Analysis of the Extracts of <i>Isatis tinctoria</i> by New Analytical Approaches of HPLC, MS and NMR

Abstract

The methods of extraction, separation and analysis of alkaloids and indole glucosinolates (GLs) of Isatis tinctoria were reviewed. Different analytical approaches such as High-pressure Liquid Chromatography (HPLC), Liquid Chromatography with Electrospray Ionization Mass Spectrometry (LC/ESI/MS), Electrospray Ionization Time-Of-FlightMass Spectrometry (ESI-TOF-MS), and Nuclear Magnetic Resonance (NMR) were used to validate and identity of these constituents. These methods provide rapid separation, identification and quantitative measurements of alkaloids and GLs of Isatis tinctoria. By connection with different detectors to HPLC such as PDA, ELSD, ESI-and APCI-MS in positive and negative ion modes, complicated compounds could be detected with at least two independent detection modes. The molecular formula can be derived in a second step of ESI-TOF-MS data. But for some constituents, UV and MS cannot provide sufficient structure identification. After peak purification, NMR by semi-preparative HPLC can be used as a complementary method.

Plant-Derived Alkaloids: The Promising Disease-Modifying Agents for Inflammatory Bowel Disease

“…Indole alkaloids are classes of alkaloids containing a structural moiety of indole with various biological properties including analgesic, regulation of central and peripheral nervous systems, antimicrobial, anti-ulcer, antioxidant, and antimalarial activities (Singh et al, 2011). Isatin ( 18 ) is a natural indole alkaloid obtained from Isatis tinctoria , an anti-inflammatory and dye medicinal plant in Europe and China (Zhou and Qu, 2011). Rabelo Socca et al (2014) reported that oral treatment of isatin (6 and 25 mg/kg of body weight in rats) was capable of protecting against TNBS-induced gut mucosa injury, which were associated with decreasing colonic TNF-α, COX-2, and PGE 2 levels, and MPO activity, and increasing colonic IL-10 and glutathione (GSH) levels, superoxide dismutase (SOD), glutathione peroxidase (GSH-Px), and glutathione reductase (GSH-Rd) activities.…”

A theoretical and spectroscopic (NMR and IR) study of indirubin in solution and in the solid state

“…4 is identical to indirubin (1), but 1 is representing any tautomer, while 4 is the 1NH1′NH of Z configuration, and it corresponds to the structure determined by X-ray crystallography ( Figure 2). The 1NH1′NH of E configuration called isoindirubin (10) has been isolated but without clear characterization (only mass spectrometry and UV) [37][38][39][40][41] In this paper, NMR data of 1 were measured in solution and solid-state phases. In conjunction with this, we simulated the 13 C and 15 N NMR by using two theoretical methods: GIAO and GIPAW (Gauge Including Projected Augmented Wave).…”

Anticancer Compounds Based on Isatin-Derivatives: Strategies to Ameliorate Selectivity and Efficiency

“…Isatin (1H-indol-2,3-dione) is a natural alkaloid extracted as a red-orange powder from plants of the Isatis genus ( Figure 1 ), found around the world in Isatis tinctoria (Europe and China) ( Zhou and Qu, 2011 ), Couroupita guianensis Aubl (Central America and Amazon region) ( Bergman et al, 1985 ), Melochia tomentosa (United States, Mexico) and Boronia koniamboensis (New Caledonia) species ( Da Silva et al, 2001 ; Bayly et al, 2015 ). Those plants contain indolic compounds that have shown medicinal properties, being already used as anti-inflammatory, and antineoplastic agents.…”