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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Antiproliferative Amaryllidaceae alkaloids from the bulbs of Hymenocallis littoralis (Jacq.) Salisb

    Ma, WenjingWang, SiyuWang, YihaiZeng, Jia...
    12页
    查看更多>>摘要：Seven undescribed Amaryllidaceae alkaloids classified into four types, including the plicamine-type, secoplicamine-type, belladine-type and pretazettine-type, along with another three alkaloids that have not been isolated from plant material and seven known alkaloids, were isolated from the bulbs of Hymenocallis littoralis (Jacq.) Salisb. The structures were elucidated on the basis of various spectroscopic methods (UV, IR, MS, NMR, ECD). The isolated alkaloids were screened for antiproliferative activity against four human tumour cell lines (HepG2, HeLa, SPC-A-1, FaDu) through MTT assay, and some alkaloids exhibited potent cytotoxicity. Meanwhile, cell morphological assessment, flow cytometric analysis, Western blot analysis, clone formation and scratch wound assays were utilized for an undescribed belladine-type alkaloid and two known alkaloids, which had anti proliferative effects on the HepG2 cell line via induction of apoptosis in a dose-dependent manner. A pair of diastereoisomers of Amaryllidaceae alkaloids exhibited significant differences in antiproliferative activity. In addition, the alkaloids also possessed the potential to inhibit tumour cell migration.
      原文链接:
    • NSTL
    • Elsevier

    Pimarane, abietane, and labdane diterpenoids from Euphorbia pekinensis Rupr. and their anti-tumor activities

    Zeng, Xiao-TaoXu, Ding-QiaoYue, Shi-JunChen, Yan-Yan...
    8页
    查看更多>>摘要：Chemical investigation of the roots of Euphorbia pekinensis Rupr. led to the isolation of five undescribed labdane diterpenoids "(4S, 5S, 9R, 10S, 13R)-18-O-galloyl-labda-8(17), 14(15)-dien-13-ol; (4S, 5S, 9R, 10S, 13R)-13-hydroxy-labda-8(17), 14(15)-dien-18-one; (4S, 5S, 9R, 10S, 13R)-18-O-acetyl-labda-8(17), 14(15)-dien-13-ol; (4S, 5S, 9R, 10S)-labda-8(17), 13(16), 14(15)-trien-18-ol; (5R, 6R, 9R, 10S, 13R)-labda-8(17), 14(15)-dien-6,13-diol", two undescribed pimarane diterpenoids "(2R, 5S, 9R, 10S, 12R, 13R)-2,12-dihydroxy-isopimara-7,15-dien-3-one; (5S, 9R, 10S, 12R, 13R)-2, 12-dihydroxy-isopimara-1, 7, 15-trien-3-one)", together with nine known diterpenoids, including three pimarane-type "(3 beta,11 alpha,13 alpha)-3,11-dihydroxypimara-7,15-diene-2,12-dione; (11R, 12S)-2,11,12-trihydroxy-ent-isopimara-1,7,15-trien-3-one; isopimara-7,15-dien-3 beta-ol)", five abietane-type "helioscopinolide A-C; helioscopinolide E; helioscopinolide I '', and one lathyrane-type jolkinol B". The structures of these compounds were elucidated by analysis of HRESIMS, 1D NMR, 2D NMR, and X-ray diffraction. These sixteen compounds were evaluated for cytotoxic activity in vitro against three human cancer cell lines, U-937, LOVO, and K-562. Jolkinol B exhibited IC50 of 3.60 mu M and 8.44 mu M against U-937 and LOVO cell lines, (4S, 5S, 9R, 10S, 13R)-18-O-galloyl-labda-8(17), 14(15)-dien-13-ol displayed IC50 of 5.92 mu M against U-937 cell lines, isopimara-7,15-dien-3 beta-ol showed IC50 of 0.87 mu M against K-562 cell lines.
      原文链接:
    • NSTL
    • Elsevier

    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.
      原文链接:
    • NSTL
    • Elsevier

    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.
      原文链接:
    • NSTL
    • Elsevier

    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.
      原文链接:
    • NSTL
    • Elsevier

    Protochlorophylls in Cucurbitaceae-Distribution, biosynthesis and phylogeny

    Kruk, JerzyGabruk, MichalKryszczak, MarianWasik, Piotr...
    8页
    查看更多>>摘要：Using high-resolution chromatography we resolved monovinyl (MV)-and divinyl (DV)-protochlorophylls (Pchls) and detected all of their side-chain homologues in the inner seed coat of Cucurbita maxima, C. pepo and their varieties. Furthermore, we analyzed other less common representatives of the Cucurbitaceae family that were found to accumulate mostly MV-Pchls. All these species and varieties showed the characteristic composition of individual Pchls. Additionally, we also detected all of the corresponding protopheophytins, which accounted for between 1.1 and 35.5% of Pchls and are supposed to be degradation products of Pchls, formed during seed storage. A pigment composition analysis of C. maxima seedlings performed during deetiolation revealed that chlorophyll (Chl) a content increased gradually, while the levels of Pchl-GG and Chl-GG, a precursor of Chl a, were low and did not change significantly. However, when the seedlings were incubated with the precursor of tetrapyrrole biosynthesis (delta-aminolevulinic acid) before illumination, the Chl-GG content increased dramatically, while synthesis of Chl a was inhibited. These data indicate that in C. maxima seedlings, Chl a is not synthesized from geranylgeranyl-pyrophoshate via Chl-GG, but rather directly from phytyl-pyrophosphate. Phylogenetic analysis of Chl synthase genes revealed that many species, including those of the Cucurbitaceae family, have two or more Chl synthase genes. This suggests that these additional genes, at least in some species, might encode isoforms involved in Pchl synthesis.
      原文链接:
    • NSTL
    • Elsevier

    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.
      原文链接:
    • NSTL
    • Elsevier