Mori Ramulus (Chin.Ph.)—the Dried Twigs of Morus alba L./Part 1: Discovery of Two Novel Coumarin Glycosides from the Anti-Hyperuricemic Ethanol Extract

Abstract

In Traditional Chinese Medicine (TCM), Mori ramulus (Chin.Ph.)—the dried twigs of Morus alba L.—is extensively used as an antirheumatic agent and also finds additional use in asthma therapy. As a pathological high xanthine oxidase (XO, EC 1.1.3.22) activity is strongly correlated to hyperuricemy and gout, standard anti-hyperuremic therapy typically involves XO inhibitors like allopurinol, which often cause adverse effects by inhibiting other enzymes involved in purine metabolism. Mori ramulus may therefore be a promissing source for the development of new antirheumatic therapeutics with less side effects. Coumarins, one of the dominant groups of bioactive constituents of M. alba, have been demonstrated to possess anti-inflammatory, antiplatelet aggregation, antitumor, and acetylcholinesterase (AChE) inhibitory activities. The combination of HPLC (DAD) and Q-TOF technique could give excellent separating and good structural characterization abilities which make it suitable to analyze complex multi-herbal extracts in TCM. The aim of this study was to develop a HPLC (DAD)/ESI-Q-TOF-MS/MS method for the identification and profiling of pharmacologically active coumarin glycosides in Mori ramulus refined extracts for used in TCM. This HPLC (DAD)/ESI-Q-TOF-MS/MS method provided a rapid and accurate method for identification of coumarin glycosides—including new natural products described here for the first time—in the crude extract of M. alba L. In the course of this project, two novel natural products moriramulosid A (umbelliferone-6-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside) and moriramulosid B (6-[[6-O-(6-deoxy-α-l-mannopyranosyl)-β-d-glucopyranosyl]oxy]-2H-1-benzopyran-1-one) were newly discovered and the known natural product Scopolin was identified in M. alba L. for the first time.

Phytochemical Analysis Using UPLC-MS/MS Combined with Network Pharmacology Methods to Explore the Biomarkers for the Quality Control of Lingguizhugan Decoction

“…Coumarins generally have many CO, CO 2 , OH, H 2 O, CH 3, and OCH 3 connected to aromatic rings, so that a series of neutral ion peaks with continuous loss often appear. In addition, coumarins often have common functional groups such as isopentenyl, acetoxy, and 5-carbon unsaturated acyloxy groups, which are also the main characteristics of coumarin compounds [ 21 , 22 ]. Glycycoumarin displayed the ions at m/ z 367.1193 (C 21 H 19 O 6 , [M-H] − , P104), with the following diagnostic fragment ions provided by the MS/MS spectrum at m/ z 337.0719 (C 19 H 13 O 6 , [M-H-2CH 3 ] − ), 309.0414 (C 18 H 13 O 5 , [M-H-2CH 3 –CO] − ), 297.0408 (C 16 H 9 O 6 , [M-H-2CH 3 –C 3 H 4 ] − ), 284.0336 (C 16 H 12 O 5 , [M-H-2CH 3 –O–C 2 H] − ), and 203.0718 (C 11 H 7 O 4 , [M-H–C 6 H 5 O 2 –C 4 H 7 ] − ) ( Figure 7(b) ).…”

Toxicity and Anti-Proliferative Properties of Anisomeles indica Ethanol Extract on Cervical Cancer HeLa Cells and Zebrafish Embryos

“…This means that the ethanol crude extract surely contains an amount of ovatodiolide. Moreover, other phytochemicals such as phenolics and flavonoids are easily dissolved in ethanol/methanol [ 20 , 28 , 47 , 48 , 49 , 50 ], and therefore they certainly present in the ethanol extract. In fact, previous studies found that ovatodiolide (isolated from Anisomeles indica) induced cell cycle at G2/M arrest in lung cancer cells [ 22 ] and squamous carcinoma cancer cells [ 24 ]; while, in this study, we revealed that the Anisomeles indica ethanol extract induced HeLa cell arrest at G1.…”

Comprehensive characterization of naturally occurring antioxidants from the twigs of mulberry (Morus alba) using on‐line high‐performance liquid chromatography coupled with chemical detection and high‐resolution mass spectrometry

“…O-β-D-apiofuranosyl-β-D-glucopyranoside,40 isoscopoletin 6-(6-O-β-apiofuranosyl-β-glucopyranoside)41 and umbelliferone-6-β-D-apiofuranosyl-(1 ! 6)-β-D-glucopyranoside 42. The only source of2 from the Moraceae family has been the stem bark of Sorocea ilicifolia 29 however, this is the first report of compound 2 from M. alba twigs.…”

“…As an example, M. alba produces a large variety of secondary metabolites, including the mulberrosides based on stilbenes, flavonoids, benzofuran derivatives and coumarins. 42 The major biological properties discovered for M. alba metabolites include (i) inhibition of ultraviolet B irradiation-induced melanogenesis by mulberroside A, 43 (ii) anti-inflammatory properties of oxyresveratrol 44 and…”