Journal of Natural Medicines最新文献

{"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}

{"title":"Correction: Preparation and pharmaceutical properties of Hangeshashinto oral ointment and its safety and efficacy in Syrian hamsters with 5-fluorouracil-induced oral mucositis","authors":"Takashi Ogihara,&nbsp;Masato Kagawa,&nbsp;Rintarou Yamanaka,&nbsp;Satoshi Imai,&nbsp;Kotaro Itohara,&nbsp;Daiki Hira,&nbsp;Shunsaku Nakagawa,&nbsp;Atsushi Yonezawa,&nbsp;Michiho Ito,&nbsp;Takayuki Nakagawa,&nbsp;Tomohiro Terada,&nbsp;Kazuo Matsubara","doi":"10.1007/s11418-024-01806-1","DOIUrl":"10.1007/s11418-024-01806-1","url":null,"abstract":"","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"803 - 803"},"PeriodicalIF":2.5,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11101564/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140334241","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":"Bajitianwan formula extract ameliorates bone loss induced by iron overload via activating RAGE/PI3K/AKT pathway based on network pharmacology and transcriptomic analysis","authors":"Weifan Xu,&nbsp;Tao Jiang,&nbsp;Luying Ding,&nbsp;Yiping Jiang,&nbsp;Lichao Zhang,&nbsp;Tianshuang Xia,&nbsp;Hailiang Xin","doi":"10.1007/s11418-024-01779-1","DOIUrl":"10.1007/s11418-024-01779-1","url":null,"abstract":"<div><p>Osteoporosis (OP) is closely related to iron overload. Bajitianwan (BJTW) is a traditional Chinese medicine formulation used for treating senile diseases such as dementia and osteoporosis. Modern pharmacological researches have found that BJTW has beneficial effect on bone loss and memory impairment in aging rats. This paper aimed to explore the role and mechanism of BJTW in ameliorating iron overload-induced bone loss. Furthermore, BJTW effectively improved the bone micro-structure of the femur in mice, and altered bone metabolism biomarkers alkaline phosphatase (ALP) and osteocalcin (OCN) in serum, as well as oxidative indexes superoxide dismutase (SOD), catalase (CAT), glutathione reductase (GR) glutathione (GSH) and malondialdehyde (MDA) in liver. As for network pharmacology, 73 components collected from BJTW regulated 99 common targets merged in the BJTW and OP. The results of RNA-seq indicated that there were 418 potential targets in BJTW low dose group (BJTW-L) and 347 potential targets in BJTW high dose group (BJTW-H). Intriguingly, both PI3K-AKT signaling pathway and the AGEs-RAGE signaling pathway were contained in the KEGG pathways enrichment results of network pharmacology and transcriptomics, which were considered as the potential mechanism. Additionally, we verified that BJTW regulated the expression of related proteins in RAGE/PI3K-AKT pathways in MC3T3-E1 cells. In summary, BJTW has potent effect on protecting against iron overload-induced OP, and its mechanism may be related to the activation of the RAGE/PI3K-AKT signaling pathways.</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":"488 - 504"},"PeriodicalIF":2.5,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140292430","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}