Four Meroterpenoids with Novel Aminoglycoside Moiety from the Basidiomycete Clitocybe clavipes with Cytotoxic Activity.

Four new meroterpenoids, Clavilactone M-P, possessing novel aminoglycoside moiety (1-4) and a 10-membered carbocycle fused with an α,ß-epoxy-γ-lactone, were isolated from Clitocybe clavipes, a basidiomycete. Their structures with absolute configurations were determined by extensive analysis of their spectroscopic data, and the ECD method. All the isolated compounds (1-4) were evaluated for their antitumor activity against three human cancer cell lines using the MTT assay. Compound 1 and 2 exhibited a significant suppression of cell viability in the Hela (IC50 = 22.8 and 19.7 µM) cell line.

Two New Compounds from Allii Macrostemonis Bulbus and Their In Vitro Antioxidant Activities.

Two new compounds named 4,4'-bis(ß-D-glucopyranosyloxy)biphenyl (1) and spirostane-25(27)-en-2α,3ß-diol-3-O-ß-D-xylopyranosyl(1→3)-ß-D-glucopyranosyl(1→4)-ß-D-galactopyranoside (2) were isolated from n-butanol extraction part of 80% ethanol extract of Allii Macrostemonis Bulbus. Alongside these, ten known compounds (3-12) were also identified, including a flavonoid glycoside (3), seven steroids (4-10), a nucleoside (11), and a phenylpropanoid glycoside (12) were found. Notably, compounds 3-6 were isolated from this plant for the first time. The structures of all compounds were confirmed using high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D, and 2D NMR spectroscopy. Some of these compounds showed strong antioxidant activity, and compound 1 demonstrated the most potent reduction of ferric ions (Fe3+) with an IC50 value of 0.59 ± 0.18 mg/mL. Compounds 2 and 3 exhibited the highest scavenging activity against superoxide anion radicals (O2-·) with an IC50 value of 0.02 ± 0.01 mg/mL. Additionally, compound 3 displayed substantial scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) with IC50 values of 0.21 ± 0.17 mg/mL and 0.02 ± 0.01 mg/mL, respectively. The discovery of these two new compounds is a reference for identifying Allii Macrostemonis Bulbus quality markers. Moreover, their exceptional antioxidant activity offers a promising avenue for uncovering novel natural antioxidants.

Daphnane-Type Diterpenes from Stelleropsis tianschanica and Their Antitumor Activity.

Four new daphnane-type diterpenes named tianchaterpenes C-F (1-4) and six known ones were isolated from Stelleropsis tianschanica. Their structures were elucidated based on chemical and spectral analyses. The comparisons of calculated and experimental electronic circular dichroism (ECD) methods were used to determine the absolute configurations of new compounds. Additionally, compounds 1-10 were evaluated for their cytotoxic activities against HGC-27 cell lines; the results demonstrate that compound 2 had strong cytotoxic activities with IC50 values of 8.8 µM, for which activity was better than that of cisplatin (13.2 ± 0.67 µM).

Inflammatory and Cytotoxic Activities of Abietane Terpenoids from Nepeta bracteata Benth.

Nepeta bracteata Benth. is used clinically to treat tracheal inflammation, coughs, asthma, colds, fevers, adverse urination, and other symptoms, along with functions in clearing heat and removing dampness. However, there have been few studies characterizing the material basis of its efficacy. Therefore, the aim of this study was to screen for compounds with anti-inflammatory activities in N. bracteata Benth. Using silica gel, ODS C18, and Sephadex LH-20 column chromatography, as well as semipreparative HPLC, 10 compounds were separated from N. bracteata Benth. extract, including four new diterpenoids (1-4), one amide alkaloid (5), and five known diterpenoids (6-10). The structures of all the isolates were elucidated by HR-ESI-MS, NMR, and CD analyses. Using lipopolysaccharide (LPS)-stimulated RAW 264.7 cells, we investigated the anti-inflammatory activities of compounds 1-10. It is worth noting that all were able to inhibit nitric oxide (NO) production with IC50 values < 50 µM and little effect on RAW 264.7 macrophage viability. Compounds 2 and 4 displayed remarkable inhibition with IC50 values of 19.2 and 18.8 µM, respectively. Meanwhile, screening on HCT-8 cells demonstrated that compounds 2 and 4 also had moderate cytotoxic activities with IC50 values of 36.3 and 41.4 µM, respectively, which is related to their anti-inflammatory effects.

[Distribution characteristics of Chinese medicine resources in Turpan Basin, Xinjiang].

Based on the results of the fourth national survey of traditional Chinese medicine resources in Turpan city, Xinjiang, this study counted the types of traditional Chinese medicine resources in Turpan Basin. The spatial distribution differences of traditional Chinese medicine resources in Turpan Basin of Xinjiang were analyzed by using grid technology, trend surface analysis, global spatial autocorrelation analysis, and local spatial autocorrelation analysis, so as to clarify the overall change trend and aggregation degree of traditional Chinese medicine resources in Turpan Basin in horizontal and vertical directions. The results showed the following: in the horizontal direction, the species richness of traditional Chinese medicine resources in the central part of Turpan Basin was high, and there were great differences in the species richness of traditional Chinese medicine resources in Turpan Basin under different grid sizes. The spatial scale effect of the richness of traditional Chinese medicine resources in Turpan Basin is obvious. Among them, under the 30 km×30 km scale, the richness of the types of Chinese medicine resources shows a high spatial correlation, and the richness of the types of Chinese medicine resources at 5 km×5 km scale presents a near random distribution state, and the richness of the types of Chinese medicine resources at 80, 90, and 100 km scale sits negatively related. Vertical direction, Chinese medicine resources appear rich at the range of-154-150 m and 900-1 050 m following by range of 1 050-1 200 m.

A Review on Daphnane-Type Diterpenoids and Their Bioactive Studies.

Natural daphnane diterpenoids, mainly distributed in plants of the Thymelaeaceae and Euphorbiaceae families, usually include a 5/7/6-tricyclic ring system with poly-hydroxyl groups located at C-3, C-4, C-5, C-9, C-13, C-14, or C-20, while some special types have a characteristic orthoester motif triaxially connectedat C-9, C-13, and C-14. The daphnane-type diterpenoids can be classified into five types: 6-epoxy daphnane diterpenoids, resiniferonoids, genkwanines, 1-alkyldaphnanes and rediocides, based on the oxygen-containing functions at rings B and C, as well as the substitution pattern of ring A. Up to now, nearly 200 daphnane-type diterpenoids have been isolated and elucidated from the Thymelaeaceae and Euphorbiaceae families. In-vitro and in-vivo experiments of these compounds have shown that they possess a wide range of biological activities, including anti-HIV, anti-cancer, anti-leukemic, neurotrophic, pesticidal and cytotoxic effects. A comprehensive account of the structural diversity is given in this review, along with the cytotoxic activities of daphnane-type diterpenoids, up to April 2019.

[Chemical constituents from green walnut husks and their antitumor activity in vitro].

Fourteen chemical constituents, including 5-hydroxy-4-methoxy-1-tetralone(1), 4,8-dihydroxy-1-tetralone(2), 4,5-dihydroxy-α-tetralone(3), blumenol B(4), dehydrovomifoliol(5), megastigm-5-ene-3,9-diol(6), juglanin B(7), blumenol C(8), loliolide(9), oleracone B(10), syringarsinol(11), pinoresinol(12), methyl 4-hydroxy-3-methoxybenzoate(13), and isovanillic acid(14), were isolated from the dichloromethane fraction of 95% methanol extract of green walnut husks by silica gel and MCI column chromatography, and Pre-HPLC. Their structures were determined by spectroscopic methods, such as NMR, MS and so on. Among them, compounds 1, 4-6, 8-13 were isolated from the green walnut husks for the first time, and compounds 4-6, 8, 10, 12, 13 were isolated from the Juglans genus for the first time. All of isolates were detected their inhibitory activities against HeLa, HGC-27 and Ht-29 cell lines by the MTT assay. The result showed that compounds 2, 3, 7, 9 and 11 exhibited inhibitory activity against the tested cell line. The IC_(50) of 7 were 26.5, 9.0, 25.4 µmol·L~(-1), respectively.

Two new daphnane diterpenes from the roots of Stelleropsis tianschanica.

Two new daphnane diterpenes named tianchaterpenes A and B were isolated from the roots of Stelleropsis tianschanica. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses and HRESIMS. Compounds 1 and 2 were evaluated for their cytotoxic activities against HeLa and HCT-8 cell lines. The results showed that all compounds displayed weak cytotoxicities to the HeLa cells and were inactive to the HCT-8 cells.

Four New Sesquiterpenoids from the Roots of Diarthron Tianschanica with Their Antineoplastic Activity.

Four new sesquiterpenoids, known as diarthronchas A⁻D (1⁻4), and one known daphnauranol B (5) were isolated from the methanol extract of the roots of Diarthron tianschanica. The compounds structures were determined on the basis of spectroscopic data. All of the isolated compounds were profiled for their antineoplastic activity.

Cryptoporic acid S, a new drimane-type sesquiterpene ether of isocitric acid from the fruiting bodies of Cryptoporus volvatus.

A new drimane-type sesquiterpene with an isocitric acid moiety, cryptoporic acid S (1), together with six known compounds, cryptoporic acid D (2), ß-sitosterol (3), ß-daucosterol (4), stigmast-4-en-3-one (5), ergosterol (6), and (22E,24R)-ergosta-7,22-diene-3ß,5α,6ß-triol (7), was isolated from the fruiting bodies of Cryptoporus volvatus. The structures of these compounds were established on the basis of UV, IR, MS, 1D and 2D NMR analysis. In the meanwhile, compounds 1 and 2 were evaluated for antioxidant activity using the methods of 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity (DPPH-RSA) and ferric reducing antioxidant power (FRAP) assay, and they exhibited moderate antioxidant activities.

[Chemical constituents from roots of Stelleropsis tianschanica].

The constituents from 95% ethanol extract of the roots of Stelleropsis tianschanica were purified by column chromatography techniques, leading to the isolation of 17 compounds. Their structures were elucidated by spectroscopic dataas 5'-methoxy lariciresinol(1), pinoresinol(2), daphnoretin(3), acutissimalignan B(4),(+)-secoisolariciresinol(5),(+)-epipinoresinol(6), 7-methyi-daphnoretin(7), thero-8S-7-methoxysyringylglycerol(8), 1-O-methyl-guaiacylglycerol(9), 2R-22'-ferulic acid ester-2,3-dihydroxypropyl ester(10), vesiculosin(11), 4ß,5ßH-guai-9,7(11)-dien-12,8-olide-1α,8α-diol(12),(-)-nortrachelogenin(13), 4α,5ßH-guai-9,7(11)-dien-12,8-olide-1α,8α-diol(14), matairesinol(15), lariciresinol(16)and isolariciresinol(17). Among them, compounds 1-13 wereobtained for the first time fromthe genus Stelleropsis. Compounds 3, 7, 10-14 were tested for their activation of orphan nuclear receptor TR3 with the immunofluorescence technology in 50 µmol•L⁻¹. The results showed that compound 10 displayed moderate activity with the activity ratio of 76.38%, and the others were only about 50.0%.

Diarylpentanol constituents from the aerial part of Stelleropsis tianschanica.

Five diarylpentanol derivatives including two new compounds stellerasme A (1), stellerasme B (2) were isolated from the aerial parts of Stelleropsis tianschanica. Their structures were elucidated by various spectroscopic techniques (UV, IR, MS, CD, 1D and 2D NMR). All compounds were evaluated for their cytotoxicity activity against HeLa and KB cell lines, and compound 1 showed selective activities against HeLa cell line with an IC50 value of 7.4 µM.

Sesquiterpenes and Sesquiterpene Derivatives from Ferula: Their Chemical Structures, Biosynthetic Pathways, and Biological Properties.

Ferula is a genus of flowering plants known for its edible and medicinal properties. Since ancient times, many species of Ferula have been used in traditional medicine to treat various health issues across countries, such as digestive disorders, respiratory problems, and even as a remedy for headaches and toothaches. In addition, they are also used as a flavoring agent in various cuisines. As the main active ingredients in Ferula, sesquiterpenes and their derivatives, especially sesquiterpene coumarins, sesquiterpene phenylpropanoids, and sesquiterpene chromones, have attracted the attention of scientists due to the diversity of their chemical structures, as well as their extensive and promising biological properties, such as antioxidative, anti-inflammatory, antibacterial properties. However, there has not been a comprehensive review of sesquiterpenes and their derivatives from this plant. This review aims to provide an overview of the chemical structures, biosynthetic pathways, and biological properties of sesquiterpenes and sesquiterpene derivatives from Ferula, which may help guide future research directions and possible application methods for this valuable edible and medicinal plant.

Carbon Dots Derived from Traditional Chinese Medicines with Bioactivities: A Rising Star in Clinical Treatment.

In the field of carbon nanomaterials, carbon dots (CDs) have become a preferable choice in biomedical applications. Based on the concept of green chemistry, CDs derived from traditional Chinese medicines (TCMs) have attracted extensive attention, including TCM charcoal drugs, TCM extracts, and TCM small molecules. The design and preparation of CDs from TCMs (TCMs-CDs) can improve the inherent characteristics of TCMs, such as solubility, particle size distribution, and so on. Compared with other precursor materials, TCMs-CDs have outstanding intrinsic bioactivities and potential pharmacological effects. However, the research of TCMs-CDs in biomedicine is not comprehensive, and their mechanisms have not been understood deeply either. In this review, we will provide concise insights into the recent development of TCMs-CDs, with a major focus on their preparation, formation, precursors, and bioactivities. Then we will discuss the perfect transformation from TCMs to TCMs-CDs. Finally, we discuss the opportunities and challenges for the application of TCMs-CDs in clinical treatment.

Natural carrier-free self-assembled diterpene nanoparticles with its efficient anti-inflammation through the inhibition of NF-κB pathway for accelerated wound healing.

Nanoscience has set off a wave in biomedicine to improve the performance of drugs in recent years, but additional materials are usually required for supramolecular nanoconstruction, undoubtedly increasing the health risks. Herein, we discovered a novel diterpene supramolecular self-assembly system without additional chemicals, Nepebracteatalic Acid nanoparticles (NA NPs), mediated through hydrogen bond, hydrophobic and electrostatic interaction. NA NPs performed sustained release behavior, lower expression levels for IL-6 and TNF-α than clinical anti-inflammatory drug Indometacin. Furthermore, the effect of NA NPs on the related protein p65 expression levels of nuclear factor-κB (NFκB) signaling pathway is quantified to confirm the enhanced anti-inflammatory property based on the self-assembly strategy. Meanwhile, the prepared nanoparticles have good biocompatibility which ensures outstanding inflammation inhibition, collagen deposition, angiogenesis during wound healing. This work opens up new prospects that carrier-free nanoparticles from NPMs have great potential to exert clinical application value, meanwhile providing reference for developing green nanoscience.

Filamin FLN-2 promotes MVB biogenesis by mediating vesicle docking on the actin cytoskeleton.

Multivesicular bodies (MVBs) contain intralumenal vesicles that are delivered to lysosomes for degradation or released extracellularly for intercellular signaling. Here, we identified Caenorhabditis elegans filamin FLN-2 as a novel regulator of MVB biogenesis. FLN-2 co-localizes with V-ATPase subunits on MVBs, and the loss of FLN-2 affects MVB biogenesis, reducing the number of MVBs in C. elegans hypodermis. FLN-2 associates with actin filaments and is required for F-actin organization. Like fln-2(lf) mutation, inactivation of the V0 or V1 sector of V-ATPase or inhibition of actin polymerization impairs MVB biogenesis. Super-resolution imaging shows that FLN-2 docks V-ATPase-decorated MVBs onto actin filaments. FLN-2 interacts via its calponin-homology domains with F-actin and the V1-E subunit, VHA-8. Our data suggest that FLN-2 mediates the docking of MVBs on the actin cytoskeleton, which is required for MVB biogenesis.

Abietane-Type Diterpenoids From Nepeta bracteata Benth. and Their Anti-Inflammatory Activity.

Terpenes possess a wide range of structural features and pharmaceutical activities and are promising for drug candidates. With the aim to find bioactive terpene molecules, eight new compounds were isolated from the medicinal plant Nepeta bracteata Benth., including seven new abietane-type diterpenoids (1-7), along with a new ursane-type triterpenoid (8). The structures of compounds 1-8 were elucidated through the detailed spectroscopic analyses of their 1D and 2D NMR and MS data, and the absolute configurations of compounds 1-7 were determined by comparing their experimental and calculated ECD spectra. Compound 1 was a novel degraded carbon diterpene with the disappearing of methyl signal at C-19, while compound 7 possessed a new norabietane-type diterpenoid carbon skeleton with the presence of five-membered lactone arising from ring rearrangement. The anti-inflammatory of all obtained isolates were evaluated on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and the results of anti-inflammatory activity screening showed that compared with the LPS model group, all compounds were significantly down-regulation the TNF-α inflammatory factor at the specific concentration, except for compound 6.