New Lycopodium alkaloids with neuroprotective activities from Lycopodium japonicum Thunb.

One new lycopodine-type alkaloid (1), one new natural product (2), and eight known analogs (3-10) were isolated from the whole plants of Lycopodium japonicum Thunb. The structures of 1-10 were determined based on extensive comprehensive spectroscopic analyses, including UV, IR, NMR, and HRESIMS. Moreover, the isolated alkaloids were evaluated for their neuroprotective activity against Hemin-induced HT22 cell damage. Notably, compounds 1 and 10 exhibited potential neuroprotective activities, with 21.45% and 20.55% increase in cell survival at 20 µM, respectively. Moreover, compounds 1 and 10 revealed protective effects on Hemin-induced apoptosis in HT22 cells.

Lycopodium Alkaloids from Phlegmariurus carinatus with Cytotoxic and Neuroprotective Effects.

One new fawcettimine-type alkaloid, phlecarinadine A (1), and twelve known ones (2-13) were isolated from the whole plant of Phlegmariurus carinatus. Their chemical structures were unambiguously established by extensive spectroscopic analyses, including nuclear magnetic resonance (NMR) spectroscopic and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). The absolute configuration of 1 was elucidated by the electronic circular dichroism (ECD) technique. These compounds were tested for their cytotoxic and neuroprotective activities. None of these compounds revealed cytotoxic activity against five tumor cells. Phlegmariurine B (2) exhibited potential neuroprotective effects against hemin-induced HT22 cell damage, with a 17.76 % increase in cell survival at 10 µM. In further study, 2 can ameliorate hemin-induced neuronal cell death via an anti-apoptotic pathway. These findings suggest that 2 might be a valuable lead compound with neuroprotective activity.

Lycopodiastrum casuarinoides: An overview of their phytochemicals, biological activities, structure-activity relationship, biosynthetic pathway and 13C NMR data.

Huperzine A, a lycodine-type alkaloid, exhibits potent inhibitory activity against acetylcholinesterase (AChE) and has been utilized to treat neurodegenerative diseases' symptoms. Lycopodiastrum casuarinoides, a member of the family Lycopodiaceae, is renowned for its lycodine-type alkaloids. Some of these alkaloids show various pharmacological benefits, such as anti-cholinesterase, neuroprotective, and cytotoxic effects. To date, 113 chemical compounds, including seventy-four lycodine-type alkaloids, ten terpenoids, eleven aliphatics, and eighteen other compounds, have been isolated from this plant. In this review, we have discussed phytochemicals and biological activities of the reported compounds of L. casuarinoides. Moreover, structure-activity relationship (SAR), plausible biosynthetic pathways, and 13C nuclear magnetic resonance spectroscopy (13C NMR) data of the lycodine-type alkaloids are also summarized.

Abietane diterpenoids from Phlegmariurus carinatus and their biological activities.

Five undescribed abietane diterpenoids, along with eight known analogs, were isolated from Phlegmariurus carinatus. Their structures were unambiguously elucidated by extensive analysis of spectroscopic data and comparison between the literature. The absolute configuration of phlecarinatone C was determined by evaluating ECD spectra. Four undescribed abietane diterpenoids and eight known analogs were tested for their neuroprotective and cytotoxic activities, separately. Teuvincenone C showed potential neuroprotective effect against Hemin-induced HT22 cell damage. Importantly, phlecarinatone C showed pronounced cytotoxic effect against U251 cells in vitro assays. The biological evaluation revealed that phlecarinatone C could inhibit proliferation, migration, and invasion in a concentration-dependent manner of U251 cells. Meanwhile, phlecarinatone C effectively reversed epithelial-to-mesenchymal transition (EMT) and promoted U251 cells apoptosis via a mitochondrial apoptotic pathway. Taken together, phlecarinatone C might be a valuable candidate for anti-metastatic agents against glioblastoma treatment.

Abietane diterpenoids with neuroprotective activities from Phlegmariurus carinatus.

Two new abietane diterpenoids, phlecarinatone A (1) and phlecarinatone B (2), along with two known analogues (3 and 4), were isolated from Phlegmariurus carinatus. The structures of 1 - 4 were unambiguously elucidated by comprehensive spectroscopic analyses. Abietane diterpenoids were isolated from the plant for the first time. All isolates were tested for their neuroprotective activities against H2O2-induced SH-SY5Y cells injury, and compound 2 showed moderate effect at the concentrations ranging from 5 ∼ 20 µM in vitro assay.

[Study on HPLC fingerprint of Callicarpa nudiflora and determination of ten components].

This study is to establish the HPLC fingerprint and determine eight components of Callicarpa nudiflora, and provide a scientific basis for the identification and quality control. The Waters sunfire C18 column (4.6 mm x 250 mm, 5 µm) was used and the detection wavelength was 330 nm . The column temperature was 30 °C. The mobile phases were acetonitrile (A) and 0.1% formic acid (B) eluting in a gradient program at a flow rate of 1.0 mL · min(-1). The chromatographic fingerprint similarity evaluation system for tradition Chinese medicine(2012) was used for analysis. C. nudiflora from different samples were of high similarity in fingerprint and the separation of ten components was good. There was an obvious difference between other samples and C. nudiflora leaves. In quantitative analysis, the ten components showed good regression(R2 > 0 999 0) with linear ranges, and their recoveries were in the range of 96.0%-105.0%. The established qualitative and quantitative methods are highly specific, simple and accurate, which can be used for the identification and quality control of C. nudiflora.

[Study on in vitro metabolic rate and metabolites or 9-dehydro-17-dehydro-andrographolide].

To investigate the metabolic rate and metabolites of 9-dehydro-17-dehydro-andrographolide, which is the main active ingredient in Xiyanping injection, by using the in vitro rat liver microsome incubation system. 9-dehydro-17-dehydro-andrographolide was incubated together with liver microsome mixed with NADPH. Its metabolic rate was studied by determining its residual concentrations with the UHPLC-MS/MS method; Its metabolites were identified by the UPLC-TOF-MS(E) method. The results showed that 9-dehydro-17-dehydro-andrographolide was metabolized faster than rat liver microsomes mixed with coenzymes, with t½ and CL of (19.7 ± 0.5) min and (35.1 ± 0.8) mL x min(-1) x g(-1) (protein), respectively. Based on the high resolution mass spectrum data and information from literatures, altogether nine metabolites of 9-dehydro-17-dehydro-andrographolide were identified in the incubation system, particularly hydroxylated and dehydrogenized products. The results of identification would provide a basis for screening out more active andrographolide derivatives.