Phytochemistry最新文献_第6页

Unusual norcucurbitacin glycosides from the roots of Siraitia grosvenorii 从 Siraitia grosvenorii 的根中提取的不同寻常的葫芦巴苷。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-08-03 DOI: 10.1016/j.phytochem.2024.114230

{"title":"Unusual norcucurbitacin glycosides from the roots of Siraitia grosvenorii","authors":"","doi":"10.1016/j.phytochem.2024.114230","DOIUrl":"10.1016/j.phytochem.2024.114230","url":null,"abstract":"<div>Siraitia grosvenorii Swingle is one of the first approved medicine food homology species in China, and it has been used as a natural sweetener in the food industry and as a traditional medicine to relieve cough and reduce phlegm. However, many S. grosvenorii roots are discarded yearly, which results in a great waste of resources. Twelve undescribed norcucurbitacin-type triterpenoid glycosides, siraitiaosides A-L (1–12), and six known analogs (13–18) were isolated from the roots of S. grosvenorii. The structures of isolated norcucurbitacin glycosides were elucidated by comprehensive data analyses, including HRESIMS, UV, IR, NMR, ECD calculations, and X-ray crystallography analysis. Siraitiaosides A-E (1–5) featured an unusual 19,29-norcucurbitacin framework while siraitiaosides F-L (6–12) featured a rare 29-norcucurbitacin framework. Notably, compound 4 displayed moderate anti-acetylcholinesterase (AChE) activity with an IC50 of 21.0 μM, meanwhile, compounds 16 and 18 exhibited pronounced cytotoxic activities against MCF-7, CNE-1, and HeLa cancer cell lines with IC50 values of 2.1–15.2 μM. In silico studies showed that compound 4 bound closely to AChE with a binding energy of −5.04 kcal/mol, and compound 18 could tightly bind to PI3K, AKT1, ERK2, and MMP9 proteins that related to autophagy, apoptosis, migration/invasion, and growth/proliferation. In summary, the roots of Siraitia grosvenorii have potential medicinal values due to the multiple bioactive components.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141894011","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

Bioassay-guided isolation of antibacterial and anti-inflammatory components from Atractylodes lancea 生物测定指导下从白术中分离抗菌和消炎成分。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-08-02 DOI: 10.1016/j.phytochem.2024.114232

{"title":"Bioassay-guided isolation of antibacterial and anti-inflammatory components from Atractylodes lancea","authors":"","doi":"10.1016/j.phytochem.2024.114232","DOIUrl":"10.1016/j.phytochem.2024.114232","url":null,"abstract":"<div>A bioassay-guided isolation from Atractylodes lancea (Thunb.) DC. obtained 22 compounds, including eight previously undescribed sesquiterpenoids and polyacetylenes (1, 3 and 12–17), as well as fourteen known analogues, and their structures were confirmed by extensive spectroscopic methods. This study evaluated their antibacterial activity against methicillin resistant Staphylococcus aureus (MRSA) for the first time, as well as anti-inflammatory activity. Most of them, including new compounds, showed varying degrees of antibacterial activity against S. aureus and MRSA. Notably, compound 21 exhibited significant antibacterial activity against four different bacteria (MIC 6.25–20.00 μg/mL). This suggested that 21 may have the potential to be developed into a broad-spectrum antibacterial agent. Moreover, except for 9 and 11, most compounds exhibited great anti-inflammatory activity (IC50 1.92–37.91 μM), and iNOS might be a potential target of these compounds according to the molecular docking analysis.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141889914","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

An efficient flavonoid glycosyltransferase NjUGT73B1 from Nardostachys jatamansi of alpine Himalayas discovered by structure-based protein clustering 通过基于结构的蛋白质聚类发现喜马拉雅山高山蕨类植物中的高效黄酮糖基转移酶 NjUGT73B1。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-27 DOI: 10.1016/j.phytochem.2024.114228

{"title":"An efficient flavonoid glycosyltransferase NjUGT73B1 from Nardostachys jatamansi of alpine Himalayas discovered by structure-based protein clustering","authors":"","doi":"10.1016/j.phytochem.2024.114228","DOIUrl":"10.1016/j.phytochem.2024.114228","url":null,"abstract":"<div>Tilianin and linarin, two rare glycosylated flavonoids in the aromatic endangered medicinal plant Nardostachys jatamansi (D.on)DC., play an important role in the fields of medicine, cosmetics, food and dye industries. However, there remains a lack of comprehensive understanding regarding their biosynthetic pathway. In this study, the phytochemical investigation of N. jatamansi resulted in the isolation of linarin. With help of AlphaFold2 to cluster the entire glycosyltransferase family based on predicted structure similarities, we successfully identified a flavonoid glycosyltransferase NjUGT73B1, which could efficiently catalyze the glucosylation of acacetin at 7-OH to produce tilianin, also the key precursor in the biosynthesis of linarin. Additionally, NjUGT73B1 displayed a high degree of substrate promiscuity, enabling glucosylation at 7-OH of many flavonoids. Molecular modeling and site-directed mutagenesis revealed that H19, H21, H370, F126, and F127 play the crucial roles in the glycosylation ability of NjUGT73B1. Notably, comparation with the wild NjUGT73B1, mutant H19K led to a 50% increase in the activity of producing tilianin from acacetin.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141793024","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

Identification and bioactivity evaluation of twelve previously undescribed depsidone derivatives from Garcinia oligantha 鉴定和评估 12 种以前未曾描述过的来自寡甘草的去苷酮衍生物。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-26 DOI: 10.1016/j.phytochem.2024.114227

{"title":"Identification and bioactivity evaluation of twelve previously undescribed depsidone derivatives from Garcinia oligantha","authors":"","doi":"10.1016/j.phytochem.2024.114227","DOIUrl":"10.1016/j.phytochem.2024.114227","url":null,"abstract":"<div><h3>Abstract</h3>Phytochemical studies on the leaves and twigs of Garcinia oligantha Merr. led to the isolation of twelve previously undescribed depsidone derivatives (oliganthdepsidones A-L, 1–12). Their structures were elucidated by extensive spectroscopic analysis including 1H and 13C NMR, HSQC, HMBC and NOESY along with HRESIMS. The structures of oliganthdepsidones G and J were finally determined using DFT-NMR chemical shift calculations and DP4+ methods. Cytotoxicity test in four human cancer cell lines indicated that oliganthdepsidone F had relatively strong cytotoxic effect against A375 (melanoma), A549 (lung cancer), HepG2 (liver cancer), and MCF-7 (breast cancer) cell lines with IC50 of 18.71, 15.44, 10.92, and 15.90 μM, respectively. The dose- and time-dependent antiproliferative effects of oliganthdepsidone F on these cell lines were also observed by CCK-8 test. As determined by fluorescent microscopy and flow cytometry in these cell lines, oliganthdepsidone F could promote cell apoptosis, leading to the inhibition of cell proliferation. The results of wound healing assay and transwell assay showed that oliganthdepsidone F could inhibit the migration and invasion of A549 and MCF-7 cell lines in a concentration-dependent manner.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141788888","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

Differentiated response of Hypericum perforatum to foliar application of selected metabolic modulators: Elicitation potential of chitosan, selenium, and salicylic acid mediated by redox imbalance 贯叶连翘对叶面喷施精选代谢调节剂的不同反应：壳聚糖、硒和水杨酸通过氧化还原失衡介导的激发潜力。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-26 DOI: 10.1016/j.phytochem.2024.114231

{"title":"Differentiated response of Hypericum perforatum to foliar application of selected metabolic modulators: Elicitation potential of chitosan, selenium, and salicylic acid mediated by redox imbalance","authors":"","doi":"10.1016/j.phytochem.2024.114231","DOIUrl":"10.1016/j.phytochem.2024.114231","url":null,"abstract":"<div>Plants plastically alter their metabolism in response to environmental stimuli, which induces changes in the accumulation of specialized metabolites. This ability can be utilized to manipulate plant phytochemistry in a desired direction. However, the abundance of secondary metabolites in the different plant species, especially medicinal, is enormous; therefore, it is difficult to establish a clear direction for the effects of metabolic modulators on phytochemical composition, especially given the possibility of using different types thereof. In order to gain insight into these changes, we investigated the effects of foliar-applied chitosan (ChL, 100 mg/L), selenium (Se, 10 mg/L), salicylic acid (SA, 150 mg/L), or an equal volume mixture thereof on Hypericum perforatum L. metabolism. Selenium and SA proved to be the more effective than ChL in enhancing the accumulation of phenolic compounds. The greatest increase was found in the concentration of neochlorogenic acid after Se-spraying. The treatment with the elicitors generally increased the concentration of identified flavonoids, but not the level of naphthodianthrone or phloroglucinol metabolites. The most pronounced response was observed on day 10 following the application of the compounds, and is likely the consequence of elevated levels of O2−˙, free proline, and modulated activity of enzymatic antioxidants.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0031942224002681/pdfft?md5=be261de84676fca1a15dbfb67d57ec9d&pid=1-s2.0-S0031942224002681-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141788887","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Ganospirones A−G, seven undescribed spiro-meroterpenoids from Ganoderma lucidum and their biological activities Ganospirones A-G，灵芝中七种未被描述的螺旋萜类化合物及其生物活性。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-22 DOI: 10.1016/j.phytochem.2024.114226

引用次数: 0

Variation in induced responses in volatile and non-volatile metabolites among six willow species: Do willow species share responses to herbivory? 六种柳树挥发性和非挥发性代谢物的诱导反应存在差异：柳树物种对食草动物的反应是否相同？

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-22 DOI: 10.1016/j.phytochem.2024.114222

{"title":"Variation in induced responses in volatile and non-volatile metabolites among six willow species: Do willow species share responses to herbivory?","authors":"","doi":"10.1016/j.phytochem.2024.114222","DOIUrl":"10.1016/j.phytochem.2024.114222","url":null,"abstract":"<div>Chemical variation is a critical aspect affecting performance among co-occurring plants. High chemical variation in metabolites with direct effects on insect herbivores supports chemical niche partitioning, and it can reduce the number of herbivores shared by co-occurring plant species. In contrast, low intraspecific variation in metabolites with indirect effects, such as induced volatile organic compounds (VOCs), may improve the attraction of specialist predators or parasitoids as they show high specificity to insect herbivores. We explored whether induced chemical variation following herbivory by various insect herbivores differs between VOCs vs. secondary non-volatile metabolites (non-VOCs) and salicinoids with direct effects on herbivores in six closely related willow species. Willow species identity explained most variation in VOCs (18.4%), secondary non-VOCs (41.1%) and salicinoids (60.7%). The variation explained by the independent effect of the herbivore treatment was higher in VOCs (2.8%) compared to secondary non-VOCs (0.5%) and salicinoids (0.5%). At the level of individual VOCs, willow species formed groups, as some responded similarly to the same herbivores. Most non-VOCs and salicinoids were upregulated by sap-suckers compared to other herbivore treatments and control across the willow species. In contrast, induced responses in non-VOCs and salicinoids to other herbivores largely differed between the willows. Our results suggest that induced responses broadly differ between various types of chemical defences, with VOCs and non-VOCs showing different levels of specificity and similarity across plant species. This may further contribute to flexible plant responses to herbivory and affect how closely related plants share or partition their chemical niches.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141760348","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

Antimicrobial isoflavans and other metabolites of Dalea nana Dalea nana 的抗菌异黄酮及其他代谢物。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-19 DOI: 10.1016/j.phytochem.2024.114224

{"title":"Antimicrobial isoflavans and other metabolites of Dalea nana","authors":"","doi":"10.1016/j.phytochem.2024.114224","DOIUrl":"10.1016/j.phytochem.2024.114224","url":null,"abstract":"<div>The phytochemical investigation of extracts from Dalea nana roots and aerial parts led to the isolation of thirteen phenolic compounds. Three previously undescribed isoflavans, named verdeans A-C (1, 3, and 7), were characterized. Two additional isoflavans (2 and 5) were previously undescribed enantiomers of known compounds. A previously undescribed isoflavone (verdean D, 10) was found, and the known specialized metabolites, isoflavans 4, 6, 8, and 9, isoflavone 11, flavone 12, and a 2-arylbenzofuran 13, were also isolated. All but one (7) of the isoflavans were prenylated. The structures of the previously undescribed compounds were deduced by NMR spectroscopy, supported by HRESI mass spectrometry. The absolute configurations of 1–3, 5, and 7–9 were determined by ECD. Compounds 1, 3, 4, 6, and 8 exhibited in vitro antimicrobial activities, causing complete growth inhibition (MIC) at concentrations between 6.7 and 37.0 μM against Cryptococcus neoformans and between 8.9 and 25.0 μM against methicillin resistant Staphylococcus aureus (MRSA). The most broadly active previously undescribed compound was verdean A (1), with MIC values of 6.7 and 12.9 μM toward C. neoformans and MRSA, respectively, and an MIC of 10.0 μM against the often-intractable C. albicans.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141734929","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

Identification of substituted variants of plastoquinone-9 as potent and specific photosynthetic inhibitors in cyanobacteria and plants 鉴定蓝藻和植物中作为强效特异性光合作用抑制剂的质醌-9 取代变体。

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-19 DOI: 10.1016/j.phytochem.2024.114225

{"title":"Identification of substituted variants of plastoquinone-9 as potent and specific photosynthetic inhibitors in cyanobacteria and plants","authors":"","doi":"10.1016/j.phytochem.2024.114225","DOIUrl":"10.1016/j.phytochem.2024.114225","url":null,"abstract":"<div>The unprenylated benzoquinones 2,3,5,6-tetramethyl-1,4-benzoquinone (duroquinone), 2-chloro-1,4-benzoquinone (CBQ), 2,6-dimethyl-1,4-benzoquinone (DMBQ), 2,6-dichloro-1,4-benzoquinone (DCBQ), and 2,6-dimethoxy-1,4-benzoquinone (DMOBQ) were tested as putative antimetabolites of plastoquinone-9, a vital electron and proton carrier of oxygenic phototrophs. Duroquinone and CBQ were the most effective at inhibiting the growth of the cyanobacterium Synechocystis sp. PCC 6803 either in photomixotrophic or photoautotrophic conditions. Duroquinone, a close structural analog of the photosynthetic inhibitor methyl-plastoquinone-9, was found to possess genuine bactericidal activity towards Synechocystis at a concentration as low as 10 μM, while at the same concentration CBQ acted only as a mild bacteriostat. In contrast, only duroquinone displayed marked cytotoxicity in axenically-grown Arabidopsis, resulting in damages to photosystem II and hindered net CO2 assimilation. Metabolite profiling targeted to photosynthetic cofactors and pigments indicated that in Arabidopsis duroquinone does not directly inhibit plastoquinone-9 biosynthesis. Taken together, these data indicate that duroquinone offers prospects as an algicide and herbicide.</div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141734931","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

Guaianolide sesquiterpene lactones from Cichorium glandulosum and their anti-neuroinflammation activities 刺五加中的愈创木内酯倍半萜内酯及其抗神经炎症活性

IF 3.2 2区生物学

Phytochemistry Pub Date : 2024-07-19 DOI: 10.1016/j.phytochem.2024.114223

引用次数: 0