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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

    Induction of volatile organic compounds in Triticum aestivum (wheat) plants following infection by different Rhizoctonia pathogens is species specific

    Piesik, DariuszLemanczyk, GrzegorzBocianowski, JanBuszewski, Boguslaw...
    9页
    查看更多>>摘要：The most popular means of plant protection is the chemical method, but this control is often connected with the need for repeating chemical treatments. Thus, eco-friendly strategies should be developed where, under the European Green Deal, aromatic plants and their repellent properties seem to constitute a good alternative. In earlier studies, we have shown that insect injury, bacteria infestation and pathogen infection induce plant volatile organic compounds (VOCs) emission, which can provide defensive functions to plants.& nbsp;In this study, Triticum aestivum L. (Poaceae) cv. 'Jenga' wheat plants were intentionally infected with one of four Rhizoctonia species (R. cerealis, R. solani, R. zeae, and R. oryzae). The soil was inoculated by the pathogens during sowing, whereas shoots were inoculated at stage BBCH 33. In greenhouse experiments, we measured VOCs from wheat 3, 7 and 11 days following stem infestation, or 42 days following soil inoculation of Rhizoctonia spp. VOC emissions were found to be largest on days 7 or 11 post-stem inoculation (> 3 days post-stem inoculation > 42 days post-soil inoculation). T. aestivum infected by pathogens induced five common green leaf volatiles (GLVs), namely (Z)-3-hexenal = (Z)-3-HAL, (E)-2-hexenal = (E)-2-HAL, (Z)-3-hexen-1-ol= (Z)-3HOL, (E)2-hexenol = (E)-2-HOL, (Z)-3-hexen-1-yl acetate = (Z)-3-HAC], six common terpenes (beta-pinene = beta-PIN, beta-myrcene = beta-MYR, Z-ocimene = Z-OCI, linalool = LIN, benzyl acetate = BAC, beta-caryophyllene =beta-CAR), and indole = IND. We found that R. cerealis infested T. aestivum emitted the largest amounts of (Z)-3-HAL and (Z)-3HAC, while T. aestivum infested by R. solani released the largest amount of LIN (7 or 11 days following stem infestation). VOCs released by the T. aestivum after R. cerealis (AGD I) and R. solani (AG 5) infestations were significantly larger in comparison to R. zeae (WAG-Z) and R. oryzae (WAG-O) for the volatiles (Z)-3-HAL, (E)-2HAL, (Z)-3-HOL, (E)-2-HOL, (Z)-3-HAC, beta-PIN, beta-MYR, and LIN. With the exception of (E)-2-HOL, beta-MYR, LIN, BAC, beta-CAR, the other VOCs were emitted in similar amounts by infected T. aestivum 3 days following stem and soil inoculation. The quantities of induced VOCs were higher at days 7 and 11 than at 3 days post-infection, and greater when T. aestivum was infected with Rhizoctonia on the stem base than through the soil.
      原文链接:
    • NSTL
    • Elsevier

    Guided isolation of daphnane-type diterpenes from Daphne genkwa by molecular network strategies

    Zhang, HaoGuo, RuiLiu, Yu-YangLin, Bin...
    8页
    查看更多>>摘要：A molecular networking-guided study on the Daphne genkwa Sieb. et Zucc led to the isolation of twelve daphnane-type diterpenoids including four undescribed compounds, yuanhuakines A-D. Their structures were elucidated by spectroscopic analyses, ECD calculations, and single-crystal X-ray diffraction analysis. All isolates were evaluated for their inhibitory activity against the A549, Hep3B, and MCF-7 cell lines. The majority of compounds inhibited A549 cells with IC50 values ranging from 7.77 to 20.56 mu M, and their structure-activity relationship is preliminarily discussed. Five of these compounds were selected for further experiments, and they appear to inhibit A549 cell lines by inducing apoptosis.
      原文链接:
    • NSTL
    • Elsevier

    Intramolecular transesterification of depsides yields fluorescent 1H-isochromen-1-ones: Application as a chemical probe for lichen determination

    Ferron, S.Jehan, P.Guillory, X.Uriac, P....
    10页
    查看更多>>摘要：The reactivity of eight purified depsides obtained from six european lichens and that display as 2-oxoalkyl chain in ortho-position of the ester bond was explored. These depsides were found to lead to 1H-Isochromen-1-ones, which exhibit a distinctive blue fluorescence at 365 nm, in the presence of a 10% aqueous solution of KOH. A mechanistic explanation, involving the formation of an enolate intermediate and intramolecular transesterification, was proposed and validated by DFT. By exploiting this fluorescent phenomenon, we conceived a chemical probe (the KUV probe) that is useful for lichen determination, as exemplified on a selection of European Porpidia species.
      原文链接:
    • NSTL
    • Elsevier

    Isoindolines and phthalides from the rhizomes of Ligusticum chuanxiong and their relaxant effects on the uterine smooth muscle

    Liu, JuanFeng, RuiDai, OuNi, Hong...
    8页
    查看更多>>摘要：Three undescribed isoindoline alkaloids, (+)-(R)-3-butyl-3-ethoxyisoindolin-1-one, (+)-(3S,6S,7R)-3-butyl-6,7-dihydroxy-3-methoxy-4,5,6,7-tetrahydroisoindolin-1-one, and (- )-(3R,6S,7R)-3-butyl-6,7-dihydroxy-3-methoxy-4,5,6,7-tetrahydroisoindolin-1-one, along with nine known phthalides were isolated from a water decoction of the rhizomes of Ligusticum chuanxiong using chromatographic methods. Their structures and absolute configurations were determined by extensive spectroscopic analyses and ECD data calculations. The relaxant effects of the isolated compounds on uterine contractions induced by oxytocin were investigated using a rat uterine smooth muscle contraction model. Furthermore, the effects of riligustilide on extracellular Ca2+ influx and intracellular Ca2+ release were assessed using high-KCl solution-induced and oxytocin-induced uterine smooth muscle contraction in a Ca2+-free balanced salt solution. The results showed that all the tested phthalides had inhibitory effects on oxytocin-induced uterine smooth muscle contraction. Riligustilide, a phthalide dimer, was the most active. Further examinations indicated that riligustilide reduced uterine smooth muscle contraction by inhibiting extracellular Ca2+ influx and intracellular Ca2+ release.
      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

    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

    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

    Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

    Shi, ZhengyiTan, XiaoshengHu, HongZhang, Na...
    8页
    查看更多>>摘要：Acylphlorostylums A-G (1-7), seven undescribed monoterpenoid polyprenylated acylphloroglucinols, were isolated and identified from Hypericum longistylum. Significantly, acylphlorostylums A and B were the first monoterpenoid polyprenylated acylphloroglucinols possessing a dodecahydro-1H-benzo [b]cyclopenta [e]oxepine moiety bearing a 6/7/5 fused tricyclic ring system that assembled by the attack from 4-OH to C-13. In addition, acylphlorostylums A-G exhibited moderate in vitro immunosuppressive activity in anti-CD3/anti-CD28 monoclonal antibodies, lipopolysaccharide and concanavalin A-induced murine splenocyte proliferation, with IC50 values ranging from 1.51 +/- 0.12 to 18.49 +/- 1.67 mu M, underscoring those isolates as novel chemical templates in the development of novel immunosuppressors.
      原文链接:
    • NSTL
    • Elsevier

    Oblongolides from endophytic fungus Phoma bellidis Neerg. harbored in Tricyrtis maculata (D. Don) JFMacbr

    Zhang, XianYang, Hui-XiangYe, KeWei, Pan-Pan...
    8页
    查看更多>>摘要：Five previously undescribed oblongolides, namely phomaones A-E, along with four known compounds, were isolated from the endophytic fungus Phoma bellidis Neerg.. Their structures and absolute configurations were determined by extensive experimental spectroscopic methods as well as single crystal X-ray diffractions, ECD calculations and GIAO C-13 NMR calculations. Phomaone A represent the first example of oblongolides with glycol directly linked by two C-C bonds, and its biosynthetic pathway were proposed. The cytotoxicity of obtained compounds was evaluated against human cancer cell lines MCF-7, DU145, and SW480. All compounds except phomaone A showed the cytotoxicity against MCF-7 with IC50 value ranging from 12.45 to 49.84 mu M.
      原文链接:
    • NSTL
    • Elsevier