Chemical & pharmaceutical bulletin最新文献_第6页

Identification of Acidic Triterpenoid Saponins from Silene vulgaris Using a Methylation-Based Isolation and LC-MS Analysis Strategy. 用甲基化分离和LC-MS分析方法鉴定麝香中酸性三萜皂苷。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00809

Takashi Kikuchi, Danyang Liu, Kouharu Otsuki, Kazuo Koike, Wei Li

{"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":"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.","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}

引用次数: 0

Isoflavone Constituents of the Underground Parts of Iris florentina and Their Inhibitory Activity on the Formation of Advanced Glycation End Products. 鸢尾地下部位异黄酮成分及其对晚期糖基化终产物形成的抑制作用。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00776

Yuka Yoshizawa, Nana Fujita, Akihito Yokosuka, Yoshihiro Mimaki

引用次数: 0

Isolation and Identification of Three New Iridoid Glucosides from the Aerial Parts of Paederia scandens. 三种新的环烯醚萜苷类化合物的分离鉴定。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00777

Masashi Fukaya, Kaori Ryu, Tetsuro Ito

引用次数: 0

Design, Synthesis, and Antitumor Activity of Novel Eupatilin Derivatives Based on the Mannich Reaction. 基于曼尼希反应的新型尤帕汀衍生物的设计、合成及抗肿瘤活性研究。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00599

Yaqi Meng, Yuqing Wang, Shujiao Li, Zhiyan Cai, Guo Zhuang, Yanli Yang

{"title":"Design, Synthesis, and Antitumor Activity of Novel Eupatilin Derivatives Based on the Mannich Reaction.","authors":"Yaqi Meng, Yuqing Wang, Shujiao Li, Zhiyan Cai, Guo Zhuang, Yanli Yang","doi":"10.1248/cpb.c24-00599","DOIUrl":"10.1248/cpb.c24-00599","url":null,"abstract":"Eupatilin, a natural bioactive flavone, is the active ingredient in traditional Chinese medicine Artemisia argyi Levl. et Vant. To enhance the antitumor effect of eupatilin, we designed a series of novel eupatilin-Mannich derivatives and investigated antitumor activity against several human cancer cell lines, including gastric cancer cells (AGS), esophageal cancer cells (Eca-109), and breast cancer cells (MDA-MB-231). Among all derivatives, the majority demonstrated superior antitumor activity compared to eupatilin, with compound 3d exhibiting the most effective antitumor activity against AGS cells. Furthermore, compound 3d effectively inhibited colony formation and migration of AGS cells. Network pharmacology combined with molecular docking studies indicated that compound 3d exerts antitumor activity by targeting the Hsp90AA1 and multiple signaling pathways. In addition, the Western blot experiment results showed that compound 3d reduced the expression of Hsp90AA1 in AGS cells, indicating that Hsp90AA1 may be the potential target of compound 3d. In summary, several novel eupatilin derivatives were prepared via the Mannich reaction, representing the first structure modification study of eupatilin. The mechanism of action of compound 3d was estimated through cell experiments, network pharmacology, molecular docking, and Western blot experiments, to provide lead compounds for the discovery of natural product-based antitumor candidates.","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 2","pages":"112-120"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143514806","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}

引用次数: 0

In-Situ Monitoring of Dissolution and Crystallization Processes of Carbamazepine Using Low-Frequency Raman Spectroscopy and Multivariate Analysis. 利用低频拉曼光谱和多变量分析原位监测卡马西平的溶出和结晶过程。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00745

Takayuki Kudo, Haruka Uchida, Mana Yamato, Ryo Ohashi, Vasanthi Palanisamy, Toshiro Fukami

{"title":"In-Situ Monitoring of Dissolution and Crystallization Processes of Carbamazepine Using Low-Frequency Raman Spectroscopy and Multivariate Analysis.","authors":"Takayuki Kudo, Haruka Uchida, Mana Yamato, Ryo Ohashi, Vasanthi Palanisamy, Toshiro Fukami","doi":"10.1248/cpb.c24-00745","DOIUrl":"10.1248/cpb.c24-00745","url":null,"abstract":"Optimization of the manufacturing process based on scientific evidence is essential for quality control of active pharmaceutical ingredients. Real-time monitoring can ensure the production of stable quality crystals in the crystallization process. Raman spectroscopy is an attractive tool for pharmaceutical quality evaluation and process analytical technology because of its ability to analyze samples non-destructively and rapidly. In this study, we attempted to monitor the crystal polymorphs of carbamazepine (CBZ I and CBZ III) during the dissolution and crystallization processes using low-frequency Raman spectroscopy, which can reflect differences in lattice vibrations originating from polymorphs in the scattering peaks. Furthermore, using multivariate analysis of the obtained spectra, we attempted to develop a model that enables the quantification of each polymorph. A partial least squares was performed to build the prediction model. The prediction model was built using a set of 33 calibration samples, and an external set of 12 validation samples was used to evaluate the model. The model presents a good prediction capacity. The quantitative results for the solid amount of carbamazepine in suspension calculated using the model during the dissolution and crystallization process showed results that correlated very well with the particle view results. It is suggested that low-frequency Raman spectroscopy can be used as a useful process analytical technology tool.","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 1","pages":"58-62"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143064081","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}

引用次数: 0

Development of Suzuki-Miyaura Coupling between 4-Pyridine Boronate Derivatives and Aryl Halide to Suppress Phenylated Impurities Derived from Phosphorus Ligands. 4-吡啶硼酸衍生物与芳基卤化物之间的Suzuki-Miyaura偶联抑制磷配体衍生的苯基化杂质。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00874

Yoshitaka Kitano, Mitsuhiro Arisawa

引用次数: 0

Chemoenzymatic Dynamic Kinetic Resolution of a Tertiary Alcohol Based on Compartmentalization of Oxovanadium and Lipase Catalysts by Means of a Polydimethylsiloxane Thimble. 基于氧化钒区隔化和脂肪酶催化剂的叔醇化学酶动力学拆分。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00065

Karla Wagner, Satoshi Horino, Anke Hummel, Kyohei Kanomata, Shuji Akai, Harald Gröger

引用次数: 0

Tantalum-Catalyzed Peptide Elongation of Unprotected Amino Acids Using N-Trimethylsilylimidazole. 钽催化n -三甲基硅基咪唑对未保护氨基酸的肽延伸。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00281

Tomohiro Hattori, Haruna Watanabe, Yuki Matsunaga, Hisashi Yamamoto

引用次数: 0

Design, Synthesis and Radioprotective Activity Evaluation of Novel N-Phenyl-2H-chromene-3-carboxamides Derived from Ex-RAD. 新型n -苯基- 2h -铬-3-羧胺的设计、合成及辐射防护活性评价。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00105

Xin-Ru Liu, Han-Yin Feng, Xiao-Han Liu, Jing Xu, Shu-Chen Liu, Shou-Guo Zhang, Tao Peng

{"title":"Design, Synthesis and Radioprotective Activity Evaluation of Novel N-Phenyl-2H-chromene-3-carboxamides Derived from Ex-RAD.","authors":"Xin-Ru Liu, Han-Yin Feng, Xiao-Han Liu, Jing Xu, Shu-Chen Liu, Shou-Guo Zhang, Tao Peng","doi":"10.1248/cpb.c25-00105","DOIUrl":"https://doi.org/10.1248/cpb.c25-00105","url":null,"abstract":"Exposures to ionizing radiation can cause serious damages to human body, and the development of radiation countermeasures is urgently needed. In this paper, a series of N-phenyl-2H-chromene-3-carboxamides were designed and synthesized as potential radiation countermeasures. Their radioprotective activities were evaluated in vitro and in vivo, and compound B5 was identified as the most effective molecule among the target compounds. B5 can not only accelerate the recovery of peripheral blood cells in mice exposed to total body irradiation, but also alleviate damage to the small intestine, spleen and thymus in mice exposed to abdominal irradiation. Furthermore, B5 exhibited superior ability to mitigate radiation-induced DNA damage and apoptosis in irradiated AHH-1 cells. Western blot analysis indicated that the radioprotection provided by B5 resulted in the downregulation of pro-apoptosis proteins p53 and upregulation of anti-apoptosis protein Bcl-2. In addition, the RNA-Sequencing analysis revealed that B5 primarily exerts its radioprotective effects through the Wnt signaling pathway and the mitogen-activated protein kinase (MAPK) signaling pathway. In conclusion, we identified B5 as a promising radioprotective compound, and B5 is valuable for further research in the future.","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 7","pages":"600-615"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144599511","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}

引用次数: 0

Synthetic Studies on Vitamin D Derivatives with Diverse but Selective Biological Activities. 具有多种选择性生物活性维生素D衍生物的合成研究。

IF 1.5 4区医学

Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00598

Atsushi Kittaka

{"title":"Synthetic Studies on Vitamin D Derivatives with Diverse but Selective Biological Activities.","authors":"Atsushi Kittaka","doi":"10.1248/cpb.c24-00598","DOIUrl":"https://doi.org/10.1248/cpb.c24-00598","url":null,"abstract":"2α-Functionalization of 1α,25-dihydroxyvitamin D3 (active vitamin D3) A-ring enhances binding affinity for the vitamin D receptor (VDR) and prolongs the half-life in target cells due to gaining resistance to CYP24A1-dependant metabolism. The wide variety of modified A-ring precursor enynes for Trost coupling with CD-ring bromoolefin were synthesized from d-glucose. The A-ring modification provided potent, selective biological activities without calcemic side-effects in vivo; for example, 2α-(3-hydroxypropyl)-19-nor-1α,25-dihydroxyvitamin D3 (MART-10) exhibits potent antitumor activity (0.3µg/kg/d, twice/week for 3 weeks) in nude mice inoculated with BxpC-3 cancer cells, 2α-[2-(tetrazol-2-yl)ethyl]-1α,25-dihydroxyvitamin D3 (AH-1) shows better bone-forming effects (0.02µg/kg/d, 5d/week for 4 weeks) in ovariectomized (OVX) rats as an osteoporosis model than natural active vitamin D3, and NS-74c exhibits potent VDR-antagonistic activity (IC50 7.4pM) in HL-60 culture cells. The A-ring modification was also applicable to the synthesis of stable 14-epi-19-nortachysterols, and their novel VDR binding mode was confirmed by X-ray co-crystallographic analysis. 25-Hydroxyvitamin D3 has two independent target molecules: VDR and a sterol regulatory element-binding protein (SREBP)/SREBP cleavage-activating protein (SCAP) complex, and 25-hydroxyvitamin D3 shows SREBP/SCAP inhibitory activity. The VDR-silent vitamin D analog KK-052 with selective SREBP/SCAP inhibitory activity in vivo was developed. A chemical library of side-chain fluorinated vitamin D analogs is currently under construction, and some analogs have shown potent anti-inflammatory activity and therapeutic effects on psoriasis model mice.","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 1","pages":"1-17"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142930797","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}

引用次数: 0