Dan Xu, Yajun Chen, Xu-Xu Cao, Jingjie Zheng, Yao Wang, Yan-Yan Ma, Kun Zhang, Deng-Gao Zhao
{"title":"Anti-inflammatory activity of phenolics from Dianella ensifolia","authors":"Dan Xu, Yajun Chen, Xu-Xu Cao, Jingjie Zheng, Yao Wang, Yan-Yan Ma, Kun Zhang, Deng-Gao Zhao","doi":"10.1016/j.phytol.2024.05.001","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.05.001","url":null,"abstract":"<div><p>A new diarylpropane (<strong>1</strong>) along with seventeen known compounds (<strong>2</strong>–<strong>18</strong>), were extracted from the entire plant of <em>Dianella ensifolia</em>. The compounds <strong>1</strong>–<strong>3</strong> were identified as a distinctive group of diarylpropanes. Their structures were determined through comprehensive spectral analysis. An anti-inflammatory activity assay revealed that compound <strong>7</strong> demonstrated significant inhibitory effects on NO generation in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells, with an IC<sub>50</sub> value of 9.93 μg/mL. Further in-depth mechanistic studies indicated that compound <strong>7</strong> suppresses LPS-induced NO production by inhibiting the activation of NF-κB, which subsequently led to a decrease in the expression of nitric oxide synthase enzymes (iNOS).</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 187-190"},"PeriodicalIF":1.7,"publicationDate":"2024-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140893485","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}
Xue-Xue Cheng , Ya-Feng Wang , Rui-Jie He , Bing-Yuan Yang , Zhang-Bin Liu , Yong-Lin Huang
{"title":"Three new quinic acid derivatives and a new shikimic acid derivative from the leaves of Castanopsis orthacantha","authors":"Xue-Xue Cheng , Ya-Feng Wang , Rui-Jie He , Bing-Yuan Yang , Zhang-Bin Liu , Yong-Lin Huang","doi":"10.1016/j.phytol.2024.04.014","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.014","url":null,"abstract":"<div><p>Three new quinic acids derivatives, 3-<em>O</em>-<em>trans-</em>caffeoyl-5-<em>O</em>-galloylquinic acid (<strong>1</strong>), 3-<em>O</em>-<em>trans</em>-caffeoly-5-<em>O</em>-galloylquinic acid methyl ester (<strong>2</strong>), 3-<em>O</em>-<em>trans</em>-caffeoyl-4-<em>O</em>-galloylquinic acid methyl ester (<strong>3</strong>), and a new shikimic acid derivative as orthacanthain A (<strong>4</strong>), along with three known compounds, 3-<em>O</em>-caffeoylquinic acid (<strong>5</strong>), methyl-3-<em>O</em>-galloylquinic acid (<strong>6</strong>), and emblifatmin (<strong>7</strong>), were isolated from the 70% methanol extract of the leaves of <em>Castanopsis orthacantha</em> France. The structures of all compounds were identified by optical rotation, MS, UV, IR, 1D and 2D NMR spectral data and comparison with literature. The IC<sub>50</sub> value of compound <strong>3</strong> was (0.024±0.009) mmol/L, which had strong inhibitory activity on α-glucosidase.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 182-186"},"PeriodicalIF":1.7,"publicationDate":"2024-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140878765","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}
Li-Guo Zheng , You-Yan Chen , Chia-Ching Liaw , Yu-Chi Lin , Su-Ying Chien , Yi-Hao Lo , Yu-Chi Tsai , Hao-Chun Hu , You-Ying Chen , Tsong-Long Hwang , Tzu-Ming Ou , Ping-Jyun Sung
{"title":"Isolation of 24-homoscalarane sesterterpenoids from a sponge of the genus Lendenfeldia","authors":"Li-Guo Zheng , You-Yan Chen , Chia-Ching Liaw , Yu-Chi Lin , Su-Ying Chien , Yi-Hao Lo , Yu-Chi Tsai , Hao-Chun Hu , You-Ying Chen , Tsong-Long Hwang , Tzu-Ming Ou , Ping-Jyun Sung","doi":"10.1016/j.phytol.2024.04.013","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.013","url":null,"abstract":"<div><p>The chemical screening of an algae-containing marine sponge identified as <em>Lendenfeldia</em> species has isolated two 24-homoscalarane sesterterpenoids, including a known compound, felixin A (<strong>1</strong>) and a new analogue, lendenfeldarane V (<strong>2</strong>). The structure of <strong>1</strong>, obtained in a previous study, was cited for the first time in this study via single-crystal X-ray diffraction analysis. The structure of <strong>2</strong> was ascertained via 2D NMR experiments and a literature review. The absolute configurations of <strong>1</strong> and <strong>2</strong> were delineated with DP4+ computation and specific optical rotation. Homoscalarane <strong>1</strong> exhibited cytotoxicity towards MG63 human osteosarcoma cells.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 177-181"},"PeriodicalIF":1.7,"publicationDate":"2024-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140807122","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}
{"title":"Four new sesquiterpenes from Carpesium faberi","authors":"Xiang-yu Zheng , Hong-xu Wan","doi":"10.1016/j.phytol.2024.04.001","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.001","url":null,"abstract":"<div><p>Four undescribed sesquiterpenes, namely faberivax A-B (<strong>1</strong>-<strong>2</strong>) and faberine A-B (<strong>3</strong>-<strong>4</strong>), were isolated from the whole plant of <em>Carpesium faberi</em>, along with nine known sesquiterpenes (<strong>5</strong>−<strong>13</strong>). The structures were identified using NMR, HRESIMS, and ECD analysis, and by comparing them with literature data. To initially explore the presence of multidrug resistance (MDR) reversal activities, molecular docking was conducted to explore the binding energies and conformations between all the isolates and P-glycoprotein. The computed binding energy data suggested that six sesquiterpenes docked into the P-glycoprotein with good binding affinity as evidenced by the lower computed binding energies ranging between −7.14 to −7.85 kcal/mol.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 171-176"},"PeriodicalIF":1.7,"publicationDate":"2024-04-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140647539","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}
Ninh Khac Thanh Tung , Hoang Thi Tuyet Lan , Tran Thuy Nga , Nguyen Thi Mai , Vu Mai Thao , Nguyen Viet Dung , Nguyen Tien Dat , Nguyen Xuan Nhiem , Nguyen Bao Tan , Hyung Min Kim , Jong Seong Kang
{"title":"Flavonoids glycosides from Camellia phanii","authors":"Ninh Khac Thanh Tung , Hoang Thi Tuyet Lan , Tran Thuy Nga , Nguyen Thi Mai , Vu Mai Thao , Nguyen Viet Dung , Nguyen Tien Dat , Nguyen Xuan Nhiem , Nguyen Bao Tan , Hyung Min Kim , Jong Seong Kang","doi":"10.1016/j.phytol.2024.04.012","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.012","url":null,"abstract":"<div><p>By combining chromatography methods, three new flavonoid glycosides, kaempferol 3-<em>O</em>-<em>α</em>-L-rhamnopyranosyl-(1→2)-<em>β</em>-D-glucopyranosyl-(1→2)-<em>α</em>-L-rhamnopyranoside (<strong>1</strong>), kaempferol 3-<em>O-</em>(4-acetyl)-<em>α</em>-L-rhamnopyranosyl-(1→2)-<em>β</em>-D-glucopyranosyl-(1→2)-<em>α</em>-L-rhamnopyranoside (<strong>2</strong>), and (2 <em>R</em>,3 <em>S</em>) 5,7,4′-tetrahydroxyflavanonol 3-<em>O-</em>(4-acetyl)-<em>α</em>-L-rhamnopyranosyl-(1→2)-<em>β</em>-D-glucopyranosyl-(1→2)-<em>α</em>-L-rhamnopyranoside (<strong>3</strong>) as well as three known compounds, chrysandroside A (<strong>4</strong>), <em>p</em>-hydroxybenzaldehyde (<strong>5</strong>), and <em>p</em>-hydroxybenzoic acid (<strong>6</strong>) were isolated from the leaves of <em>Camellia phanii</em> Hakoda & Ninh. Their structure was elucidated by 1D and 2D-NMR spectra and compared to previously published in literature. In addition, all compounds were evaluated for their ability to inhibit <em>α</em>-glucosidase activity. As the results, flavonoid glycosides <strong>1</strong>-<strong>3</strong> inhibited <em>α</em>-glucosidase activity with IC<sub>50</sub> values of 276.8 ± 19.4, 258.9 ± 24.3, and 341.4 ± 25.6 µM; phenolics (<strong>5</strong> and <strong>6</strong>) inhibited <em>α</em>-glucosidase activity with IC<sub>50</sub> values of 295.5 ± 15.1 and 217.4 ± 23.6 µM, respectively.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 166-170"},"PeriodicalIF":1.7,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140640981","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}
Juliane M. dos S. Silva , Larissa A. Rolim , Jackson R.G. da S. Almeida , Thiala A. Feitosa , Daniel A. Nery , Camila de Souza Araújo , Ana Paula de Oliveira
{"title":"Chemometric studies in Hymenaea martiana","authors":"Juliane M. dos S. Silva , Larissa A. Rolim , Jackson R.G. da S. Almeida , Thiala A. Feitosa , Daniel A. Nery , Camila de Souza Araújo , Ana Paula de Oliveira","doi":"10.1016/j.phytol.2024.04.008","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.008","url":null,"abstract":"<div><p><em>Hymenaea martiana</em> Hayne's bark and resin are widely used in folk medicine for the treatment of various diseases, however the indiscriminate extractivism of its barks brings damage to its metabolism and development. In view this, the discovery of ways for a more rational use of the species becomes relevant. This study aims to evaluate possible similarities in chemical composition profile of different parts from <em>H</em>. <em>martiana</em> (barks, stalks and leaves) through the fingerprint by ¹H-NMR and FT-IR techniques. The principal component analysis (PCA) showed metabolic similarities between the barks and stalks in two spectroscopic techniques used. The similarity is explained by presence of sucrose and pinitol in both segments as main compounds of segments. The antioxidant activity profile, showed similarity corroborating thus, with observed in metabolic analysis, where IC<sub>50</sub> values showed no statistical difference between the barks (10.73 ± 0.12 µg.mL<sup>−1</sup>) and stalks (8.40 ± 0.58 µg.mL<sup>−1</sup>). In our results, the PCA showed a difference in the leaves fingerprint of one specimen collected. As pointed also by PCA analysis, this individual was over stress situation which promoted the biosynthesis of monoterpene linalool, a compound with defensor properties from plants. Furthermore, the similarities between the barks and stalks observed may be an indication of similar biological activity and may direct other studies in order to reduce the extraction of the barks and minimize the damage to the species.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 158-165"},"PeriodicalIF":1.7,"publicationDate":"2024-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140632802","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}
{"title":"Two new pregnane glycosides from the flower buds of Dregea volubilis","authors":"Xiao-Dong Zhang , Bin Qiu , Jie Yu , Ni-Man Bao","doi":"10.1016/j.phytol.2024.04.006","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.006","url":null,"abstract":"<div><p>Two new pregnane glycosides, drevoluoside R (<strong>1</strong>) and drevoluoside S (<strong>2</strong>), along with one known analogue, degeoside A<sub><em>a</em>1</sub> (<strong>3</strong>), were isolated from the fresh flower buds of <em>Dregea</em>. <em>volubilis.</em> The structures of the new metabolites were established on the basis of detailed spectroscopic analysis. Compounds <strong>1–3</strong> were evaluated for their cytotoxicity against five human cancer cell lines with cisplantin as a positive control.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 149-152"},"PeriodicalIF":1.7,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140558907","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}
Shaymaa M. Mohamed , Anber F. Mohammed , Samir A. Ross
{"title":"Thunbergiside A: An unprecedented neolignan isolated from Gardenia thunbergia L. f. and the antifungal activity of selected phytochemicals","authors":"Shaymaa M. Mohamed , Anber F. Mohammed , Samir A. Ross","doi":"10.1016/j.phytol.2024.04.009","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.009","url":null,"abstract":"<div><p>Phytochemical investigation of <em>Gardenia thunbergia</em> L. f. aerial parts led to the isolation of a previously undescribed neolignan <strong>13,</strong> designated (thunbergiside A). This compound is classified as 2,3-dihydrobenzofuran that features a unique, highly substituted skeleton with functional diversity. The absolute configuration was established by comparing its experimental ECD spectrum and optical rotation values with those of related neolignans. In addition, seventeen diverse phytoconstituents were identified for the first time from this plant, expanding our knowledge of its chemical composition. These included oleanane-type saponins, phenolic derivatives, lignans, and neolignans, which serve as valuable chemotaxonomic markers. Considering the frequent emergence of infectious diseases, it is worth exploring additional antimicrobial agents. Selected isolated compounds were assessed for their antimycotic properties in an investigation for potential anti-infective agents. Various chromatographic procedures, spectroscopic, spectrometric analyses, and molecular modelling studies were employed for phytochemical investigation and structural characterization. Furthermore, the alamarBlue-based viability assay was employed for antifungal evaluation against three pathogenic fungi. Specifically, saponin <strong>17</strong>, 3-<em>O</em>-(β-ᴅ-glucuronopyranoside) oleanolic acid, displayed moderate antifungal activity (IC<sub>50</sub> = 11 µg/mL) against <em>Candida albicans</em>. Overall, this study identified an unprecedented neolignan along with other diverse constituents from <em>Gardenia thunbergia</em>. Moreover, the study presented a potential scaffold for antifungal drug development.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 153-157"},"PeriodicalIF":1.7,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140558908","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}
Chi Song , Ze-Yu Zhao , Jin-Xin Zhu , Yi Zang , Juan Xiong , Jia Li , Jin-Feng Hu
{"title":"Annamiacids A and B: Two dissymmetric bis-diterpenes containing a rare ketal-γ-lactone motif from Podocarpus annamiensis and their inhibitory effects on ATP-citrate lyase","authors":"Chi Song , Ze-Yu Zhao , Jin-Xin Zhu , Yi Zang , Juan Xiong , Jia Li , Jin-Feng Hu","doi":"10.1016/j.phytol.2024.04.010","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.010","url":null,"abstract":"<div><p>Two undescribed dissymmetric <em>bis</em>-diterpenes, annamiacids A (<strong>1</strong>) and B (<strong>2</strong>), were isolated from the renewable twigs and leaves of <em>Podocarpus annamiensis,</em> a ‘vulnerable’ conifer endemic to China. Their structures and absolute configurations were determined by spectroscopic and computational methods. The homodimeric (abietane-<em>O</em>-abietane, <strong>1</strong>) and heterodimeric (abietane-<em>O</em>-totarane, <strong>2</strong>) dimers were constructed from an identical phenolic abietane unit through an ether linkage with a phenolic abietane acid and a phenolic totarane acid, respectively. Both comprise a rare intramolecular 6-ketal-19,6-<em>γ</em>-lactone motif. Compound <strong>2</strong> could significantly inhibit ATP-citrate lyase with an IC<sub>50</sub> value of 5.92 <em>μ</em>M. A molecular docking study disclosed alternative H-bonds/interacting amino acid residues and binding pockets between <strong>2</strong> and the ACL enzyme when compared with those of compound <strong>1</strong>, which supports their <em>in vitro</em> data.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 142-148"},"PeriodicalIF":1.7,"publicationDate":"2024-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140555332","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}
Yong-xun Yang , Qun Wang , Xiao-nian Li , Hai-yan Huang , Hao Geng
{"title":"Absolute stereochemistry and anti-inflammatory activity of cycloisobrachycoumarin, brachycromone, cyclobrachycoumarin, and cyclobrachycoumarin 2’-epimer from Gerbera delavayi","authors":"Yong-xun Yang , Qun Wang , Xiao-nian Li , Hai-yan Huang , Hao Geng","doi":"10.1016/j.phytol.2024.04.011","DOIUrl":"https://doi.org/10.1016/j.phytol.2024.04.011","url":null,"abstract":"<div><p>Four isomeric 5-methyl-4-hydroxycoumarin-monoterpene hybrids (MMHs) comprising three known MMHs, cycloisobrachycoumarin (<strong>1</strong>), brachycromone (<strong>2</strong>), cyclobrachycoumarin (<strong>3</strong>), and a new epimer of <strong>3</strong>, cyclobrachycoumarin 2’-epimer (<strong>4</strong>) were isolated from <em>Gerbera delavayi</em>. The absolute configuration of <strong>1–4</strong> was elucidated by utilizing ECD calculations and X-ray diffraction analysis. As a result, the absolute configurations of C-2’ and C-3’ in <strong>1</strong> and <strong>2</strong> were revised to be 2′<em>S</em>, 3′<em>R</em> and 2′<em>R</em>, 3′<em>S</em> respectively. Consequently, the diagnostic negative/positive cotton effect (CE) at around 210–220 nm for the stereochemistry of angular/linear furano-MMHs is discussed and formulated. Moreover, compounds <strong>1</strong>–<strong>4</strong> were tested for the nitric oxide (NO) inhibitory activity by using lipopolysaccharide (LPS)-induced RAW 264.7 cells <em>in vitro</em>. The results showed that <strong>1</strong>–<strong>4</strong> significantly inhibited NO production at the concentration of 10.0 μM, indicating that <strong>1–4</strong> possessed potent anti-inflammatory activity.</p></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"61 ","pages":"Pages 135-141"},"PeriodicalIF":1.7,"publicationDate":"2024-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140555331","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}