Dihydroisocoumarins from Radix Glycyrrhizae

Abstract

BackgroundRadix Glycyrrhizae is the rhizome of Glycyrrhiza inflata Bat., Glycyrrhiza uralensis Fisch. or Glycyrrhiza glabra L. The present paper describes the isolation and the structural elucidation of three new dihydroisocoumarins obtained from the 70% EtOH extract of Radix Glycyrrhizae. And the cytotoxic activities of these new compounds were also evaluated using four cell lines, subsequently.ResultsA pair of new dihydroisocoumarin epimers ((3R,4S)-4,8-dihydroxy-3-methyl-1-oxoisochroman-5-yl)methyl acetate (1) and ((3R,4R)-4,8-dihydroxy-3-methyl-1-oxoisochroman-5-yl)methyl acetate (2) along with a new dihydroisocoumarin (3R,4R)-4,8-dihydroxy-3,5-dimethylisochroman-1-one (3) were isolated from Radix Glycyrrhizae. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HR–ESI–MSand ECD calculation comparing with those of experimental CD spectra. Cytotoxic activities of the three compounds were evaluated using the HepG2, A549, LoVo and Hela cell lines, respectively. IC50 values indicated compounds 1–3 exhibited moderate or less cytotoxic activity in vitro.ConclusionsDihydroisocoumarin is not the common components in Radix Glycyrrhizae, a series of dihydroisocoumarin were obtained in this plant could be a supplement to the chemical study of this plant.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0427-0) contains supplementary material, which is available to authorized users.

Bioactivity‐guided isolation of anti‐inflammatory limonins from Chukrasia tabularis

“…According to the above results, the relative configuration of 1 was completed, as shown in Figure 1 . By comparing experiments and computational ECD data, the absolute configuration of 1 was finally proved, which is a suitable method for solving the absolute configuration of natural products (Michalska et al, 2017 ; Zhao et al, 2018 ). ECD spectra were calculated by systematic conformational search, geometric optimization, and time‐dependent density functional theory calculations using Gaussian‐16 software.…”

Limonoids from the barks of Chukrasia tabularis and their anti-inflammatory activity

“…2. By comparing experimental and calculated ECD data, the absolute configuration of 1 is finally demonstrated, which is a suitable method for solving absolute configuration of natural product [18,19].…”

“…Research have shown that phragmalin limonoid has a variety of bioactivities such as antifeeding [7], antibacterial [8], blocking potassium channels [9], anti-inflammatory [10], etc. As part of our ongoing study project to separate new limonoids from Meliaceae family, a novel phragmalin limonoid with 13/14/18-cyclopropane ring (1) and a novel 16-norphragmalin limonoid (18) were separated from the bark of C. tabularis, together with 16 known phragmalin orthoesters (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) and 6 known norphragmalin limonoids (19)(20)(21)(22)(23)(24). In addition, the antitumor and antiinflammatory activity of these limonoids was also investigated.…”

PHYTOCHEMICAL AND PHARMACOLOGICAL REVIEW OF LICORICE (Glycyrrhiza sp.) - A TRADITIONAL LOCAL HERB FOR THE FUTURE OF MEDICINE

“…Licorice was a medicinal herb prevalently used in traditional Chinese medicine to treat hepatitis, influenza flu, and stomach ulcers [10]. It has pharmacological activities on various systems such as the central nervous system and endocrine system; liver, renal, and pancreatic protection function; anti-ulcer, anti-inflammatory, anti-allergic, anti-viral, antibacterial, and immune system boosting effects, antioxidant, anti-diabetic and memory impairment prevention [16]. In addition, Licorice also has effects on reducing cough, reducing spasms, loosening phlegm, and eliminating agents that cause upper respiratory tract obstruction due to the effect of increasing mucus secretion in the trachea.…”