Rubropunctatin

• CAT Number: I035802
• CAS Number: 514-67-0
• Molecular Formula: C21H22O5
• Molecular Weight: 354.40
• Purity: ≥95%
• Synonyms: (9aR)-3-hexanoyl-9a-methyl-6-[(E)-prop-1-enyl]furo[3,2-g]isochromene-2,9-dione
• InChI: InChI=1S/C21H22O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10-12H,4,6-7,9H2,1-3H3/b8-5+/t21-/m1/s1
• InChIKey: SULYDLFVUNXAMP-WKOQKXSESA-N
• SMILES: CCCCCC(=O)C1=C2C=C3C=C(OC=C3C(=O)C2(OC1=O)C)C=CC

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].
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].
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].

Reference

[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.
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[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.
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[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.
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