Chemical & pharmaceutical bulletin最新文献

{"title":"A New Class of Hybrid Anti-inflammatory Agents of Silibinin A Modified Using Gamma Irradiation.","authors":"Gyeong Han Jeong, Hanui Lee, Byung Yeoup Chung, Hyoung-Woo Bai","doi":"10.1248/cpb.c25-00040","DOIUrl":"https://doi.org/10.1248/cpb.c25-00040","url":null,"abstract":"<p><p>Silibinin is the major active constituent of the medicinal plant milk thistle seeds and possesses hepatoprotective functions. In this study, silibinin A was irradiated with gamma rays to produce 2 novel flavonolignans, silibinosins A (2) and B (3). The structures of these compounds were determined using spectroscopy and spectrometry. The anti-inflammatory effects of the flavonolignan derivatives were assessed using lipopolysaccharide (LPS)-stimulated RAW264.7 and DH82 macrophages. Silibinosin A (2) effectively suppressed the LPS-induced overproduction of pro-inflammatory mediators and cytokines in murine RAW264.7 cells. Western blot analysis revealed that compound 2 decreased the LPS-induced expression of inducible nitric oxide synthase, cyclooxygenase, and phosphorylated nuclear factor-κB and inhibitor-κBα compared to the original silibinin. Furthermore, the inhibitory effects on nitric oxide and prostaglandin E₂ production were observed in LPS-stimulated DH82 canine macrophages. Our results suggest that the newly generated flavonolignans can be novel anti-inflammatory agents for use as therapeutics or ingredients in functional foods.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 4","pages":"401-411"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143978405","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":"Systematic Review of Natural Briaranes in Marine Organisms (2020-2024): Chemical Structures and Bioactivities.","authors":"Li-Guo Zheng, Yu-Chia Chang, Yu-Chi Tsai, Yi-Hao Lo, Wei-Chiung Chi, Mingzi M Zhang, Lun Kelvin Tsou, Zhi-Hong Wen, Tsong-Long Hwang, You-Ying Chen, Ping-Jyun Sung","doi":"10.1248/cpb.c25-00255","DOIUrl":"https://doi.org/10.1248/cpb.c25-00255","url":null,"abstract":"<p><p>This review summarizes the structures, names, and bioactivities of 207 briarane-type diterpenoids, including 113 newly identified metabolites, isolated between 2020 and 2024. All the briaranes discussed were derived from octocorals belonging to the genera Briareum, Dichotella, Ellisella, Junceella, and Erythropodium. Some of these compounds have demonstrated potential biomedical activities.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 7","pages":"581-594"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144552464","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":"Effectively Determining Dopamine Based on Dopamine Self-polymerization through Fluorescent Method Using Silicon Quantum Dots as Probe.","authors":"Qiuyan Lian, Zhengjun Huang, Yuebin Liu, Xiaoyan Lin, Lili Zheng, Shuai Zhan, Yao Wang, Shaohuang Weng","doi":"10.1248/cpb.c25-00099","DOIUrl":"https://doi.org/10.1248/cpb.c25-00099","url":null,"abstract":"<p><p>Dopamine, a catecholamine neurotransmitter found in both neural tissue and body fluids, plays a critical role in brain function. Its distribution in specific brain regions affects the coordination of pituitary endocrine functions and is directly involved in neural activities, making dopamine concentration detection vital. In this study, highly fluorescent silicon quantum dots (silicon nanoparticles: SiNPs) were synthesized and employed as a fluorescent probe for convenient dopamine detection in Tris buffer. This detection mechanism relies on dopamine's self-polymerization, which results in polydopamine absorbing and quenching the fluorescence of SiNPs through a clarified inner filter effect in a concentration-dependent manner. Under optimized experimental conditions, the method demonstrated a robust linear relationship between the fluorescence quenching efficiency of SiNPs and dopamine concentration (C_DA) within the range of 0.5-40 μM. The linear equation was found to be Y = 0.0074 C_DA + 0.0142, with a limit of detection of 0.06 μM. Moreover, the method was successfully applied to detect dopamine in injection solutions and serum samples, offering a sensitive and selective approach for dopamine detection with promising potential for practical applications.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 8","pages":"724-731"},"PeriodicalIF":1.3,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144944365","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":"Total Synthesis and Biological Evaluation of Prealnumycin B.","authors":"Kei Kitamura, Tatsuro Yoneyama, Masaaki Noji, Hiroto Kaku","doi":"10.1248/cpb.c25-00299","DOIUrl":"https://doi.org/10.1248/cpb.c25-00299","url":null,"abstract":"<p><p>Prealnumycin B is an aromatic polyketide characterized as a reduced form of prealnumycin with a 6S-alcohol. As an extension of our earlier work on the synthesis of prealnumycin, the C7-C8 double bond was hydrogenated using Wilkinson's catalyst, and the C6 carbonyl group was stereoselectively reduced via asymmetric transfer hydrogenation with the (S,S)-Ts-DENEB catalyst, where the use of methanol as a solvent was crucial for achieving high regioselectivity. By comparing its spectroscopic data with those of the natural isolate, the absolute configuration of prealnumycin B was determined to be 1R,6S. In addition, the antibacterial activities of prealnumycin B and related compounds were evaluated.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 8","pages":"707-712"},"PeriodicalIF":1.3,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144944381","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":"Elucidating the Light-Emitting Species Generated from Aminoluciferin in Firefly/Beetle Bioluminescence.","authors":"Hideo Takakura, Ryosuke Kojima, Takeaki Ozawa, Yasuteru Urano","doi":"10.1248/cpb.c25-00302","DOIUrl":"https://doi.org/10.1248/cpb.c25-00302","url":null,"abstract":"<p><p>Oxyluciferin is the key photon emitter in the firefly/beetle luciferase-catalyzed bioluminescence reaction, and elucidating its chemical form within the active site of luciferase is essential for understanding and modulating emission wavelength. In this study, we focused on aminoluciferin (AL), a d-luciferin (d-LH₂) analog in which the hydroxy group is substituted with an amino group. AL has been widely used as an alternative substrate to d-LH₂ and in the development of bioluminescence probes. To identify the emissive form of AL in bioluminescence, we synthesized OxyAL (the emitter derived from AL) and 5-methyl-OxyAL, and measured their fluorescence spectra under various conditions. We assigned the range of emission wavelengths of keto-, enol- and enolate-OxyAL using 5,5-dimethyl-OxyAL, fixed in the keto form, as a reference. Based on spectral assignments and comparison with the bioluminescence spectra of AL, we conclude that enolate-OxyAL is the most probable light-emitting species in the active site of luciferase. These findings provide new insight into AL-based bioluminescence.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 8","pages":"678-686"},"PeriodicalIF":1.3,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144820686","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":"Development of Fluorogenic Reagent that Enables Simultaneous Detection and Labeling of Hydropersulfide.","authors":"Mitsuyasu Kawaguchi, Hisayuki Wakamori, Shingo Kasamatsu, Haruki Yamaguchi, Keisho Hirao, Naoya Ieda, Yuhei Ohta, Hideshi Ihara, Hidehiko Nakagawa","doi":"10.1248/cpb.c25-00462","DOIUrl":"https://doi.org/10.1248/cpb.c25-00462","url":null,"abstract":"<p><p>Real-time detection and identification of modified cysteine sulfhydryl (Cys-SH) residues are important because supersulfidation (S-sulfhydrylation) alters protein function and thereby modulates the activity of biological systems. Although fluorescence probes for rapid, sensitive detection and biotin tag-switch methods for comprehensive labeling of modified residues at the proteome level have been developed, simultaneous detection and labeling have not been achieved in a single system. Herein, we describe dinitrobenzene-based fluorogenic probes with tunable electrophilicity, which react rapidly and selectively with highly nucleophilic supersulfides such as cysteine persulfide (Cys-SSH) and Na₂S₂ and simultaneously label Cys-SSH itself with a dinitrobenzene tag.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 9","pages":"890-895"},"PeriodicalIF":1.3,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145136817","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":"Photocatalytic C-I Borylation via Halogen Bond-Enabled Electron Transfer: A Strategy for Generating Aryl Radicals from Haloarenes.","authors":"Eiji Yamaguchi, Tomohiro Yasuda, Akichika Itoh","doi":"10.1248/cpb.c25-00375","DOIUrl":"https://doi.org/10.1248/cpb.c25-00375","url":null,"abstract":"<p><p>We report the development of triarylphenol-based photocatalysts that promote C-I bond borylation via halogen bonding (XB) interactions under visible-light irradiation. Traditional phenol system reactions often suffer from phenoxyl radical instability, limiting their catalytic utility. To overcome this issue, we designed sterically and electronically tuned triarylphenols that stabilize radical intermediates while maintaining high photoreactivity. Systematic evaluation revealed that 2,4,6-triphenylphenol efficiently facilitates photoinduced electron transfer (PET) and suppresses undesired side reactions such as phenol decomposition. The optimized reaction conditions enabled a broad substrate scope, showing efficient arylboronic ester formation. Density functional theory calculations confirmed the formation of XB complexes with charge-transfer character, providing mechanistic support for the PET pathway. This work shows the potential of rationally designed phenols as XB acceptors and offers a sustainable approach for C-I bond functionalization.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 10","pages":"944-950"},"PeriodicalIF":1.3,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145205787","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":"¹H-NMR-Based Biochemometric Strategy to Identify Transient Receptor Potential Vanilloid 1-Stimulating Compounds from Alpinia officinarum Rhizome.","authors":"Tomohisa Kanai, Tatsuya Shirahata, Shunsuke Nakamori, Rin Sato, Akito Hayashi, Yota Koizumi, Kenichiro Nagai, Susumu Ohkawara, Takayuki Hoshino, Toshiko Tanaka-Kagawa, Hideto Jinno, Yoshinori Kobayashi","doi":"10.1248/cpb.c24-00707","DOIUrl":"https://doi.org/10.1248/cpb.c24-00707","url":null,"abstract":"<p><p>This study established a ¹H-NMR-based biochemometric approach for the isolation of biologically active compounds from complex extracts. In both pharmacognosy and natural product chemistry, reliably isolating bioactive compounds typically necessitates repeating time-consuming and laborious isolation and purification steps, presenting a bottleneck in many studies. We applied biochemometric methods to accurately estimate active compounds, thus minimizing the number of assays and isolation steps. The rhizomes of Alpinia officinarum Hance (Zingiberaceae) have been continuously prescribed in traditional Japanese medicine as stomachics and analgesics, despite a limited understanding of the mechanisms underlying these effects. Additionally, transient receptor potential vanilloid subtype 1 (TRPV1) plays a role in modulating nociception, respiratory defense responses, and gastrointestinal protection. Accordingly, ¹H-NMR-based biochemometry was employed to search for TRPV1-active components in A. officinarum rhizome extracts by combining TRPV1 activity intensity with ¹H-NMR data. However, initially, the active component could not be identified because the principal component analysis loading plot primarily displayed only buckets of primary metabolites. Consequently, we applied orthogonal partial least squares to the ¹H-NMR spectra, which allowed us to identify specific spectral bins at 1.66 ppm (aliphatic) and 7.02, 6.98, 6.82, and 6.74-6.58 ppm (aromatic), correlating with TRPV1-stimulating activity. Based on this prediction, diarylheptanoids were swiftly identified, and their potential to activate TRPV1 was confirmed by administering the identified compounds to TRPV1-expressing cells. These findings highlight the potential of chemometric analysis using ¹H-NMR spectroscopy for identifying the chemical classes responsible for the bioactive properties of complex crude drug extracts.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 3","pages":"195-204"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143584865","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":"Identification of a Novel Retinoid X Receptor Agonist from Boenninghausenia albiflora var. japonica.","authors":"Ryura Tateiwa, Yudai Nakama, Ayaka Murase, Tomoki Mizoguchi, Makoto Inoue, Ken-Ichi Nakashima","doi":"10.1248/cpb.c24-00728","DOIUrl":"https://doi.org/10.1248/cpb.c24-00728","url":null,"abstract":"<p><p>Retinoid X receptors (RXRs) are nuclear receptors involved in various crucial biological processes, such as gene regulation, metabolism, and cell differentiation. They predominantly function as heterodimers with other nuclear receptors and modulate gene expression in response to ligand binding. Additionally, they act as therapeutic targets for different conditions, such as cancer and metabolic disorders. Although synthetic RXR agonists, such as bexarotene, are used in clinical settings, they exert adverse side effects. In this study, to explore insights into potential natural RXR agonists as alternatives to existing drugs, we isolated 14 coumarins, including 1 new compound from Boenninghausenia albiflora var. japonica (Rutaceae). Among them, daphnoretin methyl ether (14), a known biscoumarin, was found to exhibit subtype-nonspecific RXR agonist activity.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 3","pages":"173-178"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143584870","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":"Identification of Acidic Triterpenoid Saponins from Silene vulgaris Using a Methylation-Based Isolation and LC-MS Analysis Strategy.","authors":"Takashi Kikuchi, Danyang Liu, Kouharu Otsuki, Kazuo Koike, Wei Li","doi":"10.1248/cpb.c24-00809","DOIUrl":"https://doi.org/10.1248/cpb.c24-00809","url":null,"abstract":"<p><p>The Silene genus plants in the Caryophyllaceae family are a large genus with over 850 species. It has been known that Silene genus plants contain triterpenoid saponins. These saponins have glucuronic acid in the sugar chain and are difficult to separate in chromatography. In this study, a strategy was developed to clarify the distribution of triterpenoid saponins in whole plants of Silene vulgaris by isolation of neutralized saponins using methylation reactions, which were used as standard substances for LC-MS analysis, and elucidating their characteristic MS and MS/MS fragment patterns. The n-butanol fraction of the methanol extract from the whole plant of S. vulgaris was separated to obtain fractions including saponins by octadecyl silica column chromatography. Then, each fraction was treated with trimethylsilyl diazomethane for methylation of the carboxyl groups of glucuronic acid in the molecules, and five triterpenoid methylated saponins (7a, 13a, 14a, 16a, and 17a) were isolated using HPLC. The chemical structures of the isolated compounds were determined by spectroscopic analyses including NMR and MS, and their characteristic fragmentations were also clarified in LC-MS and MS/MS. It was performed on the n-butanol fraction from the whole plant of S. vulgaris, and the chemical structures of 22 triterpenoid saponins were estimated based on the MS and MS/MS fragmentation patterns of the isolated triterpenoid saponins.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 3","pages":"179-188"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143584872","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}