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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Profiling alkaloids in Aconitum pendulum N. Busch collected from different elevations of Qinghai province using widely targeted metabolomics

    Wang, Jun-JieLou, Hua-YongLiu, YingHan, Hong-Ping...
    10页
    查看更多>>摘要：Aconitum pendulum N. Busch (Ranunculaceae) is rich in alkaloids with anti-inflammatory and analgesic activities. Many studies have focused on the identification or quantification of alkaloid components using low-throughput tests. However, the metabolic differences of plants from environmentally distinct regions remain unclear. The present study profiled alkaloid chemical compounds in the rhizomes of A. pendulum from different regions. A total of 80 chemical compounds were identified using a widely targeted ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) approach. Principal component, hierarchical clustering, and orthogonal partial least squares-discriminant analyses of the chemical compounds indicated that the plants from 6 regions clearly separated into distinct groups. A total of 19 compounds contributed the most to the metabolite differences between collection areas and were identified as potential metabolic markers. The antiinflammatory activities of the A. pendulum extracts were also evaluated and the potential environmental effects on the regulation of metabolite composition and bioactivity were explored. These results improve our understanding of the variation in chemical composition of plants from different regions and will serve as a reference for evaluating the medicinal value of A. pendulum in different environments.
      原文链接:
    • NSTL
    • Elsevier

    Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP74L2) and hydroperoxide lyase (CYP74L1)

    Toporkova, Yana Y.Askarova, Elena K.Gorina, Svetlana S.Mukhtarova, Lucia S....
    12页
    查看更多>>摘要：Nonclassical P450s of the CYP74 family catalyse the secondary conversions of fatty acid hydroperoxides to bioactive oxylipins in plants. The model organism, spikemoss Selaginella moellendorffii Hieron, possesses at least ten CYP74 genes of novel J, K, L, and M subfamilies. The cloning of three CYP74L genes and catalytic properties of recombinant proteins are described in the present work. The CYP74L1 possessed mainly hydroperoxide lyase (HPL) activity towards the 13(S)-hydroperoxide of a linolenic acids (13-HPOT) and nearly equal HPL and allene oxide synthase (AOS) activities towards the 13(S)-hydroperoxide of linoleic acids (13-HPOD). The 9-hydroperoxides were poor substrates for CYP74L1 and led to the production of mainly the a ketols (AOS products) and minorities of HPL and epoxyalcohol synthase (EAS) products. The CYP74L2 possessed the AOS activity towards all tested hydroperoxides. CYP74L3 possessed low HPL/EAS activity. Besides, the aerial parts of S. moellendorffii plants possessed complex oxylipins patterns including divinyl ethers, epoxyalcohols, and 12-oxo-phytodienoic acid. Characterization of the CYP74L enzymes and oxylipin pattern updates the knowledge on the complex oxylipin biosynthetic machinery in the surviving oldest taxa of vascular plants.
      原文链接:
    • NSTL
    • Elsevier

    Serratene triterpenoids from Lycopodium cernuum L. as alpha-glucosidase inhibitors: Identification, structure-activity relationship and molecular docking studies

    Wei, Guo-ZhuZhang, Pu-ZhaoLiu, Bing-RuiZheng, Hai-Rong...
    11页
    查看更多>>摘要：Phytochemical investigation of Lycopodium cernuum L. afforded seven undescribed serratene triterpenoids named 3 beta, 21 beta-dihydroxyserra-14-en-24-oic acid-3 beta-(5'-hydroxybenzoate) (1), 3 beta, 21 beta, 24-trihydroxyserrat-14-en-3 beta- (5'-hydroxyl benzoate) (2), 3 beta, 14 alpha, 15 alpha, 21 beta-tetrahydroxyserratane-24-methyl ester (3), 3 beta, 14 alpha, 21 beta-trihy-droxyserratane-15 alpha-(4'-methoxy-5'-hydroxybenzoate)-24-methyl ester (4), 3 beta, 14 alpha, 21 beta-trihydroxyserratane-15 alpha-(4'-methoxy-5'-hydroxybenzoate) (5), 3 beta-hydroxy-21 beta-acetate-16-oxoserrat-14-en-24-oic acid (6), 3 beta, 21 beta-dihydroxy-16 alpha, 29-epoxyserrat-14-en-24-methyl ester (7), together with eleven known compounds (8-18), whose chemical structures were elucidated through spectroscopic analysis of HRESIMS, 1D NMR, 2D NMR and comparison between the literature. All compounds were evaluated for their a-glucosidase inhibitory activity for the first time. The results showed that compounds 1, 2, 4, 5, 6, 10, 13, 15, and 16 were among the most potent alpha-glucosidase inhibitors, with IC50 values ranging from 23.22 +/- 0.64 to 50.65 +/- 0.82 mu M. Structure-activity relationship (SAR) studies indicated that the combined properties of the 5-hydroxybenzoate moiety at C-3, beta-OH at C-21, COOH-at C-24, and Delta(14,15) groups enabled an increase in the alpha-glucosidase inhibitory effect. In addition, molecular docking studies showed that the potential inhibitors mainly interact with key amino acid residues in the active site of alpha-glucosidase through hydrogen bonds and hydrophobic forces.
      原文链接:
    • NSTL
    • Elsevier

    Hypoglycemic flavonoids from Selaginella tamariscina (P.Beauv.) Spring

    Long, Hong-PingLiu, JianXu, Ping-ShengXu, Kang-Ping...
    8页
    查看更多>>摘要：Six flavonoids, namely, three undescribed biflavonoids, one undescribed 8-aryl flavonoid, and two known compounds, were isolated from Selaginella tamariscina (P.Beauv.) Spring. The structures and absolute configu-rations of those undescribed compounds were established by NMR spectroscopy data, HRESIMS analyses and electronic circular dichroism (ECD) analyses. In addition, all the isolates were evaluated for their hypoglycemic activity in HepG2 cells. Involvenflavone H, I, and J significantly increased glucose consumption in both normal and insulin-resistant HepG2 cells. Interestingly, these three compounds can effectively upregulate the protein expression of glucokinase (GCK) and adenylate cyclases (ADCYs). These results suggested that involvenflavone H, I, and J (especially involvenflavone J) may have potent hypoglycemic activity, which also provided promising molecular targets for the treatment of diabetes.
      原文链接:
    • NSTL
    • Elsevier

    What Socrates drank? Comparative chemical investigation of two Greek Conium taxa exhibiting diverse chemical profiles

    Vlassi, AnthiKoutsaviti, AikateriniConstantinidis, TheophanisIoannou, Efstathia...
    10页
    查看更多>>摘要：Conium divaricatum, even though exhibiting morphological differences in comparison to its congener of European origin Conium maculatum, is still considered a disputed taxon often referred to as a synonym of the latter. Herein, essential oils of various plant tissues from several populations of both taxa were comparatively investigated, showing distinct chemical profiles. In the case of C. divaricatum, the essential oils were dominated by hydrocarbon esters, among which the main constituents 4 '-oxodecyl hexanoate, 4 '-oxododecyl hexanoate and 4 ' oxooctyl hexanoate were isolated and identified as undescribed natural products. In contrast, the essential oils of C. maculatum were dominated by hydrocarbon alkanes, alkenes and ketones, as well as the polyacetylene (Z)falcarinol. Even though determination of the total alkaloids content and toxicity assessment against the crustacean Artemia salina did not reveal significant differences, the distinct chemical profiles and the morphological differences observed for both taxa, strongly support their distinction as separate species.
      原文链接:
    • NSTL
    • Elsevier

    Undescribed polyether ionophores from Streptomyces cacaoi and their antibacterial and antiproliferative activities

    Gezer, EmreUner, GoklemKucuksolak, MelisKurt, Mustafa Unver...
    9页
    查看更多>>摘要：Polyether ionophores represent a large group of naturally occurring compounds mainly produced by Streptomyces species. With previously proven varieties of bioactivity including antibacterial, antifungal, antiparasitic, antiviral and anti-tumor effects, the discovery of undescribed polyethers leading to development of efficient therapeutics has become important. As part of our research on polyether-rich Streptomyces cacaoi, we previously performed modification studies on fermentation conditions to induce synthesis of specialized metabolites. Here, we report four undescribed and nine known polyether compounds from S. cacaoi grown in optimized conditions. Antimicrobial activity assays revealed that four compounds, including the undescribed (6), showed strong inhibitory effects over both Bacillus subtilis and methicillin-resistant Staphylococcus aureus (MRSA) growth. Additionally, K41-A and its C15-demethoxy derivative exhibited significant cytotoxicity. These results signified that selectivity of C15-demethoxy K41-A towards cancer cells was higher than K41-A, which prompted us to conduct mechanistic experiments. These studies showed that this uninvestigated compound acts as a multitarget compound by inhibiting autophagic flux, inducing reactive oxygen species formation, abolishing proteasome activity, and stimulating ER stress. Consequently, the optimized fermentation conditions of S. cacaoi led to the isolation of undescribed and known polyethers displaying promising activities.
      原文链接:
    • NSTL
    • Elsevier

    Structural characterization of three cytotoxic steroidal saponins from the leaves of Agave desmetiana hort

    Gabr, Nagwan M.Ghaly, Neveen S.Mina, Suzan A.
    6页
    查看更多>>摘要：Three steroidal saponins detected by LC-MS were isolated from the leaves of Agave desmetiana hort. The three saponins were characterized as; Tigogenin 3 - [{O - beta - D -xylopyranosyl (1 -> 2) - alpha - L-rhamnopyranosyl (1 -> 3)}-beta-D-glucopyranoside), Tigogenin- 3 - ([O-alpha-L-rhamnopyranosyl (1 -> 3) - beta - D -glalactopyranosyl (1 -> 2)] - beta - D - glucopyranoside) and Tigogenin- 3 -([{O - alpha - L - rhamnopyranosyl (1 -> 4)} - beta - D - gal-actopyranosyl (1 -> 3) - beta - D - xylopyranosyl (1 -> 2)] - beta - D - glucopyranoside). Identification and structure elucidation of the isolates were done via 1D and 2D NMR techniques, and chemical methods. Cytotoxic activity for the crude saponins and the three isolated compounds were evaluated against Hepg-2 and Mcf-7 cell lines. Compound 2 proved to be the most cytotoxic against tested cell lines with an IC50 2.97 and 2.49 mu g/ml respectively.
      原文链接:
    • NSTL
    • Elsevier

    A/D-rings-seco limonoids from the fruits of Aglaia edulis and their bioactivities

    Sun, YujinCui, LetianSun, YunpengLi, Qiurong...
    9页
    查看更多>>摘要：Agledulines A-K, eleven previously undescribed limonoids, including eight biogenic A/D-rings-seco limonoid analogs (agledulines A-H), one D-ring-seco limonoid (agleduline I) and two A-ring-seco limonoids with a rare Delta(4,28) moiety (agledulines J-K), together with twelve reported limonoids, were isolated from the fruits of Aglaia edulis. Their structures were determined by NMR data, HRESIMS, X-ray diffraction, ECD spectra and the CD exciton chirality method. Observably, the absolute configurations of agleduline A, agleduline C and nymania 2 were unambiguously elucidated by single-crystal X-ray diffraction analyses. The biological evaluation showed that agleduline C exhibited significant cytotoxic activities with IC50 values of 10.05 mu M, and 11 alpha-acetoxygedunin showed notable anti-inflammatory activity (IC50: 4.70 mu M). In addition, agleduline I and 11 alpha-acetoxygedunin reversed the multidrug resistance with IC50 values of 5.05 and 1.49 mu M (RI: 4.64 and 15.77) in the MCF-7/Dox cells.
      原文链接:
    • NSTL
    • Elsevier

    Bioactive polyketide derivatives from the endophytic fungus Phaeosphaeriopsis musa

    Zhong, JinqianChen, YuchanLiu, ZhaomingHu, Caiyun...
    7页
    查看更多>>摘要：Two undescribed phenolic derivatives musaones A and B, six undescribed gamma-butyrolactone musaolides A-F, together with two undescribed cyclopentanone musaolides G and H were isolated from the solid culture of an endophytic strain Phaeosphaeriopsis musae M. Arzanlou & Crous (Phaeosphaeriaceae). Their structures were unambiguously elucidated by extensive spectral analyses. The absolute configurations of two diastereomers musaolides G and H were assigned by comparing their experimental and calculated ECD data. Moreover, the in vitro alpha-glucosidase inhibition and cytotoxic activities of isolated compounds (except musaolide D) were evaluated to understand their biological effects, wherein musaone B and musaolide F displayed promising alpha-glucosidase inhibition with IC50 values of 37.3 +/- 0.59 mu M and 105.18 +/- 2.76 mu M respectively, compared to the positive control acarbose (24.99 +/- 1.28 mu M).
      原文链接:
    • NSTL
    • Elsevier

    Sesquiterpenes with diverse skeletons from histone deacetylase inhibitor modified cultures of the basidiomycete Cyathus stercoreus (Schwein.) De Toni HFG134

    Liu, Shui-LinZhou, LinChen, He-PingLiu, Ji-Kai...
    9页
    查看更多>>摘要：Epigenetic modifiers are proved to be effective specialized products-mining tools by rationally regulating the gene expression of fungal biosynthetic pathways. Chemical investigation on the histone deacetylase inhibitor (HDI) vorinostat (also known as SAHA)-modified cultures of the basidiomycete Cyathus stercoreus (Schwein.) De Toni (Nidulariaceae) led to the isolation of nine previously undescribed sesquiterpenes, and four previously described ones. The structures of the nine undescribed compounds were determined by extensive NMR spectroscopic analysis, HRESIMS analysis, as well as ECD and NMR calculations. Notably, the isolated sesquiterpenes are exclusive or overproduced from the epigenetic modified cultures compared to the negative control cultures. Additionally, the skeleton types of the isolated sesquiterpenes include protoilludalane, illudalane, 1,11-seco-protoilludalane, 10,11-seco-illudalane, and 14(11 -> 10)abeo-illudalane. It is noteworthy that the 14(11 -> 10)abeoilludalane skeleton is reported for the first time. Cystercorodiol A, 4-O-acetylcybrodol, cystercorotone, and cybrodol showed weak inhibitory activity against the bacterium Escherichia coli ATCC25922 with the inhibitory rates 34.7%, 33.0%, 32.3%, and 29.6% at the concentration 200 mu M, respectively. This study suggested that epigenetic modifiers are also an effective tool for specialized metabolite-mining in basidiomycetes.
      原文链接:
    • NSTL
    • Elsevier