A new alkaloid glycoside from the rhizomes of <i>Aristolochia fordiana</i>

<div><p>A new alkaloid glycoside named fordianoside (<b>1</b>), together with three known compounds arabinothalictoside (<b>2</b>), 6-<i>O</i>-<i>p</i>-coumaroyl-β-fructofuranosyl-(2 → 1)-α-d-glucopyranoside (<b>3</b>) and 4-[formyl-5-(hydroxymethyl)-1<i>H</i>-pyrrol-1-yl] butanoic acid (<b>4</b>), was isolated from the rhizomes of <i>Aristolochia fordiana</i>. The structure of <b>1</b> was established as (1<i>S</i>)-1,2,3,4-tetrahydro-7-hydroxy-1-[(4-hydroxybenzyl) methyl]-2,2-dimethyl-8-<i>O</i>-isoquinolinyl β-d-glucopyranoside by using chemical and spectroscopic methods including HR-ESI-MS, 1D and 2D NMR.</p></div

Simultaneous enrichment and separation of flavonoids from Herba Epimedii by macroporous resins coupled with preparative chromatographic method

<div><p>An efficient, feasible enrichment and separation method of epimedins A, B, C and icariin from Herba Epimedii was developed by the combination of microwave-assisted extraction, macroporous resins and preparative HPLC. WDX-5 macroporous resin shows better recoveries at 96.2%, 97.0%, 98.2% and 97.1% for epimedins A, B, C and icariin than other macroporous resins used in the experiments. As a result, epimedins A (5.1 mg), B (15.3 mg), C (7.6 mg) and icariin (14.3 mg) were obtained from 6.0 g crude Herba Epimedii with the recoveries at 70.8%, 68.9%, 66.7% and 95.3%, respectively. The method developed in this study may provide scientific references for the enrichment and separation of flavonoids from Herba Epimedii.</p></div

Flavonostilbenes from <i>Sophora alopecuroides</i> L. as multidrug resistance associated protein 1 (MRP1) inhibitors

<div><p>Flavonoids have always attracted much attention due to their reversal activity on multidrug resistance (MDR). Eight flavonoids isolated from traditional Chinese medicine <i>Sophora alopecuroides</i> L. were applied to test their effect on MDR associated protein 1 (MRP1) through the established predicting assay. Three flavonostilbenes (alopecurone A, B and D) were first found exhibiting potent inhibitory activity on MRP1. All of them dramatically increased 6-carboxyfluorescein diacetate and doxorubicin accumulation in MRP1-transfected U-2 OS cells. The compounds significantly increased the cytotoxicity and decreased the IC₅₀ value of doxorubicin on the MDR cells (12-, 5- and 8-fold, respectively) at a non-toxic concentration (20 μM). Besides, Q-PCR analysis reveals that the MRP1 mRNA level in U-2 OS/MRP1 was also markedly decreased by the three compounds. These findings indicate a new therapeutic role of the herb. The three flavonostilbenes may have the possibility for further development as novel therapeutic reversal agents against MDR.</p></div

Two new β-carboline alkaloids from the roots of <i>Gypsophila oldhamiana</i>

<div><p>Phytochemical investigation of the roots of <i>Gypsophila oldhamiana</i> afforded two new β-carboline alkaloids, oldhamiaines A and B (<b>1</b> and <b>2</b>), along with a known analogue (<b>3</b>). Their structures were elucidated by using spectroscopic and chemical methods. This is the first report of β-carboline alkaloids in the genus <i>Gypsophila.</i></p></div

Red-Emitting Fluorescent Probe for Detection of γ‑Glutamyltranspeptidase and Its Application of Real-Time Imaging under Oxidative Stress in Cells and <i>in Vivo</i>

γ-Glutamyltranspeptidase (GGT) plays critical roles in regulating various physiological/pathophysiological processes including the intracellular redox homeostasis. However, an effective fluorescent probe for dissecting the relationships between GGT and oxidative stress <i>in vivo</i> remains largely unexplored. Herein, we present a light-up fluorescent probe (<b>DCDHF-Glu</b>) with long wavelength emission (613 nm) for the highly sensitive and selective detection of GGT using dicyanomethylenedihydrofuran derivative as the fluorescent reporter and γ-glutamyl group as the enzyme-active trigger. <b>DCDHF-Glu</b> is competent to real-time image endogenous GGT in live cells and mice. In particular, <b>DCDHF-Glu</b> enables the direct real-time visualization of the upregulation of GGT under drug-induced oxidative stress in the HepG2 cells and the LO2 cells, as well as <i>in vivo</i>, vividly implying its excellent capacity in elucidation of GGT function in GGT-related biological events

Red-Emitting Fluorescent Probe for Detection of γ‑Glutamyltranspeptidase and Its Application of Real-Time Imaging under Oxidative Stress in Cells and <i>in Vivo</i>

γ-Glutamyltranspeptidase (GGT) plays critical roles in regulating various physiological/pathophysiological processes including the intracellular redox homeostasis. However, an effective fluorescent probe for dissecting the relationships between GGT and oxidative stress <i>in vivo</i> remains largely unexplored. Herein, we present a light-up fluorescent probe (<b>DCDHF-Glu</b>) with long wavelength emission (613 nm) for the highly sensitive and selective detection of GGT using dicyanomethylenedihydrofuran derivative as the fluorescent reporter and γ-glutamyl group as the enzyme-active trigger. <b>DCDHF-Glu</b> is competent to real-time image endogenous GGT in live cells and mice. In particular, <b>DCDHF-Glu</b> enables the direct real-time visualization of the upregulation of GGT under drug-induced oxidative stress in the HepG2 cells and the LO2 cells, as well as <i>in vivo</i>, vividly implying its excellent capacity in elucidation of GGT function in GGT-related biological events

Tabercarpamines A–J, Apoptosis-Inducing Indole Alkaloids from the Leaves of <i>Tabernaemontana corymbosa</i>

A total of 10 new indole alkaloids, tabercarpamines A–J (<b>1</b>–<b>10</b>), were isolated from the leaves of <i>Tabernaemontana corymbosa</i>. Tabercarpamines C–F (<b>3</b>–<b>6</b>) are rare C-14/C-15-<i>seco</i>-tabersonine-type monoterpenoid indole alkaloids, and <b>5</b> and <b>6</b> are the first examples with a lactone linkage between C-14 and C-20. The structures of these alkaloids were elucidated using spectroscopic methods, and the absolute configurations of <b>1</b> and <b>2</b> were determined using the ECD exciton chirality method. In addition, an MTT assay was used to examine the growth-inhibitory effects of all new isolates and of two known isolates on MCF-7, HepG2, and SMMC-7721 cells; <b>1</b> exhibited significant inhibitory effects against these three human cancer cell lines with IC₅₀ values of 8.54, 3.31, and 6.76 μM, respectively. Additionally, the results from the annexin-V/PI double-staining assay indicated that <b>1</b> might inhibit the proliferation of HepG2 cells by inducing apoptosis

Cytotoxic withanolides from <i>Physalis angulata</i>

<p>A new withanolide (<b>1</b>), physagulide P, together with five known withanolides (<b>2–6</b>), was isolated from the aerial parts of <i>Physalis angulata</i> L. The structure of new compound was elucidated on the basis of extensive spectroscopic techniques, including 1D, 2D NMR and HRESIMS. The activity screening indicated that compound <b>1</b> showed significant cytotoxicities against the human osteosarcoma cell line MG-63, HepG-2 hepatoma cells and breast cancer cells MDA-MB-231 with the IC₅₀ value of 3.50, 4.22 and 15.74 μM.</p

Natural and Pseudonatural Lindenane Heterodimers from <i>Sarcandra glabra</i> by Molecular Networking

Sarglaoxolane A (1), the first lindenane–normonoterpene heterodimer fused by tetrahydrofuran, was discovered in Sarcandra glabra guided by the first proposed single-node-based molecular networking approach. Moreover, two pseudonatural derivatives (2 and 3) with an oxa-difuranofurone moiety were transformed from 1 and confirmed by X-ray diffraction, and also proven to exist in the plant extract. A combination of molecular networking and biomimetic transformation can significantly promote the discovery and structural elucidation of novel natural products

Schematic diagram of the metabolic pathways disturbed by VB.

<p>Metabolites in red and blue denoted the increase and decrease in their levels; those in black were not detected but are relevant.</p