Phytochemistry最新文献_第8页

Millettia dubia De Wild. (Fabaceae): Structural analysis of the oleanane-type glycosides and stimulation of the sweet taste receptors TAS1R2/TAS1R3 Millettia dubia De Wild.(豆科）：齐墩果烷型苷的结构分析和对甜味受体 TAS1R2/TAS1R3 的刺激。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-04 DOI: 10.1016/j.phytochem.2024.114204

David Pertuit , Christine Belloir , Younes Bouizi , Clément Delaude , Mpuza Kapundu , Marie-Aleth Lacaille-Dubois , Loïc Briand , Anne-Claire Mitaine-Offer

引用次数: 0

The Nicotiana tabacum UGT89A2 enzyme catalyzes the glycosylation of di- and trihydroxylated benzoic acid derivatives 烟草 UGT89A2 酶催化二羟基和三羟基苯甲酸衍生物的糖基化。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-03 DOI: 10.1016/j.phytochem.2024.114203

Arianna Duque-Ortiz , José Rivera-Chávez , Guillermo Pastor-Palacios , Samuel Lara-González

{"title":"The Nicotiana tabacum UGT89A2 enzyme catalyzes the glycosylation of di- and trihydroxylated benzoic acid derivatives","authors":"Arianna Duque-Ortiz , José Rivera-Chávez , Guillermo Pastor-Palacios , Samuel Lara-González","doi":"10.1016/j.phytochem.2024.114203","DOIUrl":"10.1016/j.phytochem.2024.114203","url":null,"abstract":"<div>Glycosyltransferases catalyze the transfer of a glycoside group to a wide range of acceptor compounds to produce glycoconjugates with diverse biological and pharmacological activities. The present work reports the identification and biochemical characterization of Nicotiana tabacum UGT89A2 glycosyltransferase (NtUGT89A2). The enzyme is a monomer in solution that catalyzes the O-β-glucosylation of di- and tri-hydroxylated and chlorinated derivatives of benzoic acid. NtUGT89A2 has a preference for 2,5-dihydroxybenzoic acid (2,5-DHBA) over 2,3-dihydroxybenzoic acid (2,3-DHBA) and 2,4-dihydroxybenzoic acid (2,4-DHBA). Other substrates that can be used by NtUGT89A2 include 3,4,5-trihydroxybenzoic acid and chlorinated derivatives such as 2-chloro-5-hydroxybenzoic acid (2-Cl-5-HBA). The substrates of NtUGT89A2 were identified by thermal stability experiments, where we observed a maximum increase of the thermal denaturation midpoint (Tm) of 10 °C in the presence of 2,5-DHBA and UDP-glucose. On the other hand, the highest specific activity was obtained with 2,5-DHBA (225 ± 1.7 nkat/mg). Further characterization revealed that the enzyme has a micromolar affinity for its substrates. Notably, the enzyme retains full activity after incubation at 70 °C for 1 h. These results provide a basis for future functional and structural studies of NtUGT89A2.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141538308","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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

Monoterpene-chalcone conjugates and diarylheptanoids isolated from the seeds of Alpinia katsumadai Hayata with cytotoxic activity 从Alpinia katsumadai Hayata种子中分离出的具有细胞毒性活性的单萜查尔酮共轭物和二芳基庚烷类化合物。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-06-28 DOI: 10.1016/j.phytochem.2024.114197

Hua-Lin You , Bo Zhou , Meng-Jia Guo , Xin-Man Zhao , Xiao-Long Li , Xiang-Chun Shen , Nen-Ling Zhang

引用次数: 0

Andrastin-type meroterpenoids, α-pyrone polyketides, and sesquicarane derivatives from Penicillium sp., a fungus isolated from Pinus koraiensis seed 从柯来松种子中分离出的一种真菌--青霉菌中提取出的安达信类美拉特萜类化合物、α-吡喃酮多酮类化合物和芝麻烷衍生物。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-06-27 DOI: 10.1016/j.phytochem.2024.114202

Shouye Han , Huabin Ma , Yumeng Wu , Chunying Wang , Yuanli Li , Qin Li , Zhongbin Cheng

{"title":"Andrastin-type meroterpenoids, α-pyrone polyketides, and sesquicarane derivatives from Penicillium sp., a fungus isolated from Pinus koraiensis seed","authors":"Shouye Han , Huabin Ma , Yumeng Wu , Chunying Wang , Yuanli Li , Qin Li , Zhongbin Cheng","doi":"10.1016/j.phytochem.2024.114202","DOIUrl":"10.1016/j.phytochem.2024.114202","url":null,"abstract":"<div>The genus Penicillium has provided us with the household antibiotic penicillin and the well-known lipid-lowering agent mevastatin. The strain Penicillium sp. SZ-1 was found to grow vigorously in an intact Pinus koraiensis seed, it is inferred that the strain may develop unique mechanisms associated with the biosynthesis of rare metabolites. Further fermentation of the strain on solid rice medium yielded thirteen undescribed compounds, including three andrastin-type meroterpenoids (1−3), two α-pyrone polyketides (4 and 5), and eight sesquicarane derivatives (6−13), along with seven known compounds (14−20). Their structures were determined by detailed analysis of the spectroscopic and spectrometric data (NMR and HRESIMS), in addition to comparisons of the experimental and calculated ECD data for absolute configurational assignments. The hemiacetal moiety in compounds 1 and 2 and the 3α-hydroxy group in compound 3 were rarely found in the andrastin-type meroterpenoid family. The sesquicaranes belong to a small group of sesquiterpenoid that are rarely reported. Bioassay study showed that compound 1 exhibited inhibitory effects against Staphylococcus aureus ATCC 29213 and Escherichia coli ATCC 25922 with MIC values of 64 and 32 μg/mL, respectively. In addition, compounds 1 and 3 displayed weak DPPH radical scavenging activities. The andrastins and sesquicaranes in this study enriched the structural diversity of these classes of terpenoids. Of note, this study is the first report on the metabolites of a fungus isolated from P. koraiensis seed.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141470129","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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

Daldiconoids A-G: 3,4-Secolanostane triterpenoids from the fruiting bodies of Daldinia concentrica and their anti-inflammatory activity Daldiconoids A-G：Daldinia concentrica 子实体中的 3,4-癸烷三萜类化合物及其抗炎活性。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-06-26 DOI: 10.1016/j.phytochem.2024.114201

Dingwei Gong , Baoping Xie , Yijun Sun , Yuanyuan Cheng , Xiaofei Tian , Zhengzheng Zhou , Li-Wen Tian

{"title":"Daldiconoids A-G: 3,4-Secolanostane triterpenoids from the fruiting bodies of Daldinia concentrica and their anti-inflammatory activity","authors":"Dingwei Gong , Baoping Xie , Yijun Sun , Yuanyuan Cheng , Xiaofei Tian , Zhengzheng Zhou , Li-Wen Tian","doi":"10.1016/j.phytochem.2024.114201","DOIUrl":"10.1016/j.phytochem.2024.114201","url":null,"abstract":"<div>Seven undescribed 3,4-secolanostane triterpenoids, daldiconoids A-G (1–7), were isolated from the fruiting bodies of Daldinia concentrica. Daldiconoid A (1) was a highly modified 4,6,28,29-tetranorlanostane triterpenoid alkaloid featuring an unusual δ-lactam fused with a flanking cyclopentenone architecture. Their structures were determined by spectroscopic data, NMR calculations coupled with the DP4+ analysis, X-ray single-crystal diffraction, and chemical transformation. The plausible biosynthetic pathway for 1 was proposed. Compounds 1, 2, and 4–6 inhibited the expressions of IL-1β, IL-6, and TNF-α in lipopolysaccharide stimulated RAW264.7 cells at a concentration of 10 μM. Mechanistically, Compounds 1 and 2 blocked the JAK2/STAT3 signaling pathway induced by lipopolysaccharide.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141470135","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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

Atranones and dolabellanes with cardiomyocyte protective activity against cold ischemic injury from a coral-associated fungus Stachybotrys chartarum 与珊瑚有关的真菌 Stachybotrys chartarum 中的 Atranones 和 dolabellanees 具有保护心肌细胞免受冷缺血性损伤的活性。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-06-25 DOI: 10.1016/j.phytochem.2024.114199

Shuang Lin , Zixue Chai , Hanxiao Zeng , Beiye Yang , Jiangyang Chi , Yonghui Zhang , Zhengxi Hu

{"title":"Atranones and dolabellanes with cardiomyocyte protective activity against cold ischemic injury from a coral-associated fungus Stachybotrys chartarum","authors":"Shuang Lin , Zixue Chai , Hanxiao Zeng , Beiye Yang , Jiangyang Chi , Yonghui Zhang , Zhengxi Hu","doi":"10.1016/j.phytochem.2024.114199","DOIUrl":"10.1016/j.phytochem.2024.114199","url":null,"abstract":"<div>Five undescribed atranones, namely atranones V–Z (1–5), three undescribed dolabellane-type diterpenoids, namely stachatranones D–F (7–9), together with four known congeners (6 and 10–12), were obtained from a coral-associated strain of the toxigenic fungus Stachybotrys chartarum. Their structures were elucidated via extensive spectroscopic analyses, mainly including the HRESIMS and NMR data, single-crystal X-ray diffraction analysis, electronic circular dichroism calculation, and [Mo2(OAc)4] induced circular dichroism spectrum. The cardiomyocyte protective activity assay revealed that compound 9 significantly ameliorated cold ischemic injury at 24 h post cold ischemia (CI) in a dose-dependent manner. Moreover, compound 9 prevented CI induced dephosphorylation of phosphatidylinositol-3-kinase and RAC-α serine/threonine-protein kinase at 12 h post CI in a dose-dependent manner. In this work, the undescribed compound 9 could significantly protect cardiomyocytes against cold ischemic injury, highlighting the promising potential to be designed and developed as a novel cardioprotectant in heart transplant medicine.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141470130","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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

Immunosuppressive alkaloids from Narcissus tazetta subsp. Chinensis and the mechanism of (+)-narciclasine in vitro and in vivo 中国水仙亚种中的免疫抑制生物碱以及(+)-narciclasine在体外和体内的作用机制。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-06-25 DOI: 10.1016/j.phytochem.2024.114198

Wen-Ling Wang , Xiu-Yin Wu , Xing-Yan Luo , Yu-Qin Tang , Jia Cui , Xin-Yue Huang , Yu-Chen Jiang , Yang Liu , Li-Mei Li

引用次数: 0

Cytotoxic xanthanolide sesquiterpenes from the fruits of Xanthium italicum Moretti 从意大利黄刺玫果实中提取的具有细胞毒性的黄烷内酯倍半萜。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-06-25 DOI: 10.1016/j.phytochem.2024.114196

Yu-Tong Li, Cheng-Yong Tan, Jiang Fu, Hai-Qiang Wang, Yun-Bao Liu, Shuang-Gang Ma, Yong Li, Jing Qu, Shi-Shan Yu

{"title":"Cytotoxic xanthanolide sesquiterpenes from the fruits of Xanthium italicum Moretti","authors":"Yu-Tong Li, Cheng-Yong Tan, Jiang Fu, Hai-Qiang Wang, Yun-Bao Liu, Shuang-Gang Ma, Yong Li, Jing Qu, Shi-Shan Yu","doi":"10.1016/j.phytochem.2024.114196","DOIUrl":"10.1016/j.phytochem.2024.114196","url":null,"abstract":"<div>One previously undescribed xanthanolide sesquiterpene dimer pungiolide P (1), possessing an unprecedented scaffold with a 5/7/5/7/5 ring system skeleton and its intermediate pungiolide Q (2), ten xanthanolide sesquiterpenes (3–12), two eudesmene sesquiterpene derivatives (13–14), one phenylpropionic acid derivative (15), together with eleven known compounds (16–26) were obtained from the fruits of Xanthium italicum Moretti. A possible biosynthetic pathway for pungiolide P (1) was also proposed, which was supported by its bio-synthetic intermediate (2). Compounds 1, 4–5, 18–21, and 25 exhibited cytotoxic activity against a variety of human cancer cell lines. Furthermore, compounds 1, 4–5, could cause blockage of the cell cycle in the G2/M phase and induce apoptosis in H460 cells. Notably, pungiolide P (1) exhibited significantly superior cytotoxicity compared to previously reported compounds, providing valuable insights for natural anti-tumor sources.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141470134","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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

Chromene meroterpenoids from Rhododendron dauricum L. and their anti-inflammatory effects 杜鹃花中的 Chromene meroterpenoids 及其抗炎作用。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-06-25 DOI: 10.1016/j.phytochem.2024.114200

Na Zhang , Yang Xu , Dejuan Sun , Yuxia Li , Hua Li , Lixia Chen

{"title":"Chromene meroterpenoids from Rhododendron dauricum L. and their anti-inflammatory effects","authors":"Na Zhang , Yang Xu , Dejuan Sun , Yuxia Li , Hua Li , Lixia Chen","doi":"10.1016/j.phytochem.2024.114200","DOIUrl":"10.1016/j.phytochem.2024.114200","url":null,"abstract":"<div>Rhododendron dauricum L. is a perennial herb belonging to the genus Rhododendron, commonly utilized in formulations for treating coughs and bronchitis, as well as in herbal teas for enhancing immunity and preventing tracheitis. In this study, fifteen previously undescribed chromene meroterpenoids (1a/1b-4a/4b, 5–8, 9b, 10a, 11b), along with twenty-one known compounds were isolated from the dried twigs and leaves of Rhododendron dauricum L. Of these, (−)-rhodonoid E (9b), (+)-confluentin (10a), and (−)-rubiginosin D (11b) were separated for the first time by chiral HPLC separation. The elucidation of their structures, including absolute configurations, was achieved through a combination of techniques such as NMR, HRESIMS, modified Mosher's method and quantum-chemical calculation of electronic circular dichroism (ECD) spectra. Seven pairs of enantiomers, compounds 1a/1b-4a/4b and 9a/9b-11a/11b, were initially obtained in a racemic manner and were further separated by chiral HPLC preparation. The biological assessment of these compounds against NO production was conducted in the LPS-induced RAW264.7 macrophage cells model. Compounds 9a, 9b, and 11a displayed inhibitory rates exceeding 80%, with IC50 values ranging from 8.69 ± 0.94 to 13.01 ± 1.11 μM. A preliminary examination of the structure-activity relationship (SAR) for these isolates indicated that chromene meroterpenoids with α, β-unsaturated ketone carbonyl and Δ12(13) double bond functionalities exhibited enhanced anti-inflammatory properties.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141470133","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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α-Glucosidase inhibitory flavonol glycosides from Cyclocarya paliurus (Batalin) Iljinskaja and their kinetics characteristics 来自 Cyclocarya paliurus (Batalin) Iljinskaja 的 α-Glucosidase 抑制性黄酮醇苷及其动力学特征。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-06-24 DOI: 10.1016/j.phytochem.2024.114195

Yong Yang , Tingsi Guo , Feibing Huang , Hao Zheng , Wenchu Li , Hanwen Yuan , Qingling Xie , Nusrat Hussain , Wei Wang , Yuqing Jian

{"title":"α-Glucosidase inhibitory flavonol glycosides from Cyclocarya paliurus (Batalin) Iljinskaja and their kinetics characteristics","authors":"Yong Yang , Tingsi Guo , Feibing Huang , Hao Zheng , Wenchu Li , Hanwen Yuan , Qingling Xie , Nusrat Hussain , Wei Wang , Yuqing Jian","doi":"10.1016/j.phytochem.2024.114195","DOIUrl":"10.1016/j.phytochem.2024.114195","url":null,"abstract":"<div>Seven previously undescribed flavonol glycosides including four rare flavonol glycoside cyclodimers, dicyclopaliosides A-C (1-3) with truxinate type and dicyclopalioside D (4) with truxillate type, as well as three kaempferol glycoside derivatives cyclopaliosides A-C (5–7), were obtained from the leaves of Cyclocarya paliurus. Their structures were elucidated by extensive spectroscopic methods and chemical analyses. All compounds were evaluated for their inhibitory α-glucosidase activities. Among them, compounds 1–4 display strong inhibitory activities with IC50 values of 82.76 ± 1.41, 62.70 ± 4.00, 443.35 ± 16.48, and 6.31 ± 0.88 nM, respectively, while compounds 5–7 showed moderate activities with IC50 values of 4.91 ± 0.75, 3.64 ± 0.68, and 5.32 ± 0.53 μΜ, respectively. The structure-activity relationship analysis assumed that the cyclobutane cores likely contribute to the enhancement of α-glucosidase inhibitory activities of dimers. Also, the interaction mechanism between flavonol glycoside dimers and α-glucosidase were explored by the enzyme kinetic assay, indicating that compounds 1–3 exhibited mixed-type inhibition, while 4 showed uncompetitive inhibition. Additionally, the active compounds have also undergone molecular docking evaluation.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141458706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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