Cassiaside B

Rubrofusarin as a Dual Protein Tyrosine Phosphate 1B and Human Monoamine Oxidase-A Inhibitor: An in Vitro and in Silico Study.[Pubmed:31460269]

ACS Omega. 2019 Jul 3;4(7):11621-11630.

A number of nature-derived biologically active compounds comprise glycosides. In some cases, the glycosidic residue is needed for bioactivity; however, in other cases, glycosylation just improves some pharmacokinetic/dynamic parameters. The patterns of protein tyrosine phosphatase 1B (PTP1B) and human monoamine oxidase A (hMAO-A) inhibition by rubrofusarin 6-O-beta-d-glucopyranoside (1), rubrofusarin 6-O-beta-d-gentiobioside (2), rubrofusarin triglucoside (3), and Cassiaside B2 (4) were compared with the aglycone, rubrofusarin, isolated from Cassia obtusifolia seeds. Rubrofusarin showed potent inhibition against the PTP1B enzyme (IC50; 16.95 +/- 0.49 muM), and its glycosides reduced activity (IC50; 87.36 +/- 1.08 muM for 1 and >100 muM for 2-4) than did the reference drug, ursolic acid (IC50; 2.29 +/- 0.04 muM). Similarly, in hMAO-A inhibition, rubrofusarin displayed the most potent activity with an IC50 value of 5.90 +/- 0.99 muM, which was twice better than the reference drug, deprenyl HCl (IC50; 10.23 +/- 0.82 muM). An enzyme kinetic and molecular docking study revealed rubrofusarin to be a mixed-competitive inhibitor of both these enzymes. In a western blot analysis, rubrofusarin increased glucose uptake significantly and decreased the PTP1B expression in a dose-dependent manner in insulin-resistant HepG2 cells, increased the expression of phosphorylated protein kinase B (p-Akt) and phosphorylated insulin receptor substrate-1 (p-IRS1) (Tyr 895), and decreased the expression of glucose-6-phosphatase (G6Pase) and phosphoenol pyruvate carboxykinase (PEPCK), key enzymes of gluconeogenesis. Our overall results show that glycosylation retards activity; however, it reduces toxicity. Thus, Cassia seed as functional food and rubrofusarin as a base can be used for the development of therapeutic agents against comorbid diabetes and depression.

[UPLC-MS~n analysis and certification evaluation of main chemical composition in naphthopyrone reference extract of Cassiae Semen].[Pubmed:31355568]

Zhongguo Zhong Yao Za Zhi. 2019 May;44(10):2102-2109.

The main chemical constituents of naphthopyrone reference extract( NRE) with definite content and relatively fixed chemical composition were analyzed and determined. Ultra-high performance liquid chromatography-LTQ-Orbitrap XL mass spectrometry and high performance liquid chromatography were used to systematically study NRE from the aspects of main chemical components and determination. The results showed that the chemical composition of naphthopyrone reference extract of Cassiae Semen was relatively fixed,and seven naphthalopyranones were identified. Cassiaside B_2,cassiaside C_2,rubrofusarin-6-O-beta-D-gentiobioside and cassiaside C were the main chemical constituents of NRE,of which the determination and uncertainty results were( 11. 40+ 0. 26) %,( 11. 68+0. 24) %,( 16. 60+0. 22) %,( 28. 8+0. 48) %,respectively. This study contributed to the accurate evaluation of NRE and the foundation for the application of NRE in the quality control of Cassiae Semen,and provided a new idea for the replacement of single chemical reference substance by the reference extract of traditional Chinese medicine.

An anthraquinone and three naphthopyrone derivatives from Cassia pudibunda.[Pubmed:1367272]

Phytochemistry. 1991;30(2):708-10.

Chemical examination of the methanolic extract of the roots of Cassia pudibunda led to isolation of the new rubrofusarin-6-O-beta-D-glucopyranoside, quinquangulin-6-O-beta- D-apiofuranosyl-(1----6)-O-beta-D-glucopyranoside, quinquangulin-6-O-beta-D-glucopyranoside and chrysophanol dimethyl ether. Moreover the known chrysophanol, physcion, cis-3,3',5,5'-tetrahydroxy-4-methoxystilbene, trans-3,3',5,5' -tetrahydroxy-4-methoxystilbene, and Cassiaside B were identified. The antimicrobial activity of some of these compounds is also reported.