Pub Date : 2025-11-25DOI: 10.1016/j.phytol.2025.104085
Jiaxing Yu , Adila Abudurexiti , Guangmin Yao
Two new compounds, a norditerpenoid and a megastigmane sesquiterpenoid, were isolated from the ethyl acetate extract of Pieris formosa leaves collected in Yichang, Hubei, China, together with eight known megastigmane sesquiterpenoids. Their structures were elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Pormoside A (1) represents the first example of a 17-β-D-glucopyranosyloxy-substituted 14,15-di-nor-cyclophytane diterpenoid. All isolates were evaluated for α-glucosidase inhibitory activity. Pormoside A (1) (IC50 = 112.90 ± 3.98 μM) showed significantly more potent inhibition than the positive control acarbose (IC50 = 219.55 ± 3.95 μM). Molecular docking studies of pormoside A and B further revealed their binding interactions with α-glucosidase.
从湖北宜昌产的枫香叶乙酸乙酯提取物中分离得到两个新化合物，一个为北二萜类化合物，一个为大芪甲素倍半萜类化合物，另外还有8个已知的大芪甲素倍半萜类化合物。通过光谱数据分析和电子圆二色性（ECD）计算对其结构进行了表征。Pormoside A(1)是17-β- d - glucopyranosyloy取代的14,15-二-非环植烷二萜的第一个例子。对所有菌株进行α-葡萄糖苷酶抑制活性评价。Pormoside A (1) （IC50 = 112.90 ± 3.98 μM）比阳性对照阿卡波糖（IC50 = 219.55 ± 3.95 μM）具有更强的抑制作用。卟啉苷A和卟啉苷B的分子对接研究进一步揭示了它们与α-葡萄糖苷酶的结合作用。
{"title":"Discovery of diterpenoid and sesquiterpenoids as α-glucosidase inhibitors from the leaves of Pieris formosa","authors":"Jiaxing Yu , Adila Abudurexiti , Guangmin Yao","doi":"10.1016/j.phytol.2025.104085","DOIUrl":"10.1016/j.phytol.2025.104085","url":null,"abstract":"<div><div>Two new compounds, a norditerpenoid and a megastigmane sesquiterpenoid, were isolated from the ethyl acetate extract of <em>Pieris formosa</em> leaves collected in Yichang, Hubei, China, together with eight known megastigmane sesquiterpenoids. Their structures were elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Pormoside A (<strong>1</strong>) represents the first example of a 17-<em>β</em>-<span>D</span>-glucopyranosyloxy-substituted 14,15-di-<em>nor</em>-cyclophytane diterpenoid. All isolates were evaluated for <em>α</em>-glucosidase inhibitory activity. Pormoside A (<strong>1</strong>) (IC<sub>50</sub> = 112.90 ± 3.98 <em>μ</em>M) showed significantly more potent inhibition than the positive control acarbose (IC<sub>50</sub> = 219.55 ± 3.95 <em>μ</em>M). Molecular docking studies of pormoside A and B further revealed their binding interactions with <em>α</em>-glucosidase.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"71 ","pages":"Article 104085"},"PeriodicalIF":1.4,"publicationDate":"2025-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616947","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 : 2025-11-25DOI: 10.1016/j.phytol.2025.104077
Natsu Tanikawa , Hiroshi Ueda , Fumi Tatsuzawa
Radish (Raphanus sativus L.) is a widely used cruciferous vegetable. Japanese radish, daikon, is one of the most consumed vegetables in Japan. Its large white roots are mainly used as root vegetables. The leaves are not widely used but are known to possess high nutritional value, and contain flavonoids, the plant-derived food components with various human health benefits. In general, flavonoids need to be hydrolyzed to aglycones before absorption and the biological efficacy of flavonoids has been mainly examined in terms of the type of aglycone present. However, it has been reported that flavonoids can also exert various effects in their native state before absorption. In this study, we used HPLC analysis and detected multiple flavonoid components in daikon leaves, but not in the roots. In order to clarify which flavonoids are present in daikon leaves, we isolated them from the leaves and elucidated their structures by HR-MS and NMR analyses. We identified two new flavonols, kaempferol 3-O-β-arabinopyranoside-7-O-[3-O-(4-O-β-glucopyranosyl-6-O-trans-caffeoyl-β-glucopyranosyl)-α-rhamnopyranoside] and kaempferol 3-O-α-rhamnopyranoside-7-O-[3-O-(4-O-β-glucopyranosyl-6-O-trans-caffeoyl-β-glucopyranosyl)-α-rhamnopyranoside] along with two known quercetin glycosides and four known kaempferol glycosides. A unique characteristic we observed in them was their glycosylation pattern with rhamnose at the 7-position and with sugars of different kinds (galactose, glucose, arabinose, or rhamnose) at the 3-position of aglycone. These glycosylation patterns and types of sugars were different from those identified in members of the genus Brassica that are used as vegetables, indicating different mechanisms of action for these compounds in daikon.
萝卜（Raphanus sativus L.）是一种广泛使用的十字花科蔬菜。日本萝卜，白萝卜，是日本消费最多的蔬菜之一。其白色的大根主要用作根茎类蔬菜。这种叶子并没有被广泛使用，但众所周知，它具有很高的营养价值，并且含有黄酮类化合物，这是一种植物来源的食物成分，对人体健康有各种好处。一般来说，黄酮类化合物在吸收前需要水解成苷元，黄酮类化合物的生物功效主要从存在的苷元类型来考察。然而，据报道，黄酮类化合物在吸收前的天然状态下也能发挥各种作用。本研究采用高效液相色谱法对白萝卜叶片中多种黄酮类成分进行了检测，但未检测到白萝卜根中的黄酮类成分。为了明确白萝卜叶中存在的黄酮类化合物，我们从白萝卜叶中分离出黄酮类化合物，并通过核磁共振和质谱分析对其结构进行了鉴定。我们鉴定了两种新的黄酮醇，山奈酚3-O-β-阿拉伯吡喃苷-7- o -[3-O-（4-O-β-葡萄糖吡喃基-6- o -反式咖啡因基-β-葡萄糖吡喃基）-α-鼠李糖苷]和山奈酚3-O-α-鼠李糖苷-7- o -[3-O-（4-O-β-葡萄糖吡喃基-6- o -反式咖啡因基-β-葡萄糖吡喃基）-α-鼠李糖苷]以及两种已知的槲皮素糖苷和四种已知的山奈酚糖苷。我们观察到它们的一个独特特征是它们的糖基化模式与鼠李糖在7位，与不同种类的糖（半乳糖、葡萄糖、阿拉伯糖或鼠李糖）在糖苷元的3位。这些糖基化模式和糖的类型与用作蔬菜的芸苔属成员的糖基化模式和糖的类型不同，表明这些化合物在白萝卜中的作用机制不同。
{"title":"Identification of flavonols in the leaves of daikon (Raphanus sativus L.)","authors":"Natsu Tanikawa , Hiroshi Ueda , Fumi Tatsuzawa","doi":"10.1016/j.phytol.2025.104077","DOIUrl":"10.1016/j.phytol.2025.104077","url":null,"abstract":"<div><div>Radish (<em>Raphanus sativus</em> L.) is a widely used cruciferous vegetable. Japanese radish, daikon, is one of the most consumed vegetables in Japan. Its large white roots are mainly used as root vegetables. The leaves are not widely used but are known to possess high nutritional value, and contain flavonoids, the plant-derived food components with various human health benefits. In general, flavonoids need to be hydrolyzed to aglycones before absorption and the biological efficacy of flavonoids has been mainly examined in terms of the type of aglycone present. However, it has been reported that flavonoids can also exert various effects in their native state before absorption. In this study, we used HPLC analysis and detected multiple flavonoid components in daikon leaves, but not in the roots. In order to clarify which flavonoids are present in daikon leaves, we isolated them from the leaves and elucidated their structures by HR-MS and NMR analyses. We identified two new flavonols, kaempferol 3-<em>O</em>-β-arabinopyranoside-7-<em>O</em>-[3-<em>O</em>-(4-<em>O</em>-β-glucopyranosyl-6-<em>O</em>-<em>trans</em>-caffeoyl-β-glucopyranosyl)-α-rhamnopyranoside] and kaempferol 3-<em>O</em>-α-rhamnopyranoside-7-<em>O</em>-[3-<em>O</em>-(4-<em>O</em>-β-glucopyranosyl-6-<em>O</em>-<em>trans</em>-caffeoyl-β-glucopyranosyl)-α-rhamnopyranoside] along with two known quercetin glycosides and four known kaempferol glycosides. A unique characteristic we observed in them was their glycosylation pattern with rhamnose at the 7-position and with sugars of different kinds (galactose, glucose, arabinose, or rhamnose) at the 3-position of aglycone. These glycosylation patterns and types of sugars were different from those identified in members of the genus <em>Brassica</em> that are used as vegetables, indicating different mechanisms of action for these compounds in daikon.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"71 ","pages":"Article 104077"},"PeriodicalIF":1.4,"publicationDate":"2025-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616948","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 : 2025-11-22DOI: 10.1016/j.phytol.2025.104080
Mungyeong Gwon , Dae-Won Ki , Dae-Cheol Choi , Ji-Yul Kim , Won-Gi Seo , Yongkuk Lee , In-Kyoung Lee , Bong-Sik Yun
Seven compounds including a new pyrone, towyspyrone A (1), and six known naphthalenes, 8-methoxy-1-naphthol (2), 5-methoxy-1-naphthol (3), 3,4,5-trihydroxy-1-tetralone (4), 3,4-dihydro-3,4,6,8-tetrahydroxy-1(2 H)-naphthalenone (5), scytalone (6), and 4,6,8-trihydroxy-3,4-dihydronaphthalene-1(2 H)-one (7), were isolated from culture broth of the marine-derived fungus Towyspora aestuari. Their structures were determined by extensive NMR and mass analyses. Free radical scavenging activity of the isolated compounds was assessed using 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Compounds 2 and 3 showed potent free radical scavenging activity with IC50 values of 12.6 µM and 10.8 µM, respectively, against the ABTS radical and of 224.0 µM and 191.1 µM against the DPPH radical.
{"title":"Chemical constituents of culture broth of the marine-derived fungus Towyspora aestuari and their antioxidant activity","authors":"Mungyeong Gwon , Dae-Won Ki , Dae-Cheol Choi , Ji-Yul Kim , Won-Gi Seo , Yongkuk Lee , In-Kyoung Lee , Bong-Sik Yun","doi":"10.1016/j.phytol.2025.104080","DOIUrl":"10.1016/j.phytol.2025.104080","url":null,"abstract":"<div><div>Seven compounds including a new pyrone, towyspyrone A (<strong>1</strong>), and six known naphthalenes, 8-methoxy-1-naphthol (<strong>2</strong>), 5-methoxy-1-naphthol (<strong>3</strong>), 3,4,5-trihydroxy-1-tetralone (<strong>4</strong>), 3,4-dihydro-3,4,6,8-tetrahydroxy-1(2 H)-naphthalenone (<strong>5</strong>), scytalone (<strong>6</strong>), and 4,6,8-trihydroxy-3,4-dihydronaphthalene-1(2 H)-one (<strong>7</strong>), were isolated from culture broth of the marine-derived fungus <em>Towyspora aestuari</em>. Their structures were determined by extensive NMR and mass analyses. Free radical scavenging activity of the isolated compounds was assessed using 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Compounds <strong>2</strong> and <strong>3</strong> showed potent free radical scavenging activity with IC<sub>50</sub> values of 12.6 µM and 10.8 µM, respectively, against the ABTS radical and of 224.0 µM and 191.1 µM against the DPPH radical.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104080"},"PeriodicalIF":1.4,"publicationDate":"2025-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145568323","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 : 2025-11-21DOI: 10.1016/j.phytol.2025.104084
Xu-Ping Zhang, Xue-Kai Zhao, Wei-Guang Wang, Qian-Qian Yin, Lu Gao
Phomalactones A (1) and B (2), two new γ-lactam derivatives, and one known compound, namely, phaeosphaeride A (3), were isolated from Paraphoma sp. AC-G1, an endophytic fungus isolated from Artemisia argyi. Their structures were determined using 1D and 2D NMR spectra, HRESIMS, and optical rotation measurements. Compounds 1–3 were assessed for their antimicrobial activities on Ralstonia solanacearum, Fusarium oxysporum, and Alternaria alternata. The results showed that compounds 1 and 3 exhibited significant inhibition on F. oxysporum.
{"title":"New γ-lactams from Paraphoma sp. AC-G1 isolated from Artemisia argyi","authors":"Xu-Ping Zhang, Xue-Kai Zhao, Wei-Guang Wang, Qian-Qian Yin, Lu Gao","doi":"10.1016/j.phytol.2025.104084","DOIUrl":"10.1016/j.phytol.2025.104084","url":null,"abstract":"<div><div>Phomalactones A (<strong>1</strong>) and B (<strong>2</strong>), two new <em>γ</em>-lactam derivatives, and one known compound, namely, phaeosphaeride A (<strong>3</strong>), were isolated from <em>Paraphoma</em> sp. AC-G1, an endophytic fungus isolated from <em>Artemisia argyi</em>. Their structures were determined using 1D and 2D NMR spectra, HRESIMS, and optical rotation measurements. Compounds <strong>1–3</strong> were assessed for their antimicrobial activities on <em>Ralstonia solanacearum</em>, <em>Fusarium oxysporum</em>, and <em>Alternaria alternata</em>. The results showed that compounds <strong>1</strong> and <strong>3</strong> exhibited significant inhibition on <em>F. oxysporum</em>.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"71 ","pages":"Article 104084"},"PeriodicalIF":1.4,"publicationDate":"2025-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145570901","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 : 2025-11-20DOI: 10.1016/j.phytol.2025.104078
A.S. Tareau , P.E. Bodet , J.R. Guedes da Silva Almeida , M. Barreau , O. Lesouhaitier , A. Tahrioui , R. Gonçalves de Oliveira Junior , R. Grougnet , P. Sitarek , L. Quintans-Junior , K. Baranger , S. Chevalier , L. Picot
Pseudomonas aeruginosa is a multidrug-resistant pathogen whose virulence is tightly regulated by quorum sensing (QS). Targeting QS offers a promising anti-virulence strategy by disarming pathogens without promoting resistance. Here, we screened Brazilian medicinal plant extracts for QS inhibition and identified the ethanolic leaf extract of Spondias tuberosa Arruda (STF) as a potent suppressor of pyocyanin production in planktonic P. aeruginosa cultures, without affecting bacterial growth. STF disrupted QS signaling, as demonstrated by the decreased production of QS mediators detected using a biosensor strain. Phytochemical profiling revealed candidate compounds potentially responsible for this activity. These findings highlight S. tuberosa as a promising natural source of QS inhibitors capable of attenuating P. aeruginosa virulence, particularly during the early stages of infection, and open perspectives for future research into its potential interest in anti-virulence therapeutic approaches.
{"title":"Spondias tuberosa Arruda (Anacardiaceae) ethanolic leaf extract as a source of natural products inhibiting quorum sensing and pyocyanin production in planktonic Pseudomonas aeruginosa","authors":"A.S. Tareau , P.E. Bodet , J.R. Guedes da Silva Almeida , M. Barreau , O. Lesouhaitier , A. Tahrioui , R. Gonçalves de Oliveira Junior , R. Grougnet , P. Sitarek , L. Quintans-Junior , K. Baranger , S. Chevalier , L. Picot","doi":"10.1016/j.phytol.2025.104078","DOIUrl":"10.1016/j.phytol.2025.104078","url":null,"abstract":"<div><div><em>Pseudomonas aeruginosa</em> is a multidrug-resistant pathogen whose virulence is tightly regulated by quorum sensing (QS). Targeting QS offers a promising anti-virulence strategy by disarming pathogens without promoting resistance. Here, we screened Brazilian medicinal plant extracts for QS inhibition and identified the ethanolic leaf extract of <em>Spondias tuberosa</em> Arruda (STF) as a potent suppressor of pyocyanin production in planktonic <em>P. aeruginosa</em> cultures, without affecting bacterial growth. STF disrupted QS signaling, as demonstrated by the decreased production of QS mediators detected using a biosensor strain. Phytochemical profiling revealed candidate compounds potentially responsible for this activity. These findings highlight <em>S. tuberosa</em> as a promising natural source of QS inhibitors capable of attenuating <em>P. aeruginosa</em> virulence, particularly during the early stages of infection, and open perspectives for future research into its potential interest in anti-virulence therapeutic approaches.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104078"},"PeriodicalIF":1.4,"publicationDate":"2025-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145568324","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}
Two previously unreported meroterpenoids, euglobal-A5 (1) with a phloroglucinol moiety and eucalrobusone Z (2) containing a polymethylated β-triketone were isolated from the root bark of Eucalyptus robusta along with three known triterpenoids (3–5). Their chemical structures were elucidated by comprehensive spectral analysis, and their absolute configurations were established via electronic circular dichroism (ECD) calculations. Antimicrobial and antifungal screening assays demonstrated that compound 1 inhibited the growth of Candida albicans with a minimum inhibitory concentration (MIC) of 32 μg/mL, while 2 exhibited antibacterial activity against both Escherichia coli and Pseudomonas aeruginosa with a MIC value of 64 μg/mL for each.
{"title":"Two meroterpenoids from the root bark of Eucalyptus robusta","authors":"Yi-Yang Chen, Yong-Xin Wei, Rui-Zhen Chen, Kun-Feng Zhang, Ling-Yi Kong, Ming-Hua Yang","doi":"10.1016/j.phytol.2025.104079","DOIUrl":"10.1016/j.phytol.2025.104079","url":null,"abstract":"<div><div>Two previously unreported meroterpenoids, euglobal-A5 (<strong>1</strong>) with a phloroglucinol moiety and eucalrobusone Z (<strong>2</strong>) containing a polymethylated <em>β</em>-triketone were isolated from the root bark of <em>Eucalyptus robusta</em> along with three known triterpenoids (<strong>3</strong>–<strong>5</strong>). Their chemical structures were elucidated by comprehensive spectral analysis, and their absolute configurations were established via electronic circular dichroism (ECD) calculations. Antimicrobial and antifungal screening assays demonstrated that compound <strong>1</strong> inhibited the growth of <em>Candida albicans</em> with a minimum inhibitory concentration (MIC) of 32 <em>μ</em>g/mL, while <strong>2</strong> exhibited antibacterial activity against both <em>Escherichia coli</em> and <em>Pseudomonas aeruginosa</em> with a MIC value of 64 <em>μ</em>g/mL for each.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104079"},"PeriodicalIF":1.4,"publicationDate":"2025-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145568322","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 : 2025-11-15DOI: 10.1016/j.phytol.2025.104081
Si-Yu Bai , Bao-Jun Su , Dong Liang , Gui-Jie Zhang
Three new phenolic 14-noreudesmane sesquiterpenes (1–3), along with seven known sesquiterpenes (4–10) were isolated from Ligularia dentata (A. Gray) Hara. Their planar structures were established by spectroscopic data analysis. The absolute configurations of the new compounds were determined by ECD calculations and the ICD experiments. Compounds 1 and 2 are a pair of epimers. All isolated compounds were evaluated for anti-inflammatory activity by assessing their inhibitory effects on NO production in LPS-induced BV-2 microglial cells. Among them, compounds 4, 5, and 8–10 showed inhibitory activities with IC50 values of 10.62–20.43 μM.
{"title":"Phenolic 14-noreudesmane sesquiterpenes from the aerial parts of Ligularia dentata","authors":"Si-Yu Bai , Bao-Jun Su , Dong Liang , Gui-Jie Zhang","doi":"10.1016/j.phytol.2025.104081","DOIUrl":"10.1016/j.phytol.2025.104081","url":null,"abstract":"<div><div>Three new phenolic 14-noreudesmane sesquiterpenes (<strong>1</strong>–<strong>3</strong>), along with seven known sesquiterpenes (<strong>4</strong>–<strong>10</strong>) were isolated from <em>Ligularia dentata</em> (A. Gray) Hara. Their planar structures were established by spectroscopic data analysis. The absolute configurations of the new compounds were determined by ECD calculations and the ICD experiments. Compounds <strong>1</strong> and <strong>2</strong> are a pair of epimers. All isolated compounds were evaluated for anti-inflammatory activity by assessing their inhibitory effects on NO production in LPS-induced BV-2 microglial cells. Among them, compounds <strong>4</strong>, <strong>5</strong>, and <strong>8</strong>–<strong>10</strong> showed inhibitory activities with IC<sub>50</sub> values of 10.62–20.43 <em>μ</em>M.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104081"},"PeriodicalIF":1.4,"publicationDate":"2025-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145516683","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 : 2025-11-13DOI: 10.1016/j.phytol.2025.104074
Wen-Jing Wang , Ju-Cheng Zhang , Yan Geng , Hai-Xia Dong , Fei Xie , Tian-Peng Xie , Zhi-Feng Zi , Dan-Dan Xia , Han-Jue Zhang , Hao Zhou , Min Yin , Zhong-Tao Ding
Two undescribed spirocyclic polyketide derivatives, spiromeclones A (1) and B (2), together with four known homologous compounds penicophenone A (3), 5,5′-diacetyl-2,6,2′,6′-tetrahydroxy-3,3′-dimethyl-diphenylmethane (4), 2,4-dihydroxy-5-methylacetophenone (5), and trichrontide B (6), were isolated from the endophytye fungus Penicillium sp. YUD25002 associated with Panax notoginseng. The structures of these compounds were confirmed by NMR and HR-ESI-MS, while the absolute configurations of the novel compounds were elucidated through single-crystal X-ray diffraction and TDDFT ECD calculations. The antifungal activity of the compounds against four pathogens of Panax notoginseng was investigated.
{"title":"Spirocyclic polyketide analogues from the endophyte fungus Penicillium sp. YUD25002 associated with Panax notoginseng","authors":"Wen-Jing Wang , Ju-Cheng Zhang , Yan Geng , Hai-Xia Dong , Fei Xie , Tian-Peng Xie , Zhi-Feng Zi , Dan-Dan Xia , Han-Jue Zhang , Hao Zhou , Min Yin , Zhong-Tao Ding","doi":"10.1016/j.phytol.2025.104074","DOIUrl":"10.1016/j.phytol.2025.104074","url":null,"abstract":"<div><div>Two undescribed spirocyclic polyketide derivatives, spiromeclones A (<strong>1</strong>) and B (<strong>2</strong>), together with four known homologous compounds penicophenone A (<strong>3</strong>), 5,5′-diacetyl-2,6,2′,6′-tetrahydroxy-3,3′-dimethyl-diphenylmethane (<strong>4</strong>), 2,4-dihydroxy-5-methylacetophenone (<strong>5</strong>), and trichrontide B (<strong>6</strong>), were isolated from the endophytye fungus <em>Penicillium</em> sp. YUD25002 associated with <em>Panax notoginseng</em>. The structures of these compounds were confirmed by NMR and HR-ESI-MS, while the absolute configurations of the novel compounds were elucidated through single-crystal X-ray diffraction and TDDFT ECD calculations. The antifungal activity of the compounds against four pathogens of <em>Panax notoginseng</em> was investigated.</div></div>","PeriodicalId":20408,"journal":{"name":"Phytochemistry Letters","volume":"70 ","pages":"Article 104074"},"PeriodicalIF":1.4,"publicationDate":"2025-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145516685","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.2025.104076
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}
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