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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Highly oxygenated isoryanodane diterpenoids from the leaves of Cinnamomum cassia and their immunomodulatory activities

    Zhou, LeiZheng, GuijuanLi, HengGao, Biao...
    10页
    查看更多>>摘要：A total of twelve highly oxygenated isoryanodane (also known as cinncassiol D-type) diterpenoids including nine undescribed ones, named cinnacassins A I, were isolated from the leaves of Cinnamomum cassia. Their chemical structures were elucidated by extensive spectrometric and spectroscopic techniques including HRESIMS, 1D and 2D NMR, single-crystal X-ray diffraction analysis, calculated C-13-NMR DP4+ analysis, and chemical methods. The absolute configuration of cinnacassin A was unambiguously delineated by single-crystal X-ray diffraction analysis. Cinnacassin H represents the first example of 16-O-glucosylated isoryanodane diterpenoid, and cinnacassin I is the first isoryanod-13(18)-ene diterpenoid. The relationship of the configuration C-18 and the chemical shifts of H2-19 and C-20 in the 19-hydroxy-isoryanodane diterpenoids was discussed, and the 18S-configuration of three known 19-hydroxy-isoryanodane diterpenoids, cinncassiol D1, 19-O-beta-D-glucopyranosylcinncassiol D1, and cinncassiol D3 was assigned. All the isolated isoryanodane diterpenoids were evaluated for their immunomodulatory effects in vitro, and cinnacassin A and cinncassiol D1 enhanced the proliferation of Con A-induced murine T cells with enhancement rates ranging from 17.9% to 45.4%, which were more potent than the positive control, thymosin alpha(1). In addition, cinncassiol D-1 significantly promoted the proliferation of LPSinduced murine B cells with an enhancement rate up to 116.1%, two-fold more potent than thymosin a1 at a concentration of 1.5625 mu M.
      原文链接:
    • NSTL
    • Elsevier

    Constituents promoting osteogenesis from the fruits of Psoralea corylifolia and their structure-activity relationship study

    Xu, QingxiaZhang, YouboHe, ZichaoLiu, Zhenyu...
    13页
    查看更多>>摘要：The mature fruit of Psoralea corylifolia L. is a common traditional Chinese medicine used to tonify the kidney and yang, and as well as to treat osteoporosis. Systematic phytochemical investigations have established the most comprehensive constituent library to date, covering over 180 compounds. In this study, 109 chemical constituents containing 37 undescribed compounds were reported and incorrect structures of four known coumarins were corrected. The structures of these undescribed compounds were elucidated using spectroscopic methods, single-crystal X-ray diffraction, Rh-2(OCOCF3)(4) and Mo-2(OAc)(4)-induced circular dichroism spectra. To identify potentially active compounds and investigate their structure-activity relationship (SAR), 89 constituents in the library were evaluated for their osteogenic differentiation and mineralisation activities in MC3T3-E1 cells. We found that coumarins, isoflavones, flavonones, and meroterpenoids were the material basis for Psoralea corylifolia-based treatment of osteoporosis, with some compounds exhibiting excellent activities. These compounds function via the estrogen receptor (ER) pathway and were natural phytoestrogen. Further SAR analysis showed that compounds with an intact isopentenyl replacement possessed superior activities, which was explained by their improved affinity with the ER.
      原文链接:
    • NSTL
    • Elsevier

    Nardosinane-related antimicrobial terpenoids from Lemnalia sp. soft coral

    Liu, JingXia, FeiOuyang, HanWang, Wei...
    7页
    查看更多>>摘要：Ten nardosinane-related terpenoids, including five unreported nardosinane-type sesquiterpenoids, parathyrsoidins H-J and linardosinenes D-E, two unusual condensed nardosinanes, named nardosinoids A and B, together with three known related compounds, were isolated from the Xisha soft coral Lemnalia sp. Their structures were elucidated by extensive spectroscopic analysis and comparison of experimental and calculated electronic circular dichroism data. Nardosinoids A and B are the first condensates of two nardosinanes. All these compounds were evaluated for antimicrobial activity in vitro. Nardosinane-type sesquiterpenoids parathyrsoidin I and linardosinene E showed inhibitory effects against influenza A virus H1N1 (IC50 7.1 and 1.1 mu M, respectively). In addition, nardosinoids A and B exhibited antibacterial activity against Bacillus subtilis (MIC 4-8 mu g/mL).
      原文链接:
    • NSTL
    • Elsevier

    Bioactive specialised metabolites from the endophytic fungus Xylaria sp. of Cudrania tricuspidata

    Song, JintongXu, KeLiu, ChunyuWang, Tian...
    9页
    查看更多>>摘要：Fourteen undescribed compounds, including five 2,5-diarylcyclopentenones xylariaones A1-B2, seven a-pyrone derivatives xylaripyones A G, one.-pyrone derivative xylaripyone H, one diketopiperazine cyclo-(L-Leu-N=ethyl-L-Glu), and two known diketopiperazines, were isolated from cultures of the endophytic fungus Xylaria sp., which was separated from Cudrania tricuspidata Bureau ex Lavall ' ee. Their structures were determined by analysing extensive spectroscopic data (HRESIMS and NMR) and electronic circular dichroism (ECD) calculations. Furthermore, these compounds were evaluated for potential antiproliferative activity against the human tumour cell lines PC3 and A549, and the results showed that xylaripyone D exhibited moderate inhibitory activity against the proliferation of PC3 cell lines with an IC50 value of 14.75 mu M. Meanwhile, xylariaone A3 and xylaripyone F displayed weak inhibitory effects on NO production in RAW 264.7 murine macrophages with IC50 values of 49.76 and 69.68 mu M, respectively.
      原文链接:
    • NSTL
    • Elsevier

    Undescribed ecdysteroids and phenolic glycosides from the roots of Cyathula officinalis Kuan and their anti-inflammatory activity in LPS-induced RAW 264.7 macrophages in vitro

    Yang, Long-feiTeng, LiHuang, Yue-huiTang, Min...
    9页
    查看更多>>摘要：Six undescribed compounds, including four undescribed ecdysteroids (cyathsterones A-D) and two undescribed phenolic glycosides (cyathglucosides A-B), were isolated from the roots of Cyathula officinalis Kuan. Their structures were based on chemical analyses, NMR spectroscopic evidence, DP4+ calculations, and hydrolysis products. All compounds inhibited NO release in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages in vitro. Among them, cyathsterone A showed the strongest inhibitory effects. Moreover, cyathsterone A has been shown to inhibit the release of the proinflammatory cytokines TNF-alpha, IL-6, and IL-1 beta in LPS-induced RAW 264.7 macrophages in vitro. Further studies found that cyathsterone A present concentration-dependent suppression of the protein expression of iNOS and COX-2 in LPS-stimulated RAW 264.7 cells in vitro and exerted anti-inflammatory activity via the NF-kappa B signalling pathway.
      原文链接:
    • NSTL
    • Elsevier

    Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour

    Chen, Shun-QingJia, JiaHu, Jing-YaoWu, Jun...
    11页
    查看更多>>摘要：Phytochemical investigation on the aerial parts of Tabernaemontana bufalina Lour. (Apocynaceae) led to the identification of four undescribed monoterpenoid indole alkaloids named taberbufamines A-D, an undescribed natural product, and fourteen known indole alkaloids. The structures of the undescribed alkaloids were established by spectroscopic and computational methods, and their absolute configurations were further determined by quantum chemical TDDFT calculations and the experimental ECD spectra. Taberbufamines A and B possessed an uncommon skeleton incorporating an indolizidino [8,7-b]indole motif with a 2-hydroxymethyl-butyl group attached at the pyrrolidine ring. Biosynthetically, Taberbufamines A and B might be derived from iboga-type alkaloid through rearrangement. Vobatensine C showed significant bioactivity against A-549, Bel-7402, and HCT-116 cells with IC50 values of 2.61, 1.19, and 1.74 mu M, respectively. Ervahanine A showed antimicrobial activity against Bacillus subtilis, Mycobacterium smegmatis, and Helicobacter pylori with MIC values of 4, 8, and 16 mu g/mL, respectively. 19(S)-hydroxyibogamine was shown as butyrylcholinesterase inhibitor (IC50 of 20.06 mu M) and alpha-glycosidase inhibitor (IC50 of 17.18 mu M), while tabernamine, ervahanine B, and ervadivaricatine B only showed alpha-glycosidase inhibitory activities with IC50 values in the range of 0.95-4.61 mu M.
      原文链接:
    • NSTL
    • Elsevier

    The Phytochemical Society of Europe

    Stafford, AngelaRobins, Richard
    3页
      原文链接:
    • NSTL
    • Elsevier

    Autoproteolysis of Procerain and Procerain B mediated by structural changes

    Jamdar, Sahayog N.Srivastava, GauravGaur, NeerajMakde, Ravindra D....
    10页
    查看更多>>摘要：Procerain (Pc) and Procerain B (PcB) are two latex proteases from Calotropis procera having potential applications in food and other industries. However, autolytic degradation of these proteases limits their potential use in industry. Nevertheless, basic mechanism underlying the autoproteolysis has not been detailed. In order to understand the same, we subjected the enzymes to various denaturing and activating conditions. The results showed that structural changes induced by different denaturing conditions trigger their autoproteolysis. We also observed differential response of Pc, PcB and other papain-like proteases towards autocatalysis in presence of reducing agent in-spite of sharing the same structural fold, including the number of disulfide bonds. The possible reason underlying this intriguing observation is also discussed. Further, present work establishes that structural changes in the proteases lead to autoproteolysis and the enzymes are stable unless they experience structural perturbation. These findings could thus be useful for their practical applications in industries.
      原文链接:
    • NSTL
    • Elsevier

    Structural characterization of phenolic constituents from the rhizome of Imperata cylindrica var. major and their anti-inflammatory activity

    Han, YuZhang, YiWang, TaoRuan, Jing-Ya...
    13页
    查看更多>>摘要：As one of raw materials, the rhizome of Imperata cylindrica var. major (Nees) C.E. Hubb. is used in kinds of preparations curing inflammation related diseases, while its effective substances are not yet clear. In this paper, its chemical constituents and their anti-inflammatory activities were investigated. As results, ten compounds, named as imperphenoside A (1), imperphenols B (2) and C (3), imperphenosides D-F (4-6), and imperlignanosides A-D (7-10), along with previously reported thirty-seven known ones (11-47) were obtained from it. Their structures were ascertained basing on the extensive spectroscopic methods and electronic circular dichroism data analysis. Meanwhile, compounds 4, 11, 12, 24, 27, 31, 32, 37, 43, 45, and 47 exhibited nitric oxide inhibitory effects in concentration dependent at 3, 10, and 30 mu M on lipopolysaccharides induced RAW 264.7 cells. Moreover, the western blot analysis indicated that compounds 4, 11, 43, and 47 could restrain the phosphorylation of nuclear factor kappa-B kinase to down-regulate the protein expression of inflammatory cytokines such as inducible nitric oxide synthase, interleukin-6 and tumor necrosis factor-alpha. In conclusion, they might play the anti-inflammatory effects through regulating NF-kappa B signaling pathway.
      原文链接:
    • NSTL
    • Elsevier

    Serrulatane diterpenoids from the leaves of Eremophila glabra and their potential as antihyperglycemic drug leads

    Petersen, Malene J.Liang, ChaoKjaerulff, LouiseNdi, Chi...
    11页
    查看更多>>摘要：Eremophila (Scrophulariaceae) is a genus of Australian desert plants, which have been used by Australian Aboriginal people for various medicinal purposes. Crude extracts of the leaf resin of Eremophila glabra (R.Br.) Ostenf. showed alpha-glucosidase and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC50 values of 19.3 +/- 1.2 mu g/mL and 11.8 +/- 2.1 mu g/mL, respectively. Dual alpha-glucosidase/PTP1B high-resolution inhibition profiling combined with HPLC-PDA-HRMS and NMR were used to isolate and identify the compounds providing these activities. This resulted in isolation of seven undescribed serrulatane diterpenoids, eremoglabrane A-G, together with nine previously identified serrulatane diterpenoids and flavonoids. Three of the serrulatane diterpenoids showed PTP1B inhibitory activities with IC50 values from 63.8 +/- 5.8 mu M to 104.5 +/- 25.9 mu M.
      原文链接:
    • NSTL
    • Elsevier