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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Guaiane-type sesquiterpenes from Curcuma wenyujin

    Li, YahuiLiu, JingwenWu, YingchunLi, Yiming...
    10页
    查看更多>>摘要：Eight undescribed sesquiterpenes including seven guaianes and one pseudoguaiane which were named as wenyujinols A-H, along with ten known guaianes, were isolated from rhizomes of Curcuma wenyujin Y. H. Chen et C. Ling. The structures of wenyujinols A-H were elucidated by 1D and 2D nuclear magnetic resonance (NMR) data, high resolution mass spectrum (HRMS), electronic circular dichroism (ECD) spectra, and X-ray single crystallographic analysis. All of the isolated compounds were evaluated for antioxidant activity via activation of the Nrf2-ARE pathway in human embryonic kidney (HEK) 293 cells, for inhibitory effects on NO production in RAW 264.7 cells, and for cytotoxicity against three human cancer cell lines A549, HL60, and MCF7 in vitro. The results indicated that procurcumenol (50-200 mu M) and 9-oxo-neoprocurcumenol (25-200 mu M) exhibited anti-oxidant activity via activation of the Nrf2-ARE pathway in a dose-dependent manner.
      原文链接:
    • NSTL
    • Elsevier

    Balance of Delta(5)-and Delta(7)-sterols and stanols in halophytes in connection with salinity tolerance

    Rozentsvet, Olga A.Kotlova, Ekaterina R.Bogdanova, Elena S.Nesterov, Viktor N....
    10页
    查看更多>>摘要：Sterols (STs) have a key role in regulating the fluidity and permeability of membranes in plants (phytosterols) that have wide structural diversity. We studied the effect of structural STs diversity on salt tolerance in halophytes. Specifically, we used gas chromatography-mass spectrometry (GC-MS), including two-dimensional gas chromatography-mass spectrometry (GCxGC-MS), to assess the STs composition in leaves of 21 species of wild-growing halophytes from four families (Asteraceae, Chenopodiaceae, Plumbaginaceae, Tamaricaceae) and three ecological groups (Euhalophytes (Eu), recretophytes (Re), salt excluders (Ex)). Fifteen molecular species of STs from three main groups, & UDelta;(5)-, & UDelta;(7)-and & UDelta;(0)- STs (stanols), were detected. Plants of the genus Artemisia were characterized by a high content of stigmasterol (30-49% of the total STs), while beta-sitosterol was the major compound in two Limonium spp., where it comprised 84-92% of the total STs. Species of Chenopodiaceae were able to accumulate both & UDelta;(5)-and & UDelta;(7)-STs and stanols. The content of the predominant & UDelta;(5)-STs decreased in the order Ex & RARR; Re & RARR; Eu. Molecular species with a saturated steroid nucleus were identified in Eu and Re, suggesting their special salt-accumulating and salt-releasing functions. The structural analogues of stigmasterol, having a double bond C-22, were stigmasta-7,22-dien-3 beta-ol (spinasterol) and stigmast-22-en-3 beta-ol (& UDelta;(7-)-sitosterol). The ratio of & UDelta;(5)-stig-masterol/& UDelta;(5)-beta-sitosterol increased in Ex plants, and spinasterol/& UDelta;(7-)-sitosterol and 22-stigmastenol/sitostanol increased in Eu plants. These data support the well-known role of stigmasterol and its isomers in plant responses to abiotic and biotic factors. The variability in STs types and their ratios suggested some involvement of the sterol membrane components in plant adaptation to growth conditions. The balance of & UDelta;(5)-, & UDelta;(7)-and stanols, as well as the accumulation of molecular analogues of stigmasterol, was suggested to be associated with salt tolerance of the plant species in this investigation.
      原文链接:
    • NSTL
    • Elsevier

    MS/MS-based molecular networking accelerated discovery of germacrane-type sesquiterpene lactones from Elephantopus scaber L

    Xu, WeiBai, MingLiu, De-FengLv, Tian-Ming...
    11页
    查看更多>>摘要：Assisted by an MS/MS-based molecular networking guided strategy, six undescribed germacrane-type sesquiterpene lactones, namely scaberxones A-F, along with a known analog were obtained and characterized from Elephantopus scaber L. Their structures were unequivocally assigned by detailed spectroscopic analyses, NMR and ECD spectral calculations, and computer-assisted structure elucidation (CASE), complemented with single-crystal X-ray diffraction. All compounds were measured for their production of nitric oxide (NO) levels in lipopolysaccharide (LPS)-induced BV-2 microglial cells to assess their anti-neuroinflammatory activity. Scaberxone F showed the most potent inhibition of NO production at a concentration of 10 mu M.
      原文链接:
    • NSTL
    • Elsevier

    Derrisrobustones A-D, isoflavones from the twig extract of Derris robusta (DC.) Benth. and their alpha-glucosidase inhibitory activity

    Suthiphasilp, VirayuPayaka, ApirakChaiyosang, BoonyanootHarding, David J....
    7页
    查看更多>>摘要：Three previously undescribed isoflavones, derrisrobustones A-C, and a previously undescribed natural isoflavone, derrisrobustone D, along with eight known isoflavones, were isolated from the twig extract of Derris robusta (DC.) Benth. All structures were identified by extensive spectroscopic analysis. Derrisrobustones A-C were obtained as scalemic mixtures and were resolved by chiral HPLC. The (1 & DPRIME;R, 2 & DPRIME;R) absolute configuration of (+)-derrisrobustone B was established by single-crystal X-ray crystallography using Cu K alpha radiation. The absolute configurations of derrisrobustones A and C were determined by analysis of experimental and calculated ECD data. All compounds were evaluated for their alpha-glucosidase inhibitory activity. Of these, derrubone displayed the best alpha-glucosidase inhibitory activity with an IC50 value of 64.2 mu M.
      原文链接:
    • NSTL
    • Elsevier

    Characterization of undescribed melanoma inhibitors from Euphorbia mauritanica L. cultivated in Egypt targeting BRAF(V600E) and MEK 1 kinases via in-silico study and ADME prediction

    El-Hawary, Seham S.Emam, Sherif E.Kubacy, Tahia M.El-Khrisy, Ezz El-Din A. M....
    11页
    查看更多>>摘要：Three undescribed diterpenes including two ent-abietanes, euphomauritanol A, and euphomauritanol B, and one jatrophane, euphomauritanophane A, in addition to eight previously described metabolites were isolated from the MeOH-CH2Cl2 (1:1) extract of the Euphorbia mauritanica. The chemical structures of isolates were established based on the spectroscopic means including FT-IR, HRMS, 1D and 2D NMR. The absolute stereochemistry of the undescribed diterpenes was deduced by experimental and calculated TDDFT-electronic circular dichroism (ECD). The anti-proliferative effects of the isolated diterpenes were evaluated against B16-BL6, Hep G2, and Caco-2. The euphomauritanol A, euphomauritanol B, and euphomauritanophane A significantly inhibited the growth of murine melanoma B16-BL6 cell lines with IC50 10.28, 20.22, and 38.81 mu M, respectively with no responses against the other cells. These activities were rationalized by molecular docking of the active compounds in BRAF(V600E) and MEK1 active sites. Moreover, the in-silico pharmacokinetics predictions by Swiss ADME revealed that the active compounds possessed favorable oral bioavailability and drug-likeness properties.
      原文链接:
    • NSTL
    • Elsevier

    Liglaurates A-E, cytotoxic bis(lauric acid-12yl)lignanoates from the rhizomes of Drynaria roosii Nakaike

    He, WenwenWang, DongyangZhu, WeimingWang, Liping...
    11页
    查看更多>>摘要：Five undescribed bis(lauric acid-12-yl)lignanoates, liglaurates A-E, along with the known methyl and glyceryl 12-caffeoyloxylaurates were isolated from the rhizomes of Drynaria roosii Nakaike. Their structures including absolute configurations were determined by HRESIMS, NMR techniques, and ECD calculation. Liglaurates A-D were isolated as the racemates, among which (+/-)-liglaurate A and (+/-)-liglaurate B were synthesized by a metal-mediated oxidative coupling reaction and further resolved as the enantiomerically pure compounds. Liglaurates (+)-A, (-)-A, (+)-B, (-)-B, (+/-)-C and (+/-)-D exhibited remarkable cytotoxic activities against HeLa cell line, with the IC50 values of 0.11 +/- 0.02, 0.24 +/- 0.01, 0.02 +/- 0.00, 0.13 +/- 0.02, 0.34 +/- 0.07 and 0.17 +/- 0.01 mu M, respectively.
      原文链接:
    • NSTL
    • Elsevier

    Rosmarinic acid and hesperidin regulate gas exchange, chlorophyll fluorescence, antioxidant system and the fatty acid biosynthesis-related gene expression in Arabidopsis thaliana under heat stress

    Ozfidan-Konakci, CeydaAlp, Fatma NurZengin, GokhanYildiztugay, Evren...
    13页
    查看更多>>摘要：The impacts of exogenous rosmarinic acid (RA, 100 mu M) and/or hesperidin (HP, 100 mu M) were evaluated in improving tolerance on the gas exchange, chlorophyll fluorescence and efficiencies, phenomenological fluxes of photosystems, antioxidant system and gene expression related to the lipid biosynthesis under heat stress. For this purpose, Arabidopsis thaliana was grown under RA and HP with heat stress (S, 38 ?) for 24 h(h). As shown in gas exchange parameters, heat stress caused mesophyll efficiency and non-stomatal restrictions. Both alone and combined forms of RA and HP to stress-treated A. thaliana alleviated the disturbance of carbon assimilation, transpiration rate and internal CO2 concentrations. Stress impaired the levels of energy flow reaching reaction centers of PSII and the photon capture ability of active reaction centers. RA and/or HP enhanced photosystems' structural/functional characteristics and photosynthetic performance. Histochemical staining and biochemical analyses revealed that heat stress caused the oxidation in A. thaliana. By activating several defensive mecha-nisms, RA and/or HP could reverse the harm caused by radical production. Both alone and combined forms of RA and HP removed superoxide anion radical (O-2 & BULL;-) accumulation, inducing superoxide dismutase (SOD). The common enzyme that scavenged hydrogen peroxide (H2O2) at all three applications (S + RA, S + HP and S + RA + HP) was POX. Also, only RA could utilize the ascorbate (AsA) regeneration in response to stress, suggesting increased ascorbate peroxidase (APX), monodehydroascorbate (MDHAR) and dehydroascorbate (DHAR) activ-ities. However, the regeneration/redox state of AsA and glutathione (GSH) did not maintain under S + HP and S + RA + HP. While RA had no positive influence on the saturated fatty acids under stress, HP increased the total saturated fatty acids (primarily palmitic acid). Besides, the combined application of RA + HP effectively created the stress response by increasing the expression of genes involved in fatty acid synthesis. The synergetic in-teractions of RA and HP could explain the increased levels of saturated fatty acids in combining these com-pounds. The data obtained from the study will contribute to the responses of phenolic compounds in plants to heat stress.
      原文链接:
    • NSTL
    • Elsevier

    The ethnobotany, phytochemistry, and biological properties of Nigella damascena-A review

    Badalamenti, NataleBazan, GiuseppeMarino, PasqualeBruno, Maurizio...
    16页
    查看更多>>摘要：This review is a systematic scientific work on medicinal and traditional use, on the chemical composition of specialized metabolites, volatile and non-volatile, on aspects related to toxicology and phytotherapy of Nigella damascena L. The genus Nigella (Ranunculaceae) is distributed throughout the Mediterranean basin, extending to northern India, and has been divided into three sections. Nigella damanscena L. is traditionally used as an ingredient in food, for example, as flavouring agents in bread and cheese, but is also known in folk medicine, used to regulate menstruation; for catarrhal affections and amenorrhea; as a diuretic and sternutatory; as an analgesic, anti-oedematous, and antipyretic; and for vermifuge and its disinfectant effects. This paper reviews the most dated to the latest scientific research on this species, highlighting the single isolated metabolites and exploring their biological activity. Fifty-seven natural compounds have been isolated and characterised from the seeds, roots, and aerial parts of the plant. Among these constituents, alkaloids, flavonoids, diterpenes, triterpenes, and aromatic compounds are the main constituents. The isolated compounds and the various extracts obtained with solvents of different polarities presented a diverse spectrum of biological activities such as antibacterial, antifungal, antitumour, antioxidant, anti-inflammatory, antipyretic, anti-oedema, and antiviral activities. Various in vitro and in vivo tests have demonstrated the pharmacological potential of beta-elemene and alkaloid damascenin. Unfortunately, the largest number of biological studies on this species and its metabolites have been conducted in vitro; therefore, further investigation is necessary to evaluate the toxicological aspects and real mechanisms of action of crude extracts to confirm the therapeutic potential of N. damascena.
      原文链接:
    • NSTL
    • Elsevier

    Phorneroids A-M, diverse types of diterpenoids from Euphorbia neriifolia

    Gao, YuanZhou, Jun-SuLiu, Hong-ChunZhang, Yan...
    11页
    查看更多>>摘要：A chemical investigation on the aerial parts of Euphorbia neriifolia led to the identification of thirteen undescribed diterpenoids, phorneroids A-M, including ent-abietane (A-D), ent-kaurane (E-G), ent-atisane (H-K), and ent- isopimarane (L and M) types, together with three known compounds. Phorneroid A represents the first example of 8-spiro-fused 9,10-seco-ent-abietane diterpenoid lactone featuring a unique 6/5/6/5 spirocyclic framework. Biological assays showed that some of the compounds displayed moderate cytotoxicity against two human tumor cell lines, A549 and HL-60.
      原文链接:
    • NSTL
    • Elsevier

    Cytotoxic compounds from the leaf of Bersama abyssinica subspecies abyssinica

    Nyamboki, Divinah KwambokaBedane, Kibrom GebreheiwotHassan, KhadijaSpiteller, Michael...
    5页
    查看更多>>摘要：From the leaves of Kenyan medicinal plant Bersama abyssinica Subspecies abyssinica, four previously undescribed compounds namely, three bufadienolides, 10 beta-formylpaulliniogenin B, 10 beta-formylpaulliniogenin A and 1 beta-acetoxy-3 beta,5 beta-dihydroxy-15-methoxy-16,19-dioxobufa-14(15),20,22-trienolide, and a phenolic compound 2,6,4'-trihydroxybenzophenone-4-O-(6'''-cinnamoyl)-beta-D-glucoside were isolated together with four known compounds. The structural elucidation of the compounds was based on 1D and 2D NMR spectroscopy and HRMS data analyses. The relative configurations were defined by NOESY correlations. Cytotoxic activities on L929 and KB3.1 cell lines of the isolated compounds were investigated using MTT assay. The 1 beta-acetoxy-3 beta,5 beta-dihydroxy-15-methoxy-16,19-dioxobufa-14(15),20,22-trienolide showed significant cytotoxic activity against KB3.1 cell lines with IC50 of 3.9 +/- 0.99 mu M.
      原文链接:
    • NSTL
    • Elsevier