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Polyoxygenated cyclohexenes from the fruits of Uvaria cordata (Dunal) Alston 来自 Uvaria cordata (Dunal) Alston 果实的聚氧环己烯
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-28 DOI: 10.1016/j.phytol.2024.05.011
Virayu Suthiphasilp , Panom Winyayong , Phunrawie Promnart
{"title":"Polyoxygenated cyclohexenes from the fruits of Uvaria cordata (Dunal) Alston","authors":"Virayu Suthiphasilp ,&nbsp;Panom Winyayong ,&nbsp;Phunrawie Promnart","doi":"10.1016/j.phytol.2024.05.011","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.05.011","url":null,"abstract":"<div><p>The phytochemical investigation of <em>Uvaria cordata</em> (Dunal) Alston resulted in the isolation and identification of eight cyclohexene derivatives (<strong>1</strong>–<strong>8</strong>) and a tetrahydroxanthene-1,3(2<em>H</em>)-dione (<strong>9</strong>). Among them, compounds <strong>1</strong> and <strong>2</strong> were previously undescribed compounds, and their structures were characterized by intensive spectroscopic data and HRESITOFMS. Compound <strong>7</strong> ((+)-(5 <em>S</em>)-grandiuvarone) exhibited NO production inhibitory with an IC<sub>50</sub> value of 34.1 μM, which was better than the standard compound, indomethacin (IC<sub>50</sub> = 51.3 μM).</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 270-274"},"PeriodicalIF":1.7,"publicationDate":"2024-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141163849","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}
引用次数: 0
Recent advance in the development of N-heterocyclic derivatives as anti-SARS-CoV-2 inhibitors: A review 开发 N-杂环衍生物作为抗 SARS-CoV-2 抑制剂的最新进展:综述
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-28 DOI: 10.1016/j.phytol.2024.04.016
Walid Ettahiri , Mohamed Adardour , Siham Alaoui , Abderrazzak Elmoutaouakil Ala Allah , Maryem Aichouch , Rajae Salim , Youssef Ramli , Abdelhakim Bouyahya , Mustapha Taleb
{"title":"Recent advance in the development of N-heterocyclic derivatives as anti-SARS-CoV-2 inhibitors: A review","authors":"Walid Ettahiri ,&nbsp;Mohamed Adardour ,&nbsp;Siham Alaoui ,&nbsp;Abderrazzak Elmoutaouakil Ala Allah ,&nbsp;Maryem Aichouch ,&nbsp;Rajae Salim ,&nbsp;Youssef Ramli ,&nbsp;Abdelhakim Bouyahya ,&nbsp;Mustapha Taleb","doi":"10.1016/j.phytol.2024.04.016","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.016","url":null,"abstract":"<div><p>The pandemic caused by COVID-19 hinders everything on earth, including physical and mental health, daily life and the global economy. Currently, there are no defined drugs and few vaccines available on the market to combat SARS-CoV-2. A number of organic compounds have been designed and tested against the virus, but they have not shown promising activities. <em>N</em>-heterocycles, which are abundant in nature, is a significant source of pharmacologically active compounds. <em>N</em>-heterocycles have the potential to exert Anti- SARS-CoV-2 activity <em>via</em> various antiviral mechanisms, and some of them, have already used in clinics or under clinical evaluations for the processing of COVID-19. Therefore, <em>N</em>-heterocycles occupies an important position in the discovery of novel anti-SARS-CoV-2 agents. The current study is an effort to collect information’s covering the articles published from 2019 to the beginning of this year 2022, regarding the recent development of <em>N</em>-heterocycles derivatives; indazole, triazolopyrimidine, pyrazolopyrimidine, quinoxaline, benzimidazole, benzodiazepine, indole, and quinoline, as potential anti-SARS-CoV-2 agents, their structure-activity relationship and mechanisms of action.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 247-269"},"PeriodicalIF":1.7,"publicationDate":"2024-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141163848","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}
引用次数: 0
Five undescribed drimane-type sesquiterpenes from Polygonum hydropiper 何首乌中五种未被描述的 drimane 型倍半萜类化合物
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-22 DOI: 10.1016/j.phytol.2024.05.007
Chen-xi Wang , Chen-yue Li , Meng-kun Yan , Wen-qiong Wang , Li-jiang Xuan
{"title":"Five undescribed drimane-type sesquiterpenes from Polygonum hydropiper","authors":"Chen-xi Wang ,&nbsp;Chen-yue Li ,&nbsp;Meng-kun Yan ,&nbsp;Wen-qiong Wang ,&nbsp;Li-jiang Xuan","doi":"10.1016/j.phytol.2024.05.007","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.05.007","url":null,"abstract":"<div><p>In order to find various structural and active compounds, 95 % ethanol extract of <em>P. hydropiper</em> was investigated to obtain five undescribed drimane sesquiterpenes 3-O-angeloyl-11-O-methyldanilol (<strong>1</strong>), 3-O-tigloyl-11-O-methyldanilol (<strong>2</strong>), 3-O-(3′-methylbutenoyl)-11-O-methyldanilol (<strong>3</strong>), 3-O-(2′-metylbutanoyl)-11-O-methyldanilol (<strong>4</strong>) and 2α, 3β-ditigloyloxy-11-O-methylisodrimeninol (<strong>5</strong>). Their structures were established by extensive spectroscopic analyses. Furthermore, 3-O-angeloyl-11-O-methyldanilol (<strong>1</strong>) showed moderate anti-platelet aggregation activity according to in <em>vitro</em> pharmacological evaluation.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 236-241"},"PeriodicalIF":1.7,"publicationDate":"2024-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141078346","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}
引用次数: 0
Isolation, absolute configuration and immunosuppressant activities of pyrrole and furanone derivatives from the edible mushroom Grifola frondosa 食用菌中吡咯和呋喃酮衍生物的分离、绝对构型和免疫抑制活性
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-22 DOI: 10.1016/j.phytol.2024.05.009
Chun Tian , Fan Xu , Yu He , Hong-Lian Ai , Bao-Bao Shi , Ji-Kai Liu
{"title":"Isolation, absolute configuration and immunosuppressant activities of pyrrole and furanone derivatives from the edible mushroom Grifola frondosa","authors":"Chun Tian ,&nbsp;Fan Xu ,&nbsp;Yu He ,&nbsp;Hong-Lian Ai ,&nbsp;Bao-Bao Shi ,&nbsp;Ji-Kai Liu","doi":"10.1016/j.phytol.2024.05.009","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.05.009","url":null,"abstract":"<div><p>Chemical investigation on methanol extract of the fruiting bodies of <em>Grifola frondosa</em> led to the isolation of seven pyrrole alkaloids and two furanone metabolites, including two undescribed ones (compounds <strong>1</strong> and <strong>3</strong>). The structures were established by spectroscopic data analysis and quantum chemical calculations. The absolute configuration of <strong>2</strong> was established for the first time on the basis of its optical rotation and electronic circular dichroism aided with quantum calculations. Compound <strong>1</strong> showed the suppressive activity against the cell proliferation of LPS-induced B lymphocytes with IC<sub>50</sub> value of 30.53 <em>μ</em>M and Con A-induced T lymphocytes with IC<sub>50</sub> value of 46.79 <em>μ</em>M, respectively.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 242-246"},"PeriodicalIF":1.7,"publicationDate":"2024-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141083816","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}
引用次数: 0
Cytotoxic activities of metallic nanoparticles biosynthesized using plant extracts and pure compounds from Cephalaria species 利用头孢属植物提取物和纯化合物生物合成的金属纳米粒子的细胞毒活性
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-22 DOI: 10.1016/j.phytol.2024.05.004
Mohamed Chanfiou Mkouboi , Nazli Boke Sarikahya , Ayse Nalbantsoy , Murat Elibol
{"title":"Cytotoxic activities of metallic nanoparticles biosynthesized using plant extracts and pure compounds from Cephalaria species","authors":"Mohamed Chanfiou Mkouboi ,&nbsp;Nazli Boke Sarikahya ,&nbsp;Ayse Nalbantsoy ,&nbsp;Murat Elibol","doi":"10.1016/j.phytol.2024.05.004","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.05.004","url":null,"abstract":"<div><p>Green nanotechnology has been focused on new concepts and fundamental research to produce nanoparticles in high rates and low risks by the use of different sources such as microorganisms and plants. Due to the several constituents in secondary metabolites, plants play an important role in nanomaterial synthesis known as ecofriendly methods which acquired important potential in different studies. The current work aimed to synthesize different silver and zinc-based nanoparticles using <em>Cephalaria tchihatchewii</em> via phytobiological methods involving metallic solutions, organic extracts, and isolated compounds. Sixteen types of nanoparticles were determined in between 50 and 297 nm as diameter and characterized using ultraviolet-visible spectrophotometer, dynamic light scattering, scanning electron microscopy and fourier transform infrared spectroscopy. The cytotoxic activities of nanoparticles were evaluated against human lung cancer (A549), breast cancer (MDA-MB-231), prostate cancer (PC3), and healthy lung (CCD-34Lu) cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2 H-tetrazolium bromide MTT assay utilizing doxorubicin as a positive control. Against PC3 cells, the cytotoxic activity of silver nitrate and loganin-AgNPs show significant inhibition with IC<sub>50</sub> values of 2.39 ± 0.16 and 7.84 ± 1.21 respectively compared with doxorubicin (12.99 ± 1.57 µg/mL). A moderate inhibition activity was observed for Zinc sulfate, elmalienoside-B-AgNPs, methyl glycoside-AgNPs, and luteolin-7-<em>O</em>-glycoside-AgNPs with IC<sub>50</sub> values of 22. 27± 0.18, 11.59 ± 0.82, 12.43 ± 0.37 and 13.26 ± 1.63 µg/mL, respectively. The inhibition activity against human breast cancer cells MDA-MB-231 was significantly reported with silver nitrate (2.25 ± 0.62 µg/mL), and elmalienoside-B-AgNPs (11.48 ± 0.46 µg/mL) compared with doxorubicin (11.61± 0.68 µg/mL). The cytotoxicity activities, make <em>Cephalaria tchihatchewii</em> plant a suitable candidate in different biopharmaceutical usages especially in anticancer activities. This study will provide a clear perspective on nanoparticles containing green synthesized pure compounds and the reaction mechanism of their activities.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 226-235"},"PeriodicalIF":1.7,"publicationDate":"2024-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141078345","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}
引用次数: 0
Three new phenolic glycosides from Rhus chinensis leaves 从盐肤木叶中提取的三种新的酚苷
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-21 DOI: 10.1016/j.phytol.2024.05.002
Xin Chen , Zhengxiang Tong , Rongtao Li , Jianguo Zeng
{"title":"Three new phenolic glycosides from Rhus chinensis leaves","authors":"Xin Chen ,&nbsp;Zhengxiang Tong ,&nbsp;Rongtao Li ,&nbsp;Jianguo Zeng","doi":"10.1016/j.phytol.2024.05.002","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.05.002","url":null,"abstract":"<div><p>Three new phenolic glycosides, including 3-hydroxy-5-methylphenol 1-<em>O</em>-<em>β</em>-D-(6′-<em>O</em>-cinnamoyl)-glucopyranoside (<strong>1</strong>), 3-hydroxy-5-methylphenol 1-<em>O</em>-<em>β</em>-D-(6′-<em>O</em>-<em>p</em>-hydroxycinnamoyl)-glucopyranoside (<strong>2</strong>), 3-hydroxy-5-methylphenol 1-<em>O</em>-<em>β</em>-D-(6′-<em>O</em>-<em>p</em>-hydroxybenzoyl)-glucopyranoside (<strong>3</strong>), were isolated from the leaves of <em>Rhus chinensis</em> Mill, together with seven known compounds (<strong>4-10</strong>). Their structures were elucidated on the basis of extensive NMR spectral and high resolution mass spectrometry analysis. Among the isolated compounds, butein (4), quercetin (5), and ethyl gallate (6) exhibited moderate NO production in RAW264.7 cells induced by LPS with IC<sub>50</sub> values of 21.29 ± 0.54, 34.26 ± 2.09 and 42.59 ± 0.11 <em>μ</em>M, compared with postive control L-NMMA (a nitric oxide synthase inhibitor, IC<sub>50</sub> 38.41 ± 0.32 <em>μ</em>M).</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 222-225"},"PeriodicalIF":1.7,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141078344","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}
引用次数: 0
Albifimbrins A and B, a pair of epimeric tetrahydrofuran-containing linear polyketide derivatives from the marine-derived fungus Albifimbria verrucaria CD1-4 Albifimbrins A 和 B,一对来自海洋真菌 Albifimbria verrucaria CD1-4 的含四氢呋喃的线性多酮衍生物
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-20 DOI: 10.1016/j.phytol.2024.05.006
Sheng-Tao Fang, Yin-Ping Song, Zhen-Zhen Shi, Nai-Yun Ji
{"title":"Albifimbrins A and B, a pair of epimeric tetrahydrofuran-containing linear polyketide derivatives from the marine-derived fungus Albifimbria verrucaria CD1-4","authors":"Sheng-Tao Fang,&nbsp;Yin-Ping Song,&nbsp;Zhen-Zhen Shi,&nbsp;Nai-Yun Ji","doi":"10.1016/j.phytol.2024.05.006","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.05.006","url":null,"abstract":"<div><p>A pair of new epimeric polyketides, named albifimbrins A and B (<strong>1</strong> and <strong>2</strong>), were isolated from the cultures of the shellfish-derived fungus <em>Albifimbria verrucaria</em> CD1–4. Their structures were determined by extensive spectroscopic analysis including HR-MS, 1D and 2D NMR data, together with the CD exciton chirality method. Compounds <strong>1</strong> and <strong>2</strong> possess unusual tetrahydrofuran moiety in their linear molecule structures. The antimicroalgal assay indicated that compounds <strong>1</strong> and <strong>2</strong> shown moderate inhibitory activities against marine harmful microalgae, <em>Prorocentrum donghaiense</em>, <em>Amphidinium carterae</em> and <em>Heterocapsa circulariaquama</em>.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 218-221"},"PeriodicalIF":1.7,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141068434","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}
引用次数: 0
Simultaneous characterization and quantification of 25 flavonoid compounds in Actinidia arguta Miq. leaves by HPLC-DAD and screening for their inhibitory activity on α‑glucosidase 利用 HPLC-DAD 同时表征和定量放线菌叶中的 25 种黄酮类化合物,并筛选其对α-葡萄糖苷酶的抑制活性
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-14 DOI: 10.1016/j.phytol.2024.04.015
Yu-Fei Hou , Lu Bai , Shao-Jing Liu , Sen Guo , Ya-Long Wang , Chi-Tang Ho , Nai-Sheng Bai
{"title":"Simultaneous characterization and quantification of 25 flavonoid compounds in Actinidia arguta Miq. leaves by HPLC-DAD and screening for their inhibitory activity on α‑glucosidase","authors":"Yu-Fei Hou ,&nbsp;Lu Bai ,&nbsp;Shao-Jing Liu ,&nbsp;Sen Guo ,&nbsp;Ya-Long Wang ,&nbsp;Chi-Tang Ho ,&nbsp;Nai-Sheng Bai","doi":"10.1016/j.phytol.2024.04.015","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.015","url":null,"abstract":"<div><p><em>A. arguta</em> leaves, as an important by-product during the ripening of <em>A. arguta</em> fruits, are usually discarded. It contains numerous flavonoid components. In the present research, a simple and reproducible HPLC-DAD method was established and verified for simultaneous identification and quantification analysis of 25 flavonoid components in <em>A. arguta</em> leaves. The findings indicated that the highest concentration of flavonoid compounds in <em>A. arguta</em> leaves was quercetin (<strong>2</strong>), with a content of 8.97 ± 0.09 mg/g. The content of flavonoids in samples from different cultivation bases was different, indicating that the varied flavonoid contents are possibly determined by geographical variance. This method can be used for the quality control of <em>Actinidia arguta</em>. The 25 flavonoids showed good α-glucosidase inhibitory activity with IC<sub>50</sub> values ranging from 0.35 to 4.15 mM, and the activity difference varied with the different structures. 2\"-<em>O</em>-galloylhyperin (<strong>18</strong>) showed the best antihyperglycemic action (IC<sub>50</sub> = 0.35 ± 0.01 mM), followed by quercetin (<strong>2</strong>, IC<sub>50</sub> = 0.38 ± 0.01 mM), quercetin 4′-<em>O</em>-galactoside (<strong>19</strong>, IC<sub>50</sub> = 0.41 ± 0.01 mM), kaempferol (<strong>3</strong>, IC<sub>50</sub> = 0.42 ± 0.01 mM), and kaempferol-3-rutinoside (<strong>6</strong>, IC<sub>50</sub> = 0.53 ± 0.01 mM). Molecular docking analysis demonstrated that the interaction modes of these five stronger inhibitors with α-glucosidase were mainly hydrogen bonding and hydrophobic interaction. The results showed that compounds with different structural skeletons interacted with different amino acid residues and exerted different degrees of α-glucosidase inhibition. Therefore, <em>A. arguta</em> leaves and their flavonoids may be beneficial against diabetes, and higher levels of flavonoids are considered to have greater potential for medicinal use.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 208-217"},"PeriodicalIF":1.7,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140918223","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}
引用次数: 0
New Flavonoids from the leaves and stems of Sedum formosanum (Crassulaceae) 从景天科植物(Sedum formosanum)的叶和茎中提取的新黄酮类化合物
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-10 DOI: 10.1016/j.phytol.2024.05.003
Takayuki Mizuno , Takahisa Nakane , Hari Prasad Devkota , Takuro Ito , Goro Kokubugata , Tsukasa Iwashina
{"title":"New Flavonoids from the leaves and stems of Sedum formosanum (Crassulaceae)","authors":"Takayuki Mizuno ,&nbsp;Takahisa Nakane ,&nbsp;Hari Prasad Devkota ,&nbsp;Takuro Ito ,&nbsp;Goro Kokubugata ,&nbsp;Tsukasa Iwashina","doi":"10.1016/j.phytol.2024.05.003","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.05.003","url":null,"abstract":"<div><p>As a series of the phytochemical research of the family Crassulaceae, the flavonoids of <em>Sedum formosanum</em> from two Taiwanese and one Japanese sites were isolated and characterized by UV spectra, HR-MS, LC-MS, acid hydrolysis, NMR, and HPLC and TLC comparisons with authentic samples. Eight new flavonoids (<strong>21</strong>, <strong>22</strong>, <strong>24</strong>-<strong>26</strong> and <strong>28</strong>-<strong>30</strong>) including two flavones and six isoflavones were isolated from the leaves and stems, together with 24 known compounds (<strong>1</strong>-<strong>20</strong>, <strong>23</strong>, <strong>27</strong>, <strong>31</strong> and <strong>32</strong>), and identified as chrysoeriol 7-<em>O</em>-[6´´-(3-hydroxy-3-methylglutaroyl)glucoside] (<strong>21</strong>), chrysoeriol 7-<em>O</em>-[6´´-(5´´´-methoxy-3-hydroxy-3-methyglutaroyl)glucoside] (<strong>22</strong>), 3´-<em>O</em>-methylorobol 7-<em>O</em>-rutinoside (<strong>24</strong>), 3´-<em>O</em>-methylorobol 7-<em>O</em>-arabinosyl-(1→2)-glucoside (<strong>25</strong>), 3´-<em>O</em>-methylorobol 7-<em>O</em>-arabinosyl-(1→6)-glucoside (<strong>26</strong>), orobol 3´,4´-dimethyl ether 7-<em>O</em>-rutinoside (<strong>28</strong>), orobol 3´,4´-dimethyl ether 7-<em>O</em>-sophoroside (<strong>29</strong>) and orobol 3´,4´-dimethyl ether 7-<em>O</em>-arabinosyl-(1→6)-glucoside (<strong>30</strong>). The samples were collected in three sites of Taiwan and Japan, and geographic chemical variation was observed among their sites.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 198-207"},"PeriodicalIF":1.7,"publicationDate":"2024-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140906729","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}
引用次数: 0
Naturally occurring eugenin: Biosynthesis, distribution, bioactivity, and therapeutic potential 天然的丁香酚:生物合成、分布、生物活性和治疗潜力
IF 1.7 4区 生物学
Phytochemistry Letters Pub Date : 2024-05-09 DOI: 10.1016/j.phytol.2024.04.017
Lutfun Nahar , Waed Alsheikh , Kenneth J. Ritchie , Satyajit D. Sarker
{"title":"Naturally occurring eugenin: Biosynthesis, distribution, bioactivity, and therapeutic potential","authors":"Lutfun Nahar ,&nbsp;Waed Alsheikh ,&nbsp;Kenneth J. Ritchie ,&nbsp;Satyajit D. Sarker","doi":"10.1016/j.phytol.2024.04.017","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.017","url":null,"abstract":"<div><h3>Introduction</h3><p>Eugenin (5-hydroxy-7-methoxy-2-methyl-4H-chromen-4-one) is a bioactive phytoalexin mainly found as a bitter component in carrots (<em>Daucus carota</em> L.; Apiaceae) and cloves [<em>Syzygium aromaticum</em> (L.) Merr. &amp; L. M. Perry; Myrtaceae].</p></div><div><h3>Materials and methods</h3><p>An extensive literature search was performed involving various established databases like Web of Science, PubMed, Science Direct, Dictionary of Natural Products and Google Scholar, using the keyword ‘eugenin’. The literature reports that describe various aspects of naturally occurring eugenin, e.g., isolation, structure elucidation, biosynthesis, bioactivity studies and therapeutic potential, have been included in this review, while the papers that present total synthesis or structural modifications of eugenin have been excluded.</p></div><div><h3>Results</h3><p>Eugenin, biosynthesized from the acetate-malonate pathway, has been reported from at least 22 plant species from 13 families. It has also been found in two fungal species, <em>Aschersonia confluens</em> and <em>Chaetomium minutum</em>. <em>Dacaus carota</em> and <em>Syzygium aromaticum</em> are two major sources of this chromone. Antimalarial, antimicrobial, antioxidant, antiplatelet aggregation, antiviral, cytotoxic, immunosuppressive/immunomodulatory, osteogenesis-inducing, pyrolyl endopeptidase (PEP)-inhibitory and blue-green algae growth inhibitory activities of eugenin have been reported in the literature. Among these bioactivities, antioxidant, antiplatelet aggregation, immunosuppressive/immunomodulatory activities of eugenin and its <em>in silico</em> prediction of antiviral property against severe-acute-respiratory-syndrome-related coronavirus-2 <strong>(</strong>SARS-CoV-2) activity may have some therapeutic potential.</p></div><div><h3>Conclusion</h3><p>The distribution of eugenin is rather limited to a few plant species and only a couple of fungal species. Based on the reported bioactivities, it could be concluded that this chromone might have some potential as a template for new drug development.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 191-197"},"PeriodicalIF":1.7,"publicationDate":"2024-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140893486","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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