The search for a potent α-glucosidase inhibitor from the fungus Biscogniauxia capnodes SWUF15-40 yielded eighteen compounds. A comprehensive analysis from NMR and MS data revealed three new α-pyrones, biscogniapyrones A–C (1–3), two new isocoumarins (5 and 6), and thirteen known compounds. The configurations were assigned from calculated 13C NMR chemical shifts and ECD spectra, together with 1H NMR analysis of Mosher esters. Several compounds exhibited effective inhibitory activity against α-glucosidase with IC50 values in the range of 0.041–0.257 mM, which are lower than the positive control, acarbose (IC50 0.713 mM). The proposed non-competitive mode of inhibition was deduced from Lineweaver–Burk plots together with Km and Vmax values. In silico dockings of the strongest inhibitor, compound 3 were studied. Three out of the five determined allosteric sites of the enzyme model were favorable, with closed free binding energies of roughly − 4.00 kcal/mol. The binding interactions observed between 3 and amino acids in the pocket sites were hydrogen bonding and hydrophobic interactions. These findings, therefore, provide opportunities for drug development processes to be carried out.
{"title":"Potential α-glucosidase inhibitors from cultures of Biscogniauxia capnodes SWUF15-40 fungus","authors":"Audomsak Churat, Praewpan Katrun, Chittima Laohpongspaisan, Wiyada Mongkolthanaruk, Chamaiporn Champasri, Pairot Moontragoon, Nuttika Suwannasai, Ek Sangvichien, Pakarapon Poonsukkho, Sirirath McCloskey","doi":"10.1007/s11418-025-01876-9","DOIUrl":"10.1007/s11418-025-01876-9","url":null,"abstract":"<div><p>The search for a potent <i>α</i>-glucosidase inhibitor from the fungus <i>Biscogniauxia capnodes</i> SWUF15-40 yielded eighteen compounds. A comprehensive analysis from NMR and MS data revealed three new <i>α</i>-pyrones, biscogniapyrones A–C (<b>1</b>–<b>3</b>), two new isocoumarins (<b>5</b> and <b>6</b>), and thirteen known compounds. The configurations were assigned from calculated <sup>13</sup>C NMR chemical shifts and ECD spectra, together with <sup>1</sup>H NMR analysis of Mosher esters. Several compounds exhibited effective inhibitory activity against <i>α</i>-glucosidase with IC<sub>50</sub> values in the range of 0.041–0.257 mM, which are lower than the positive control, acarbose (IC<sub>50</sub> 0.713 mM). The proposed non-competitive mode of inhibition was deduced from Lineweaver–Burk plots together with <i>K</i><sub>m</sub> and <i>V</i><sub>max</sub> values. In silico dockings of the strongest inhibitor, compound <b>3</b> were studied. Three out of the five determined allosteric sites of the enzyme model were favorable, with closed free binding energies of roughly − 4.00 kcal/mol. The binding interactions observed between <b>3</b> and amino acids in the pocket sites were hydrogen bonding and hydrophobic interactions. These findings, therefore, provide opportunities for drug development processes to be carried out.</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":"79 3","pages":"488 - 498"},"PeriodicalIF":2.5,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143497650","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}
Pub Date : 2025-02-20DOI: 10.1007/s11418-024-01871-6
Yuwei Xie, Nali Cai, Xiaohua Liu, Liangliang He, Yiming Ma, Changyu Yan, Juan Liang, Shu-Hua Ouyang, Ao Luo, Yingzhi He, Jun Lu, Dang Ao, Jia Liu, Zhonglv Ye, Bin Liu, Rong-Rong He, Wen Li
Silent information regulator 5 (SIRT5) is the fifth member of the sirtuin family, which is mainly expressed in mitochondrial matrix. SIRT5 plays a key role in metabolism and antioxidant responses, and is an important regulator for maintaining intracellular homeostasis. Given its involvement in multiple cellular processes, dysregulation of SIRT5 activity is associated with a variety of diseases. This review explores the structural characteristics of SIRT5 that influence its substrate specificity, highlights recent research advances, and summarizes its four key enzymatic activities along with their corresponding substrates in disease contexts. We also discuss the natural products that modulate SIRT5 activity and identify potential targets of SIRT5 through virtual docking, which may provide new therapeutic avenues. Although the mechanism of SIRT5 in diseases needs to be further elucidated and deglutathionylation activities are still at an early stage, targeting SIRT5 and its substrates holds significant promise for the development of novel therapeutics.
Graphical abstract
沉默信息调节因子5 （Silent information regulator 5, SIRT5）是sirtuin家族的第五个成员，主要表达于线粒体基质中。SIRT5在代谢和抗氧化反应中起关键作用，是维持细胞内稳态的重要调节因子。考虑到SIRT5参与多种细胞过程，SIRT5活性失调与多种疾病有关。本文探讨了影响SIRT5底物特异性的结构特征，重点介绍了最近的研究进展，并总结了SIRT5在疾病背景下的四种关键酶活性及其相应的底物。我们还讨论了调节SIRT5活性的天然产物，并通过虚拟对接确定了SIRT5的潜在靶点，这可能为治疗提供新的途径。虽然SIRT5在疾病中的作用机制有待进一步阐明，去谷胱甘肽化活性仍处于早期阶段，但靶向SIRT5及其底物对开发新的治疗方法具有重要的前景。
{"title":"SIRT5: a potential target for discovering bioactive natural products","authors":"Yuwei Xie, Nali Cai, Xiaohua Liu, Liangliang He, Yiming Ma, Changyu Yan, Juan Liang, Shu-Hua Ouyang, Ao Luo, Yingzhi He, Jun Lu, Dang Ao, Jia Liu, Zhonglv Ye, Bin Liu, Rong-Rong He, Wen Li","doi":"10.1007/s11418-024-01871-6","DOIUrl":"10.1007/s11418-024-01871-6","url":null,"abstract":"<div><p>Silent information regulator 5 (SIRT5) is the fifth member of the sirtuin family, which is mainly expressed in mitochondrial matrix. SIRT5 plays a key role in metabolism and antioxidant responses, and is an important regulator for maintaining intracellular homeostasis. Given its involvement in multiple cellular processes, dysregulation of SIRT5 activity is associated with a variety of diseases. This review explores the structural characteristics of SIRT5 that influence its substrate specificity, highlights recent research advances, and summarizes its four key enzymatic activities along with their corresponding substrates in disease contexts. We also discuss the natural products that modulate SIRT5 activity and identify potential targets of SIRT5 through virtual docking, which may provide new therapeutic avenues. Although the mechanism of SIRT5 in diseases needs to be further elucidated and deglutathionylation activities are still at an early stage, targeting SIRT5 and its substrates holds significant promise for the development of novel therapeutics.</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":"79 3","pages":"441 - 464"},"PeriodicalIF":2.5,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01871-6.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143466383","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}
Pub Date : 2025-02-18DOI: 10.1007/s11418-024-01869-0
Min-Hui Zhang, Fang Liu, Wen-Hui Gao, Zhao-Kun Liu
Boletus bicolor is a kind of wild edible boletus, which is widely distributed in China. We have isolated the protein D1 from B. bicolor, and found that protein D1 has a significant inhibitory effect on the growth and proliferation of lung cancer A549 cells both in vitro and in vivo. In this paper, we found that miR-34a plays an important role in inhibiting the proliferation of A549 cells. miR-34a is the functional target of protein D1 against A549 cells. Protein D1 induces the positive feedback regulation of miR-34a and p53, which further regulates downstream Bcl-2 and CDK6, and inhibits the proliferation of A549 cells.
{"title":"Fungal protein D1 inhibits the proliferation of A549 cells via activating the p53/miR-34a signaling pathway","authors":"Min-Hui Zhang, Fang Liu, Wen-Hui Gao, Zhao-Kun Liu","doi":"10.1007/s11418-024-01869-0","DOIUrl":"10.1007/s11418-024-01869-0","url":null,"abstract":"<div><p><i>Boletus bicolor</i> is a kind of wild edible boletus, which is widely distributed in China. We have isolated the protein D1 from <i>B. bicolor</i>, and found that protein D1 has a significant inhibitory effect on the growth and proliferation of lung cancer A549 cells both in vitro and in vivo. In this paper, we found that miR-34a plays an important role in inhibiting the proliferation of A549 cells. miR-34a is the functional target of protein D1 against A549 cells. Protein D1 induces the positive feedback regulation of miR-34a and p53, which further regulates downstream Bcl-2 and CDK6, and inhibits the proliferation of A549 cells.</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":"79 3","pages":"477 - 487"},"PeriodicalIF":2.5,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447545","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}
Two previously undescribed specialized metabolites, erecricins F (1) and G (2), along with two known metabolites, erectumins A (3) and B (4), were isolated from the aerial parts of Hypericum erectum Thunb. (Hypericaceae). Detailed spectroscopic analyses revealed erecricin F (1) to be a C30 meroterpene with four isoprene units, and erecricin G (2) to be a prenylated acylphloroglucinol biogenetically related to 1. The relative configurations of erecricins F (1) and G (2) were assigned by NOESY analysis and GIAO NMR calculation, while their absolute configurations were deduced by comparison of the ECD spectra with TDDFT calculated spectra. The relative configurations of 3 and 4 were also elucidated by the similar method as for 1 and 2. Erecricins F (1) and G (2) and erectumins A (3) and B (4) were evaluated for their inhibitory effect against IL-1β release from LPS-stimulated murine microglial cells and anti-ferroptosis activity using human hepatoma Hep3B cells.
{"title":"Meroterpenes and prenylated acylphloroglucinol from the aerial parts of Hypericum erectum","authors":"Rena Takizawa, Chiaki Nagata, Sang-Yong Kim, Daisuke Tsuji, Mareshige Kojoma, Reiko Akagi, Yoshiki Kashiwada, Naonobu Tanaka","doi":"10.1007/s11418-025-01883-w","DOIUrl":"10.1007/s11418-025-01883-w","url":null,"abstract":"<div><p>Two previously undescribed specialized metabolites, erecricins F (<b>1</b>) and G (<b>2</b>), along with two known metabolites, erectumins A (<b>3</b>) and B (<b>4</b>), were isolated from the aerial parts of <i>Hypericum erectum</i> Thunb. (Hypericaceae). Detailed spectroscopic analyses revealed erecricin F (<b>1</b>) to be a C<sub>30</sub> meroterpene with four isoprene units, and erecricin G (<b>2</b>) to be a prenylated acylphloroglucinol biogenetically related to <b>1</b>. The relative configurations of erecricins F (<b>1</b>) and G (<b>2</b>) were assigned by NOESY analysis and GIAO NMR calculation, while their absolute configurations were deduced by comparison of the ECD spectra with TDDFT calculated spectra. The relative configurations of <b>3</b> and <b>4</b> were also elucidated by the similar method as for <b>1</b> and <b>2</b>. Erecricins F (<b>1</b>) and G (<b>2</b>) and erectumins A (<b>3</b>) and B (<b>4</b>) were evaluated for their inhibitory effect against IL-1<i>β</i> release from LPS-stimulated murine microglial cells and anti-ferroptosis activity using human hepatoma Hep3B cells.</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":"79 3","pages":"639 - 646"},"PeriodicalIF":2.5,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447549","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}
Resin glycosides, characteristic of plants of the Convolvulaceae family, are well-known purgative constituents found in traditional medicinal crude drugs, such as Rhizoma Jalapae, Rhizoma Jalapae Braziliensis, Orizaba Jalapa Tuber, and Pharbitidis Semen. The isolated compounds exhibited a wide range of biological activities, including antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug-resistance-modulating properties, as well as cytotoxicity against cancer cells. Ipomoea lacunosa L. (Convolvulaceae) is an herbaceous vine native to the United States. Four new acylated glycosidic acid methyl esters (1–4) and one new glycosidic acid (5) were isolated from the methanol extract of the plant seed. The structures of 1–5 were elucidated using spectroscopic data in conjunction with our previous studies on the components of the crude resin glycoside fraction from I. lacunosa seeds. Compounds 1 and 2 were identified as heptaglycosides, 3 as an octaglycoside, and 4 as a nonaglycoside, all sharing methyl 3S,11S-dihydroxytetradecanoate as a common aglycone. The saccharide moieties were partially acylated by glycosidic acid, 7S-hydroxydecanoic acid 7-O-β-d-quinovopyranoside, and organic acids, including (E)-2-methylbut-2-enoic, 2S-methylbutyric, and 2R-methyl-3R-hydroxybutyric acids. Compound 5 was identified as a triglycoside with a new aglycone, 4,11-dihydroxyhexadecanoic acid, which is the first glycosidic acid with a hydroxyl group at C-4 of the aglycone moiety.
{"title":"Four new acylated glycosidic acid methyl esters and a new glycosidic acid from Ipomoea lacunosa seeds","authors":"Masateru Ono, Renjyu Murakami, Shin Yasuda, Hiroyuki Miyashita, Hitoshi Yoshimitsu, Ryota Tsuchihashi, Masafumi Okawa, Junei Kinjo","doi":"10.1007/s11418-025-01877-8","DOIUrl":"10.1007/s11418-025-01877-8","url":null,"abstract":"<div><p>Resin glycosides, characteristic of plants of the Convolvulaceae family, are well-known purgative constituents found in traditional medicinal crude drugs, such as Rhizoma Jalapae, Rhizoma Jalapae Braziliensis, Orizaba Jalapa Tuber, and Pharbitidis Semen. The isolated compounds exhibited a wide range of biological activities, including antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug-resistance-modulating properties, as well as cytotoxicity against cancer cells. <i>Ipomoea lacunosa</i> L. (Convolvulaceae) is an herbaceous vine native to the United States. Four new acylated glycosidic acid methyl esters (<b>1</b>–<b>4</b>) and one new glycosidic acid (<b>5</b>) were isolated from the methanol extract of the plant seed. The structures of <b>1</b>–<b>5</b> were elucidated using spectroscopic data in conjunction with our previous studies on the components of the crude resin glycoside fraction from <i>I. lacunosa</i> seeds. Compounds <b>1</b> and <b>2</b> were identified as heptaglycosides, <b>3</b> as an octaglycoside, and <b>4</b> as a nonaglycoside, all sharing methyl 3<i>S</i>,11<i>S</i>-dihydroxytetradecanoate as a common aglycone. The saccharide moieties were partially acylated by glycosidic acid, 7<i>S</i>-hydroxydecanoic acid 7-<i>O</i>-<i>β</i>-<span>d</span>-quinovopyranoside, and organic acids, including (<i>E</i>)-2-methylbut-2-enoic, 2<i>S</i>-methylbutyric, and 2<i>R</i>-methyl-3<i>R</i>-hydroxybutyric acids. Compound <b>5</b> was identified as a triglycoside with a new aglycone, 4,11-dihydroxyhexadecanoic acid, which is the first glycosidic acid with a hydroxyl group at C-4 of the aglycone moiety.</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":"79 2","pages":"422 - 434"},"PeriodicalIF":2.5,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-025-01877-8.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143405086","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}
Pub Date : 2025-02-06DOI: 10.1007/s11418-025-01880-z
Takayoshi Awakawa
Fe(II)/αKG-dependent oxygenases are multifunctional oxidases responsible for the formation of unique natural product skeletons. Studies of these enzymes are important because the knowledge of their catalytic functions, enzyme structures, and reaction mechanisms can be used to create non-natural enzymes through mutation and synthesize non-natural compounds. In this review, I will introduce the research we have conducted on two fungal Fe(II)/αKG-dependent oxygenases, TlxI-J and TqaL. TlxI-J is the first Fe(II)/αKG-dependent oxygenase type enzyme heterodimer that catalyzes consecutive oxidation reactions, hydroxylation followed by retro-aldol or ketal formation, to form the complex skeletons of meroterpenoids. TqaL is the first naturally occurring aziridine synthase, and I will discuss the mechanism of its unique C–N bond formation in nonproteinogenic amino acid biosynthesis. This review will advance research on the discovery of new enzymes and the analysis of their functions by reviewing the structures and functions of these extraordinary Fe(II)/αKG-dependent oxygenases, and promote their use in the synthesis of new natural medicines.
{"title":"Biosynthesis of unique natural product scaffolds by Fe(II)/αKG-dependent oxygenases","authors":"Takayoshi Awakawa","doi":"10.1007/s11418-025-01880-z","DOIUrl":"10.1007/s11418-025-01880-z","url":null,"abstract":"<div><p>Fe(II)/αKG-dependent oxygenases are multifunctional oxidases responsible for the formation of unique natural product skeletons. Studies of these enzymes are important because the knowledge of their catalytic functions, enzyme structures, and reaction mechanisms can be used to create non-natural enzymes through mutation and synthesize non-natural compounds. In this review, I will introduce the research we have conducted on two fungal Fe(II)/αKG-dependent oxygenases, TlxI-J and TqaL. TlxI-J is the first Fe(II)/αKG-dependent oxygenase type enzyme heterodimer that catalyzes consecutive oxidation reactions, hydroxylation followed by retro-aldol or ketal formation, to form the complex skeletons of meroterpenoids. TqaL is the first naturally occurring aziridine synthase, and I will discuss the mechanism of its unique C–N bond formation in nonproteinogenic amino acid biosynthesis. This review will advance research on the discovery of new enzymes and the analysis of their functions by reviewing the structures and functions of these extraordinary Fe(II)/αKG-dependent oxygenases, and promote their use in the synthesis of new natural medicines.</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":"79 2","pages":"303 - 313"},"PeriodicalIF":2.5,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-025-01880-z.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143363517","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}
Since the coronavirus disease 2019 (COVID-19) outbreak, research has been conducted on treatment and countermeasures against the causative severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). However, the development of new seeds is urgently needed because viruses have the characteristic of becoming resistant through mutation. We hypothesize that endophytes produce antiviral substances to combat foreign viruses in host plants. According to this hypothesis, the seeds of therapeutic agents for infectious diseases could be obtained from endophytes by culture experiments. This report found that Aspergillus sp. endophyte isolated from Catharanthus roseus produced ( +)-eupenoxide and its 3-ketone form with anti-SARS-CoV-2 activity. In addition, ( +)-eupenoxide-3,6-diketon was discovered as a new compound with potent 3C-like protease inhibitory activity (IC50: 0.048 μM) by synthesis based on ( +)-eupenoxide. This finding could be an important evidence that endophytic fungi symbiosis with medicinal plants is useful as antiviral producers.
{"title":"Potent SARS-CoV-2 3C-like protease inhibitor ( +)-eupenoxide-3,6-diketone (IC50: 0.048 μM) was synthesized based on ( +)-eupenoxide; lead from ( +)-eupenoxide analogs study by endophytic fermentation","authors":"Shoji Maehara, Moeka Kumamoto, Shogo Nakajima, Yuhzo Hieda, Koichi Watashi, Toshiyuki Hata","doi":"10.1007/s11418-024-01874-3","DOIUrl":"10.1007/s11418-024-01874-3","url":null,"abstract":"<div><p>Since the coronavirus disease 2019 (COVID-19) outbreak, research has been conducted on treatment and countermeasures against the causative severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). However, the development of new seeds is urgently needed because viruses have the characteristic of becoming resistant through mutation. We hypothesize that endophytes produce antiviral substances to combat foreign viruses in host plants. According to this hypothesis, the seeds of therapeutic agents for infectious diseases could be obtained from endophytes by culture experiments. This report found that <i>Aspergillus</i> sp. endophyte isolated from <i>Catharanthus roseus</i> produced ( +)-eupenoxide and its 3-ketone form with anti-SARS-CoV-2 activity. In addition, ( +)-eupenoxide-3,6-diketon was discovered as a new compound with potent 3C-like protease inhibitory activity (IC<sub>50</sub>: 0.048 μM) by synthesis based on ( +)-eupenoxide. This finding could be an important evidence that endophytic fungi symbiosis with medicinal plants is useful as antiviral producers.</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":"79 2","pages":"357 - 370"},"PeriodicalIF":2.5,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143078405","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}
A new diterpenoid, carneadiol (1), with an unprecedented tricyclic carbon skeleton, was isolated from the culture extracts of Nocardia carnea IFM 12324. The structure of compound 1 was elucidated using spectral studies, including various NMR data. The absolute configuration of 1 was determined using X-ray crystallographic analysis with the crystalline sponge method. The biosynthetic gene of compound 1 was deduced, and it was observed that the mRNA of the gene involved in terpenoid cyclization increased significantly in the strain producing compound 1.
{"title":"A new diterpenoid, carneadiol, isolated from Nocardia carnea IFM 12324","authors":"Yasumasa Hara, Ayaka Nakamura, Teruhisa Manome, Akiko Takaya, Hiroki Takahashi, Sayaka Ban, Takashi Yaguchi, Masami Ishibashi","doi":"10.1007/s11418-025-01878-7","DOIUrl":"10.1007/s11418-025-01878-7","url":null,"abstract":"<div><p>A new diterpenoid, carneadiol (<b>1</b>), with an unprecedented tricyclic carbon skeleton, was isolated from the culture extracts of <i>Nocardia carnea</i> IFM 12324. The structure of compound <b>1</b> was elucidated using spectral studies, including various NMR data. The absolute configuration of <b>1</b> was determined using X-ray crystallographic analysis with the crystalline sponge method. The biosynthetic gene of compound <b>1</b> was deduced, and it was observed that the mRNA of the gene involved in terpenoid cyclization increased significantly in the strain producing compound <b>1</b>.</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":"79 2","pages":"435 - 440"},"PeriodicalIF":2.5,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143051146","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}
Pub Date : 2025-01-19DOI: 10.1007/s11418-024-01875-2
Yves M. Mba Nguekeu, Herman D. Sonfack Fozeng, Chika Ifeanyi Chukwuma, Saw Y. Yu Hnin, Nhat Nam Hoang, Emmanuel Mfotie Njoya, Silvère Augustin Ngouela, Mathieu Tene, Tshepiso Jan Makhafola, Hiroyuki Morita, Maurice Ducret Awouafack
Two new cerebrosides, raphimanosides A (1) and B (2), and a new ceramide, raphimanide (3), were isolated from the aerial parts of Raphidiocystis mannii Hook. f., along with ten known compounds (4–13). Their structures were fully established, based on extensive analyses of 1H, 13C, DEPT, 2D NMR, ESIMS, and HRESIMS data and chemical conversion. Subsequently, methanol extract, ethyl acetate, and n-butanol soluble portions and the isolated compounds 1–9, 12, and 13 were assayed for their cytotoxic effects against three human cancer cell lines (MCF-7, HeLa and A549). None of the new compounds demonstrated efficacy against the tested cell lines. In contrast, the methanol extract, ethyl acetate soluble portion, and compounds 6, 7, 9, 12, and 13 showed moderate to low activities against different tested cell lines. Ethyl acetate soluble portion and compounds 13 and 7 were the most potent samples with the IC50 value of 41.25 μg/mL, 36.76 μM, and 13.16 μM against MCF-7, HeLa, and A549 cell lines, respectively. To the best of our knowledge, this is the inaugural investigation into the chemical constituents of the genus Raphidiocystis, offering novel insights into the chemotaxonomy of this hitherto poorly understood genus.
{"title":"New cerebrosides and ceramide with other constituents from the aerial parts of Raphidiocystis mannii Hook. f. and their cytotoxic activities","authors":"Yves M. Mba Nguekeu, Herman D. Sonfack Fozeng, Chika Ifeanyi Chukwuma, Saw Y. Yu Hnin, Nhat Nam Hoang, Emmanuel Mfotie Njoya, Silvère Augustin Ngouela, Mathieu Tene, Tshepiso Jan Makhafola, Hiroyuki Morita, Maurice Ducret Awouafack","doi":"10.1007/s11418-024-01875-2","DOIUrl":"10.1007/s11418-024-01875-2","url":null,"abstract":"<div><p>Two new cerebrosides, raphimanosides A (<b>1</b>) and B (<b>2</b>), and a new ceramide, raphimanide (<b>3</b>), were isolated from the aerial parts of <i>Raphidiocystis mannii</i> Hook. f., along with ten known compounds (<b>4–13</b>). Their structures were fully established, based on extensive analyses of <sup>1</sup>H, <sup>13</sup>C, DEPT, 2D NMR, ESIMS, and HRESIMS data and chemical conversion. Subsequently, methanol extract, ethyl acetate, and <i>n</i>-butanol soluble portions and the isolated compounds <b>1–9</b>, <b>12</b>, and <b>13</b> were assayed for their cytotoxic effects against three human cancer cell lines (MCF-7, HeLa and A549). None of the new compounds demonstrated efficacy against the tested cell lines. In contrast, the methanol extract, ethyl acetate soluble portion, and compounds <b>6</b>, <b>7</b>,<b> 9</b>, <b>12</b>, and <b>13</b> showed moderate to low activities against different tested cell lines. Ethyl acetate soluble portion and compounds <b>13</b> and <b>7</b> were the most potent samples with the IC<sub>50</sub> value of 41.25 μg/mL, 36.76 μM, and 13.16 μM against MCF-7, HeLa, and A549 cell lines, respectively. To the best of our knowledge, this is the inaugural investigation into the chemical constituents of the genus <i>Raphidiocystis</i>, offering novel insights into the chemotaxonomy of this hitherto poorly understood genus.</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":"79 2","pages":"412 - 421"},"PeriodicalIF":2.5,"publicationDate":"2025-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142998179","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}
Pub Date : 2025-01-17DOI: 10.1007/s11418-024-01872-5
Takashi Kikuchi
Steroids are physiologically important compounds for animals, plants, and fungi, and they have significantly contributed to drug discovery for many years. Fungi mainly biosynthesize ergostane-type steroids such as ergosterol. However, after the basic skeleton is biosynthesized, chemical transformations can lead to the cleavage or rearrangement of the fundamental skeleton of steroids. The cleaved (seco) and rearranged (abeo) steroids are chemically and pharmacologically intriguing because they often exhibit biological activities. As ergostane-type steroids including the normal, seco, and abeo types have been isolated from the mushrooms of the Pleurotus genus, this review focuses on them as a resource of ergostane-type steroids, providing their distribution, structure determination, and biological activity.
{"title":"Ergostane-type steroids from mushrooms of Pleurotus genus","authors":"Takashi Kikuchi","doi":"10.1007/s11418-024-01872-5","DOIUrl":"10.1007/s11418-024-01872-5","url":null,"abstract":"<div><p>Steroids are physiologically important compounds for animals, plants, and fungi, and they have significantly contributed to drug discovery for many years. Fungi mainly biosynthesize ergostane-type steroids such as ergosterol. However, after the basic skeleton is biosynthesized, chemical transformations can lead to the cleavage or rearrangement of the fundamental skeleton of steroids. The cleaved (seco) and rearranged (<i>abeo</i>) steroids are chemically and pharmacologically intriguing because they often exhibit biological activities. As ergostane-type steroids including the normal, seco, and <i>abeo</i> types have been isolated from the mushrooms of the <i>Pleurotus</i> genus, this review focuses on them as a resource of ergostane-type steroids, providing their distribution, structure determination, and biological 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":"79 2","pages":"289 - 302"},"PeriodicalIF":2.5,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01872-5.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142998177","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}
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