{"title":"Quantitative analysis of taxiphyllin, a cyanogenic glycoside, in the leaves of Hydrangea macrophylla var. thunbergii","authors":"Junko Tsukioka, Yutaro Ohki, Momona Nakao, Seikou Nakamura","doi":"10.1007/s11418-023-01733-7","DOIUrl":"10.1007/s11418-023-01733-7","url":null,"abstract":"<div><p>The dried and fermented leaves of <i>Hydrangea macrophylla</i> var. <i>thunbergii</i> are currently used as crude drugs (Sweet Hydrangea Leaf) with a sweet taste for patients with diabetes. In recent years, cases of food poisoning with symptoms of vomiting etc. have been reported after drinking a decoction of this crude drug. Cyanogenic glycosides have been suggested as potential causative agents. However, cyanogenic glycosides from <i>H. macrophylla</i> var. <i>thunbergii</i> was ambiguous. In the present study, we found that the leaves contained the cyanogenic glycoside taxiphillin (<b>1</b>). Next, the content of <b>1</b> in leaves of different sizes, colors, parts, and growth periods was quantified. In addition, we prepared the leaves of plants grown in five types of soils with different pH values (pH 5.0–7.5). The content of <b>1</b> in the leaves of the plants grown in these soils was quantified. The content of <b>1</b> varied greatly, with more than a three-fold difference, depending on when the leaves were collected from the plants. Furthermore, we compared the content of <b>1</b> in the crude drug obtained under different processing conditions for <i>H. macrophylla</i> var. <i>thunbergii.</i> The results showed that <b>1</b> was mostly hydrolyzed during plant processing. It has been suggested that cyanogenic glycosides are not the causative constituents of food poisoning.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"978 - 985"},"PeriodicalIF":3.3,"publicationDate":"2023-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5155963","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":"Cordythiazole A, the first member of thiazole alkaloids from Chinese cordyceps, with α-glucosidase inhibitory activity","authors":"Xue Han, Li-Hua Liu, Xiao-Ying Fang, Shu-Tai Jiang, Huan Zhao, Zheng-Ming Qian, Zhi-Nan Yin, Li-Gong Lu, Chuan-Xi Wang, Xin-Sheng Yao, Hao Gao","doi":"10.1007/s11418-023-01732-8","DOIUrl":"10.1007/s11418-023-01732-8","url":null,"abstract":"<div><p>Chinese cordyceps, also known as Dong-Chong-Xia-Cao, is widely recognized as a famous precious tonic herb, and used as traditional Chinese medicine for centuries. It is mainly used for regulating the immune system and improving functions of the lung and kidney, with anti-tumor, anti-inflammatory, and anti-diabetic activities. Due to its rarity and preciousness, a few chemical components are isolated and identified. Moreover, most of them are common chemical components and widely distributed in other natural resources, such as nucleosides, sterols, fatty acids, sugar alcohols, and peptides. Therefore, a large number of active substances of Chinese cordyceps is still unclear. During our search for chemical constituents of Chinese cordyceps, a new thiazole alkaloid, cordythiazole A (1), was isolated and identified. Its structure was elucidated by comprehensive spectroscopic analysis and single-crystal X-ray diffraction analysis. This is the first report of the presence of thiazole alkaloid in Chinese cordyceps, which adds a new class of metabolite of Chinese cordyceps. Furthermore, a putative biosynthesis pathway of cordythiazole A was proposed based on possible biogenic precursor, genes, and literatures. In addition, it showed <i>α</i>-glucosidase inhibitory activity with potency close to that of acarbose. The discovery of cordythiazole A with α-glucosidase inhibitory activity adds a new class of potential anti-diabetes ingredient in Chinese cordyceps.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"986 - 991"},"PeriodicalIF":3.3,"publicationDate":"2023-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-023-01732-8.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5118533","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":"A monoacylglyceryltrimethylhomoserine, 21F121-A, containing a branched acyl group from Penicillium glaucoroseum","authors":"Ichiro Kimura, Yuki Hitora, Yusaku Sadahiro, Teppei Kawahara, Sachiko Tsukamoto","doi":"10.1007/s11418-023-01735-5","DOIUrl":"10.1007/s11418-023-01735-5","url":null,"abstract":"<div><p>A new monoacylglyceryltrimethylhomoserine, 21F121-A (<b>1</b>), was isolated from the culture of <i>Penicillium glaucoroseum</i> (21F00121) by LCMS-guided purification. The structure was elucidated by NMR and mass spectrometries. The absolute configuration of the homoserine moiety was analyzed by the ECD spectrum after acid hydrolysis, and the <i>S</i>-configuration of the glycerol moiety was determined based on the spectrum of the 1,2-dibenzoyl derivative after acid hydrolysis. Although a variety of diacylglyceryltrimethylhomoserine is distributed in lower plants and fungi, a limited number of studies on monoacyl derivatives have been reported. This is the fourth sample of monoacylglyceryltrimethylhomoserine discovered from a natural source, and the second sample isolated from a fungus. Compound <b>1</b> contains an unusual branched pentaene chain attached at the <i>sn</i>-1 position of glycerol and weakly inhibited the growth of HCT116 cells.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"992 - 997"},"PeriodicalIF":3.3,"publicationDate":"2023-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-023-01735-5.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5118800","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}
Li Li, Jia-Min Dong, He-He Ye, Man-Jing Jiang, Huan-Hua Yang, Lin-Pan Liang, Li-Jun Ning, Ying Wu
{"title":"Baicalin promotes antiviral IFNs production and alleviates type I IFN-induced neutrophil inflammation","authors":"Li Li, Jia-Min Dong, He-He Ye, Man-Jing Jiang, Huan-Hua Yang, Lin-Pan Liang, Li-Jun Ning, Ying Wu","doi":"10.1007/s11418-023-01702-0","DOIUrl":"10.1007/s11418-023-01702-0","url":null,"abstract":"<div><p>Type I and III interferons (IFNs) both serve as pivotal components of the host antiviral innate immune system. Although they exert similar antiviral effects, type I IFNs can also activate neutrophil inflammation, a function not born by type III IFNs. Baicalin, the main bioactive component of <i>Scutellariae radix</i>, has been shown to exert therapeutic effects on viral diseases due to its anti-viral, anti-inflammatory and immunomulatory activities. There is uncertainty, however, on the association between the antiviral effects of baicalin and the modulation of anti-viral IFNs production and the immunological effects of type I IFNs. Here, a Poly (I:C)-stimulated A549 cell line was established to mimic a viral infection model. Our results demonstrated that baicalin could elevate the expression of type I and III IFNs and their receptors in Poly (I:C)-stimulated A549 cells. Moreover, the potential regulation effects of baicalin for type I IFN-induced neutrophil inflammation was further explored. Results showed that baicalin diminished the production of the pro-inflammatory cytokines (IL-1β, IL-6, IL-17 and TNF-α), ROS, and neutrophil extracellular traps and suppressed chemotaxis. Collectively, all these data indicated that baicalin had a dual role on IFNs production and effects: (1) Baicalin was able to elevate the expression of type I and III IFNs and their receptors, (2) and it alleviated type I IFN-mediated neutrophil inflammatory response. This meant that baicalin has the potential to act as an eximious immunomodulator, exerting antiviral effects and reducing inflammation.</p></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"677 - 687"},"PeriodicalIF":3.3,"publicationDate":"2023-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4974103","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":"Four new stilbenes and one new flavonoid with potential antibacterial and anti-SARS-CoV-2 activity from Cajanus cajan","authors":"Jia-Yan Chen, Xin Lian, Yu-Wen Fan, Zhuo-Yi Ao, Wei-Jie Zhang, Yong-Chen Pan, Li-Ping Chen, Jie Yuan, Jie-Wei Wu","doi":"10.1007/s11418-023-01727-5","DOIUrl":"10.1007/s11418-023-01727-5","url":null,"abstract":"<div><p>Four new stilbenes (<b>1</b>–<b>4</b>) and one new flavonoid (<b>5</b>), named cajanines D–H, together with three known stilbenes (<b>6</b>–<b>8</b>) were isolated from the leaves of <i>Cajanus cajan</i> (L.) Millsp. (pigeon pea). The structures of these compounds were elucidated unambiguously on the basis of IR, 1D, and 2D NMR, as well as HRESIMS data. Structurally, stilbenes <b>1</b>–<b>4</b> bore an isopentyl side chain, and further hydroxylation of compounds <b>1</b>–<b>3</b> generated a greater variety of structural forms. Compound <b>5</b> was a flavonoid owning an isopentyl side chain. Besides, antibacterial activity of the isolated compounds against <i>Staphylococcus aureus</i>, <i>Bacillus cereus</i>, and <i>Escherichia coli</i> was studied in vitro. Compounds <b>1</b>–<b>8</b> were endowed with profound antibacterial activity. Among them, the MIC values of compounds <b>4</b>, <b>6</b>, and <b>7</b> against <i>S. aureus</i> were 1.56, 0.78, and 0.78 µg/mL, respectively, among which <b>6</b> and <b>7</b> had better antibacterial activity than the positive control Vancomycin with the MIC values of 1.56 µg/mL. Additionally, the anti-SARS-CoV-2 main protease activity of all the isolated compounds was evaluated, and it was worth mentioning that the IC<sub>50</sub> values of compounds <b>5</b>–<b>7</b> were 8.27, 4.65, and 8.30 µM, respectively, being comparable to the positive control Ebselen. Our findings may provide valuable guidance for the application of stilbenes as lead compounds in the future for the development of drugs with antibacterial or anti-COVID-19 activity.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"858 - 866"},"PeriodicalIF":3.3,"publicationDate":"2023-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4721667","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":"Arginase inhibitory activities of guaiane sesquiterpenoids from Curcuma comosa rhizomes","authors":"Nhat Nam Hoang, Takeshi Kodama, Yu Nakashima, Kiep Minh Do, Saw Yu Yu Hnin, Yuan-E Lee, Prema, Naotaka Ikumi, Hiroyuki Morita","doi":"10.1007/s11418-023-01731-9","DOIUrl":"10.1007/s11418-023-01731-9","url":null,"abstract":"<div><p>Arginases are bimanganese enzymes involved in many human illnesses, and thus are targets for disease treatments. The screening of traditional medicinal plants demonstrated that an ethanol extract of <i>Curcuma comosa</i> rhizomes showed significant human arginase I and II inhibitory activity, and further fractionation led to the isolation of three known guaiane sesquiterpenoids, alismoxide (<b>1</b>), 7α,10α-epoxyguaiane-4α,11-diol (<b>2</b>) and guaidiol (<b>3</b>). Tests of their inhibitory activities on human arginases I and II revealed that <b>1</b> exhibited selective and potent competitive inhibition for human arginase I (IC<sub>50</sub> = 30.2 μM), whereas the other compounds lacked inhibitory activities against human arginases. To the best of our knowledge, this is the first demonstration of human arginase I inhibitory activity by a sesquiterpenoid. Thus, <b>1</b> is a primary and specific inhibitory molecule against human arginase I.</p></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"891 - 897"},"PeriodicalIF":3.3,"publicationDate":"2023-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4724592","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":"Application of the relative molar sensitivity method using GC-FID to quantify safranal in saffron (Crocus sativus L.)","authors":"Naoko Masumoto, Takumi Ohno, Toshihiro Suzuki, Tadayasu Togawa, Naoki Sugimoto","doi":"10.1007/s11418-023-01724-8","DOIUrl":"10.1007/s11418-023-01724-8","url":null,"abstract":"<div><p>Safranal is one flavor component of saffron, which is used as a spice, food additive, and crude drug. In ISO3632, safranal is defined as the compound that contributes to the quality of saffron, and many quantitative determination methods for safranal have been reported. However, safranal is volatile and degrades easily during storage, and an analytical standard with an exact known purity is not commercially available, making it difficult to quantify accurately the content of safranal in saffron. Here, we developed a method for quantifying safranal using relative molar sensitivity (<i>RMS</i>), called the RMS method, using a GC-flame ionization detector (GC-FID). We determined the <i>RMS</i> of safranal to 1,4-bis(trimethylsilyl)benzene-<i>d</i><sub>4</sub>, a certified reference material commercially available, by a combination of quantitative NMR and chromatography. Using two GC-FID instruments made by different manufacturers to evaluate inter-instrument effect, the resultant RMS was 0.770, and the inter-instrument difference was 0.6%. The test solution, with a known safranal concentration, was measured by the RMS method, with an accuracy of 99.4–101%, repeatability of 0.81%, and reproducibility of 0.81–1.3%. Given the ease of degradation, high volatility, and uncertain purity of safranal reagents, the RMS method is a more accurate quantification approach compared to the calibration curve method and methods based on absorption spectrophotometry. Moreover, our findings revealed that the GC-FID makeup gas affected the <i>RMS</i> and quantitative values.</p><h3>Graphical Abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"829 - 838"},"PeriodicalIF":3.3,"publicationDate":"2023-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4574741","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}
Dan Wang, Lin Liu, Kaiwen Li, Huiya Cao, Mengyang Liu, Qian Chen, Yuzheng Wu, Yi Zhang, Tao Wang
{"title":"Eurycoma longifolia alkaloid components ameliorate hyperuricemic nephropathy via regulating serum uric acid level and relieving inflammatory reaction","authors":"Dan Wang, Lin Liu, Kaiwen Li, Huiya Cao, Mengyang Liu, Qian Chen, Yuzheng Wu, Yi Zhang, Tao Wang","doi":"10.1007/s11418-023-01729-3","DOIUrl":"10.1007/s11418-023-01729-3","url":null,"abstract":"<div><p>\u0000Hyperuricemia is an independent risk factor for chronic kidney disease. We have previously showed the uric-acid-lowering effect of <i>Eurycoma longifolia</i> Jack, yet the renal protective effect and mechanism of <i>E. longifolia</i> remain obscure. The mouse model of hyperuricemic nephropathy was induced by adenine combined with potassium oxonate in male C57BL/6 J mice. <i>E. Longifolia</i> alkaloid components could reduce the level of serum uric acid by regulating the expression of hepatic phosphoribosyl pyrophosphate synthase (PRPS), hypoxanthine-guanine phosphoribosyl transferase (HPRT), and renal urate transporter organic anion transporter 1 (OAT1) and ATP-binding box subfamily G member 2 (ABCG2) in HN mice. Additionally, <i>E. Longifolia</i> alkaloid components alleviated renal injury and function caused by hyperuricemia, which was characterized by improving renal histopathology, reducing urea nitrogen and creatinine levels. <i>E. Longifolia</i> alkaloid components treatment could reduce the secretion of pro-inflammatory factors by inhibiting the activation of NF-κB and NLRP3 inflammatory signaling pathways, including tumor necrosis factor α (TNF-α), monocyte chemoattractant protein-1 (MCP-1), interleukin-1 β (IL-1β), and regulated activated normal T cell expression and secretion proteins (RANTES). Meanwhile, <i>E. longifolia</i> alkaloid components improved renal fibrosis, inhibited the transformation of calcium-dependent cell adhesion molecule E (E-cadherin) to α-smooth muscle actin (α-SMA) transformation, and decreased collagen 1 expression in HN mice.</p></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"867 - 879"},"PeriodicalIF":3.3,"publicationDate":"2023-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-023-01729-3.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4495384","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":"New biofunctional effects of oleanane-type triterpene saponins","authors":"Hisashi Matsuda, Toshio Morikawa, Seikou Nakamura, Osamu Muraoka, Masayuki Yoshikawa","doi":"10.1007/s11418-023-01730-w","DOIUrl":"10.1007/s11418-023-01730-w","url":null,"abstract":"<div><p>In the current review, we describe the novel biofunctional effects of oleanane-type triterpene saponins, including elatosides, momordins, senegasaponins, camelliasaponins, and escins, obtained from <i>Aralia elata</i> (bark, root cortex, young shoot), <i>Kochia scoparia</i> (fruit), <i>Polygala senega</i> var. <i>latifolia</i> (roots), <i>Camellia japonica</i> (seeds), and <i>Aesculus hippocastanum</i> (seeds), considering the following biofunctional activities: (1) inhibitory effects on elevated levels of blood alcohol and glucose in alcohol and glucose-loaded rats, respectively, (2) inhibitory effects on gastric emptying in rats and mice, (3) accelerative effects on gastrointestinal transit in mice, and (4) protective effects against gastric mucosal lesions in rats. In addition, we describe (5) suppressive effects of the extract and chakasaponins from <i>Camellia sinensis</i> (flower buds) on obesity based on inhibition of food intake in mice. The active saponins were classified into the following three types: (1) olean-12-en-28-oic acid 3-<i>O</i>-monodesmoside, (2) olean-12-ene 3,28-<i>O</i>-acylated bisdesmoside, and (3) acylated polyhydroxyolean-12-ene 3-<i>O</i>-monodesmoside. Furthermore, common modes of action, such as involvements of capsaicin-sensitive nerves, endogenous NO and PGs, and possibly sympathetic nerves, as well as common structural requirements, were observed. Based on our findings, a common mechanism of action might mediate the pharmacological effects of active saponins. It should be noted that the gastrointestinal tract is an important action site of saponins, and the role of the saponins in the gastrointestinal tract should be carefully considered.</p></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"77 4","pages":"644 - 664"},"PeriodicalIF":3.3,"publicationDate":"2023-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-023-01730-w.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4498331","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}