: Two new spirostanol glycosides, thibetanosides J and K ( 1 and 2 ), along with three known ones ( 3 - 5 ) were isolated from the roots and rhizomes of Helleborus thibetanus . Their structures were elucidated by extensive use of spectroscopic techniques and chemical evidence. In this study, compounds 1 - 5 were evaluated for their cytotoxic activity against HCT116, A549 and HepG2 tumor cell lines. Among them, compound 1 exhibited moderate cytotoxicity against A549 cells (IC 50 7.69 ± 1.13 μM) and HepG 2 cells (IC 50 8.32 ± 2.63 μM). Compound 2 exhibited moderate cytotoxicity against HCT116 cells (IC 50 20.67 ± 1.06 μM).
{"title":"Two New Spirostanol Glycosides from the Roots and Rhizomes of Helleborus thibetanus Franch.","authors":"Xiaomei Song, Yu-ze Li, Zilong Zhang, Wenli Huang, Huawei Zhang, Yi Jiang, Jianli Liu, Dongdong Zhang","doi":"10.25135/rnp.361.2207.2520","DOIUrl":"https://doi.org/10.25135/rnp.361.2207.2520","url":null,"abstract":": Two new spirostanol glycosides, thibetanosides J and K ( 1 and 2 ), along with three known ones ( 3 - 5 ) were isolated from the roots and rhizomes of Helleborus thibetanus . Their structures were elucidated by extensive use of spectroscopic techniques and chemical evidence. In this study, compounds 1 - 5 were evaluated for their cytotoxic activity against HCT116, A549 and HepG2 tumor cell lines. Among them, compound 1 exhibited moderate cytotoxicity against A549 cells (IC 50 7.69 ± 1.13 μM) and HepG 2 cells (IC 50 8.32 ± 2.63 μM). Compound 2 exhibited moderate cytotoxicity against HCT116 cells (IC 50 20.67 ± 1.06 μM).","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":" ","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48602106","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: A new isoflavipucine derivative, (8 S , 9 R )-dihydroisoflavipucine ( 1 ), is isolated from an ethyl acetate extract of endophytic fungi Botryosphaeria dothidea (D4-2) derived from Taxus mairei . The structure of 1 is elucidated based on nuclear magnetic resonance, circular dichroism, and mass spectrometry. The antiproliferative activity of the isolates against breast cancer cells MDA-MB-231, MCF7 and 4T1 are evaluated.
{"title":"8S, 9R)-Dihydroisoflavipucine, a New Isoflavipucine Derivative from the Endophytic Fungi Botryosphaeria dothidea","authors":"Zhangshuang Deng, Hui Chen, Wendan Li, Liangmin Xue, Xiu-Jin Liu, Yiqing Zhou","doi":"10.25135/rnp.360.2206.2500","DOIUrl":"https://doi.org/10.25135/rnp.360.2206.2500","url":null,"abstract":": A new isoflavipucine derivative, (8 S , 9 R )-dihydroisoflavipucine ( 1 ), is isolated from an ethyl acetate extract of endophytic fungi Botryosphaeria dothidea (D4-2) derived from Taxus mairei . The structure of 1 is elucidated based on nuclear magnetic resonance, circular dichroism, and mass spectrometry. The antiproliferative activity of the isolates against breast cancer cells MDA-MB-231, MCF7 and 4T1 are evaluated.","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":" ","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47309217","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-10-11DOI: 10.25135/rnp.357.2207.2504
H. Džudžević-Čančar, Emina Boškailo, A. Dedić, Z. Marijanović, A. Alispahić, Ismet Fatih Čančar, Danijela Vidic, I. Jerković
: The samples of Clinopodium nepeta (L.) Kuntze (Lamiaceae) aerial parts were collected from four different localities in sub-Mediterranean area of Bosnia and Herzegovina and subjected to phytochemical profiling. Shade-dried and fresh samples were used to determine their headspace volatile organic composition by solid-phase microextraction on two differently coated fibers. Corresponding essential oils were obtained by hydrodistillation. Both headspace and essential oil were analysed by gas chromatography-mass spectrometry Among detected compounds, piperitenone oxide and pulegone were dominant in the headspace of shade-dried and fresh C. nepeta samples. The essential oils contained 42 compounds including pulegone (44.8%), piperitenone (48.8%) and piperitenone oxide (60.2%) as the major compounds, followed by limonene, cis piperitone oxide, p -menthone and dihydrocarvyl acetate. In this work, a wide range of volatile compounds present in C. nepeta samples from Bosnia and Herzegovina was determined. The obtained data provides detail phytochemical analysis of the volatiles of C. nepeta and therefore completes earlier researches of this plant from the other geographical areas.
{"title":"Clinopodium nepeta (L.) Kuntze from Bosnia and Herzegovina: Chemical Characterisation of Headspace and Essential Oil of Fresh and Dried Samples","authors":"H. Džudžević-Čančar, Emina Boškailo, A. Dedić, Z. Marijanović, A. Alispahić, Ismet Fatih Čančar, Danijela Vidic, I. Jerković","doi":"10.25135/rnp.357.2207.2504","DOIUrl":"https://doi.org/10.25135/rnp.357.2207.2504","url":null,"abstract":": The samples of Clinopodium nepeta (L.) Kuntze (Lamiaceae) aerial parts were collected from four different localities in sub-Mediterranean area of Bosnia and Herzegovina and subjected to phytochemical profiling. Shade-dried and fresh samples were used to determine their headspace volatile organic composition by solid-phase microextraction on two differently coated fibers. Corresponding essential oils were obtained by hydrodistillation. Both headspace and essential oil were analysed by gas chromatography-mass spectrometry Among detected compounds, piperitenone oxide and pulegone were dominant in the headspace of shade-dried and fresh C. nepeta samples. The essential oils contained 42 compounds including pulegone (44.8%), piperitenone (48.8%) and piperitenone oxide (60.2%) as the major compounds, followed by limonene, cis piperitone oxide, p -menthone and dihydrocarvyl acetate. In this work, a wide range of volatile compounds present in C. nepeta samples from Bosnia and Herzegovina was determined. The obtained data provides detail phytochemical analysis of the volatiles of C. nepeta and therefore completes earlier researches of this plant from the other geographical areas.","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":" ","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49651524","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: A new lignan eplignan A ( 1 ), along with six konwn lignans ( 2 – 7 ) was isolated from the herbaceous stems of Ephedra intermedia Schrenket C. A. Meyer. Their structures were elucidated based on the spectroscopic evidence, mainly including NMR and HRESIMS data. The absolute configuration of 1 was determined by comparing calculated and experimental electronic circular dichroic (ECD) spectra. Moreover, all compounds ( 1 – 7 ) were evaluated for their protective effects against the BEAS-2B cells injury induced by TGF- β 1 in vitro , and the results showed that compounds 1 , 2 , 4 , and 6 exhibited significantly protective activities at the concentration of 10 μ M.
{"title":"A New Lignan from the Herbaceous stems of Ephedra intermedia Schrenket C. A. Meyer.","authors":"Weisheng Feng, Xi-ling Fan, Yan-gang Cao, Mengnan Zeng, Ru Wang, Yanling Liu, Chenxiang Xu, Xin-yi Ma, Ying-jie Ren, Chen He, Xiangda Li, Xiaoke Zheng","doi":"10.25135/rnp.359.2207.2519","DOIUrl":"https://doi.org/10.25135/rnp.359.2207.2519","url":null,"abstract":": A new lignan eplignan A ( 1 ), along with six konwn lignans ( 2 – 7 ) was isolated from the herbaceous stems of Ephedra intermedia Schrenket C. A. Meyer. Their structures were elucidated based on the spectroscopic evidence, mainly including NMR and HRESIMS data. The absolute configuration of 1 was determined by comparing calculated and experimental electronic circular dichroic (ECD) spectra. Moreover, all compounds ( 1 – 7 ) were evaluated for their protective effects against the BEAS-2B cells injury induced by TGF- β 1 in vitro , and the results showed that compounds 1 , 2 , 4 , and 6 exhibited significantly protective activities at the concentration of 10 μ M.","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":" ","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42499729","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-08-30DOI: 10.25135/rnp.356.2206.2486
T. Lin, Lijing Cai, Mengying Zhang, Jie He
: A new sesquiterpene, named todasinoid A ( 1 ), together with eight known compounds ( 2 − 9 ) were isolated from the roots of Toddalia asiatica . The gross structure of todasinoid A were established by analyses of the NMR and HRESIMS data. A comparison of the experimental ECD spectrum of 1 with the calculated ECD spectra for a model compound ( 1a ) resolved the absolute configuration of 1 . The known compounds were identified to be bullatantriol ( 2 ), aculeatin ( 3 ), 6-(3-ethoxy-2-hydroxy-3-methylbutyl)-5,7-dimethoxy-2H-1-benzopyran-2-one ( 4 ), trans -N-p-coumaroyltyramine ( 5 ), feruloyltyramine ( 6 ), − sitosterol ( 7 ), sitosterol D -glucoside( 8 ), 7 α -hydroxysitosterol ( 9 ) by comparing the NMR data and specific rotations with reported data in literature. Compound 1 is an eremophilane-type sesquiterpenoid containing a mercaptolactate side-chain that is rarely found in nature. Compounds 2 , 5 , and 9 were isolated from this plant for the first time. Bioassay study revealed that compound 5 exhibited inhibitory effects against -glucosidase with an IC 50 of 320 M, being more active than the positive control acarbose.
{"title":"Todasinoid A, a New Eremophilane-type Sesquiterpene from the Plant Toddalia asiatica","authors":"T. Lin, Lijing Cai, Mengying Zhang, Jie He","doi":"10.25135/rnp.356.2206.2486","DOIUrl":"https://doi.org/10.25135/rnp.356.2206.2486","url":null,"abstract":": A new sesquiterpene, named todasinoid A ( 1 ), together with eight known compounds ( 2 − 9 ) were isolated from the roots of Toddalia asiatica . The gross structure of todasinoid A were established by analyses of the NMR and HRESIMS data. A comparison of the experimental ECD spectrum of 1 with the calculated ECD spectra for a model compound ( 1a ) resolved the absolute configuration of 1 . The known compounds were identified to be bullatantriol ( 2 ), aculeatin ( 3 ), 6-(3-ethoxy-2-hydroxy-3-methylbutyl)-5,7-dimethoxy-2H-1-benzopyran-2-one ( 4 ), trans -N-p-coumaroyltyramine ( 5 ), feruloyltyramine ( 6 ), − sitosterol ( 7 ), sitosterol D -glucoside( 8 ), 7 α -hydroxysitosterol ( 9 ) by comparing the NMR data and specific rotations with reported data in literature. Compound 1 is an eremophilane-type sesquiterpenoid containing a mercaptolactate side-chain that is rarely found in nature. Compounds 2 , 5 , and 9 were isolated from this plant for the first time. Bioassay study revealed that compound 5 exhibited inhibitory effects against -glucosidase with an IC 50 of 320 M, being more active than the positive control acarbose.","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":"1 1","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"69542896","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-08-29DOI: 10.25135/rnp.334.2203.2387
U. Supratman, Aprilia Sari, N. Nurlelasari, A. Azhari, D. Harneti, R. Maharani, T. Mayanti, K. Farabi, Darwati Darwati, S. Fajriah, M. N. Azmi, Y. Shiono
{"title":"New Ergostane-type Sterol Produced by an Endophytic Fungus Fusarium phaseoli Isolated from Chisocheton macrophyllus (Meliaceae)","authors":"U. Supratman, Aprilia Sari, N. Nurlelasari, A. Azhari, D. Harneti, R. Maharani, T. Mayanti, K. Farabi, Darwati Darwati, S. Fajriah, M. N. Azmi, Y. Shiono","doi":"10.25135/rnp.334.2203.2387","DOIUrl":"https://doi.org/10.25135/rnp.334.2203.2387","url":null,"abstract":"","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":" ","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48453557","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-08-26DOI: 10.25135/rnp.354.2207.2510
Yang Yu, Ju-tao Wang, Lan Ding, Ren-nai Yang, Liang-ping Zha, Shuang Gui
: A novel β -carboline, namely Plagranline A ( 1 ), and a known alkaloid ( 2 ) were isolated from the roots of Platycodon grandiflorus . Their structure was elucidated using a combination of spectroscopic analyses and computational chemistry, including electronic circular dichroism (ECD) and optical rotatory dispersion (ORD). Alkaloids 1 and 2 exhibited moderate inhibitory effects against NO production. Interestingly, 1 and 2 are the first alkaloid constituents reported from the plant P. grandifloras.
{"title":"Plagranline A, a Novel β-carboline and the First Alkaloid Isolated from Platycodon grandiflorus","authors":"Yang Yu, Ju-tao Wang, Lan Ding, Ren-nai Yang, Liang-ping Zha, Shuang Gui","doi":"10.25135/rnp.354.2207.2510","DOIUrl":"https://doi.org/10.25135/rnp.354.2207.2510","url":null,"abstract":": A novel β -carboline, namely Plagranline A ( 1 ), and a known alkaloid ( 2 ) were isolated from the roots of Platycodon grandiflorus . Their structure was elucidated using a combination of spectroscopic analyses and computational chemistry, including electronic circular dichroism (ECD) and optical rotatory dispersion (ORD). Alkaloids 1 and 2 exhibited moderate inhibitory effects against NO production. Interestingly, 1 and 2 are the first alkaloid constituents reported from the plant P. grandifloras.","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":" ","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49271880","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-08-26DOI: 10.25135/rnp.353.2204.2432
Guanqun Zhan, Kailing Yang, Tao Yang, Xiaolei Li, Ruixi Zhou, Rongkun Miao, Yuyan Guan, Y. Teng, Zengjun Guo
: One new monoterpene alkaloid ( 1 ) and eight known compounds ( 2 – 9 ), belonging to two monoterpene alkaloids ( 1 – 2 ), one pyridine alkaloid ( 3 ), four phenylpropanoid derivatives ( 4 – 7 ), and two matrine-type alkaloids ( 8 – 9 ), were isolated from Rauvolfia vomitoria Afzel. The structure of new compound 1 was determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation. Notably, this is the first reported monoterpene alkaloids from R. vomitoria . Besides, compounds 3 , 5 , and 7 – 9 were first discovered in the Apocynaceae family and compounds 4 and 6 were first reported in the Rauvolfia genus. This is also the first example of matrine-type alkaloids reported in the Apocynaceae family, indicating that matrine-type alkaloids are not unique to the Leguminosae/Fabaceae family. All isolated compounds were evaluated for their anti-acetylcholinesterase, anti-α-glucosidase, and antioxidant activities. Compound 6 showed significant α-glucosidase inhibitory activity and remarkable DPPH radical scavenging capacity, both of which are superior to the positive controls. Molecular docking of compound 6 with α-glucosidase was further performed, suggesting that compound 6 could form hydrogen bonds with residues ALA-292, ASN-259, and ARG-263.
{"title":"A New Monoterpene Alkaloid From the Stems of Rauvolfia vomitoria","authors":"Guanqun Zhan, Kailing Yang, Tao Yang, Xiaolei Li, Ruixi Zhou, Rongkun Miao, Yuyan Guan, Y. Teng, Zengjun Guo","doi":"10.25135/rnp.353.2204.2432","DOIUrl":"https://doi.org/10.25135/rnp.353.2204.2432","url":null,"abstract":": One new monoterpene alkaloid ( 1 ) and eight known compounds ( 2 – 9 ), belonging to two monoterpene alkaloids ( 1 – 2 ), one pyridine alkaloid ( 3 ), four phenylpropanoid derivatives ( 4 – 7 ), and two matrine-type alkaloids ( 8 – 9 ), were isolated from Rauvolfia vomitoria Afzel. The structure of new compound 1 was determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation. Notably, this is the first reported monoterpene alkaloids from R. vomitoria . Besides, compounds 3 , 5 , and 7 – 9 were first discovered in the Apocynaceae family and compounds 4 and 6 were first reported in the Rauvolfia genus. This is also the first example of matrine-type alkaloids reported in the Apocynaceae family, indicating that matrine-type alkaloids are not unique to the Leguminosae/Fabaceae family. All isolated compounds were evaluated for their anti-acetylcholinesterase, anti-α-glucosidase, and antioxidant activities. Compound 6 showed significant α-glucosidase inhibitory activity and remarkable DPPH radical scavenging capacity, both of which are superior to the positive controls. Molecular docking of compound 6 with α-glucosidase was further performed, suggesting that compound 6 could form hydrogen bonds with residues ALA-292, ASN-259, and ARG-263.","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":" ","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43918064","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-08-21DOI: 10.25135/rnp.350.2205-2474
Fatma M. Abdel Bar, Nouran H. Abdel Fatah, Yhiya Amen, A. Halim, H. Saad
: Genus Lactuca L. belongs to one of the major families of flowering plants, Asteraceae. It includes about 150 species, distributed in warm and temperate areas, commonly in the Northern Hemisphere. Since ancient times, numerous Lactuca L. species have been cultivated for their economic and medicinal significance. Cultivated lettuce ( Lactuca sativa ), a representative member of the genus, is the most important leafy salad vegetable. The current review aims to provide comprehensive information on the taxonomy, phytochemistry, traditional uses, and biological activities of plants of the genus Lactuca . in L. indica -exposed cells. These results showed that, in addition to its diuretic action, L. indica exerts other actions directly on epithelial cells to protect against
{"title":"Genus Lactuca (Asteraceae): A Comprehensive Review","authors":"Fatma M. Abdel Bar, Nouran H. Abdel Fatah, Yhiya Amen, A. Halim, H. Saad","doi":"10.25135/rnp.350.2205-2474","DOIUrl":"https://doi.org/10.25135/rnp.350.2205-2474","url":null,"abstract":": Genus Lactuca L. belongs to one of the major families of flowering plants, Asteraceae. It includes about 150 species, distributed in warm and temperate areas, commonly in the Northern Hemisphere. Since ancient times, numerous Lactuca L. species have been cultivated for their economic and medicinal significance. Cultivated lettuce ( Lactuca sativa ), a representative member of the genus, is the most important leafy salad vegetable. The current review aims to provide comprehensive information on the taxonomy, phytochemistry, traditional uses, and biological activities of plants of the genus Lactuca . in L. indica -exposed cells. These results showed that, in addition to its diuretic action, L. indica exerts other actions directly on epithelial cells to protect against","PeriodicalId":21053,"journal":{"name":"Records of Natural Products","volume":" ","pages":""},"PeriodicalIF":1.9,"publicationDate":"2022-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41816476","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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