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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Interactions of fungi with non-isothiocyanate products of the plant glucosinolate pathway: A review on product formation, antifungal activity, mode of action and biotransformation

    Plaszko T.Szucs Z.Vasas G.Gonda S....
    30页
    查看更多>>摘要：? 2022 The Author(s)The glucosinolate pathway, which is present in the order Brassicales, is one of the most researched defensive natural product biosynthesis pathways. Its core molecules, the glucosinolates are broken down upon pathogen challenge or tissue damage to yield an array of natural products that may help plants defend against the stressor. Though the most widely known glucosinolate decomposition products are the antimicrobial isothiocyanates, there is a wide range of other volatile and non-volatile natural products that arise from this biosynthetic pathway. This review summarizes our current knowledge on the interaction of these much less examined, non-isothiocyanate products with fungi. It deals with compounds including (1) glucosinolates and their biosynthesis precursors; (2) glucosinolate-derived nitriles (e.g. derivatives of 1H-indole-3-acetonitrile), thiocyanates, epithionitriles and oxazolidine-2-thiones; (3) putative isothiocyanate downstream products such as raphanusamic acid, 1H-indole-3-methanol (= indole-3-carbinol) and its oligomers, 1H-indol-3-ylmethanamine and ascorbigen; (4) 1H-indole-3-acetonitrile downstream products such as 1H-indole-3-carbaldehyde (indole-3-carboxaldehyde), 1H-indole-3-carboxylic acid and their derivatives; and (5) indole phytoalexins including brassinin, cyclobrassinin and brassilexin. Herein, a literature review on the following aspects is provided: their direct antifungal activity and the proposed mechanisms of antifungal action, increased biosynthesis after fungal challenge, as well as data on their biotransformation/detoxification by fungi, including but not limited to fungal myrosinase activity.
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    • NSTL
    • Elsevier

    Terpenoids from Nardostachys jatamansi and their cytotoxic activity against human pancreatic cancer cell lines

    Ma L.-M.Wang K.Meng X.-H.Wang C.-B....
    10页
    查看更多>>摘要：? 2022 Elsevier LtdFive previously unreported terpenoids, together with fifteen known analogs, were isolated from a methanol extract of the roots and rhizomes of Nardostachys jatamansi. Their structures, including absolute configurations, were elucidated by spectroscopic data and electronic circular dichroism (ECD) spectra analyses, as well as single-crystal X-ray diffraction for crystalline compounds. Structurally, (4R,5S,6S,7R)-1(10)-aristolane-8,9-diacid is a novel 8,9-dicarboxylic acid derivative of aristolane-type sesquiterpenoid. (4R,6S,7R,10S)-10-Hydroxyguaia-1(5)-6,7-epoxy-2-one is an undescribed analogue of nardoguaianone K, with a rare 6,7-epoxide group. (4R,5R,6R,8R)-1(10)-Isonardosinone-8-ol-9-one-7,11-lactone is an isonardosinane-type sesquiterpene bearing a γ-lactone ring. Dinardokanshone F is a rare example of a sesquiterpene dimer from N. jatamansi connected by an oxo bridge. The isolates were evaluated for their cytotoxic activity against four human pancreatic cancer cell lines (CFPAC-1, PANC-1, CAPAN-2 and SW1990). Compound epoxynardosinone exhibited significant cytotoxicity against CAPAN-2 cell lines with IC50 value of 2.60 ± 1.85 μM. 1-Hydroxylaristolone displayed comparable cytotoxicity on CFPAC-1 cell lines (IC50 1.12 ± 1.19 μM), compared to Taxol (IC50 0.32 ± 0.13 μM). 1-Hydroxylaristolone, 1(10)-aristolane-9β-ol, 1(10)-aristolen-2-one, alpinenone, valtrate isovaleroyloxyhydrine and nardostachin displayed stronger cytotoxicity against PANC-1 cell lines with IC50 values ranging from 0.01 ± 0.01 to 6.50 ± 1.10 μM. 1(10)-Aristolane-9β-ol, 10-hydroxyguaia-1(5)-6,7-epoxy-2-one, nardoguaianone K, nardonoxide, epoxynardosinone, 1(10)-isonardosinone-8-ol-9-one-7,11-lactone, valtrate isovaleroyloxyhydrine and nardostachin showed remarkable cytotoxicity against SW1990 cell lines with IC50 values ranging from 0.07 ± 0.05 to 4.82 ± 6.96 μM. Furthermore, the primary mechanistic study of nardostachin demonstrated that it induced cell apoptosis via the mitochondria-dependent pathway, and induced SW1900 cell arrest at G2/M phase.
      原文链接:
    • NSTL
    • Elsevier

    Enzyme activity and population genetic structure analysis in wheat associated with resistance to Bipolaris sorokiniana-common root rot diseases

    Qalavand F.Esfahani M.N.Azarm D.A.Vatandoost J....
    10页
    查看更多>>摘要：? 2022 Elsevier LtdCommon root rot disease (CRR) caused by Bipolaris sorokiniana (Sacc.) (Pleosporaceae), is an important fungal disease of wheat, Triticum aestivum (Poaceae), causing considerable yield losses globally. Incorporating genetic resistance in cultivated crops is considered the most efficient and sustainable solution to counter root rot diseases. Moreover, resistance to CCR is quantitative in nature, and thus the mechanism is poorly understood. To this aim, we analyzed the activities of defense-related enzymes; peroxidase (POX), superoxide dismutase (SOD), polyphenol oxidase (PPO), catalase (CAT), phenylalanine ammonia-lyase (PAL), β-1,3-glucanase (GLU) and chitinase (CHI), as well as total phenol content (TPC) to CRR on the three known resistant wheat ‘Alvand’ and ‘Bam’, ‘Mehregan’ at different time points (wpi) following CRR pathogen, B. sorokiniana inoculation. Of which, were selected out of 33 wheat cultivars previously screened for resistance to CRR. We also analyzed the genetic variability of the entire germplasm, 33 wheat cultivars using seven simple sequence repeat (SSR) primer pairs. The activity of antioxidant enzymes was increased in the related resistant genotypes. Of which, ‘Bam’ had the highest increase in PPO, and GLU activities, followed by ‘Alvand’ in SOD, PAL, and CHI significantly. Whereas, ‘Mehregan’ showed the highest level of TPC, POX, and CAT activities. In addition, five out of seven used SSR primers produced a total of 20 polymorphic bands, of which the number of alleles in each gene locus varied within 3–7 bands. The polymorphism information content (PIC) value also ranged from 0.44 to 0.81, with the mean of 0.65, Shannon Information Index (I) between 0.29 and 0.63 with an average of 0.47 per locus, and Nei's gene diversity (h) value varied from 0.16 to 0.44 with an average of 0.32. The average number of effective alleles was 1.52, ranging between 1.21 and 1.8. The gene locus Xgwm 140 showed the highest diversity in the population genetic structure, which explains the ability of the primers to resolve the assayed germplasm. Thus, resistance to CRR in wheat was mainly related to the enhancement of antioxidant enzymes, although the specific metabolic pathways require further study. This study presents new insights for understanding resistance mechanisms of the selected wheat cultivars to CRR, thus improving wheat yield in the future.
      原文链接:
    • NSTL
    • Elsevier

    Acanthoic acid, unique potential pimaradiene diterpene isolated from Acanthopanax koreanum Nakai (Araliaceae): A review on its pharmacology, molecular mechanism, and structural modification

    Dou J.-Y.Jiang Y.-C.Cui Z.-Y.Lian L.-H....
    11页
    查看更多>>摘要：? 2022 Elsevier LtdAcanthoic acid (AA) is a pimaradiene diterpene isolated from the root bark of Acanthopanax koreanum Nakai (Araliaceae) with a wide range of pharmacological activities, including anti-cancer, anti-inflammatory, anti-diabetes, liver protection, gastrointestinal protection, and cardiovascular protection. In addition, AA promotes its pharmacological effects by targeting liver X receptors (LXRs), nuclear factor-kappa B (NF-κB), Toll-Like Receptor 4 (TLR4) and IL-1 receptor-associated kinase (IRAK) signaling pathways, or AMP-activated protein kinase (AMPK) signaling pathway, etc. Also, some studies focus on the structural modification of AA to improve its pharmacological activities. The review summarizes the pharmacological activities, molecular mechanism, and the structural modification of AA, which might supply information for the development of AA in the future.
      原文链接:
    • NSTL
    • Elsevier

    Novel methods to characterise spatial distribution and enantiomeric composition of usnic acids in four Icelandic lichens

    Xu M.Oddsson S.Gylfason A.E.Snorradottir B.S....
    11页
    查看更多>>摘要：? 2022 Elsevier LtdUsnic acid is an antibiotic metabolite produced by a wide variety of lichenized fungal lineages. The enantiomers of usnic acid have been shown to display contrasting bioactivities, and hence it is important to determine their spatial distribution, amounts and enantiomeric ratios in lichens to understand their roles in nature and grasp their pharmaceutical potential. The overall aim of the study was to characterise the spatial distribution of the predominant usnic acid enantiomer in lichens by combining spatial imaging and chiral chromatography. Specifically, separation and quantification of usnic acid enantiomers in four common lichens in Iceland was performed using a validated chiral chromatographic method. Molecular dynamics simulation was carried out to rationalize the chiral separation mechanism. Spatial distribution of usnic acid in the lichen thallus cross-sections were analysed using Desorption Electrospray Ionization-Imaging Mass Spectrometry (DESI-IMS) and fluorescence microscopy. DESI-IMS confirmed usnic acid as a cortical compound, and revealed that usnic acid can be more concentrated around the algal vicinity. Fluorescence microscopy complemented DESI-IMS by providing more detailed distribution information. By combining results from spatial imaging and chiral separation, we were able to visualize the distribution of the predominant usnic acid enantiomer in lichen cross-sections: (+)-usnic acid in Cladonia arbuscula and Ramalina siliquosa, and (?)-usnic acid in Alectoria ochroleuca and Flavocetraria nivalis. This study provides an analytical foundation for future environmental and functional studies of usnic acid enantiomers in lichens.
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    • NSTL
    • Elsevier

    Complexity of the auxin biosynthetic network in Arabidopsis hypocotyls is revealed by multiple stable-labeled precursors

    Tillmann M.Tang Q.Gardner G.Cohen J.D....
    9页
    查看更多>>摘要：? 2022 Elsevier LtdAuxin is a key regulator of plant development and in Arabidopsis thaliana can be synthesized through multiple pathways; however, the contributions of various biosynthetic pathways to specific developmental processes are largely unknown. To trace the involvement of various biosynthetic routes to indole-3-acetic acid (IAA) under conditions that induce adventitious root formation in Arabidopsis hypocotyls, we treated seedlings with three different stable isotope-labeled precursors ([13C6]anthranilate, [15N1]indole, and [13C3]serine) and monitored label incorporation into a number of proposed biosynthesis intermediates as well as IAA. We also employed inhibitors targeting tryptophan aminotransferases and flavin monooxygenases of the IPyA pathway, and treatment with these inhibitors differentially altered the labeling patterns from all three precursors into intermediate compounds and IAA. [13C3]Serine was used to trace utilization of tryptophan (Trp) and downstream intermediates by monitoring 13C incorporation into Trp, indole-3-pyruvic acid (IPyA), and IAA; most 13C incorporation into IAA was eliminated with inhibitor treatments, suggesting Trp-dependent IAA biosynthesis through the IPyA pathway is a dominant contributor to the auxin pool in de-etiolating hypocotyls that can be effectively blocked using chemical inhibitors. Labeling treatment with both [13C6]anthranilate and [15N1]indole simultaneously resulted in higher label incorporation into IAA through [15N1]indole than through [13C6]anthranilate; however, this trend was reversed in the proposed precursors that were monitored, with the majority of isotope label originating from [13C6]anthranilate. An even greater proportion of IAA became [15N1]-labeled compared to [13C6]-labeled in seedlings treated with IPyA pathway inhibitors, suggesting that, when the IPyA pathway is blocked, IAA biosynthesis from labeled indole may also come from an origin independent of the measured pool of Trp in these tissues.
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    • NSTL
    • Elsevier

    Berberine alkaloids inhibit the proliferation and metastasis of breast carcinoma cells involving Wnt/β-catenin signaling and EMT

    Horak I.Dian L.Xu Z.Sun Y....
    14页
    查看更多>>摘要：? 2022Berberine alkaloids belong to the class of isoquinoline alkaloids that have been shown to possess anticancer potential, berberine exhibits inhibitory effects on breast cancer development. However, the exact mechanisms of action for anti-breast carcinoma of the alkaloids, including epiberberine, berberrubine and dihydroberberine are still unclear. MTT assay, colony formation, wound healing and transwell invasion assays detected these alkaloids suppressed proliferation, migration and invasion of breast cancer cells. Hoechst and Annexin V-FITC/PI staining were used to analyze the apoptosis of breast cancer cells. Western blotting investigated the changes noted in the expression levels of the key proteins involved in the Wnt/β-catenin signaling pathway and epithelial to mesenchymal transition (EMT). The results showed that inhibited the proliferation of breast cancer cells. Berberine alkaloids inhibited the cell cycle at G2/M phase in MCF-7 cells, but in MDA-MB-231 cells berberine alkaloids arrested the cell cycle in G0/G1 and G2/M phases. By decreasing β-catenin expression, increasing GSK-3β expression and decreasing N-cadherin expression, increasing E-cadherin expression, which proved that epiberberine, berberrubine and dihydroberberine inhibited of metastasis of breast cancer cells through Wnt signaling pathway and reversed EMT except berberine. Furthermore, berberine alkaloids exert their anti-breast cancer effects through the synergistic action of intrinsic and extrinsic pathways of apoptosis. These findings highlight the different effects of different berberine alkaloids on breast cancer cells and confirm that berberine alkaloids may be potentially used in the treatment of breast cancer.
      原文链接:
    • NSTL
    • Elsevier

    Eleven undescribed alkaloids from the rhizomes of Sinomenium acutum and their IDO1 and TDO inhibitory activities

    Peng L.-Y.Zhao Q.-S.Liu J.-X.Bi R....
    15页
    查看更多>>摘要：? 2022 Elsevier LtdEleven previously undescribed alkaloids, named sinometumines A-K, along with three known alkaloids, were isolated from the rhizomes of Sinomenium acutum. The chemical structures of these unreported compounds were established using extensive spectroscopic methods (IR, UV, HRESIMS, and NMR), and their absolute configurations were determined by single crystal X-ray diffraction analyses and calculated electronic circular dichroism spectroscopy (ECD). Sinometumine D was the first aporphine-type derived alkaloid inner salt with a rearranged dibenzofuran ring backbone. Sinometumine E was a rare protoberberine-type alkaloid with a complex 6/6/6/6/6/6 hexacyclic skeleton. This was the first report of alkaloids with these two skeletons isolated from S. acutum. All isolates were evaluated for their inhibitory activities against indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO). Lysicamine possessed noteworthy inhibitory activities as an IDO1/TDO dual inhibitor with IC50 values of 6.22 ± 0.26 μM and 23.76 ± 2.93 μM, respectively, and liriodenine revealed moderate dual inhibition with IC50 values of 31.65 ± 4.44 μM and 15.64 ± 0.26 μM. The intermolecular interactions and binding modes between lysicamine and IDO1/TDO were elaborated by molecular docking studies.
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    • NSTL
    • Elsevier

    Bioactive pulvinones from a marine algicolous fungus Aspergillus terreus NTU243

    Hsiao G.Chi W.-C.Chang C.-H.Fu Y.-J....
    7页
    查看更多>>摘要：? 2022 Elsevier LtdMarine fungi are regarded as an under-explored source of structurally interesting and bioactive natural products with the potential to provide attractive lead compounds for drug discovery. In this study, several fungal strains were isolated from marine algae collected from the northeastern coast of Taiwan. In the preliminary antimicrobial screening against bacteria and fungi, the ethyl acetate extract of the fermented products of Aspergillus terreus NTU243 derived from a green alga Ulva lactuca was found to exhibit significant antimicrobial activities. Therefore, bioassay-guided separations of the active principle from liquid and solid fermented products of A. terreus NTU243 were undertaken, which resulted in the isolation and purification of 16 compounds. Their structures were elucidated by spectroscopic analysis to be four previously undescribed aspulvinones S–V as well as twelve known compounds. All the isolates were assessed for anti-inflammatory activity by measuring the amount of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 cells, and aspulvinone V, butyrolactone I, and (+)-terrein inhibited 45.0%, 34.5%, and 49.2% of NO production, respectively, at 10 μM concentration. Additionally, zymography showed that the conditioned medium of THP-1 cells post-LPS challenged significantly enhanced matrix metalloproteinase (MMP)-9-mediated gelatinolysis, and pretreatment with aspulvinones U and V significantly attenuated MMP-9-mediated gelatinolysis by 56.0% and 67.8%, separately.
      原文链接:
    • NSTL
    • Elsevier

    Isoquinoline alkaloids from the Corydalis tomentella with potential anti-hepatoma and antibacterial activities

    Du K.Liu Y.Zong K.Wang Y....
    7页
    查看更多>>摘要：? 2022 Elsevier LtdSix undescribed isoquinolines, including one rarely reported N-benzyl isoquinoline together with sixteen known ones were isolated from C. tomentella. Their planar structures and absolute configurations were elucidated by extensive analyses of UV, IR, NMR, HRESIMS, DP4+ probability analysis as well as ECD calculations. Biological evaluations revealed that 3,4-2H-tomentelline C (6) showed significant cytotoxicity (IC50 = 7.42 μM) against the HepG2 cell line while (1′R, 2′S)-coptichine B (3) exhibited stronger antibacterial activities.
      原文链接:
    • NSTL
    • Elsevier