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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Cephalotaxine homologous alkaloids from seeds of Cephalotaxus oliveri Mast

    Jing-WuCai X.-H.Zeng L.-H.Schinnerl J....
    6页
    查看更多>>摘要：? 2022 Elsevier LtdSix undescribed isoquinoline alkaloids, named as cephaloliverines A?F, were isolated from the seeds of Cephalotaxus oliveri. They were identified by NMR and MS spectroscopic data analyses, combined with the time-dependent density functional theory ECD calculation for cephaloliverines A and B and also by X-ray crystal diffraction for cephaloliverine E. Biosynthetic considerations suggest that cephaloliverines A?D are homologous of cephalotaxine-, homoerythrina- and Erythrina-type alkaloids. The performed bioassay revealed no cytotoxic activity against cancer cells and no neuroprotective properties on HEI–OC–1 cells model.
      原文链接:
    • NSTL
    • Elsevier

    Sesquiterpene lactone and its unique proaporphine hybrids from Magnolia grandiflora L. and their anti-inflammatory activity

    Cho H.M.Park E.J.Park Y.J.Ponce-Zea J....
    10页
    查看更多>>摘要：? 2022 Elsevier LtdTwo undescribed sesquiterpene lactone-proaporphine hybrid skeletons, two undescribed sesquiterpenes, and four known compounds were isolated from the aerial part of Magnolia grandiflora L. The structures of isolated compounds were unambiguously determined based on the interpretation of a combination of NMR spectroscopy, HRESIMS, DP4+ probability calculation of carbon data, X-ray crystallographic analyses, and ECD calculation. The isolated compounds were investigated for their anti-inflammatory activity against nitric oxide production and the protein expression of COX-2 in LPS-stimulated RAW 264.7 cells.
      原文链接:
    • NSTL
    • Elsevier

    Marginaols G–M, anti-in?ammatory isopimarane diterpenoids, from the rhizomes of Kaempferia marginata

    Chunglok W.Yotnoi B.Chulrik W.Chokchaisiri S....
    8页
    查看更多>>摘要：? 2022 Elsevier LtdMarginaols G–M, a series of undescribed isopimarane diterpenoids, together with four known analogs were isolated from the rhizomes of Kaempferia marginata. The structures of these isolated compounds were characterized using high-resolution mass spectrometry and extensive 1D- and 2D-nuclear magnetic resonance (NMR) analyses. In addition, the absolute con?gurations of marginaol G and H were determined by X-ray crystallographic analysis and comparison with the literature values. When compared to the standard drug dexamethasone (IC50 4.7 μM), marginaol G, H, and 6β-acetoxysandaracopimaradien-1α,9α-diol had an intriguing anti-inflammatory effect on NO inhibition in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages, with IC50 values ranging from 4.5 to 7.3 μM and being less cytotoxic to the cells. The anti-inflammatory action of these isopimarane diterpenoids from K. marginata supports the use of Thai traditional medicine for inflammation treatment.
      原文链接:
    • NSTL
    • Elsevier

    Cytotoxic cardiac glycosides from the root of Streblus asper

    Osman Mohammed R.M.Huang Y.Huang X.Deng S....
    11页
    查看更多>>摘要：? 2022 Elsevier LtdBioassay-guided separation of the root of Streblus asper led to the identification of six undescribed cardiac glycosides, including a rare cardiac glycoside dimer, along with twelve previously reported analogues. Their structures were determined on the basis of analyses of spectroscopic methods (1D and 2D-NMR spectroscopy), high-resolution electrospray ionization mass spectrometry (HRESIMS), circular dichroism (CD), and comparison of their spectroscopic data with previously reported data. Regarding their cytotoxic activities, microculture tetrazolium assays showed that all isolated cardiac glycosides strongly inhibited MCC-803, T24, SKOV-3, HepG2, Wi-38, and A549 cancer cell lines, with IC50 values ranging from 0.075 μM to 0.752 μM. One cardiac glycoside, a rare cardiac glycoside dimer, exhibited the strongest activity against the six cancer cell lines, with IC50 values ranging from 0.075 μM to 0.214 μM. In addition, the structure-activity relationships (SARs) of cardiac glycosides were investigated. In summary, S. asper showed marked cytotoxicity to several cancer cell lines, which could be meaningful for discovering new anticancer agents.
      原文链接:
    • NSTL
    • Elsevier

    Naming of new natural products: Standard, pitfalls and tips-and-tricks

    Bailly C.
    13页
    查看更多>>摘要：? 2022 Elsevier LtdNaming a newly discovered natural product (NP) is a pleasant but difficult exercise. In most cases, the NP name will be given with reference to the species of origin, be it a plant, a marine organism, a mammalian or microbial species. For a long time, the use of biologically-based trivial names has been recommended to identify the parental linkage between the product and the originating genus or species. But the recommendation is not always followed and a multiplicity of trivial names have been attributed to NP, based on locations (country, region, city), foods, music, animals, forenames, etc. Tips-and-tricks associated with the naming of NP are underlined here. Usually, NP are differentiated across a homogeneous chemical series with a letter (from the Latin or Greek alphabet), followed or not with a number. In other cases, the change of a single letter distinguishes a series of NP. Common pitfalls associated with the naming of NP are enumerated, including the complexity of names, use of synonyms, duplicated names, confusing names and inappropriate terminology. The difficulties regularly encountered with the naming of NP are discussed. Four essential recommendations are recalled: (i) a thorough analysis of the existing products to avoid duplicated names and confusion, (ii) the use of a biologically-based trivial name to retrace the origin of the product, (iii) the strict adherence to the codes of chemical nomenclature, and (iv) the preference for simple names to facilitate transmission. Naming a new NP is a rewarding task, which shall be performed with all due skill, care and diligence.
      原文链接:
    • NSTL
    • Elsevier

    Dammarane-type triterpenoids from Gynostemma compressum X. X. Chen & D. R. Liang (Cucurbitaceae) and their AMPK activation effect in 3T3-L1 cells

    Tran T.H.Le B.V.Pham H.T.T.Pham T.K....
    10页
    查看更多>>摘要：? 2022 Elsevier LtdBioassay-guided fractionation of the 80% ethanol extract of Gynostemma compressum X. X. Chen & D. R. Liang (Cucurbitaceae) resulted in the isolation and identification of eight undescribed triterpenoids, gycomol VN1, gycomol VN2, and gycomosides VN1–6 from the bioactive n-butanol fraction. The structures of these compounds were elucidated by one- and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution electrospray ionisation mass spectrometry, and chemical methods. All isolated compounds were evaluated for their 5′-adenosine monophosphate-activated protein kinase (AMPK) and acetyl-coenzyme A carboxylase (ACC) activation effects on 3T3-L1 cells. Importantly, gycomol VN2, gycomoside VN1, and gycomosides VN3–5 activated the phosphorylation of AMPK and its downstream substrate ACC in 3T3-L1 cells at a dose of 10 μM. These effects imply that the activation of AMPK and ACC by active compounds from G. compressum has considerable potential for the prevention of obesity and its related disorders by activating AMPK signaling pathways.
      原文链接:
    • NSTL
    • Elsevier

    Lignans and terpenoids from the stem of Ephedra equisetina Bunge

    Li M.Hao Z.-Y.Zheng X.-K.Feng W.-S....
    8页
    查看更多>>摘要：? 2022 Elsevier LtdSeven undescribed lignans, equiselignan A–F, and six undescribed terpenoids, equiseterpenoid A–E (including two pairs of enantiomers, (+/?)-equiselignan A and (+/?)-equiseterpenoid E), were isolated from the stems of Ephedra equisetina Bunge. Their structures were elucidated by spectroscopic methods, and the absolute configurations of the undescribed compounds were determined by interpretation of their electronic circular dichroic (ECD) and optical rotation data. In β-hexosaminidase (β-Hex) release assay, anti-asthmatic activities of all of the compounds were evaluated by releasing β-Hex in C48/80-induced RBL-2H3 cells. The β-Hex release rates of equiselignan B and equiseterpenoid B were 0.86 ± 0.094 and 0.86 ± 0.012 by comparing with model group, whereupon equiselignan B and equiseterpenoid B exhibited significant anti-asthmatic activities.
      原文链接:
    • NSTL
    • Elsevier

    Ten undescribed diterpenoid quinones derived from the Salvia miltiorrhiza

    He C.Chen X.Fan X.-L.Li X.-D....
    8页
    查看更多>>摘要：? 2022 Elsevier LtdThis study aimed to report the structure elucidation of the compounds isolated from Salvia miltiorrhiza, and their biological evaluations. Ten undescribed diterpenoid quinones and 10 known analogues were isolated from the dried roots of S. miltiorrhiza. Their structures were elucidated by extensive analysis, including nuclear magnetic resonance, high-resolution mass spectra, and ultraviolet and infrared spectra. Their absolute configurations were determined by comparing the experimental and calculated electronic circular dichroism spectra. In the evaluation of bioactivities, Salvianolactone acid I, epi-danshenspiroketallactone F, danshinspiroketallactone, grandifolia G, and 2H-Naphtho [1,8-bc]furan (10 μM) significantly increased cell viability and decreased the nuclear transport of p-P65 in lipopolysaccharide-induced bronchial epithelial cells. It was concluded that the diterpenoid quinones might belong to potent targeted lung-protective agents.
      原文链接:
    • NSTL
    • Elsevier

    The production of broad-spectrum antibiotics from phytopathogen Epicoccum sorghinum by culturing in host edible mushroom Thelephora ganbajun extract

    Wang C.-F.Yang X.-Q.Shi W.-Z.Long X....
    8页
    查看更多>>摘要：? 2022 Elsevier LtdMetabolism of special endophytes and phytopathogens can be induced by the symbiotic interactions with the host. A phytopathogen Epicoccum sorghinum cultured in host mushroom Thelephora ganbajun medium exhibited different metabolites compared with that of ordinary medium. An unprecedented scaffold possessing the same substructure as perylenequinone mycotoxin, a first methyl rearrangement product of phytotoxin, epoxydon 6-methylsalicylate ester, three undescribed compounds, and an undescribed natural product were isolated from E. sorghinum cultured in T. ganbajun. Episorin A and epicosorin A were produced from E. sorghinum induced by culturing in host medium. Episorin A was the first example of perylenequinone analogue in the natural products. These induced compounds and other metabolites showed notable antibiosis against endogenous fungi, and insect existing in mushroom. Induced episorin A showed significant inhibitory effects on nitric oxide production in LPS-activated macrophages, and anti-acetylcholinesterase with the IC50 at 5.40 ± 0.25 μM, and 4.32 μM, respectively, and cytotoxicity against HL-60, A-549, SMMC-7721, MCF-7 and SW480 with IC50 at 14.21 ± 0.53, 17.93 ± 0.22, 18.17 ± 0.63, 28.36 ± 0.43, and 18.20 ± 1.03 μM.
      原文链接:
    • NSTL
    • Elsevier

    Chemical and genetic variation in feral Cannabis sativa populations across the Nebraska climate gradient

    Busta L.Cahoon E.B.Sato S.J.Clemente T.E....
    10页
    查看更多>>摘要：? 2022Cannabis sativa is a versatile crop that can be cultivated for fiber, seed, or phytochemicals. To take advantage of this versatility and the potential of Cannabis as a feedstock for the bioeconomy, genomics-enabled breeding programs must be strengthened and expanded. This work contributes to the foundation for such by investigating the phytochemistry and genomics of feral Cannabis populations collected from seventeen counties across the climate gradient of Nebraska. Flower tissue from male and female plants (28 total) was studied using (i) gas chromatography-mass spectrometry to assess cannabinoid profiles and (ii) RNA sequencing to determine transcript abundances. Both male and female flower tissues produced cannabinoids, and, though the compounds were more abundant in female flower tissue, the primary cannabinoid in both was usually cannabidiol. The expression of genes that mediate early steps on the cannabinoid biosynthetic pathway were upregulated in female relative to male flowers, suggesting that female versus male flower tissue cannabinoid abundance may be controlled at least in part at the transcriptional level. DNA sequencing was used to place feral Cannabis plants from Nebraska into a previously described genomic context, revealing that all the plants studied here are much more similar to previously characterized hemp-type Cannabis plants than to drug-type Cannabis plants, at least at the genetic level. This work provides foundational phytochemical knowledge and a large set of high-quality single nucleotide polymorphism markers for future studies of feral Nebraska Cannabis.
      原文链接:
    • NSTL
    • Elsevier