
  • Molecular Formula: C21H22O5
  • Molecular Weight: 354.39600
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2017-09-27 12:55:59
  • Modify Date: 2024-01-10 18:12:29
  • Rubropunctatin, an orange azaphilone pigment, is isolated from the extracts of Monascus pilosus-fermented rice (red-mold rice). Rubropunctatin has anti-inflammatory, immunosuppressive and antioxidative effects, and also exhibits anti-tumor activity[1][2][3].

Name (9aR)-3-hexanoyl-9a-methyl-6-[(E)-prop-1-enyl]furo[3,2-g]isochromene-2,9-dione
Synonyms Rubropunctatin
Description Rubropunctatin, an orange azaphilone pigment, is isolated from the extracts of Monascus pilosus-fermented rice (red-mold rice). Rubropunctatin has anti-inflammatory, immunosuppressive and antioxidative effects, and also exhibits anti-tumor activity[1][2][3].
Related Catalog
In Vitro Rubropunctatin (1.5-30 μM; 24 h) shows selective tumoricidal effect on the human gastric carcinoma BGC-823 cells and no significant toxicity toward normal epithelial cell GES-1[1]. Rubropunctatin (5-30 μM; 6-24 h) induces apoptosis in a dose- and time-dependent manner in BGC-823 cells[1]. Rubropunctatin (0.75-8.0 µg/ml) exhibits DDPH radical scavenging activity, inhibition of super oxide radical generation and ferric reducing activity[2]. Cell Viability Assay[1] Cell Line: BGC-823 and GES-1cells Concentration: 1.5, 3, 6, 12, 15, 18, 30 μM Incubation Time: 24 hours Result: Decreased the viability of BGC-823 cells with an IC50 of 12.57 μM for 24 h. Did not show obvious cytotoxic effects on the normal cells. Cell Cycle Analysis[1] Cell Line: BGC-823 cells Concentration: 0, 5, 10, 30 μM Incubation Time: 0, 6, 12, 24 hours Result: Increased the percentage of cells in sub-G1 phase in a dose- and time-dependent manner.
In Vivo Rubropunctatin (8-32 mg/kg; i.v. for 5 times) has anti-tumor effect mice[1]. Rubropunctamine inhibits 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice, with an ID50 of 0.11 mg/ear[3]. Animal Model: Male nude mice (5 weeks) are inoculated with BGC-823 cells[1] Dosage: 8, 32 mg/kg Administration: I.v. five times (day 1st, 4th, 7th, 10th, and 13th) Result: Diminished the tumor volume by 11.1% (8 mg/kg) and 24.2% (32 mg/kg). Reduced the tumor weight by 23.5% (8 mg/kg) and 37.7% (32 mg/kg). No significant difference was observed on the body weight.
References

[1]. Zheng Y, et, al. Anti-cancer effect of rubropunctatin against human gastric carcinoma cells BGC-823. Appl Microbiol Biotechnol. 2010 Nov;88(5):1169-77.

[2]. Dhale MA, et, al. Protective and antioxidative effect of rubropunctatin against oxidative protein damage induced by metal catalyzed reaction. Int J Biol Macromol. 2018 Sep;116:409-416.

[3]. Akihisa T, et, al. Azaphilones, furanoisophthalides, and amino acids from the extracts of Monascus pilosus-fermented rice (red-mold rice) and their chemopreventive effects. J Agric Food Chem. 2005 Feb 9;53(3):562-5.

Density 1.23g/cm3
Boiling Point 638.8ºC at 760 mmHg
Molecular Formula C21H22O5
Molecular Weight 354.39600
Flash Point 280ºC
Exact Mass 354.14700
PSA 69.67000
LogP 3.63110
Index of Refraction 1.58