Chloranthus Japonicus Research Articles

Extraction and Isolation of Two Polysaccharides from Chloranthus japonicus Sieb. and Evaluation of Their Anti-Gastric Cancer Activities.

Two unreported heteropolysaccharides, denoted as YCJP-1 and YCJP-2, were isolated from the herbs of Chloranthus japonicus. YCJP-1 was a heteropolysaccharide composed of glucose, galactose, arabinose, mannose, rhamnose, and a minor proportion of uronic acids, with the molecular weight mainly distributed in the 74,475-228,443 Da range. YCJP-2 was mainly composed of glucose, mannose, and galactose, with the molecular weights ranging from 848 to 5810 Da. To further evaluate the anti-gastric cancer effects of C. japonicus, the inhibitory effects of the crude polysaccharide (YCJP) and the purified polysaccharides (YCJP-1 and YCJP-2) were determined using a CCK-8 assay and colon-forming assay on MGC-803 and AGS gastric cancer cell lines. Our results showed that YCJP, YCJP-1, and YCJP-2 possess prominent inhibitory effects on the proliferation of MGC-803 and AGS cells, and the AGS cell was more sensitive to YCJP, YCJP-1, and YCJP-2. Moreover, YCJP-2 demonstrated superior anti-gastric cancer effects compared to YCJP-1. This could potentially be attributed to YCJP-2's higher glucose content and narrower molecular weight distribution.

Chlorajaponins A—Q, Lindenane‐Related Sesquiterpenoid Dimers from Chloranthus japonicus and Their Biological Activities

Comprehensive SummarySeventeen undescribed lindenane‐related sesquiterpenoid dimers, chlorajaponins A—Q (1—17), and 13 reported analogs (18—30) were isolated from Chloranthus japonicus Sieb. Compound 1 possesses an unprecedented 3/5/7/5/5/6/5/3 fused octacyclic scaffold, featuring a 6(5→4)‐abeo‐lindenane monomer, while 2 exhibits a 3/5/6/6/5/6/5/3 fused octacyclic scaffold. Their structures were determined through a combination of spectroscopic analyses and X‐ray crystallography. Compounds 1, 2, and 18 demonstrated significant inhibitory effects on lipid accumulation and effectively reduced the levels of triglycerides and total cholesterol, as well as the levels of aspartate aminotransferase and alanine aminotransferase in a HepG2 cell model. In addition, compounds 1, 2, and 18 significantly suppressed the protein expression of the fatty acid synthase (FASN) and the sterol regulatory element‐binding protein 1 (SREBP1). Moreover, the anti‐inflammatory assay showed that compounds 19—22 and 25 inhibited the NO production induced by lipopolysaccharide in RAW 264.7 macrophages with IC50 values of 7.89 ± 0.44, 6.25 ± 0.46, 2.98 ± 0.29, 10.77 ± 0.60, and 3.60 ± 0.28 μmol/L.

Lindenane sesquiterpenoid dimers from Chloranthus japonicus improve LDL uptake by regulating PCSK9 and LDLR

UPLC-TOF-MS/MDF directed phytochemical research of Chloranthus japonicus led to the isolation of 46 lindenane sesquiterpenoid dimers, which included 13 new analogs. Their structures with absolute configurations were elucidated by analysis of spectroscopic data. Fourteen compounds with ester chains significantly decreased PCSK9 protein level in medium of HepG2 cells, especially for compounds 14 and 29 (5 µM) with inhibition rates of 69.0% and 72.8%, respectively. Compound 14 in HepG2 cells was evaluated via DiI-LDL uptake assays and found to increase LDL uptake by upregulating LDLR mRNA and protein level. Meanwhile, 14 decreased the secretion of PCSK9 protein in medium and downregulated intracellular PCSK9 protein and mRNA level. The discovery of these natural small molecule compounds provides a novel structure basis for design PCSK9 regulators, making them a promising lead for development of new lipid-lowering agents.

Richard Maack and his contributions to the botany of Siberia

A brief account of the biography of Richard Maack (1825–1886) is provided, with an emphasis on his botanical travels and research presented in the context of contemporary politics and sciences. The history of three Siberian expeditions of the Imperial Russian Geographical Society is detailed: to the Viluy River in 1853–1855, to the Amur River in 1855–1856 and to the Ussuri River in 1859–1860. Scientific and curatorial treatments of botanical collections of these expeditions are reviewed. The botanical works based on the Amur and Ussuri expeditions are analysed, and more precise dates of their effective publication are traced from contemporary sources. The corrected nomenclature is provided for Carex wiluica, Chloranthus mandshuricus, Ligustrina and Nymphaea wenzelii. Chloranthus japonicus is re‐established as the correct name for C. mandshuricus in place of the recently resurrected C. quadrifolius. Lectotypes are designated for Carex wiluica, Chloranthus japonicus and C. mandshuricus; the previously designated lectotype of C. japonicus is superseded because of being in conflict with the protologue.

Phenylpropenol ester and sesquiterpenoids with antimetastatic activities from the whole plants of Chloranthus japonicus

One new phenylpropenol ester (1) and three new lindenane sesquiterpenes (2–4) were isolated from the whole plant of Chloranthus japonicus together with three known lindenane derivatives (5–7). Their structures were determined based on detailed spectroscopic and electronic circular dichroism computational analyses. Compound 4 showed moderate efficacy in inhibiting cell migration, invasion, and vasculogenic mimicry (VM) in human of hepatocarcinoma (HCC) HepG2 cells. Furthermore, compound 4 could alter the expression of the proteins Vimentin, N-cadherin, Snail1 and E-cadherin by down-regulating the expression of Twist1, which indicated that its antimetastatic effect was associated with restraining the epithelial-mesenchymal transition (EMT) in HepG2 cells.

Crystal structure and Hirshfeld analysis of (1aS,3aR,4aS,5aR)-15-acet-oxy-linden-7(11),8-trieno-12,8-lactone.

The structure of the title com-pound, C17H20O4 [systematic name: (1aS,3aR,4aS,5aR)-15-(acet-oxy)linden-7(11),8-trieno-12,8-lactone or (4aR,5S,5aR,6aS,6bR)-5-(acet-oxy-meth-yl)-4a,5,5a,6,6a,6b-hexa-hydro-3,6b-di-methyl-cyclo-propa[2,3]indeno-[5,6-b]furan-2(4H)-one, ent-chloranthalactone C], a natural product iso-lated from the whole plant Chloranthus japonicus Sieb., is a typical lin-den-ane-type sesquiterpenoid. The mol-ecule com-prises a bi-cyclo-[3.1.0]hexane ring (A/B system) bearing an acetoxymethyl (C-4) group, a bi-cyclo-[4.3.0]nonane ring (B/C system) containing a double bond (C-8/9) and a chiral quaternary carbon (C-10), and a 7(11)-en-12,8-olide structural moiety on the cyclo-hexan-8-ene (C ring). In the tetra-cyclic skeleton, the 1,3-cyclo-propane ring has a β-con-figuration, and atoms H-5 and H3-14 have α- and β-orientations, respectively. In the crystal, the mol-ecules are assembled into a two-dimensional network by weak O⋯H/H⋯O inter-actions. Hirshfeld surface analysis illustrates that the greatest contributions are from H⋯H (55.2%), O⋯H/H⋯O (34.6%) and C⋯H/H⋯C (8.9%) contacts.

Hexane Extract of Chloranthus japonicus Increases Adipocyte Differentiation by Acting on Wnt/β-Catenin Signaling Pathway.

Chloranthus japonicus has been heavily investigated for the treatment of various diseases. This paper attempts to show that Chloranthus japonicus can modulate adipocyte differentiation of preadipocytes. To establish this, we investigated the effects of Chloranthus japonicus extract in peroxisome proliferator-activated receptor γ (PPARγ) expression, adipogenesis, and the underlying molecular mechanisms in C3H10T1/2 and 3T3-L1 cells. Our data showed that Chloranthus japonicus methanol extract increased lipid accumulation and promoted adipocyte differentiation. Further studies on the fractionation with various solvents led to the identification of Chloranthus japonicus hexane extract (CJHE) as the most potent inducer of adipocyte differentiation. CJHE consistently increased lipid accumulation and adipocyte marker expression including Pparγ and it acted during the early stages of adipocyte differentiation. Mechanistic studies revealed that CJHE and a Wnt inhibitor similarly stimulated adipogenesis and were active in Wnt-selective reporter assays. The effects of CJHE were inhibited by Wnt3a protein treatment and were significantly blunted in β-catenin-silenced cells, further suggesting that CJHE acted on Wnt pathways to promote adipogenesis. We also showed that Chloranthus japonicus extracts generated from different plant parts similarly promoted adipocyte differentiation. These results identified Chloranthus japonicus as a pro-adipogenic natural product and suggest its potential use in metabolic syndrome.

Gold at 7-month low on strong US treasury yields

This study investigated the distribution of vascular plants in Mt. Anam located in Haksa-ri in Kimwha-eup, Cheorwon-gun, Gangwon-do. Eight surveys were conducted from March 2015 to May 2018. In this survey, a total of 416 taxa of vascular plants were observed, comprising 354 species, 4 subspecies, 52 varieties, and 6 forms belonging to 260 genera and 86 families. This included five taxa of endemic plants (such as Salix koriyanagi Kimura, Clematis brachyura Maxim., and Berberis koreana Palib.), nine taxa of rare plants designated by the Korea Forest Service, two taxa of vulnerable plants (such as Epimedium koreanum Nakai), and seven taxa of least concern plants (such as Aristolochia contorta Bunge). Forty-nine taxa of plants with floristic characteristics were found—1 taxon in Grade V (Epimedium koreanum Nakai), 3 taxa in Grade IV (such as Athyrium iseanum Rosenst.), 12 taxa in Grade III (such as Berberis koreana Palib.), 10 taxa in Grade II (such as Thalictrum rochebrunnianum var. grandisepalum (H. Lév.) Nakai), and 23 taxa in Grade I (such as Chloranthus japonicus Siebold). For invasive alien plants, there were 25 taxa comprising 25 species belonging to 23 genera and 10 families (such as Rumex crispus L., Lepidium virginicum L., and Ambrosia artemisiifolia L.).

The vascular plants of Mt. Anam (Cheorwon-gun, Gangwon-do) area adjacent to the Korean demilitarized zone

This study investigated the distribution of vascular plants in Mt. Anam located in Haksa-ri in Kimwha-eup, Cheorwon-gun, Gangwon-do. Eight surveys were conducted from March 2015 to May 2018. In this survey, a total of 416 taxa of vascular plants were observed, comprising 354 species, 4 subspecies, 52 varieties, and 6 forms belonging to 260 genera and 86 families. This included five taxa of endemic plants (such as Salix koriyanagi Kimura, Clematis brachyura Maxim., and Berberis koreana Palib.), nine taxa of rare plants designated by the Korea Forest Service, two taxa of vulnerable plants (such as Epimedium koreanum Nakai), and seven taxa of least concern plants (such as Aristolochia contorta Bunge). Forty-nine taxa of plants with floristic characteristics were found—1 taxon in Grade V (Epimedium koreanum Nakai), 3 taxa in Grade IV (such as Athyrium iseanum Rosenst.), 12 taxa in Grade III (such as Berberis koreana Palib.), 10 taxa in Grade II (such as Thalictrum rochebrunnianum var. grandisepalum (H. Lév.) Nakai), and 23 taxa in Grade I (such as Chloranthus japonicus Siebold). For invasive alien plants, there were 25 taxa comprising 25 species belonging to 23 genera and 10 families (such as Rumex crispus L., Lepidium virginicum L., and Ambrosia artemisiifolia L.).

Underlying mechanisms of development: pollen wall ontogeny inChloranthus japonicusand a reconsideration of pollen ontogeny in early-diverging lineages of angiosperms

AbstractDespite the large amount of knowledge accumulated, a precise understanding of the morphogenesis of the intricate and complex pollen walls (exines) is incomplete. A new factor (simple physico-chemical interactions) is shown to be involved in exine development. The stages of exine development in many species show remarkable similarity with successive micellar self-assembling mesophases of a colloidal system. Currently, > 100 genes have been reported to play a role in exine deposition, but nothing contradicts the view that specific patterns of exines are based on physico-chemical principles of space-filling operations taking place after genomic control of the concentrations of the source materials. On the examples of Chloranthus japonicus, magnoliids and other early-diverging angiosperms we show that exine development unfolds by two physico-chemical processes (phase separation and self-assembly) after genomic control, revealing an interplay between genomic and physical processes.

Diversity and Antimicrobial Activity of Endophytic Fungi Isolated from Chloranthus japonicus Sieb in Qinling Mountains, China.

The plant Chloranthus japonicus Sieb is known for its anticancer properties and mainly distributed in China, Japan, and Korea. In this study, we firstly investigated the diversity and antimicrobial activity of the culturable endophytic fungi from C. japonicus. A total of 332 fungal colonies were successfully isolated from 555 tissue segments of the medicinal plant C. japonicus collected from Qinling Mountains, China. One hundred and thirty representative morphotype strains were identified according to ITS rDNA sequence analyses and were grouped into three phyla (Ascomycota, Basidiomycota, Mucoromycota), five classes (Dothideomycetes, Sordariomycetes, Eurotiomycetes, Agaricomycetes, Mucoromycetes), and at least 30 genera. Colletotrichum (RA, 60.54%) was the most abundant genus, followed by Aspergillus (RA, 11.75%) and Diaporthe (RA, 9.34%). The Species Richness Index (S, 56) and the Shannon-Wiener Index (H′, 2.7076) indicated that C. japonicus harbored abundant fungal resources. Thirteen out of 130 endophytic fungal ethyl acetate extracts exhibited inhibitory activities against at least one pathogenic bacterium or fungus. Among of these, F8158, which was identified as Trichoderma cf. harzianum, exhibited good antagonistic capacities (the percent inhibition of mycelial growth ranged from 47.72~88.18) for different pathogens and has a potential application in biological control. In addition, it is noteworthy that the strain F8157 (Thanatephorus cucumeris, an opportunistic pathogen) showed antibacterial and antifungal activity, which is reported firstly in this study, and should be investigated further. Taken together, these results indicated that the endophytic fungi from C. japonicus may be of potential interest in screening bio-control agents and discovering of new bioactive compounds.

The Stages of Gametophyte and Sporoderm Development in Pollen Grains

Based on several modern plant species (Aristolochia clematitis, A. manshuriensis, Alliaria petiolata, Chloranthus japonicus, Symphytum officinale, Ambrosia trifida, Polemonium caeruleum, Plantago major, Populus tremula and P. × berolinensis), grown in botanical gardens of Moscow and Saint Petersburg, the stages of gametophyte and sporoderm development were compared. The most common regularities in the development of male gametophyte and its sporoderm were revealed. It is shown that the thicker the endexine, the later the intine starts to develop. The formation of tubular intine at the first mitosis of male gametophyte can occur after initiation of the intine, as it is observed in spores with endosporous spore germination in gametophyte. The dehydration of a pollen grain that is expressed in deposition of lipids and starch can start before the maturation of sporoderm that is observed in inaperturate pollen grains. Angiosperms show the broadest possibilities of variability in the sporoderm structure without losing the capacity for reproduction.

Chlojaponilactone B Attenuates Lipopolysaccharide-Induced Inflammatory Responses by Suppressing TLR4-Mediated ROS Generation and NF-κB Signaling Pathway.

The lindenane-type sesquiterpenoid chlojaponilactone B (1), isolated from Chloranthus japonicus, has been reported to possess anti-inflammatory properties. The present study aimed to further explore the molecular mechanisms underlying the anti-inflammatory activity of 1. RNA-seq analyses revealed the significant changes in the expression levels of genes related to multiple inflammatory pathways upon treatment of lipopolysaccharide (LPS)-induced RAW 264.7 murine macrophages with 1. Real time PCR (RT-PCR) and Western blotting were used to confirm the modulations in the expression of essential molecules related to inflammatory responses. Compound 1 inhibited toll like receptor 4 (TLR4) and myeloid differentiation factor 88 (MyD88) activation upon LPS stimulation, influencing the expression of NF-κB and pro-inflammatory mediators. Molecular docking studies showed that 1 bound to TLR4 in a manner similar to that of TAK-242, a TLR4 inhibitor. Moreover, our results showed that 1 suppressed inflammatory responses by inhibiting TLR4 and subsequently decreasing reactive oxygen species (ROS) generation, downregulating the NF-κB, thus reducing the expression of the pro-inflammatory cytokines iNOS, NO, COX-2, IL-6 and TNF-α; these effects were similar to those of TAK-242. We proposed that 1 should be considered as a potential anti-inflammatory compound in future research.

Japonicones A-C: Three lindenane sesquiterpenoid dimers with a 12-membered ring core from Chloranthus japonicus

Japonicones A–C (1–3), three new dimeric lindenane-type sesquiterpenoids featuring a rare 12-membered ring framework, were isolated from the whole plants of Chloranthus japonicus Sieb. Their structures and absolute configurations were unequivocally established by a combination of spectroscopic data, ECD calculation, and X-ray crystallography. Compounds 1–3 were evaluated for their DNA Topoisomerase Ⅰ (Top1) inhibitory, cytotoxic, and antibacterial activities.

Complete sequence of the chloroplast genome of Asarum heterotropoides (Aristolochiales: Asarum L.)

This article aims to introduce the Asarum heterotropoides complete chloroplast genome sequence information. Asarum heterotropoides complete length of 159,944 BP and the total content of GC was 38.5%, with SSC (16,677 BP) and LSC (88,253 BP) to a separate IR (27,261 BP) consisting of four typical structures. Asarum heterotropoides CP genome encodes 152 unique genes, including 103 protein-encoding genes, 41 tRNA genes, and eight rRNA genes, and 44 copies in the IR region. One gene contains two genes in the 15 genes which contain one intron. The phylogenetic trees are based on 15 plants. The determination of A. heterotropoides was closely related to the phylogenetic position of Ceratophyllum demersum and its relationship with Chloranthus japonicus.

A new lindenane-type sesquiterpenoid lactone from Chloranthus japonicus

Chromatographic fractionation of the EtOH extracts of the Traditional Chinese Medicine (TCM) Chloranthus japonicus, has led to the isolation of a new lindenane-type sesquiterpenoid lactone derivative (1). Rosmarylchloranthalactone E (1), which consists of lindenane sesquiterpenoid lactone and rosmarinic acid moieties linked via an ester bridge, was structurally elucidated by 1D and 2D NMR and HRMS data. Compound 1 was a potent phosphodiesterase-4 (PDE4) inhibitor with an IC50 value of 0.96 ± 0.04 μM.

Antifungal Activities of Dimeric Sesquiterpenes, Shizukaols C and F, Isolated from Chloranthus japonicus Sieb.

Two dimeric sesquiterpenes were separated from Chloranthus japonicus Sieb. and identified as shizukaols C and F. They exhibited potent antifungal activities (MICs = 4-16 μg/ml) in vitro against various plant pathogenic fungi (Pythium ultimum, Phytophthora infestans, Botrytis cinerea, Colletotrichum lagenarium, Alternaria kikuchiana, and Magnaporthe grisea). Shizukaol C showed 88% and 91% protective activities in the greenhouse against Puccinia recondita (wheat leaf rust) and Phytophthora infestans (tomato late blight), respectively, at 100 μg/ml; shizukaol F exhibited 93% antifungal activity against Puccinia recondita at the same concentration. Therefore, these compounds might serve as interesting candidates for effective antifungal agents.

Two new sesquiterpenoids and a new lindenane sesquiterpenoid dimer from Chloranthus japonicus

A structurally novel 8,9-seco-eudesma-9,4:8,12-dilactone sesquiterpenoid, chlorajapodiolide (1), a new eudesmane sesquiterpenoid, chlorajapotriol (2), a new lindenane-type sesquiterpenoid dimer, chlorajaponilide I (3), and four known lindenane-type sesquiterpenoid dimers were isolated from the whole plant of Chloranthus japonicus. Their structures were established through extensive analysis of NMR spectroscopic data in combination with mass spectrometry. All compounds were evaluated for cytotoxicities against four human cancer cell lines A549, HCT116, MGC803, and HepG2.

Modulation of glucose metabolism by a natural compound from Chloranthus japonicus via activation of AMP-activated protein kinase

AMP-activated protein kinase (AMPK) is a key sensor and regulator of glucose metabolism. Here, we demonstrated that shizukaol F, a natural compound isolated from Chloranthus japonicus, can activate AMPK and modulate glucose metabolism both in vitro and in vivo. Shizukaol F increased glucose uptake in differentiated C2C12 myotubes by stimulating glucose transporter-4 (GLUT-4) membraned translocation. Treatment of primary mouse hepatocytes with shizukaol F decreased the expression of phosphoenolpyruvate carboxykinase 2 (PEPCK), glucose-6-phosphatase (G6Pase) and suppressed hepatic gluconeogenesis. Meanwhile, a single oral dose of shizukaol F reduced gluconeogenesis in C57BL/6 J mice. Further studies indicated that shizukaol F modulates glucose metabolism mainly by AMPKa phosphorylation activity. In addition, we also found that shizukaol F depolarizes the mitochondrial membrane and inhibits respiratory complex I, which may result in AMPK activation. Our results highlight the potential value of shizukaol F as a possible treatment of metabolic syndrome.

Chlorajaponols A–F, sesquiterpenoids from Chloranthus japonicus and their in vitro anti-inflammatory and anti-tumor activities

Two new eudesmane sesquiterpenoids, chlorajaponols A–B (1–2), two new guaiane sesquiterpenoids, chlorajaponols C–D (3–4), a new germacrane sesquiterpenoid, chlorajaponol E (5), and a new lindenane sesquiterpenoid, chlorajaponol F (6), along with 8 known sesquiterpenoids and 6 known disesquiterpenoids, were isolated from the whole plant of Chloranthus japonicus. Their structures were established by extensive analysis of NMR spectroscopic data in combination with mass spectrometry. The structures of compounds 1–4 were confirmed by single crystal X-ray diffraction (CuKα radiation). The possible biogenetic pathways of compounds 1–6 were discussed. Chlorajaponol B (2) showed significant inhibition against nitric oxide (NO) release in LPS-induced RAW264.7 macrophages with the IC50 value of 9.56±0.71μM, comparable to that of positive control amino guanidine (8.50±0.35μM). Shizukaol C (18) strongly suppressed the proliferation of three human tumor cell lines MGC803, HepG2, and HL-60 with IC50 values of 4.60±1.05μM, 3.17±0.66μM, and 1.57±0.27μM, respectively.