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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    A full set of 8,4 '-oxy-8 '-phenylneolignan stereoisomers from Sophora tonkinensis and their absolute configurations by TDDFT

    He, Hao-KeLi, XinYang, Sheng-LiTian, Meng-Yin...
    8页
    查看更多>>摘要:A full set of 8,4'-oxy-8'-phenylneolignans with four chiral carbons, named (+)/(-)-leptolepisols D1-D2 and (+)/(-)-sophorols A-F, were isolated from the roots and rhizomes of Sophora tonkinensis Gagnep., including 14 previously undescribed stereoisomers, along with 2 known leptolepisol D diastereomers. Their planar structures and relative configurations were elucidated by detailed spectroscopic analysis (HRESIMS and NMR). Based on a highly accurate conformer filtering protocol at low computational cost, the absolute configurations of full set 8,4'-oxy-8'-phenylneolignans were completely assigned by TDDFT calculations of ECD spectra for the first time. Furthermore, (+)/(-)-sophorol A, (-)-sophorol B, and (-)-sophorol E could moderately suppress the lipopolysaccharide-induced nitric oxide production in murine macrophages at 10 mu m, with inhibitory ratios of 48.4-52.9%.

    Anti-tumor alkaloids from Peganum harmala

    Peng, Xiao-HuiLin, BinZan, Yan-HuiYang, Han-Gao...
    7页
    查看更多>>摘要:Six alkaloids peharmalines F-K, along with 14 known ones, were isolated from the aerial part of Peganum harmala L.. The structures of the isolated compounds were determined based on their HR-ESI-MS data, extensive NMR spectroscopic analyses, and ECD calculations. 3-(4-Hydroxyphenyl)quinoline exhibited potent antiproliferative activity against the HepG-2 cell lines with an IC50 value of 3.05 mu M. Norharmane displayed a moderate inhibition against A549 and HepG-2 cells with IC50 values of 16.45 mu M and 17.27 mu M, respectively.

    Identification of seven undescribed cucurbitacins in Cucumis sativus (cucumber) and their cytotoxic activity

    Han, LidaLi, PengkunZha, ZiouLiu, Chang...
    9页
    查看更多>>摘要:Cucurbitacin C-type cucurbitacins that are only identified in Cucumis sativus (cucumber) are, in part, responsible for the health benefits and bitter flavor. Nevertheless, detailed information about those functional ingredients in cucumber is scarce. In this study, ten cucurbitacin C analogues including seven undescribed ones have been isolated from the bitter leaves of cucumber, in which six compounds showed growth inhibition capabilities against tumor cell lines HepG2, A549, DU145 and HCT116. Intriguingly, cucurbitacin C6 and C7 exhibited a significant inhibition effect compared to the positive control taxol (IC50 = 1.86 +/- 0.17 mu M) on HepG2 cell line with IC50 values of 10.06 +/- 0.34 mu M and 4.16 +/- 0.42 mu M, respectively. The mechanism of cucurbitacin-induced apoptosis is likely down-regulating the expression of caspase-related proteins. This work enlarges the knowledge of the cucurbitacins in cucumber and highlights the importance of cucumber as a source of specialized metabolites in the food and medicinal industries.

    Bridged cassane derivatives from the seeds of Caesalpinia sappan L. and their cytotoxic activities

    Jin, YueWang, MiaoYan, Yan-FangZhang, Xin-Xin...
    12页
    查看更多>>摘要:Two undescribed nitrogen bridged cassane alkaloids (caesanamides A-B) and five undescribed oxygen bridged cassane diterpenoids (caesalpinins JA-JE), together with six known analogs, were isolated and identified from the seeds of Caesalpinia sappan. Their structures, including the absolute configurations, were unequivocally elucidated by the analysis of comprehensive spectroscopic data, ECD calculations, single-crystal X-ray diffraction and the CASE algorithm. Among them, caesanamides A and B represent the first examples of cassane alkaloids bearing unique ring systems of an amide bridge between C-19/C-20 incorporating a 1,3-oxazolidine (6/6/6/5/6/5) or a 7-one-1,3-oxazepine (6/6/6/5/6/7). Caesalpinin JA is an A/B cis-20-norcassane diterpenoid with a rare five-membered oxygen bridge between C-10/C-18. Biological evaluation showed that cassane alkaloids exhibited significant cytotoxicity against HepG2 cells with IC50 values of 13.48 +/- 1.07 mu M (caesanamide A), 18.91 +/- 0.98 mu M (caesanamide B), and 7.82 +/- 0.65 mu M (caesanine B). Further flow cytometry analysis revealed that caesanine B could cause GOG1 cell cycle arrest and promote apoptosis in a dose- and time-dependent manner in HepG2 cells.

    Phytoceramides and acylated phytosterol glucosides from Pterospermum acerifolium Willd. Seed coat and their osteogenic activity (vol 81, pg 117, 2012)

    Dixit, PreetyChand, KailashKhan, Mohd ParvezSiddiqui, Jawed Akhtar...
    1页

    Phenylpropanoids from Brachybotrys paridiformis Maxim. ex Oliv. and their anti-HBV activities

    Wu, Si-TongWang, Yi-XiaoYu, Bai-HongMa, Chun-Liu...
    8页
    查看更多>>摘要:Using chemical and spectroscopic data, this study on Brachybotrys paridiformis Maxim. ex Oliv. identified four undescribed phenylpropanoids, brachin A-C and brachoside A, together with nine other known compounds. The isolated compounds were tested for anti-hepatitis B virus activities in the HepG2.2.15 cell line. Among them, caffeic anhydride showed the most potent activity.

    Guaianolides and unusual 3-oxa-guaianolides from Artemisia macrocephala

    Zhao, Yan-rongZou, Guo-anAisa, Haji Akber
    7页
    查看更多>>摘要:Eight undescribed guaianolides (macrocephalolides A-H) and two known analogues (parishin C, artabsinolide E) were isolated from the whole plant of Artemisia macrocephala growing in Xinjiang, China. Their structures were determined on the basis of extensive spectroscopic analysis, with absolute configurations established by comparison of experimental and calculated ECD data, as well as confirmation of single-crystal X-ray diffraction crystallography. Macmcephalolides A-B featured an unusual type of 3-oxa-guaianolide with a cyclopentenone moiety. Macrocephalolides C-E possessed a dihydro-2H-pyran acetal segment, representing an unprecedented 2, 3-secoguaianolide skeleton with 6/7/5 tricyclic ring system in natural sesquiterpenes. The X-ray crystal structures of parishin C and artabsinolide E were reported for the first time.