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Secondary Metabolites of an Endophytic Fungus from Ligularia fischeri Ligularia fischeri 内生真菌的次级代谢物
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-23 DOI: 10.1007/s10600-024-04501-5
Rui Dong, Taofeng Zhang, Jian Lu, Tao Wang, Aimei Yang, Jinlong Pu, Lingling Li, Deyi Luo
{"title":"Secondary Metabolites of an Endophytic Fungus from Ligularia fischeri","authors":"Rui Dong, Taofeng Zhang, Jian Lu, Tao Wang, Aimei Yang, Jinlong Pu, Lingling Li, Deyi Luo","doi":"10.1007/s10600-024-04501-5","DOIUrl":"10.1007/s10600-024-04501-5","url":null,"abstract":"","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142413398","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Bromination of Acetylhaplophyllidine by Molecular Br2 and N-Bromosuccinimide 分子 Br2 和 N-溴丁二酰亚胺对乙酰基茶碱的溴化作用
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-20 DOI: 10.1007/s10600-024-04473-6
A. U. Ubaydullaev, Sh. N. Zhurakulov, V. I. Vinogradova, K. K. Turgunov, B. Tashkhodzhaev, N. I. Mukarramov
{"title":"Bromination of Acetylhaplophyllidine by Molecular Br2 and N-Bromosuccinimide","authors":"A. U. Ubaydullaev,&nbsp;Sh. N. Zhurakulov,&nbsp;V. I. Vinogradova,&nbsp;K. K. Turgunov,&nbsp;B. Tashkhodzhaev,&nbsp;N. I. Mukarramov","doi":"10.1007/s10600-024-04473-6","DOIUrl":"10.1007/s10600-024-04473-6","url":null,"abstract":"<p>The influence of the 7-<i>O</i>-acetyl group of acetylhaplophyllidine (<b>2</b>) on the bromination process was studied. Acetylhaplophyllidine in bromination by molecular Br<sub>2</sub> and <i>N</i>-bromosuccinimide under various conditions formed multicomponent mixtures consisting of bromination products of intramolecular annelation (<b>3</b>, <b>4</b>, and <b>6</b>) and bromo-derivatives of 4-oxofuranoquinolines (<b>5</b> and <b>7</b>).</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142412692","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of β-D-Glucopyranosides of 12α-Epimers of 20S-Protopanaxadiol and Betulafolientriol 20S-Protopanaxadiol 和 Betulafolientriol 的 12α-Epimers 的 β-D-Glucopyranosides 的合成
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-19 DOI: 10.1007/s10600-024-04464-7
L. N. Atopkina, A. I. Kalinovsky
{"title":"Synthesis of β-D-Glucopyranosides of 12α-Epimers of 20S-Protopanaxadiol and Betulafolientriol","authors":"L. N. Atopkina,&nbsp;A. I. Kalinovsky","doi":"10.1007/s10600-024-04464-7","DOIUrl":"10.1007/s10600-024-04464-7","url":null,"abstract":"<p><i>β</i>-D-Glucopyranosides of 3<i>β</i>, 12<i>α</i>,20<i>S</i>-trihydroxydammar-24-ene (<b>1</b>) and 3<i>α</i>,12<i>α</i>,20<i>S</i>-trihydroxydammar-24-ene (<b>2</b>), close structural analogs of ginsenoside-Rh2 and a metabolite of <i>Panax ginseng</i> glycosides (compound K), were synthesized. Glycosylation of 20<i>S</i>-hydroxydammar-24-ene-3,12-dione (<b>5</b>) and 3<i>α</i>-acetoxy-20<i>S</i>-hydroxydammar-24-en-12-one (<b>6</b>) by 2,3,4,6-tetra-<i>O</i>-acetyl-<i>α</i>-D-glucopyranosyl bromide (<b>8</b>) under classical Koenig-Knorr reaction conditions followed by deacetylation by NaOMe in MeOH gave free 20-<i>O</i>-<i>β</i>-D-glucopyranosides <b>10</b> and <b>13</b>, treatment of which with NaBH<sub>4</sub> in i-PrOH formed 20-<i>O</i>-<i>β</i>-D- glucopyranosides of the 12<i>α</i>-epimers of 20S-protopanaxadiol <b>11</b> and betulafolientriol <b>14</b>. Condensation of 3<i>β</i>,12<i>α</i>,20<i>S</i>-trihydroxydammar-24-ene (<b>1</b>) and glycosyl donor <b>8</b> in the presence of Ag<sub>2</sub>O in CH<sub>2</sub>Cl<sub>2</sub> followed by removal of the protecting groups gave 3-<i>O</i>-<i>β</i>-D-glucopyranoside <b>16</b>; of 3<i>α</i>,12<i>α</i>,20<i>S</i>-trihydroxydammar-24-ene (<b>2</b>) under the same conditions, a mixture of 3- and 12-<i>O</i>-<i>β</i>-D-glucopyranosides <b>19</b> and <b>20</b>.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142254974","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
New Synthetic Method for Betulin 3-O-Propionate 28-O-Acylates 桦木醇 3-O-丙酸 28-O-酰化物的新合成方法
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-19 DOI: 10.1007/s10600-024-04465-6
A. V. Levdansky, N. V. Garyntseva, V. A. Levdansky
{"title":"New Synthetic Method for Betulin 3-O-Propionate 28-O-Acylates","authors":"A. V. Levdansky,&nbsp;N. V. Garyntseva,&nbsp;V. A. Levdansky","doi":"10.1007/s10600-024-04465-6","DOIUrl":"10.1007/s10600-024-04465-6","url":null,"abstract":"<p>A synthetic method for betulin 3-<i>O</i>-propionate 28-<i>O</i>-acylates via the reaction of betulin 3-<i>O</i>-propionate with melts of benzoic, phthalic, cinnamic, and succinic acids at 185–195°C for 5–6 min was proposed.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142254973","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A New Benzylisoquinoline of Michelia compressa var. compressa 蜜雪草变种新的苄基异喹啉
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-18 DOI: 10.1007/s10600-024-04468-3
T. L. Yang, T. H. Wang, C. L. Kao, H. C. Yeh, H. T. Li, C. Y. Chen
{"title":"A New Benzylisoquinoline of Michelia compressa var. compressa","authors":"T. L. Yang,&nbsp;T. H. Wang,&nbsp;C. L. Kao,&nbsp;H. C. Yeh,&nbsp;H. T. Li,&nbsp;C. Y. Chen","doi":"10.1007/s10600-024-04468-3","DOIUrl":"10.1007/s10600-024-04468-3","url":null,"abstract":"<p>(+)-Zishenine (<b>1</b>), a new benzylisoquinoline, along with eight known compounds including two oxoaporphines, liriodenine (<b>2</b>), and oxoxylopine (<b>3</b>), two aporphines, (–)-anonaine (<b>4</b>) and (–)-xylopine (<b>5</b>), two lignans, (+)-sesamin (<b>6</b>) and (+)-diasesamin (<b>7</b>) and two benzenoids, ferulic acid (<b>8</b>) and <i>p</i>-hydroxybenzaldehyde (<b>9</b>), were isolated from the fruits of <i>Michelia compressa</i> var. <i>compressa</i> (Magnoliaceae). The structure was characterized and identified by spectral analysis.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142268991","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Two New Isoindole Alkaloids from Aspergillus fumigatus as Potential Activators for Tobacco Powdery Mildew 来自烟曲霉的两种新的异吲哚生物碱是烟草白粉病的潜在激活剂
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-18 DOI: 10.1007/s10600-024-04469-2
Yu-Ping Wu, Hua-Yin Liu, Wen-Yu Liu, Gao-Kun Zhao, Guang-Hai Zhang, Heng Yao, Wei Li, Wei-Guang Wang, Guang-Hui Kong, Bo Yang
{"title":"Two New Isoindole Alkaloids from Aspergillus fumigatus as Potential Activators for Tobacco Powdery Mildew","authors":"Yu-Ping Wu,&nbsp;Hua-Yin Liu,&nbsp;Wen-Yu Liu,&nbsp;Gao-Kun Zhao,&nbsp;Guang-Hai Zhang,&nbsp;Heng Yao,&nbsp;Wei Li,&nbsp;Wei-Guang Wang,&nbsp;Guang-Hui Kong,&nbsp;Bo Yang","doi":"10.1007/s10600-024-04469-2","DOIUrl":"10.1007/s10600-024-04469-2","url":null,"abstract":"<p>To further explore powdery mildew (caused by <i>Golovinomyces cichoracearum</i>) natural products, an extract from the fermentation of endophytic <i>Aspergillus fumigatus</i> was investigated. As a result, six isoindole alkaloid derivatives (<b>1–6</b>) were isolated. Among them, two compounds (<b>1</b> and <b>2</b>) were newly discovered and the activity evaluation of the purified compounds <b>1–6</b> against <i>G. cichoracearum</i> was studied. The results revealed that compounds <b>1–6</b> demonstrated obvious anti-<i>G. cichoracearum</i> activities for cigar tobacco in the range of 40.6% ± 5.4 to 66.5% ± 4.9 at a concentration of 250 μg/mL, respectively. However, these rates are lower than that of positive control. By isolating and structurally identifying the above isoindole alkaloids, new materials conducive to improving the utilization of <i>N. tabacum</i>-derived fungi could be developed for screening anti-powdery mildew drugs.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142254976","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Discovery of New Compound Comazaphilone I from Mycolicibacterium aurum 从金耳霉菌中发现新化合物 Comazaphilone I
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-18 DOI: 10.1007/s10600-024-04458-5
Peng Li, Yunqiang Wu, Shufen He, Hongmei Lu, Shan He, Liwei Liu
{"title":"Discovery of New Compound Comazaphilone I from Mycolicibacterium aurum","authors":"Peng Li,&nbsp;Yunqiang Wu,&nbsp;Shufen He,&nbsp;Hongmei Lu,&nbsp;Shan He,&nbsp;Liwei Liu","doi":"10.1007/s10600-024-04458-5","DOIUrl":"10.1007/s10600-024-04458-5","url":null,"abstract":"<p>A new compound, comazaphilone I (<b>1</b>), was isolated from <i>Mycolicibacterium aurum</i> WYQ isolated from marine sediment samples collected in the East China Sea. Its structure was elucidated based on spectroscopic data, comparison with literature data, and ECD calculation. The newly discovered compound, while bearing a similar planar structure to the known compound comazaphilone A, features a distinct 6S7S configuration. However, no bioactivities were screened from the bioassay experiments.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142254977","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A New Minor Hederagenin-Type Triterpene Saponin from Cassia fistula 肉桂中一种新的次要 Hederagenin 型三萜皂苷
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-18 DOI: 10.1007/s10600-024-04466-5
Thuy Thi Thu Vu, Nga Thi Thu Nguyen, Hong Thi Tran, Thu Thi Mai Lo, Hung Duc Nguyen, Mau Hoang Chu
{"title":"A New Minor Hederagenin-Type Triterpene Saponin from Cassia fistula","authors":"Thuy Thi Thu Vu,&nbsp;Nga Thi Thu Nguyen,&nbsp;Hong Thi Tran,&nbsp;Thu Thi Mai Lo,&nbsp;Hung Duc Nguyen,&nbsp;Mau Hoang Chu","doi":"10.1007/s10600-024-04466-5","DOIUrl":"10.1007/s10600-024-04466-5","url":null,"abstract":"<p>A new hederagenin-type triterpene saponin was found in the aqueous-ethanolic extract of the seeds of <i>Cassia fistula</i> L. The structure of this compound was established as 3-<i>O</i>-<i>β</i>-D-xylopyranosyl-(1→2)-<i>β</i>-D- xylopyranosylhederagenin 28-<i>O</i>-<i>α</i>-L-rhamnopyranosyl-(1→2)-<i>β</i>-D-glucopyranosyl ester (<b>1</b>), mainly by extensive 2D NMR analysis in combination with spectral data of known compounds.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142254978","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemical Constituents from the Fungus Inonotus sinensis 猪笼草真菌的化学成分
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-18 DOI: 10.1007/s10600-024-04463-8
Jian-Hai Ding, Yu-Qin Yang, Chen-Xi Quan, Cai-Zhi Xiong, Wen-Guan Luo, Jia-Min Zhao, Yang Xiao, Tian-Yin Chen, Dan-Min Zhang, Jin-Fen Cao, Shi-Wei Liu, Ji-Kai Liu
{"title":"Chemical Constituents from the Fungus Inonotus sinensis","authors":"Jian-Hai Ding,&nbsp;Yu-Qin Yang,&nbsp;Chen-Xi Quan,&nbsp;Cai-Zhi Xiong,&nbsp;Wen-Guan Luo,&nbsp;Jia-Min Zhao,&nbsp;Yang Xiao,&nbsp;Tian-Yin Chen,&nbsp;Dan-Min Zhang,&nbsp;Jin-Fen Cao,&nbsp;Shi-Wei Liu,&nbsp;Ji-Kai Liu","doi":"10.1007/s10600-024-04463-8","DOIUrl":"10.1007/s10600-024-04463-8","url":null,"abstract":"<p>A new isopimarane-type diterpenoid, named inonotolide E (<b>1</b>), and four known compounds (<b>2–5</b>) were isolated from cultures of the fungus <i>Inonotus sinensis</i>. The new structure was established by extensive spectroscopic techniques (1D and 2D NMR and HR-ESI-MS). Compound <b>1</b> was evaluated for its cytotoxicities against five human cancer cell lines.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142268992","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A New Lanostane-Type Triterpene from the Branches of Thai Uvaria siamensis 泰国暹罗乌蔹莓枝条中的一种新的兰氏三萜类化合物
IF 0.8 4区 化学
Chemistry of Natural Compounds Pub Date : 2024-09-18 DOI: 10.1007/s10600-024-04467-4
Ngoc-Hong Nguyen, Boi-Phong Vuong, Dinh-Manh Nguyen, Thuc-Huy Duong, Hoang-Thanh Kpa, Thi-Kim-Dung Le, Thi-Ngoc-Duyen Nguyen, Huy Truong Nguyen, Jirapast Sichaem
{"title":"A New Lanostane-Type Triterpene from the Branches of Thai Uvaria siamensis","authors":"Ngoc-Hong Nguyen,&nbsp;Boi-Phong Vuong,&nbsp;Dinh-Manh Nguyen,&nbsp;Thuc-Huy Duong,&nbsp;Hoang-Thanh Kpa,&nbsp;Thi-Kim-Dung Le,&nbsp;Thi-Ngoc-Duyen Nguyen,&nbsp;Huy Truong Nguyen,&nbsp;Jirapast Sichaem","doi":"10.1007/s10600-024-04467-4","DOIUrl":"10.1007/s10600-024-04467-4","url":null,"abstract":"<p>A new lanostane-type triterpene, uvariaol (<b>1</b>), was isolated from the branches of Thai <i>Uvaria siamensis</i>, along with three known compounds, polycarpol (<b>2</b>), fisetinidol (<b>3</b>), and stigmast-4-en-3-one (<b>4</b>). Their structures were elucidated through extensive spectroscopic analyses and comparison with existing literature. The <i>α</i>-glucosidase inhibitory potential of compounds <b>1–4</b> was evaluated. Compound <b>1</b> exhibited significant inhibitory activity against <i>α</i>-glucosidase, surpassing the potency of the positive control, with an IC<sub>50</sub> value of 30.8 ± 1.5 μM.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142255062","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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