Structure elucidation of a sodium salified anthraquinone from the seeds of Cassia obtusifolia by NMR technique assisted with acid–alkali titration

Abstract

A new sodium salt of anthraquinone named sodium emodin-1-O-β-gentiobioside, together with nine known compounds, viz. rubrofusarin-6-O-β-D-gentiobioside, chrysophanol-1-O-β-D-glucopyranosyl-(1-3)-β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside, obtusifolin-2-O-β-D-glucopyranoside, aurantio-obtusin-6-O-β-D-glucopyranoside, physcion-8-O-β-D-glucopyranoside, 1-hydroxyl-2-acetyl-3,8-dimethoxy-6-O-β-D-apiofuranosyl-(1-2)-β-D-glucosylnaphthalene, toralactone-9-O-β-D-gentiobioside, aurantio-obtusin, rubrofusarin-6-O-β-D-apiofuranosyl-(1-6)-O-β-D-glucopyranoside, was isolated from the seeds of Cassia obtusifolia and its structure was elucidated by (1)H and (13)C NMR technique assisted with acid-alkali titration. The change of chemical shifts of sodium emodin-1-O-β-gentiobioside before and after acid-alkali titration was also characterized.

Cassia tora Seed Extract and Its Active Compound Aurantio-obtusin Inhibit Allergic Responses in IgE-Mediated Mast Cells and Anaphylactic Models

“…Senna tora) and Cassia obtusifolia L. (syn. Senna obtusifolia), , and may possess anti-inflammation, antioxidant, and anticancer properties. − Moreover, anthraquinones inhibit chemical mediators of mast cell activation. For instance, emodin, rhein, and citreorosein, three naturally occurring anthraquinone derivatives, suppress the IgE-mediated anaphylactic reaction, mast cell activation, and LT generation. − Among anthraquinone derivatives isolated from C. tora , aurantio-obtusin is the major compound.…”

Anti-Inflammatory Effects of Aurantio-Obtusin from Seed of Cassia obtusifolia L. through Modulation of the NF-κB Pathway

“…Senna obtusifolia ; Fabaceae) and Cassia tora L. (syn. Senna tora ) [25,26,27] as well as a phytochemical marker of quality control in the Chinese Pharmacopeia (Version 2015) [28].…”

Hepatoprotective effect of Cassia obtusifolia seed extract and constituents against oxidative damage induced by tert -butyl hydroperoxide in human hepatic HepG2 cells

“…The seeds of C. obtusifolia have a number of beneficial effects against various types of degenerative diseases in humans, largely because the major ingredients of C. obtusifolia have very potent antioxidant activity (Jung et al, ; Yen & Chung, ). Moreover, anthraquinones are predominantly reported in and isolated from the seeds of C. obtusifolia (Zhang, Wang, Liu, & Tu, ). In previous studies, anthraquinones compounds, which are widely distributed in plants, were considered to play an important role as dietary antioxidants for the prevention of oxidative liver damage (Jung et al, ; Wong et al, ; Xie et al, ; Yoon & Kim, ).…”