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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Unravelling the key aroma compounds in the characteristic fragrance of Dendrobium officinale flowers for potential industrial application

    Yang Y.-H.Zhao J.Du Z.-Z.
    8页
    查看更多>>摘要：? 2022 Elsevier LtdDendrobium officinale Kimura et Migo, one of the most important orchids because of its medicinal and edible value, has a typical Dendrobium Sw. flora scent, which has great application potential and commercial value to be characterized. The aroma-active compounds originating from D. officinale fresh flowers (DFF) were investigated using a sensomics approach. A combined solid phase microextraction and solvent-assisted flavor evaporation method were used to accurately capture the overall aromatic profile. Exactly 34 odorants were detected and identified by aroma extract dilution analysis (AEDA) coupled with gas chromatography/olfactometry?mass spectrometry (GC/O?MS) in DFF, of which nine odorants had a flavor dilution (FD) factor ≥27. All 34 odorants were further quantified. The odor activity values (OAVs) were calculated with the highest value of 7444, in which 18 compounds were confirmed to be key odorants, including 1-octen-3-ol, hexanal, nonanal, phenylacetaldehyde, linalool, 4-oxoisophorone, theaspirane, methyl salicylate, etc. Among the studies above, 42 out of 78 volatiles and 14 out of 34 odorants were identified in DFF for the first time. Then, the aroma profile of the DFF was simulated successfully by aroma recombination experiments based on the quantitation results, and the omission test suggested that alcohols are the decisive type of compounds in the DFF key odorants. In addition, a progressive addition test showed that the aroma recombinate prepared with 18 reference key odorants was able to reconstruct the characteristic aroma of DFF. In comparison, the recombinate constituted by mixing all 34 reference odorants in the same concentrations as determined in the DDF sample could mimic the flower scent and closely match the sensory attributes of the original D. officinale fresh flower.
      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

    Identification of meroterpenoids from Bipolaris victoriae S27 and their potential activity against tumor metastasis and inhibition of the NF-κB signaling pathway

    Feng L.Wang X.-J.Li L.Zhang A.-X....
    11页
    查看更多>>摘要：? 2022 Elsevier LtdThree undescribed meroterpenoids, named bipolacochlioquinones A–C, together with seven known compounds, were isolated from the plant endophytic fungus Bipolaris victoriae S27 derived from the fresh stems of Rubia podantha Diels. Their structures were mainly determined by extensive spectroscopic analysis. The relative configurations of bipolacochlioquinones A–C were assigned using the ROESY spectrum, comparison of their spectral data with that reported in the literatures, and NMR calculations. Moreover, their complete absolute configurations were further established by electronic circular dichroism calculations using density functional theory. Among them, bipolacochlioquinone A is found to represent the first example of previously undescribed 6/6/6/6/6 pentacyclic dioxane-containing cochlioquinones, and bipolacochlioquinone B possesses a rare 6/6/6/6/5 pentacyclic system bearing a tetrahydrofuran ring fused to a polyketide and a sesquiterpenoid subunit. All compounds were evaluated for their inhibitory effects on tumor growth, metastasis, and the NF-κB signaling pathway. Among them, bipolacochlioquinone C and cochlioquinone A show the most potent cytotoxicities and NF-κB inhibitory activities. The effects of bipolacochlioquinone C and cochlioquinone A on the expression of NF-κB-associated proteins were also evaluated using western blotting. These results indicate that bipolacochlioquinone C and cochlioquinone A can inhibit the growth and metastasis of HCT116 and MDA-MB-231 cells by suppressing the NF-κB signaling pathway.
      原文链接:
    • NSTL
    • Elsevier

    Interactions of fungi with non-isothiocyanate products of the plant glucosinolate pathway: A review on product formation, antifungal activity, mode of action and biotransformation

    Plaszko T.Szucs Z.Vasas G.Gonda S....
    30页
    查看更多>>摘要：? 2022 The Author(s)The glucosinolate pathway, which is present in the order Brassicales, is one of the most researched defensive natural product biosynthesis pathways. Its core molecules, the glucosinolates are broken down upon pathogen challenge or tissue damage to yield an array of natural products that may help plants defend against the stressor. Though the most widely known glucosinolate decomposition products are the antimicrobial isothiocyanates, there is a wide range of other volatile and non-volatile natural products that arise from this biosynthetic pathway. This review summarizes our current knowledge on the interaction of these much less examined, non-isothiocyanate products with fungi. It deals with compounds including (1) glucosinolates and their biosynthesis precursors; (2) glucosinolate-derived nitriles (e.g. derivatives of 1H-indole-3-acetonitrile), thiocyanates, epithionitriles and oxazolidine-2-thiones; (3) putative isothiocyanate downstream products such as raphanusamic acid, 1H-indole-3-methanol (= indole-3-carbinol) and its oligomers, 1H-indol-3-ylmethanamine and ascorbigen; (4) 1H-indole-3-acetonitrile downstream products such as 1H-indole-3-carbaldehyde (indole-3-carboxaldehyde), 1H-indole-3-carboxylic acid and their derivatives; and (5) indole phytoalexins including brassinin, cyclobrassinin and brassilexin. Herein, a literature review on the following aspects is provided: their direct antifungal activity and the proposed mechanisms of antifungal action, increased biosynthesis after fungal challenge, as well as data on their biotransformation/detoxification by fungi, including but not limited to fungal myrosinase activity.
      原文链接:
    • NSTL
    • Elsevier

    Protein profiling of fast neutron soybean mutant seeds reveals differential accumulation of seed and iron storage proteins

    Islam N.Natarajan S.S.Krishnan H.B.
    8页
    查看更多>>摘要：? 2022A fast neutron (FN) radiated mutant soybean (Glycine max (L.) Merr., Fabaceae) displaying large duplications exhibited an increase in total seed protein content. A tandem mass tag (TMT) based protein profiling of matured seeds resulted in the identification of 4338 proteins. Gene duplication resulted in a significant increase in several seed storage proteins and protease inhibitors. Among the storage proteins, basic 7 S globulin, glycinin G4, and beta-conglycinin showed higher abundance in matured FN mutant seeds in addition to protease inhibitors. A significantly higher abundance of L-ascorbate peroxidases, acid phosphatases, and iron storage proteins was also observed. A higher amount of albumin, sucrose synthase, iron storage, and ascorbate family proteins in the mutant seeds was observed at the mid-stage of seed filling. We anticipate that the duplicated genes might have a cascading effect on the genome constituents, thus, resulting in increased storage and iron-containing protein content in the mutant seeds.
      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

    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

    Isoquinoline alkaloids from the Corydalis tomentella with potential anti-hepatoma and antibacterial activities

    Du K.Liu Y.Zong K.Wang Y....
    7页
    查看更多>>摘要：? 2022 Elsevier LtdSix undescribed isoquinolines, including one rarely reported N-benzyl isoquinoline together with sixteen known ones were isolated from C. tomentella. Their planar structures and absolute configurations were elucidated by extensive analyses of UV, IR, NMR, HRESIMS, DP4+ probability analysis as well as ECD calculations. Biological evaluations revealed that 3,4-2H-tomentelline C (6) showed significant cytotoxicity (IC50 = 7.42 μM) against the HepG2 cell line while (1′R, 2′S)-coptichine B (3) exhibited stronger antibacterial activities.
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    • NSTL
    • Elsevier

    Eleven undescribed alkaloids from the rhizomes of Sinomenium acutum and their IDO1 and TDO inhibitory activities

    Peng L.-Y.Zhao Q.-S.Liu J.-X.Bi R....
    15页
    查看更多>>摘要：? 2022 Elsevier LtdEleven previously undescribed alkaloids, named sinometumines A-K, along with three known alkaloids, were isolated from the rhizomes of Sinomenium acutum. The chemical structures of these unreported compounds were established using extensive spectroscopic methods (IR, UV, HRESIMS, and NMR), and their absolute configurations were determined by single crystal X-ray diffraction analyses and calculated electronic circular dichroism spectroscopy (ECD). Sinometumine D was the first aporphine-type derived alkaloid inner salt with a rearranged dibenzofuran ring backbone. Sinometumine E was a rare protoberberine-type alkaloid with a complex 6/6/6/6/6/6 hexacyclic skeleton. This was the first report of alkaloids with these two skeletons isolated from S. acutum. All isolates were evaluated for their inhibitory activities against indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO). Lysicamine possessed noteworthy inhibitory activities as an IDO1/TDO dual inhibitor with IC50 values of 6.22 ± 0.26 μM and 23.76 ± 2.93 μM, respectively, and liriodenine revealed moderate dual inhibition with IC50 values of 31.65 ± 4.44 μM and 15.64 ± 0.26 μM. The intermolecular interactions and binding modes between lysicamine and IDO1/TDO were elaborated by molecular docking studies.
      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