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Phytochemistry Letters
Elsevier B.V.
Phytochemistry Letters

Elsevier B.V.

1874-3900

Phytochemistry Letters/Journal Phytochemistry LettersSCIISTP
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    Occurrence of a resveratrol trimer diglucoside derivative with a fused heptacyclic skeleton in Shorea uliginosa

    Ito T.Fukaya M.Ryu K.Nishiguchi M....
    5页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeUliginoside H (1) is a new resveratrol trimer diglucoside derivative with fused heptacycles. It was discovered from the acetone extract of the stem bark of Shorea uliginosa (Dipterocarpaceae). Spectroscopic analysis, such as NMR experiments, was used to elucidate the structure, and the absolute configuration was determined using circular dichroism data. Notably, 1 has a fused ring system composed of a dihydrobenzofuran ring, a hexahydrocyclopenta[c]chromene ring, and a cyclohex-2-enone ring, each with eight asymmetric carbons. Thus, a plausible biosynthetic pathway for 1 was proposed.
      原文链接:
    • NSTL
    • Elsevier

    Iridoids and lignans from Valeriana officinalis L. and their cytotoxic activities

    Zhang Z.Zhang D.Wu G.Sun Y....
    6页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeTwo new iridoids (1 and 2), one new lignan (3) together with one known iridoid (4) and twelve known lignans (5－16) were obtained from the roots of Valeriana officinalis L. (V. officinalis). The structures were determined using IR, MS, 1D and 2D NMR spectroscopy and the absolute configurations of the new structures were deduced by ECD experiments. All of the isolated compounds were assayed for their cytotoxic activities against three tumour cell lines (A549, HCT116 and SW620) and the results showed that compounds 9 and 10 showed cytotoxicities against A549 cells, compounds 9 and 11 showed cytotoxicities against SW620 cells and compound 10 showed cytotoxicities against HCT116 cells.
      原文链接:
    • NSTL
    • Elsevier

    Adenostemmoic acid B suppresses NO production by downregulating the expression and inhibiting the enzymatic activity of iNOS

    Kobayashi T.Tanaka N.Suzuki M.Maeda M....
    7页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeAdenostemmoic acid B (AB) is a major compound found in Adenostemma lavenia; it shows anti-melanogenic, anti-inflammatory, and cytotoxic activities. By modifying the 19th position (carboxy: involved in the avoidance of cytotoxicity) of AB, we succeed to separate these activities. Short-chain alkylation of the carboxy group enhanced anti-melanogenic activity, while long-chain alkylation (hydrophobic) resulted in the suppression of nitric oxide (NO) production and inducible NO synthase (iNOS) expression without anti-melanogenic activity. Re-modification of hydrophilic properties in these long-chain derivatives restored anti-melanogenic activity but did not suppress NO production. Unexpectedly, AB and derivatives with long chains linked by an anhydride bond were new iNOS inhibitors. These results suggest that AB modulates multiple physiological activities by regulating different targets, including iNOS.
      原文链接:
    • NSTL
    • Elsevier

    Four new compounds with cytotoxic and neuroprotective activity from Notopterygium incisum

    Ma L.-M.Chai T.Wang C.-B.Ma L....
    7页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropePhytochemical research on an extract of Notopterygium incisum yielded twenty-four compounds (1–24), including four new compounds 7, 10, 13 and 17. The structures of new compounds were elucidated by spectroscopic analysis, and the absolute configuration of 5 were assigned via Mosher's method. In addition, compounds 2, 9, 19 and 24 were analyzed by single crystal X-ray analysis for the first time. The new compound 7 exhibited remarkable cytotoxic activity against the human pancreatic cancer cell lines PANC-1, CAPAN-2, CFPAC-1, and SW1990 with IC50 values of 6.25 ± 0.54, 7.74 ± 1.12, 6.68 ± 1.11, and 5.35 ± 0.33 μM, respectively. The primary mechanistic study indicated that 7 caused cell death probably due to induced defects in the mitotic process. Moreover, compounds 2 and 7-9 effectively protected against H2O2-induced neurotoxicity in the SH-SY5Y cells, and 1, 3, 6, 10, 11, 16 and 19 exhibited strong DPPH scavenging ability.
      原文链接:
    • NSTL
    • Elsevier

    Six new dammarane-type triterpene saponins from the processed leaves of Panax notoginseng

    Zhang M.Sun X.Ren R.Su L....
    7页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeSix new dammarane-type triterpenoid saponins, notoginsenosides SFt5–SFt10 (1–6) were isolated from the processed leaves of Panax notoginseng (Burk.) F.H.Chen (Araliaceae), together with eight known notoginsenosides (7–14), fourteen known ginsenosides (15?28), two known vinaginsenosides (29?30), and one known gypenoside (31). Their structures were established by detailed spectroscopic analysis (NMR, UV, IR, HRESI-MS) and acidic hydrolysis. Four compounds notoginsenoside SFt1 (7), ginsenosides Rg5 (17), C-Mc (23) and 20(R)–Rg3 (25) have significant protective effects against L-glutamate-induced SH–SY5Y nerve injury (10 μM).
      原文链接:
    • NSTL
    • Elsevier

    Two new saponins from Paronychia capitata

    Allaoua Z.Benabdelaziz I.Benkhaled M.Haba H....
    5页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeTwo new oleanane-type triterpene glycosides, 3?O?β?D?glucopyranosyl?28?O?[β?D?glucopyranosyl?(1→2)?β?D?xylopyranosyl?(1→6)?β?D?glucopyranosyl]medicagenic acid (1) and 3?O?β?D?glucopyranosyl?28?O?[β?D?glucopyranosyl?(1→6)?β?D?glucopyranosyl?(1→2)? β?D?xylopyranosyl]oleanolic acid (2), named capitatosides A and B respectively, were isolated from the butanol extract of Paronychia capitata (L.) Lam., along with seven known compounds. The structures of the isolated compounds were established by spectroscopic methods, mainly HRMS, 1D and 2D NMR (1H, 13C, COSY, HSQC, HMBC and NOESY) techniques, whereas those of the known compounds were identified by spectral comparison with reported literature data.
      原文链接:
    • NSTL
    • Elsevier

    Limonoids from the bark of Toona ciliata var pubescens and their anti-tumor activities

    Li J.-Y.Pan W.-D.Du L.-B.Sheng D.-M....
    5页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeTwo previously undescribed B-ring seco-limonoids named toonacilinatin I (1) and toonacilinatin J (2), together with ten known analogues (3–12), were isolated from the ethyl acetate extract of the bark of Toona ciliata var pubescens. All structures were elucidated by extensive spectroscopic analysis involving IR, MS, and NMR. Among them, compounds 1–10, and 12 were discovered from this plant for the first time. All the compounds except 7 and 8 were evaluated for their anti-tumor activity by MTT method of MDA-MB-231 and A-673 cell lines, the bioassay results showed that compounds 1, 2, 5, 9 and 11 exerted superior inhibitory activity with IC50 values as 0.11–1.60 μM. Notably, those active compounds exhibited little effect on normal hepatocellular HL-7702 cells.
      原文链接:
    • NSTL
    • Elsevier

    Synthesis and structure–activity relationship of 16,17-modified gibberellin derivatives

    Ishida T.Watanabe B.Mashiguchi K.Yamaguchi S....
    5页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeGibberellins (GAs) are a group of diterpenoid plant hormones that control plant growth and development at various stages. Biologically active GAs share the common structures of a 3β-hydroxy group, a carboxy group at C-6, and a γ-lactone between C-4 and C-10. Hydroxylation at C-2β is a major deactivation step in many plant species, and hydroxylation at C-13 has been shown to weaken the binding affinity of GAs to their receptor proteins. In rice, bioactive GA4 has also been shown to be deactivated through 16α,17-epoxidation. Moreover, 16,17-dihydro-16α,17-dihydroxy GA4 has been identified as an aglycon of its glucoside from rice. However, our knowledge on the biological activity of 16,17-epoxidized GAs is currently limited to 16,17-dihydro-16α,17-epoxy GA4. Moreover, the bioactivity of 16,17-dihydro-16α,17-dihydroxy GA4 remains unknown. Here, we synthesized 16,17-epoxidized or dihydroxylated GA derivatives and performed a structure–activity relationship study using rice seedlings. 16,17-Epoxidation of bioactive GA1 and GA4 reduced their activity to promote elongation of rice leaf sheaths. Moreover, 16,17-dihydroxylation significantly decreased the activities of 16,17-dihydro-16α,17-epoxy GAs. These results suggest that GAs are deactivated in a stepwise manner via 16,17-epoxidation and hydrolysis of these epoxy groups.
      原文链接:
    • NSTL
    • Elsevier

    Pyranones from kiwi-associated fungus Fusarium tricinctum and their antibacterial activity

    Ma J.-T.Qin X.-X.Wang X.He J....
    4页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeFour new pyrone derivatives, fusaritricins A–D (1?4), together with five known analogues, were obtained from the kiwi endophytic fungus Fusarium tricinctum. Their structures were established by extensive spectroscopic data analysis and their absolute configurations were determined by quantum chemical calculations. Compounds 1, 2, 3, and 9 exhibited antibacterial activity against plant pathogen Pseudomonas syringae pv. Actinidiae (Psa) with MIC values of 128, 128, 64, and 64 μg/mL, respectively. This is the first report of anti-Psa activity of pyrone derivatives.
      原文链接:
    • NSTL
    • Elsevier

    Two new polyhydroxylated steroidal glycosides from Paris polyphylla var. yunnanensis

    Jiang X.-L.Hou X.-Y.Yang B.-B.Wang L....
    6页
    查看更多>>摘要：? 2022 Phytochemical Society of EuropeChemical investigation of Paris polyphylla smith var. yunnanensis afforded two new polyhydroxylated steroidal glycosides, named Parisyunnanosides K and L (1–2), together with nine known ones. The chemical structures of the new compounds were elucidated by 1D, 2D NMR and HR-ESI-MS techniques, together with chemical methods. Parisyunnanosides K and L (1–2) are rare C27 steroidal glycosides with two double bonds located at C-5, 6 and C-25, 26 of the aglycone, respectively. The cytotoxic activities of the isolated compounds were evaluated against Caco-2 cells by CCK-8 assay. Among them, compounds 5–11 exhibited potent cytotoxic activity with IC50 values ranging from 1.10 to 14.14 μM compared with the positive control oxaliplatin (1.38 μM).
      原文链接:
    • NSTL
    • Elsevier