Pub Date : 2025-11-11DOI: 10.1016/j.phytol.2025.104076
Xiao-Yan Duan , Hui Yan , Jun Yang , Ji-Feng Luo , Hataichanok Pandith , Terd Disayathanoowat , Angkhana Inta , Yue-Hu Wang
The role of fungi in agarwood resin formation remains incompletely understood. This study investigated the metabolic effects of Botryosphaeria dothidea strain ket49 on the nonresinous heartwood of Aquilaria sinensis. HPLC analysis revealed that, compared with the control treatment, fermentation with ket49 induced a time-dependent metabolic shift, markedly increasing the accumulation of agarotetrol, a pharmacopeial marker, by 4.5-fold. UPLCQTOFMS/MS analysis of the fermented extract tentatively revealed 14 2-(2-phenylethyl)chromones. Subsequent isolation yielded 11 compounds, including the new (R)-2-[2-hydroxy-2-(2-hydroxyphenyl)ethyl]chromone (1). These findings revealed the possibility that 2-(2-phenylethyl)chromones are hydroxylated by this fungus. The increase in agarotetrol production by fungi may be a sustainable strategy for high-quality agarwood induction.
{"title":"Botryosphaeria dothidea fermentation enhances agarotetrol accumulation in the nonresinous heartwood of Aquilaria sinensis","authors":"Xiao-Yan Duan , Hui Yan , Jun Yang , Ji-Feng Luo , Hataichanok Pandith , Terd Disayathanoowat , Angkhana Inta , Yue-Hu Wang","doi":"10.1016/j.phytol.2025.104076","DOIUrl":"10.1016/j.phytol.2025.104076","url":null,"abstract":"<div><div>The role of fungi in agarwood resin formation remains incompletely understood. This study investigated the metabolic effects of <em>Botryosphaeria dothidea</em> strain ket49 on the nonresinous heartwood of <em>Aquilaria sinensis</em>. HPLC analysis revealed that, compared with the control treatment, fermentation with ket49 induced a time-dependent metabolic shift, markedly increasing the accumulation of agarotetrol, a pharmacopeial marker, by 4.5-fold. UPLC<img>QTOF<img>MS/MS analysis of the fermented extract tentatively revealed 14 2-(2-phenylethyl)chromones. Subsequent isolation yielded 11 compounds, including the new (<em>R</em>)-2-[2-hydroxy-2-(2-hydroxyphenyl)ethyl]chromone (<strong>1</strong>). These findings revealed the possibility that 2-(2-phenylethyl)chromones are hydroxylated by this fungus. The increase in agarotetrol production by fungi may be a sustainable strategy for high-quality agarwood induction.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104076"},"PeriodicalIF":1.4,"publicationDate":"2025-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145516682","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 : 2025-11-11DOI: 10.1016/j.phytol.2025.104073
Latifah Gunawan , Al Arofatus Naini , Desi Harneti , Kindi Farabi , Sofa Fajriah , Elpri Eka Permadi , Sri Rahayu , Siriporn Jungsuttiwong , Unang Supratman
Hydroperoxides (–OOH) represent rare but biologically intriguing motifs in plant secondary metabolites, particularly within sesquiterpenoids. Phytochemical investigation of Dysoxylum amooroides yielded an undescribed sesquiterpenoid, amooroxyline A (1), together with 4β,10α-dihydroxyaromadendrane (2). The structure and absolute configuration of 1 were established by ECD analysis. Cytotoxicity assays revealed 1 inactive on MCF-7, while 2 showed moderate selective inhibition (IC₅₀ = 20.1 μM), with neither affecting normal CV-1 cells. In addition, molecular docking centered on the hydroperoxide scaffold (1 and related 10β,11-dihydroxy-1β-hydroperoxide-4αH,5αH,7αH-guaiane analogue) supported these results, showing weaker binding affinities to ESR1, ESR2, and aromatase compared to native ligands. Further in silico exploration suggested potential interactions with BACE1 and Plasmodium falciparum Falcipain-2, highlighting guaiane hydroperoxides as promising chemotypes for future studies in degenerative and infectious disease contexts.
氢过氧化物（-OOH）是植物次生代谢物中罕见但生物学上有趣的基序，特别是在倍半萜类化合物中。通过植物化学研究，得到了一种未描述的倍半萜类物质，amooroxyline A(1)和4β，10α-二羟基腺嘌呤(2)。通过ECD分析确定了1的结构和绝对构型。细胞毒性试验显示1对MCF-7无活性，而2显示中等选择性抑制（IC₅₀= 20.1 μM），两者都不影响正常的CV-1细胞。此外，以氢过氧化物支架为中心的分子对接（1和相关的10β，11-二羟基-1β-氢过氧化物-4α h，5αH，7α h -瓜蓝烷类似物）支持了这些结果，显示与天然配体相比，对ESR1， ESR2和芳香化酶的结合亲和力较弱。进一步的硅片探索提示了与BACE1和恶性疟原虫falciparum falcipin -2的潜在相互作用，突出了愈蓝烷氢过氧化物作为未来在退行性疾病和传染病背景下研究的有前途的化学型。
{"title":"Unveiling naturally occurring hydroperoxide sesquiterpenoids from Indonesian Dysoxylum amooroides Miq","authors":"Latifah Gunawan , Al Arofatus Naini , Desi Harneti , Kindi Farabi , Sofa Fajriah , Elpri Eka Permadi , Sri Rahayu , Siriporn Jungsuttiwong , Unang Supratman","doi":"10.1016/j.phytol.2025.104073","DOIUrl":"10.1016/j.phytol.2025.104073","url":null,"abstract":"<div><div>Hydroperoxides (–OOH) represent rare but biologically intriguing motifs in plant secondary metabolites, particularly within sesquiterpenoids. Phytochemical investigation of <em>Dysoxylum amooroides</em> yielded an undescribed sesquiterpenoid, amooroxyline A (<strong>1</strong>), together with 4<em>β</em>,10<em>α</em>-dihydroxyaromadendrane (<strong>2</strong>). The structure and absolute configuration of <strong>1</strong> were established by ECD analysis. Cytotoxicity assays revealed <strong>1</strong> inactive on MCF-7, while <strong>2</strong> showed moderate selective inhibition (IC₅₀ = 20.1 μM), with neither affecting normal CV-1 cells. In addition, molecular docking centered on the hydroperoxide scaffold (<strong>1</strong> and related 10β,11-dihydroxy-1β-hydroperoxide-4αH,5αH,7αH-guaiane analogue) supported these results, showing weaker binding affinities to ESR1, ESR2, and aromatase compared to native ligands. Further <em>in silico</em> exploration suggested potential interactions with BACE1 and <em>Plasmodium falciparum</em> Falcipain-2, highlighting guaiane hydroperoxides as promising chemotypes for future studies in degenerative and infectious disease contexts.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104073"},"PeriodicalIF":1.4,"publicationDate":"2025-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145516684","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 : 2025-11-10DOI: 10.1016/j.phytol.2025.104075
Shan-Shan Wei , Dao-Jun Rong , Jia-Ying Lai , Chen Chen , Si-Ran Li , Zhong-Hua Yu , Hai-Bo Tan
The further chemical investigation of the liquid fermentation of endophytic fungus Xylaria curta, which was isolated from the medicinal plant Alpinia zerumbet B. L. Burtt & R. M. Sm., had led to the isolation of one novel compound with the trivial name of xylacurtin A (1). The chemical structure was fully characterized by means of detailed spectroscopic analysis, which thus successfully revealed it to share an unprecedented 7-butyl-4-methoxyoxepin-2(5H)-one skeleton. It represents the first member of rearranged pyranone derivative with a novel seven-membered ring system in nature. Moreover, the biological activity of xylacurtin A (1) were also evaluated to show that 1 was a promising antibacterial lead compound towards the Staphylococcus aureus and Methicillin-resistant S. aureus with the MIC value of 6.3 μg/mL without any notable cytotoxicity.
药用植物Alpinia zerumbet b.l. Burtt &； R. M. Sm.液体发酵内生真菌Xylaria curta的进一步化学研究。，从而分离出一种新的化合物，它的名字很简单，叫做木curtin A(1)。通过详细的光谱分析，对其化学结构进行了充分的表征，从而成功地揭示了它具有前所未有的7-丁基-4-甲氧基氧素-2(5H)- 1骨架。它代表了自然界中具有新颖七元环体系的重排吡喃酮衍生物的第一个成员。此外，我们还对木质素A(1)的生物活性进行了评价，结果表明1对金黄色葡萄球菌和耐甲氧西林金黄色葡萄球菌的MIC值为6.3 μg/mL，无明显的细胞毒性，是一种很有前景的抗菌先导化合物。
{"title":"One new rearranged pyranone derivative with antibacterial activity from Xylaria curta YSJ-5","authors":"Shan-Shan Wei , Dao-Jun Rong , Jia-Ying Lai , Chen Chen , Si-Ran Li , Zhong-Hua Yu , Hai-Bo Tan","doi":"10.1016/j.phytol.2025.104075","DOIUrl":"10.1016/j.phytol.2025.104075","url":null,"abstract":"<div><div>The further chemical investigation of the liquid fermentation of endophytic fungus <em>Xylaria curta</em>, which was isolated from the medicinal plant <em>Alpinia zerumbet</em> B. L. Burtt & R. M. Sm., had led to the isolation of one novel compound with the trivial name of xylacurtin A (<strong>1</strong>). The chemical structure was fully characterized by means of detailed spectroscopic analysis, which thus successfully revealed it to share an unprecedented 7-butyl-4-methoxyoxepin-2(5<em>H</em>)-one skeleton. It represents the first member of rearranged pyranone derivative with a novel seven-membered ring system in nature. Moreover, the biological activity of xylacurtin A (<strong>1</strong>) were also evaluated to show that <strong>1</strong> was a promising antibacterial lead compound towards the <em>Staphylococcus aureus</em> and Methicillin-resistant <em>S. aureus</em> with the MIC value of 6.3 μg/mL without any notable cytotoxicity.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104075"},"PeriodicalIF":1.4,"publicationDate":"2025-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145516686","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 : 2025-11-05DOI: 10.1016/j.phytol.2025.104071
Chun-Lin Zhao , Kai-Wen Kang , Zhi-Cheng Su , Hong-Yan Mu , Hui-Shan Guo , Hui-Zhen Chen , Ya-Ting Chen , Jing-Wei Jin , Ju-Cai Xu , Hong-Guang Li , Li-She Gan
Fourteen alkaloids, including one new quinolone alkaloid, 4-hydroxy-2-(12-(isobutyryloxy)dodecyl)-1-methylquinolin-1-ium (1), together with nine known quinolone alkaloids (2-10), and four known indole alkaloids (11-14), were isolated from 80 % ethanol extract of the fruits of Tetradium ruticarpum. Their structures were determined by spectroscopic data analyses. These quinolone alkaloids can take 4-enol,1-ammonium ion form or 4-keto,1-tertiary amine form. Using compound 6 as a representative example, the keto-enol tautomerism of these quinolone alkaloids under various acid-base conditions was investigated. The anti-diabetic activities of compounds 1-6 were evaluated by a 2-NBDG glucose uptake assay on C2C12 myotubes. These alkaloids significantly promoted glucose uptake in their maximum safe dosage (5–10 μM). Further studies with compounds 1 and 5 revealed dose-dependent increases in glucose uptake. Western blot analyses indicated that these compounds can activate the phosphorylation of AMPK and ACC1, while upregulating GLUT4 expression in C2C12 myotubes. These molecular events collectively contribute to the observed promotion of glucose uptake and inhibition of lipid synthesis.
{"title":"Anti-diabetic quinolone alkaloids from the fruits of Tetradium ruticarpum","authors":"Chun-Lin Zhao , Kai-Wen Kang , Zhi-Cheng Su , Hong-Yan Mu , Hui-Shan Guo , Hui-Zhen Chen , Ya-Ting Chen , Jing-Wei Jin , Ju-Cai Xu , Hong-Guang Li , Li-She Gan","doi":"10.1016/j.phytol.2025.104071","DOIUrl":"10.1016/j.phytol.2025.104071","url":null,"abstract":"<div><div>Fourteen alkaloids, including one new quinolone alkaloid, 4-hydroxy-2-(12-(isobutyryloxy)dodecyl)-1-methylquinolin-1-ium (<strong>1</strong>), together with nine known quinolone alkaloids (<strong>2</strong>-<strong>10</strong>), and four known indole alkaloids (<strong>11</strong>-<strong>14</strong>), were isolated from 80 % ethanol extract of the fruits of <em>Tetradium ruticarpum.</em> Their structures were determined by spectroscopic data analyses. These quinolone alkaloids can take 4-enol,1-ammonium ion form or 4-keto,1-tertiary amine form. Using compound <strong>6</strong> as a representative example, the keto-enol tautomerism of these quinolone alkaloids under various acid-base conditions was investigated. The anti-diabetic activities of compounds <strong>1</strong>-<strong>6</strong> were evaluated by a 2-NBDG glucose uptake assay on C2C12 myotubes. These alkaloids significantly promoted glucose uptake in their maximum safe dosage (5–10 <em>μ</em>M). Further studies with compounds <strong>1</strong> and <strong>5</strong> revealed dose-dependent increases in glucose uptake. Western blot analyses indicated that these compounds can activate the phosphorylation of AMPK and ACC1, while upregulating GLUT4 expression in C2C12 myotubes. These molecular events collectively contribute to the observed promotion of glucose uptake and inhibition of lipid synthesis.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104071"},"PeriodicalIF":1.4,"publicationDate":"2025-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145466622","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}
In this study, we isolated a new anthraquinone glycoside, 6-hydroxyrubiadin-3-O-β-D-(4′,6′-O-diacetyl)glucopyranoside (6), along with five known compounds from Rubia argyi roots. Subsequently, we elucidated the chemical structures of the isolated compounds based on chemical and physicochemical evidence. Additionally, we developed qualitative and quantitative high-performance liquid chromatography methods to compare the contents of the anthraquinones, 6-hydroxyrubiadin, alizarin, and purpurin, in R. tinctorum and R. argyi collected in Japan. Notably, anthraquinones isolated from R. argyi roots significantly inhibited amyloid-β aggregation.
在这项研究中，我们分离了一个新的蒽醌苷，6 -羟基rubiadin-3- o -β- d -（4 ',6 ' - o -二乙酰）葡萄糖吡喃苷(6)，以及五个已知的化合物从苦艾根。随后，我们根据化学和物理化学证据对分离化合物的化学结构进行了分析。此外，建立了定性和定量的高效液相色谱法，比较了日本产银叶参和银叶参中蒽醌类、6-羟基茜素、茜素和紫外光素的含量。值得注意的是，从艾叶根中分离的蒽醌类物质能显著抑制淀粉样蛋白-β的聚集。
{"title":"Qualitative and quantitative analyses, and biological activities of major anthraquinones in Rubia argyi and R. tinctorum","authors":"Tomoe Ohta , Junko Tsukioka , Shota Miyanowaki , Souichi Nakashima , Hisashi Matsuda , Seikou Nakamura","doi":"10.1016/j.phytol.2025.104067","DOIUrl":"10.1016/j.phytol.2025.104067","url":null,"abstract":"<div><div>In this study, we isolated a new anthraquinone glycoside, 6-hydroxyrubiadin-3-<em>O</em>-β-D-(4′,6′-<em>O</em>-diacetyl)glucopyranoside (<strong>6</strong>), along with five known compounds from <em>Rubia argyi</em> roots. Subsequently, we elucidated the chemical structures of the isolated compounds based on chemical and physicochemical evidence. Additionally, we developed qualitative and quantitative high-performance liquid chromatography methods to compare the contents of the anthraquinones, 6-hydroxyrubiadin, alizarin, and purpurin, in <em>R. tinctorum</em> and <em>R. argyi</em> collected in Japan. Notably, anthraquinones isolated from <em>R. argyi</em> roots significantly inhibited amyloid-β aggregation.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104067"},"PeriodicalIF":1.4,"publicationDate":"2025-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145466660","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 : 2025-11-03DOI: 10.1016/j.phytol.2025.104072
Yong-xun Yang , Yan Luo , Ying Qu , Yu-lian Luo , Hai-yan Huang , Hao Geng
Four novel 6/6/6/6 tetracyclic Rhododendron chromane meroterpenoids (RCMs), designated hongzhongdujuanins A–D (1–4), along with three common 6/6/6/4 or 6/6/5/4 tetracyclic RCMs, rubiginosins A (5) and C (6), and (+)-fastinoid B (7) were isolated from the flowers of Rhododendron rubiginosum Franch. var. rubiginosum. Structurally, compounds 1 and 2 are a pair of C-12 epimers, and 4 is an irregular RCM featuring a C16 (3 × C5 + C1) terpenoid side chain rather than the regular isopentenyl C15 (3 × C5) terpenoid side chain. The absolute configurations of compounds 1–4 were resolved by a combination of biosynthetic arguments, characteristic chemical shifts of Ha-10 and H3-19 (or H2-13), and ECD calculation. Furthermore, the conformations of the B–D ring of 1–4 were deduced as half-chair, chair, and boat, respectively. Lastly, compounds 1–7 (excluding 4) were tested for COX-2 inhibitory activity. The results showed that compounds 1–3 have effective inhibition, with IC50 values ranging from 8.97 to 9.87 μM, indicating their COX-2 inhibitory potential, and demonstrating that the uncommon 6/6/6/6-ring core scaffold is necessary for COX-2 inhibitory activity.
{"title":"New 6/6/6/6 tetracyclic Rhododendron chromane meroterpenoids from flowers of Rhododendron rubiginosum Franch. var. rubiginosum with COX-2 inhibitory activity","authors":"Yong-xun Yang , Yan Luo , Ying Qu , Yu-lian Luo , Hai-yan Huang , Hao Geng","doi":"10.1016/j.phytol.2025.104072","DOIUrl":"10.1016/j.phytol.2025.104072","url":null,"abstract":"<div><div>Four novel 6/6/6/6 tetracyclic <em>Rhododendron</em> chromane meroterpenoids (RCMs), designated hongzhongdujuanins A–D (<strong>1–4</strong>), along with three common 6/6/6/4 or 6/6/5/4 tetracyclic RCMs, rubiginosins A (<strong>5</strong>) and C (<strong>6</strong>), and (+)-fastinoid B (<strong>7</strong>) were isolated from the flowers of <em>Rhododendron rubiginosum</em> Franch. var. <em>rubiginosum</em>. Structurally, compounds <strong>1</strong> and <strong>2</strong> are a pair of C-12 epimers, and <strong>4</strong> is an irregular RCM featuring a C<sub>16</sub> (3 × C<sub>5</sub> + C<sub>1</sub>) terpenoid side chain rather than the regular isopentenyl C<sub>15</sub> (3 × C<sub>5</sub>) terpenoid side chain. The absolute configurations of compounds <strong>1–4</strong> were resolved by a combination of biosynthetic arguments, characteristic chemical shifts of H<sub>a</sub>-10 and H<sub>3</sub>-19 (or H<sub>2</sub>-13), and ECD calculation. Furthermore, the conformations of the B–D ring of <strong>1–4</strong> were deduced as half-chair, chair, and boat, respectively. Lastly, compounds <strong>1–7</strong> (excluding <strong>4)</strong> were tested for COX-2 inhibitory activity. The results showed that compounds <strong>1–3</strong> have effective inhibition, with IC<sub>50</sub> values ranging from 8.97 to 9.87 μM, indicating their COX-2 inhibitory potential, and demonstrating that the uncommon 6/6/6/6-ring core scaffold is necessary for COX-2 inhibitory activity.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104072"},"PeriodicalIF":1.4,"publicationDate":"2025-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145466659","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 : 2025-11-01DOI: 10.1016/j.phytol.2025.104066
Yan Liu , Yue Sun , Yue Wang , Hai-dan Zou , Jia-Tong Wu , Juan Pan , Wei Guan , Zhi-Chao Hao , Hai-Xue Kuang , Bing-You Yang
An undescribed triterpenoid saponin, astralanosaponin M (1) along with seven previously identified triterpenoids (2–8) were isolated from the roots of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (AMM). Compound 2 was identified for the first time in a leguminous species. The structural characteristics and properties of the separated compounds were elucidated through comprehensive NMR spectroscopy, HR-ESI-MS, and by analyzing the data in relation to established compounds. The absolute configuration of sugars were determined by GC-MS. These compounds’ in vitro anti-diabetic nephropathy activity were evaluated using high glucose-induced SV40 MES 13 cells. Compounds 5 and 3 exhibited significant inhibitory activity with IC50 values of 22.4 μM and 24.6 μM, respectively.
从黄芪（Astragalus membranaceus, Fisch.）的根中分离得到一种未被描述的三萜皂苷，astralanosaponin M(1)和7个先前鉴定的三萜（2-8）。知母。蒙古变种（AMM）化合物2为首次从豆科植物中分离得到。通过综合核磁共振波谱、HR-ESI-MS以及与已建立化合物相关的数据分析，对分离化合物的结构特征和性质进行了鉴定。采用气相色谱-质谱法测定糖的绝对构型。使用高糖诱导的SV40 MES 13细胞评估这些化合物的体外抗糖尿病肾病活性。化合物5和3的IC50值分别为22.4 μM和24.6 μM。
{"title":"An undescribed triterpenoid saponin from the root of Astragalus membranaceus (Fisch.) Bge. var. mongholicus","authors":"Yan Liu , Yue Sun , Yue Wang , Hai-dan Zou , Jia-Tong Wu , Juan Pan , Wei Guan , Zhi-Chao Hao , Hai-Xue Kuang , Bing-You Yang","doi":"10.1016/j.phytol.2025.104066","DOIUrl":"10.1016/j.phytol.2025.104066","url":null,"abstract":"<div><div>An undescribed triterpenoid saponin, astralanosaponin M (<strong>1</strong>) along with seven previously identified triterpenoids (<strong>2–8</strong>) were isolated from the roots of <em>Astragalus membranaceus</em> (Fisch.) Bge<em>.</em> var. <em>mongholicus</em> (AMM). Compound <strong>2</strong> was identified for the first time in a leguminous species. The structural characteristics and properties of the separated compounds were elucidated through comprehensive NMR spectroscopy, HR-ESI-MS, and by analyzing the data in relation to established compounds. The absolute configuration of sugars were determined by GC-MS. These compounds’ <em>in vitro</em> anti-diabetic nephropathy activity were evaluated using high glucose-induced SV40 MES 13 cells. Compounds <strong>5</strong> and <strong>3</strong> exhibited significant inhibitory activity with IC<sub>50</sub> values of 22.4 μM and 24.6 μM, respectively.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104066"},"PeriodicalIF":1.4,"publicationDate":"2025-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145417143","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 : 2025-10-31DOI: 10.1016/j.phytol.2025.104070
Lin Zhang , Wei Li , Hao Wang , Jun Zeng , Wen-Hua Dong , Bei Jiang , Jing-Zhe Yuan , Fei Wu , Wen-Li Mei , Hao-Fu Dai
Four 2-(2-phenylethyl)chromone dimers were isolated from the agarwood of Aquilaria malaccensis for the first time, including two unreported 2-(2-phenylethyl)chromone dimers, aquimalaccenone A (1) and B (2) and two known ones. Their structures were determined by 1D and 2D NMR, ECD, HRESIMS and literature data comparison. The biological activity of these compounds against NO production in LPS-induced RAW264.7 cells was evaluated. Aquifilarone A (3) and 6″-hydroxy-4‴-methoxy-crassin B (4) have anti-inflammatory activity with IC50 values of 31.15 ± 1.49 μM and 43.42 ± 1.63 μM (quercetin as positive control, IC50 16.85 ± 1.22 μM).
{"title":"Two new 2-(2-phenylethyl)chromone dimers from agarwood of Aquilaria malaccensis","authors":"Lin Zhang , Wei Li , Hao Wang , Jun Zeng , Wen-Hua Dong , Bei Jiang , Jing-Zhe Yuan , Fei Wu , Wen-Li Mei , Hao-Fu Dai","doi":"10.1016/j.phytol.2025.104070","DOIUrl":"10.1016/j.phytol.2025.104070","url":null,"abstract":"<div><div>Four 2-(2-phenylethyl)chromone dimers were isolated from the agarwood of <em>Aquilaria malaccensis</em> for the first time, including two unreported 2-(2-phenylethyl)chromone dimers, aquimalaccenone A (<strong>1</strong>) and B (<strong>2</strong>) and two known ones. Their structures were determined by 1D and 2D NMR, ECD, HRESIMS and literature data comparison. The biological activity of these compounds against NO production in LPS-induced RAW264.7 cells was evaluated. Aquifilarone A (<strong>3</strong>) and 6″-hydroxy-4‴-methoxy-crassin B (<strong>4</strong>) have anti-inflammatory activity with IC<sub>50</sub> values of 31.15 ± 1.49 <em>μ</em>M and 43.42 ± 1.63 <em>μ</em>M (quercetin as positive control, IC<sub>50</sub> 16.85 ± 1.22 <em>μ</em>M).</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104070"},"PeriodicalIF":1.4,"publicationDate":"2025-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145417142","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 : 2025-10-31DOI: 10.1016/j.phytol.2025.104068
Yunhan Zhang , Yiwei Wu , Huizhen Yang , Wenjie Shangguan , Jiaping Fan , Xueli Huang , Hong Wang , Rongfei Chen , Wen Sun , Tunhai Xu , Yindi Zhu
Two novel sesquiterpenoids, wenyujinone J and wenyujinone K, alongside a new natural product (3), and three known sesquiterpenoids analogs (4–6), were isolated and identified from Curcuma wenyujin. The structures of the novel sesquiterpenoids were elucidated through comprehensive spectroscopic analysis and chemical methods. Their absolute stereochemistry was determined via electronic circular dichroism (ECD) spectroscopy and computational ECD analysis. The protective effect of all compounds (50–400 μM) against high glucose-induced apoptosis in pulmonary microvascular endothelial cells (PMVECs) were evaluated. Compounds 4, 5 and 6, particularly compound 5, exhibited significant dose-dependent protective effects. Furthermore, treatment with compound 5 markedly upregulated the nuclear protein expression of phosphorylated protein kinase B (p-AKT).
{"title":"Sesquiterpenoids from the rhizome of Curcuma wenyujin and their protective effects against high glucose-induced apoptosis in PMVECs cells","authors":"Yunhan Zhang , Yiwei Wu , Huizhen Yang , Wenjie Shangguan , Jiaping Fan , Xueli Huang , Hong Wang , Rongfei Chen , Wen Sun , Tunhai Xu , Yindi Zhu","doi":"10.1016/j.phytol.2025.104068","DOIUrl":"10.1016/j.phytol.2025.104068","url":null,"abstract":"<div><div>Two novel sesquiterpenoids, wenyujinone J and wenyujinone K, alongside a new natural product (<strong>3</strong>), and three known sesquiterpenoids analogs (<strong>4</strong>–<strong>6</strong>), were isolated and identified from <em>Curcuma wenyujin</em>. The structures of the novel sesquiterpenoids were elucidated through comprehensive spectroscopic analysis and chemical methods. Their absolute stereochemistry was determined via electronic circular dichroism (ECD) spectroscopy and computational ECD analysis. The protective effect of all compounds (50–400 μM) against high glucose-induced apoptosis in pulmonary microvascular endothelial cells (PMVECs) were evaluated. Compounds <strong>4</strong>, <strong>5</strong> and <strong>6</strong>, particularly compound <strong>5</strong>, exhibited significant dose-dependent protective effects. Furthermore, treatment with compound <strong>5</strong> markedly upregulated the nuclear protein expression of phosphorylated protein kinase B (p-AKT).</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104068"},"PeriodicalIF":1.4,"publicationDate":"2025-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145417141","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 : 2025-10-30DOI: 10.1016/j.phytol.2025.104069
Xin-Xin Liang , Lei Li , Jia-Yi Zhang , Xin-Yue Zhang , Yi-Kun Feng , Chen Gu , Si-Cheng Jin , Xiang-Guo Meng
A previously unreported bisbenzoquinone, designated as 6,6''-bis-(2,5-dihydroxy-3-heptyl-1,4-benzoquinone), was isolated from the culture of Chaetomium trilaterale. The structure of this compound was elucidated through comprehensive spectroscopic analyses, including 1D and 2D NMR, HRESIMS, and further confirmed by single-crystal X-ray diffraction. Furthermore, its cytotoxic potential was assessed, revealing dose-dependent inhibitory effects on the proliferation of human cancer cell lines 22Rv1, LNCaP, and H1975.
{"title":"A new bisbenzoquinone with cytotoxicity from Chaetomium trilaterale","authors":"Xin-Xin Liang , Lei Li , Jia-Yi Zhang , Xin-Yue Zhang , Yi-Kun Feng , Chen Gu , Si-Cheng Jin , Xiang-Guo Meng","doi":"10.1016/j.phytol.2025.104069","DOIUrl":"10.1016/j.phytol.2025.104069","url":null,"abstract":"<div><div>A previously unreported bisbenzoquinone, designated as 6,6''-bis-(2,5-dihydroxy-3-heptyl-1,4-benzoquinone), was isolated from the culture of <em>Chaetomium trilaterale</em>. The structure of this compound was elucidated through comprehensive spectroscopic analyses, including 1D and 2D NMR, HRESIMS, and further confirmed by single-crystal X-ray diffraction. Furthermore, its cytotoxic potential was assessed, revealing dose-dependent inhibitory effects on the proliferation of human cancer cell lines 22Rv1, LNCaP, and H1975.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104069"},"PeriodicalIF":1.4,"publicationDate":"2025-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145417140","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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