Saghi Hakimi Naeini, Hassan Rajabi-Maham, Abdolkarim Hosseini, Vahid Azizi
{"title":"Neuroprotective impact of glycitin on memory impairment in a pentylenetetrazol-induced chronic epileptic rat model: insights into hippocampal histology, oxidative stress, and inflammation.","authors":"Saghi Hakimi Naeini, Hassan Rajabi-Maham, Abdolkarim Hosseini, Vahid Azizi","doi":"10.1007/s11418-024-01846-7","DOIUrl":"https://doi.org/10.1007/s11418-024-01846-7","url":null,"abstract":"<p><p>Epilepsy, characterized by recurrent seizures, often accompanies neurocognitive impairments and is associated with increased oxidative stress and inflammation. This study investigates the possible neuroprotective properties of glycitin, a soy isoflavone, on memory impairment, its impact on oxidative stress responses, and inflammatory gene expression in a chronic epileptic rat model induced by pentylenetetrazol (PTZ). Glycitin was administered at varying doses to evaluate its potential neuroprotective impact on memory, oxidative stress, and inflammation in this model. Behavioural assessments, memory retention and recall capabilities, histopathological examinations, measurements of oxidative stress biomarkers, and molecular assessments were employed for comprehensive evaluation. The results demonstrated that glycitin significantly improved memory impairment and reduced oxidative stress in epileptic rats. Additionally, glycitin treatment decreased the expression of tumor necrosis factor-α (TNF-α) and nuclear factor kappa B (NF-κB), indicating its potential to modulate the inflammatory response associated with epilepsy. These observations underscore the potential of glycitin as a therapeutic candidate for mitigating memory impairments linked to chronic epilepsy due to its antioxidant and anti-inflammatory properties, offering insights into novel avenues for the development of targeted interventions aimed at preserving cognitive function and ameliorating oxidative damage and inflammation in epileptic conditions.</p>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142370691","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Research on the quality evaluation of crude drugs.","authors":"Hiroyuki Fuchino","doi":"10.1007/s11418-024-01845-8","DOIUrl":"https://doi.org/10.1007/s11418-024-01845-8","url":null,"abstract":"<p><p>As crude drugs are natural products, their quality may vary. However, the degradation of the active ingredients in the compositional changes that occur during processing and preparation also affects the medicinal properties of the Kampo formula, which uses herbal medicines; therefore, a detailed investigation of the effects of compositional changes during preparation is required. Plant constituents vary in content depending on the year of cultivation and the plant part; however, detailed studies have rarely been reported for some crude drugs. Liquid chromatography-nuclear magnetic resonance/mass spectrometry revealed the degradation process of saponins, which are unstable components of the crude drug \"Achyranthes root.\" The presence of diterpenes unstable with respect to drying temperature in the leaves of the crude drug \"Leonurus herb\" was revealed and their structures were elucidated. At the examination stage of the degradation process of perillaldehyde, the characteristic aromatic component of Perilla herb, it was elucidated that some specimens contained a small amount of perillaldehyde and that they contained more α-asarone. A trend toward lower ephedrine content was observed toward the tip of the above-ground branching of the Ephedra herb. Multivariate analysis was also introduced into the quality assessment of crude drugs and was established as a tool to identify bioactive compounds using the component diversity of crude drugs and to elucidate component differences due to the cultivation environment.</p>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142363932","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Chemical profile and biological activities of Lysiphyllum binatum (Blanco) de Wit.","authors":"Surasak Kheawchaum, Sanit Thongnest, Jutatip Boonsombat, Paratchata Batsomboon, Chulabhorn Mahidol, Hunsa Prawat, Somsak Ruchirawat","doi":"10.1007/s11418-024-01844-9","DOIUrl":"https://doi.org/10.1007/s11418-024-01844-9","url":null,"abstract":"<p><p>Lysiphyllum binatum (Blanco) de Wit in the Fabaceae family, despite its traditional medicinal uses, has not been the subject of prior scientific inquiry into its chemical and biological profile. The dichloromethane and MeOH extracts of its roots exhibited notably similar antioxidant activity, while the dichloromethane extract of the vine stems showed aromatase inhibition. This study aimed to identify the bioactive components responsible for these activities. Chemical investigation of the roots led to the isolation of six new metabolites, named lysiphans A-F (1-6), along with eight known compounds (7-14). The vine stem yielded lysiphan C (3) and compound 7, as well as five known isolates (15-19). The structures of these metabolites were determined through NMR spectral analysis, HRESIMS, quantum chemical calculations of NMR and ECD spectra, and Mosher's modifications to establish their absolute configurations. The biogenetic relationships between the new compounds were proposed. Several of the isolates were evaluated for their antioxidant, anti-aromatase, and cytotoxic properties. Lysiphan B (2) exhibited significant antioxidant activity, with an IC<sub>50</sub> value of 28.8 ± 0.4 μM in the diphenyl picrylhydrazyl radical (DPPH) assay, 3.5 ± 0.2 μM in the xanthine/xanthine oxidase (XXO) assay, and 1.5 ± 0.0 ORAC units in oxygen radical absorbance capacity (ORAC) assay. Additionally, compounds 12, 13, and 16 exhibited very strong aromatase inhibitory activity with IC<sub>50</sub> values of 0.3 ± 0.2, 4.7 ± 0.1, and 0.9 ± 0.2 µM, respectively. Compound 16 also demonstrated strong ORAC activity of 1.9 ± 0.1 ORAC units.</p>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142338948","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Azamollugin, a mollugin derivative, has inhibitory activity on MyD88- and TRIF-dependent pathways","authors":"Yuki Nakajima, Hitomi Nishino, Kazunori Takahashi, Alfarius Eko Nugroho, Yusuke Hirasawa, Toshio Kaneda, Hiroshi Morita","doi":"10.1007/s11418-024-01842-x","DOIUrl":"https://doi.org/10.1007/s11418-024-01842-x","url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>Previously, we reported that azamollugin, an aza-derivative of mollugin, exhibited potent inhibitory activity on NO production in LPS-stimulated RAW 264.7 cells. Further investigations in this study revealed that azamollugin not only suppressed iNOS gene expression regulated by NF-κB, but also inhibited LPS-induced IFN-β expression, which is known to be regulated by IRF3. Azamollugin exhibited an inhibitory activity on LPS-induced IRAK1 activation, suggesting inhibitory effect on the MyD88-dependent pathway. Furthermore, azamollugin inhibited LPS-induced phosphorylation of IRF3 and its upstream factor, TBK1/IKKε, suggesting an inhibitory effect on the TRIF-dependent pathway via TLR4. In addition, azamollugin also suppressed poly(I:C)-induced phosphorylation of TBK1 and IRF3, suggesting an inhibitory effect on the TRIF-dependent pathway via TLR3. These results suggest that azamollugin has inhibitory activity against both the MyD88-dependent and TRIF-dependent pathways, respectively.</p><h3 data-test=\"abstract-sub-heading\">Graphical abstract</h3>\u0000","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"8 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269443","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Macrocyclizing-thioesterases in bacterial non-ribosomal peptide biosynthesis.","authors":"Kenichi Matsuda","doi":"10.1007/s11418-024-01841-y","DOIUrl":"https://doi.org/10.1007/s11418-024-01841-y","url":null,"abstract":"<p><p>Macrocyclization of peptides reduces conformational flexibilities, potentially leading to improved drug-like properties. However, side reactions such as epimerization and oligomerization often pose synthetic challenges. Peptide-cyclizing biocatalysts in the biosynthesis of non-ribosomal peptides (NRPs) have remarkable potentials as chemoenzymatic tools to facilitate more straightforward access to complex macrocycles. This review highlights the biocatalytic potentials of NRP cyclases, especially those of cis-acting thioesterases, the most general cyclizing machinery in NRP biosynthesis. Growing insights into penicillin-binding protein-type thioesterases, a relatively new group of trans-acting thioesterases, are also summarized.</p>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142103217","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"High-resolution X-ray computed tomography for identifying herbal medicines was as effective as microscopic examination.","authors":"Hiroko Tokumoto, Nahoko Uchiyama, Michiho Ito","doi":"10.1007/s11418-024-01840-z","DOIUrl":"https://doi.org/10.1007/s11418-024-01840-z","url":null,"abstract":"<p><p>Microscopic examination is one of the important identification methods for crude drug test described in the 18th Japanese Pharmacopoeia. This method is useful for identification because it can be used for small amounts of samples regardless of their storage conditions; however, this method requires a lot of technical skill in sectioning intricate and/or small samples and is time-consuming. High-resolution X-ray computed tomography (HRXCT) is a novel method for observing the internal morphology of materials. Previously, we used HRXCT to visualize the internal morphology of the Ephedra Herb, obtaining observations that closely match those obtained via microscopic examination. HRXCT employs a low-energy X-ray source and the permeation distance of the X-rays is very short. Therefore, HRXCT can be used for elucidating the morphology of small herbal medicines. In this study, Artemisia Capillaris Flower (capitulum with a diameter of approximately 2 mm) and Plantago Seed (seeds with a length of approximately 2 mm) were examined. The results showed that HRXCT examination was sufficient to illustrate the internal independent organs of Artemisia Capillaris Flower and that their inflorescences remained intact. When observing Plantago Seed, the internal morphology of more than one seed can be depicted simultaneously. Therefore, observation using HRXCT was easy, simple, and effective to illustrate the internal morphology of herbal medicines, which is typically time-consuming and requires advanced microscopy skills.</p>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142103216","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yuta Koseki, Hiroaki Nishimura, Ryuji Asano, Katsuyuki Aoki, Li Shiyu, Ryosuke Sugiyama, Mami Yamazaki
{"title":"Isolation of new indole alkaloid triglucoside from the aqueous extract of Uncaria rhynchophylla.","authors":"Yuta Koseki, Hiroaki Nishimura, Ryuji Asano, Katsuyuki Aoki, Li Shiyu, Ryosuke Sugiyama, Mami Yamazaki","doi":"10.1007/s11418-024-01836-9","DOIUrl":"https://doi.org/10.1007/s11418-024-01836-9","url":null,"abstract":"<p><p>Uncaria rhynchophylla (Miq.) Miq. (Rubiaceae) is widely used as a botanical raw material for traditional Japanese and Chinese medicines. However, not all of its potentially bioactive constituents have been isolated and characterized. Herein, one new indole alkaloid triglucoside (1), nine known alkaloids (2-10) and thirteen known non-alkaloids (11-23) were isolated from the aqueous extract of Uncaria rhynchophylla hook and structurally characterized <sup>1</sup>H and <sup>13</sup>C NMR and high-resolution electrospray ionization mass spectrometry. The absolute configurations of isolated compounds (1, 2 and 3) were determined by the X-ray diffraction analysis of their single crystals obtained using a micro-drop crystallization technique. This technique allows single crystals to be obtained from samples as small as 50 µg, thus providing detailed structural information even on minor constituents and enabling the accurate quality monitoring of botanical raw materials more accurately.</p>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142034863","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Eleven new glycosidic acid methyl esters from the crude resin glycoside fraction of Ipomoea alba seeds","authors":"Nodoka Misuda, Hirotaka Nishikawa, Shin Yasuda, Hiroyuki Miyashita, Hitoshi Yoshimitsu, Ryota Tsuchihashi, Masafumi Okawa, Junei Kinjo, Masateru Ono","doi":"10.1007/s11418-024-01838-7","DOIUrl":"10.1007/s11418-024-01838-7","url":null,"abstract":"<div><p>Resin glycosides are characteristic of plants of the Convolvulaceae family and are well-known purgative ingredients in crude drugs, such as Rhizoma Jalapae, Orizaba Jalapa Tuber, and Pharbitidis Semen, which are used in traditional medicine and derived from plants belonging to this family. Isolated resin glycosides have demonstrated diverse biological activities, including antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug-resistance-modulating properties, as well as cytotoxicity against cancer cells. These compounds consist of hydroxyl fatty acid oligoglycosides (glycosidic acids), with portions of the saccharide moieties acylated with some organic acids to form the core structure. This study investigated the glycosidic acid components of a crude resin glycoside fraction obtained from a methanolic extract of <i>Ipomoea alba</i> L. seeds (Convolvulaceae). Eleven new glycosidic acid methyl esters and one known methyl ester were isolated from a glycosidic acid fraction treated with trimethylsilyldiazomethane in hexane. Their structures were determined using acidic hydrolysis and electrospray ionization-time of fight mass spectrometry and NMR spectral analyses. These compounds are penta-, tetra-, or triglycosides, with methyl 11<i>S</i>-hydroxytetradecanoate or methyl 11<i>S</i>-hydroxyhexadecanoate as the aglycone. Although <span>d</span>-quinovose and <span>l</span>-rhamnose are common monosaccharide components, the remaining monosaccharides are <span>d</span>-glucose, <span>d</span>-xylose, or <span>d</span>-fucose. The crude resin glycoside fraction showed non-negligible cytotoxicity against HL-60 human promyelocytic leukemia cells.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"1057 - 1070"},"PeriodicalIF":2.5,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01838-7.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141999210","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Isolation of C-29 oxygenated oleanane triterpenoids and a (+)-muurolene type sesquiterpenoid from the fruiting bodies of Fuscoporia torulosa and their bioactivities","authors":"Tatsuro Yoneyama, Chian Chen, Yoshihiro Ichimura, Katsuyuki Nakashima, Hiromichi Kenmoku, Hiroshi Imagawa, Akemi Umeyama, Masaaki Noji","doi":"10.1007/s11418-024-01832-z","DOIUrl":"10.1007/s11418-024-01832-z","url":null,"abstract":"<div><p>Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes (<b>1</b> and <b>2</b>) and torulosacid (<b>3</b>), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (<b>4</b>–<b>12</b>), were isolated from the MeOH extract of the fruiting bodies of <i>Fuscoporia torulosa</i>. The structures of <b>1</b>–<b>3</b> were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of <b>3</b> were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates, <b>1</b>,<b> 7</b>, and <b>9</b> showed growth inhibitory activity against methicillin-resistant <i>Staphylococcus aureus</i> and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"919 - 928"},"PeriodicalIF":2.5,"publicationDate":"2024-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141911310","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Formohyperins G–L, polycyclic prenylated benzoylphloroglucinols from the flowers of Hypericum formosanum","authors":"Rena Takizawa, Yusei Shimomoto, Daisuke Tsuji, Kiyoshi Imabayashi, Kohji Itoh, Reiko Akagi, Yoshiki Kashiwada, Naonobu Tanaka","doi":"10.1007/s11418-024-01839-6","DOIUrl":"10.1007/s11418-024-01839-6","url":null,"abstract":"<div><p>Phytochemical study on the flowers of <i>Hypericum formosanum</i> Maxim. (Hypericaceae) led to the isolation of formohyperins G–L (<b>1–6</b>), whose structures were assigned by detailed spectroscopic analysis. Formohyperins G–L (<b>1–6</b>) are new benzoylphloroglucinols substituted by a C<sub>10</sub> unit, a prenyl group, and a methyl group. Formohyperins G–J (<b>1–4</b>) possess a 6/6/6-tricyclic structure, while formohyperins K (<b>5</b>) and L (<b>6</b>) have a unique 6/6/5/4-tetracyclic structure consisting of cyclohexadienone, dihydropyrane, cyclopentane, and cyclobutane rings. The absolute configurations of <b>1–6</b> were deduced by analysis of the ECD spectra. Formohyperins G–J (<b>1–4</b>) and L (<b>6</b>) were found to show potent inhibitory activities against IL-1β release from LPS-treated murine microglial cells with EC<sub>50</sub> values of 5.0, 10.9, 6.3, 10.8, and 13.7 µM, respectively, without cytotoxicity. 6-<i>O</i>-Methylformohyperins G (<b>1a</b>) and I (<b>3a</b>) also exhibited the inhibitory activities with EC<sub>50</sub> values of 4.7 and 2.7 µM, respectively, although they were cytotoxic against microglial cells.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 4","pages":"970 - 977"},"PeriodicalIF":2.5,"publicationDate":"2024-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141911281","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}