Journal of Natural Medicines最新文献

{"title":"New biflavonoids isolated from Xylia kerrii leaves extract with selective cytotoxicity against MH7A human rheumatoid arthritis synovial fibroblast cells","authors":"Kazuki Fujii,&nbsp;Itsuki Iwata,&nbsp;Akiko Takaya,&nbsp;Masami Ishibashi,&nbsp;Yasumasa Hara","doi":"10.1007/s11418-024-01801-6","DOIUrl":"10.1007/s11418-024-01801-6","url":null,"abstract":"<div><p>Three new biflavonoids (<b>1</b>–<b>3</b>) and two known flavonoids (<b>4</b>, <b>5</b>) were isolated from <i>Xylia kerrii</i> collected in Thailand. Compounds <b>1</b>–<b>5</b> showed selective cytotoxicity against the rheumatoid fibroblast-like synovial MH7A cell line, and these compounds showed weak cytotoxicity against the human lung synovial fibroblast WI-38 VA13 sub 2 RA cell line. Notably, compound <b>1</b> was highly selective toward MH7A cells with an IC₅₀ value of 6.9 μM, whereas the IC₅₀ value for WI-38 VA13 sub 2 RA cells was &gt; 100 μM. The western blotting analysis of MH7A cells treated with compound <b>1</b> showed increased CDKN2A /p16INK4A and caspase-8 levels.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><img></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"732 - 740"},"PeriodicalIF":2.5,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01801-6.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140594532","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":"Hypoglycemic effects of mountain caviar extract and inhibitory mechanism of saponins, including momordin Ic, on glucose absorption","authors":"Kenchi Miyasaka,&nbsp;Ryuya Takada,&nbsp;Jianbo Wu,&nbsp;Shogo Takeda,&nbsp;Yoshiaki Manse,&nbsp;Toshio Morikawa,&nbsp;Hiroshi Shimoda","doi":"10.1007/s11418-024-01791-5","DOIUrl":"10.1007/s11418-024-01791-5","url":null,"abstract":"<div><p>Mountain caviar is a fruit of <i>Kochia scoparia</i> that contains momordin Ic as a major saponin constituent. Its extract (MCE) has been shown to suppress blood glucose elevations in the human oral glucose tolerance test (OGTT) as well as increases in blood glucose in OGTT, gastric emptying (GE), and glucose incorporation in the small intestine in rats. However, the effects of MCE and momordin Ic on glucose absorption in mice and these action mechanisms have not been examined for more than 2 decades. Therefore, we herein investigated the effects of MCE, its saponin fraction, and momordin Ic on blood glucose elevations in mice. Mouse blood glucose elevation tests were performed on carbohydrate-loaded mice. The mountain caviar saponin fraction significantly delayed blood glucose elevations in glucose-, sucrose-, and soluble starch-loaded mice. In glucose-loaded mice, the saponin fraction, MCE, and momordin Ic significantly suppressed rapid glucose elevations after glucose loading, but not sucrose loading. A mouse GE study was performed by loading with glucose and phenolphthalein solution. Momordin Ic and MCE strongly suppressed mouse GE. Intestinal glucose absorption was evaluated by the incorporation of 2-deoxyglucose (2-DG) into Caco-2 cell layers and mouse duodenum wall vesicles. The results obtained showed that momordin Ic inhibited the incorporation of 2-DG into Caco-2 cells and mouse duodenum vesicles. Collectively, these results suggest that MCE, particularly the principal saponin, momordin Ic, preferably suppressed glucose-induced blood glucose elevations and delayed carbohydrate-induced glucose elevations in mice. The underlying mechanism was found to involve the suppression of GE and intestinal glucose absorption.</p><h3>Graphical Abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"693 - 701"},"PeriodicalIF":2.5,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140594442","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":"Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers","authors":"Kazuki Ujiie,&nbsp;Chiaki Tanaka,&nbsp;Masayoshi Arai,&nbsp;Masaru Hashimoto,&nbsp;Yuki Yoshida,&nbsp;Tomikazu Kawano,&nbsp;Satoru Tamura","doi":"10.1007/s11418-024-01810-5","DOIUrl":"10.1007/s11418-024-01810-5","url":null,"abstract":"<div><p>The relative configuration of the epoxide functionality in pinofuranoxin A (<b>1</b>), α-alkylidene-β-hydroxy-γ-methyl-γ-butyrolactone with <i>trans</i>-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the configurational elucidation of the stereogenic centers on the conformationally flexible acyclic side-chains. Sharpless’s enantioselective epoxidations and dihydroxylations were quite effective in the reinvestigations of the configurations. As our syntheses made all diastereomers available, these would be quite effective in the next structure-biological activity relationship studies.</p><h3>Graphical Abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"608 - 617"},"PeriodicalIF":2.5,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01810-5.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140594682","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":"Compound–compound interaction analysis of baicalin and berberine derivatives in aqueous solution","authors":"Yoshinori Uekusa,&nbsp;Chiharu Tanioka,&nbsp;Kenjiro Nakamoto,&nbsp;Riina Tsutsumi,&nbsp;Chihiro Iida,&nbsp;Naoto Enshu,&nbsp;Takehiro Nishimura,&nbsp;Fumiyuki Kiuchi,&nbsp;Haruhisa Kikuchi","doi":"10.1007/s11418-024-01804-3","DOIUrl":"10.1007/s11418-024-01804-3","url":null,"abstract":"<div><p>Baicalin and berberine are biologically active constituents of the crude drugs Scutellaria root and Coptis rhizome/Phellodendron bark, respectively. Baicalin and berberine are reported to combine together as a 1:1 complex that forms yellow precipitates by electrostatic interaction in decoctions of Kampo formulae containing these crude drugs. However, the structural basis and mechanism for the precipitate formation of this compound–compound interaction in aqueous solution remains unclarified. Herein, we searched for berberine derivatives in the Coptis rhizome that interact with baicalin and identified the chemical structures involved in the precipitation formation. Precipitation assays showed that baicalin formed precipitates with berberine and coptisine but not with palmatine and epiberberine. Thus, the 2,3-methylenedioxy structure may be crucial to the formation of the precipitates, and electrostatic interaction is necessary but is not sufficient. In this multicomponent system experiment, palmatine formed a dissociable complex with baicalin and may competitively inhibit the formation of berberine and coptisine precipitation with baicalin. Therefore, the precipitation formed by berberine and baicalin was considered to be caused by the aggregation of the berberine–baicalin complex, and the 2,3-methylenedioxy structure is likely crucial to the aggregation of the complex.</p><h3>Graphic abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"590 - 598"},"PeriodicalIF":2.5,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140594444","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":"Cryptobuchanosides A–G: seven previously undescribed triterpene glycosides from Cryptolepis buchananii R.Br. ex Roem. and Schult. with nitric oxide production inhibition activity","authors":"Ngo Anh Bang,&nbsp;Nguyen Duc Duy,&nbsp;Bui Huu Tai,&nbsp;Nguyen Thi Kim Thuy,&nbsp;Pham Hai Yen,&nbsp;Duong Thi Dung,&nbsp;Nguyen Huy Hoang,&nbsp;Nguyen Xuan Nhiem,&nbsp;Ninh Khac Ban,&nbsp;Phan Van Kiem","doi":"10.1007/s11418-024-01805-2","DOIUrl":"10.1007/s11418-024-01805-2","url":null,"abstract":"<div><p>In this study, nine triterpene glycosides including seven previously undescribed compounds (<b>1</b>–<b>7</b>), were isolated from leaves of <i>Cryptolepis buchananii</i> R.Br. ex Roem. and Schult. using various chromatographic methods. The chemical structures of the compounds were elucidated to be 3<i>-O-β</i>-<span>d</span>-glucopyranosyl-(1 → 6)-<i>β</i>-<span>d</span>-glucopyranosyluncargenin C 28<i>-O-α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>1</b>), 3<i>-O-β</i>-<span>d</span>-glucopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyluncargenin C 28<i>-O-α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>2</b>), 3<i>-O-β</i>-<span>d</span>-glucopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyluncargenin C 28<i>-O-β</i>-<span>d</span>-glucopyranosyl-(1 → 4)-<i>α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>3</b>), 3<i>-O-β</i>-<span>d</span>-glucopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosylhederagenin 28<i>-O-α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>4</b>), 3<i>-O-β</i>-<span>d</span>-glucopyranosylarjunolic acid 28<i>-O-α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>5</b>), 3<i>-O-β</i>-<span>d</span>-glucopyranosyl-(1 → 2)-<i>β</i>-<span> d</span>-glucopyranosyl-6<i>β</i>,23-dihydroxyursolic acid 28<i>-O-α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>6</b>), 3<i>-O-β</i>-<span>d</span>-glucopyranosyl-6β,23-dihydroxyursolic acid 28<i>-O-α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>7</b>), asiatic acid 28<i>-O-α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>8</b>), and 3<i>-O-β</i>-<span>d</span>-glucopyranosylasiatic acid 28<i>-O-α</i>-<span>l</span>-rhamnopyranosyl-(1 → 2)-<i>β</i>-<span>d</span>-glucopyranosyl ester (<b>9</b>), through infrared, high-resolution electrospray ionization mass spectrometry, one- and two-dimensional nuclear magnetic resonance spectral analyses. The isolates inhibited nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells, with half-maximal inhibitory concentration (IC₅₀) values of 18.8–58.5 µM, compared to the positive control compound, dexamethasone, which exhibited an IC₅₀ of 14.1 µM.</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 3","pages":"741 - 752"},"PeriodicalIF":2.5,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140568986","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":"Alkylphthalides with intracellular triglyceride metabolism-promoting activity from the rhizomes of Cnidium officinale Makino","authors":"Toshio Morikawa,&nbsp;Naoki Inoue,&nbsp;Saya Yamamoto,&nbsp;Miyuki Shiotani,&nbsp;Yoshiaki Manse,&nbsp;Kiyofumi Ninomiya","doi":"10.1007/s11418-024-01799-x","DOIUrl":"10.1007/s11418-024-01799-x","url":null,"abstract":"<div><p>Methanol extract of the <i>Cnidium officinale</i> Makino rhizome, which is used as a crude drug Cnidium Rhizome (<i>Cnidii Rhizoma</i>; “<i>Senkyu</i>” in Japanese) and is listed in the Japanese Pharmacopoeia XVIII, showed intracellular triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells. Thirty-five constituents, including two new alkylphthalide glycosides, senkyunosides A (<b>1</b>) and B (<b>2</b>), and a neolignan with a new stereoisomeric structure (<b>3</b>), were isolated in the extract. Their stereostructures were elucidated based on chemical and spectroscopic evidence. Among the isolates, several alkylphthalides, (<i>Z</i>)-3-butylidene-7-methoxyphthalide (<b>9</b>) and senkyunolides G (<b>10</b>), H (<b>14</b>), and I (<b>15</b>), and a polyacetylene falcarindiol (<b>26</b>), were found to show significant activity without any cytotoxicity at 10 μM.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"709 - 721"},"PeriodicalIF":2.5,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01799-x.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140594547","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":"Correction: Heating or ginger extract reduces the content of Pinellia ternata lectin in the raphides of Pinellia tuber","authors":"Yan Liu,&nbsp;Itsuki Nose,&nbsp;Kazuyoshi Terasaka,&nbsp;Tsukasa Fueki,&nbsp;Toshiaki Makino","doi":"10.1007/s11418-024-01808-z","DOIUrl":"10.1007/s11418-024-01808-z","url":null,"abstract":"","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"805 - 805"},"PeriodicalIF":2.5,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01808-z.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140748119","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":"Correction: Evaluation of rooting characteristics of Ephedra cuttings by anatomy and promising strain selection based on rooting characteristics and alkaloid content","authors":"Yoshitomi Kudo,&nbsp;Hirokazu Ando,&nbsp;Ai Kaneda,&nbsp;Honoka Ito,&nbsp;Kazuki Umemoto,&nbsp;Si-ran Ni,&nbsp;Masayuki Mikage,&nbsp;Yohei Sasaki","doi":"10.1007/s11418-024-01807-0","DOIUrl":"10.1007/s11418-024-01807-0","url":null,"abstract":"","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"804 - 804"},"PeriodicalIF":2.5,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01807-0.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140747852","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":"Vincarostine A, a novel anti-malarial trimeric monoterpenoid indole alkaloid from Catharanthus roseus","authors":"Yusuke Hirasawa,&nbsp;Yusuke Kakizoe,&nbsp;Takahiro Tougan,&nbsp;Nahoko Uchiyama,&nbsp;Toshihiro Horii,&nbsp;Hiroshi Morita","doi":"10.1007/s11418-024-01795-1","DOIUrl":"10.1007/s11418-024-01795-1","url":null,"abstract":"<div><p>A novel trimeric monoterpenoid indole alkaloid, vincarostine A (<b>1</b>) consisting of an aspidosperma-iboga-aspidosperma type skeleton, was isolated from the whole plant of <i>Catharanthus roseus</i>. The structure including absolute stereochemistry was elucidated on the basis of 2D NMR data and CD spectrum. Vincarostine A (<b>1</b>) showed anti-malarial activity.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"768 - 773"},"PeriodicalIF":2.5,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01795-1.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140334243","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":"Oxomollugin, an oxidized substance in mollugin, inhibited LPS-induced NF-κB activation via the suppressive effects on essential activation factors of TLR4 signaling","authors":"Yuki Nakajima,&nbsp;Naohide Tsuboi,&nbsp;Kumiko Katori,&nbsp;Maigunuer Waili,&nbsp;Alfarius Eko Nugroho,&nbsp;Kazunori Takahashi,&nbsp;Hitomi Nishino,&nbsp;Yusuke Hirasawa,&nbsp;Yoko Kawasaki,&nbsp;Yukihiro Goda,&nbsp;Toshio Kaneda,&nbsp;Hiroshi Morita","doi":"10.1007/s11418-024-01798-y","DOIUrl":"10.1007/s11418-024-01798-y","url":null,"abstract":"<div><p>Oxomollugin is a degraded product of mollugin and was found to be an active compound that inhibits LPS-induced NF-κB activation. In this study, we investigated the inhibitory activity of oxomollugin, focusing on TLR4 signaling pathway, resulting in NF-κB activation. Oxomollugin inhibited the LPS-induced association of essential factors for initial activation of TLR4 signaling, MyD88, IRAK4 and TRAF6. Furthermore, oxomollugin showed suppressive effects on LPS-induced modification of IRAK1, IRAK2 and TRAF6, LPS-induced association of TRAF6-TAK1/TAB2, and followed by IKKα/β phosphorylation, which critical in signal transduction leading to LPS-induced NF-κB activation. The consistent results suggested that oxomollugin inhibits LPS-induced NF-κB activation via the suppression against signal transduction in TLR4 signaling pathway.</p><p>The activities of oxomollugin reported in this study provides a deeper understanding on biological activity of mollugin derivatives as anti-inflammatory compounds.</p><h3>Graphical Abstract</h3>\u0000<div><figure><div><div><picture><img></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"568 - 575"},"PeriodicalIF":2.5,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140334242","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}