首页期刊导航|Phytochemistry
期刊信息/Journal information
Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
正式出版
收录年代

    Density functional theory study on the coupling and reactions of diferuloylputrescine as a lignin monomer

    Elder, Thomasdel Rio, Jose C.Ralph, JohnRencoret, Jorge...
    11页
    查看更多>>摘要：Diferuloylputrescine has been found in a variety of plant species, and recent work has provided evidence of its covalent bonding into lignin. Results from nuclear magnetic resonance spectroscopy revealed the presence of bonding patterns consistent with homo-coupling of diferuloylputrescine and the possibility of cross-coupling with lignin. In the present work, density functional theory calculations have been applied to assess the energetics associated with radical coupling, rearomatization, and dehydrogenation for possible homo-coupled dimers of diferuloylputrescine and cross-coupled dimers of diferuloylputrescine and coniferyl alcohol. The values obtained for these reaction energetics are consistent with those reported for monolignols and other novel lignin monomers. As such, this study shows that there would be no thermodynamic impediment to the incorporation of diferuloylputrescine into the lignin polymer and its addition to the growing list of non-canonical lignin monomers.
      原文链接:
    • NSTL
    • Elsevier

    Prenylated cyclohexene-type meroterpenoids and sulfur-containing xanthones produced by Pseudopestalotiopsis theae

    Akone, Sergi HerveWang, HaoMouelle, Eitel Ngoh MisseMandi, Attila...
    8页
    查看更多>>摘要：Chemical investigation of the fungal endophyte Pseudopestalotiopsis theae isolated from leaves of Caloncoba welwitschii, collected in Cameroon, resulted in two previously undescribed sulfur-containing xanthone derivatives sydoxanthones D and E, in addition to three previously undescribed monomeric diisoprenyl-cyclohexene-type meroterpenoids biscognienynes D-F and five known natural products. The structures of the undescribed compounds were unambiguously identified by their mass spectra and by extensive 1D and 2D NMR spectroscopic analysis. Mosher's reaction was performed to determine the absolute configuration of sydoxanthones D and E while TDDFT-ECD calculations were used to assign the configuration of biscognienyne D. Biscognienynes B and D showed significant cytotoxicity against the mouse lymphoma cell line L5178Y with IC50 values of 7.7 and 6.7 mu M and against the human leukemic cell lines HL60, and Hal-01 with IC50 values ranging from 4.3 to 12.1 mu M.
      原文链接:
    • NSTL
    • Elsevier

    PTP1B and alpha-glucosidase inhibitory activities of the chemical constituents from Hedera rhombea fruits: Kinetic analysis and molecular docking simulation

    Ha, Manh TuanLee, Tae HyunKim, Chung SubPrajapati, Ritu...
    15页
    查看更多>>摘要：In this study, we present the first investigation of Hedera rhombea Bean fruit, which led to the isolation of six undescribed compounds including two megastigmane glucosides, two rare 1,4-dioxane neolignanes, and two quinic acid derivatives, together with 26 known compounds. Their structures and absolute configurations were elucidated by extensive analysis of NMR spectroscopic data, HRMS, and ECD calculations. This is the first report on the isolation of methyl 3-O-caffeoyl 5-O-p-coumamylquinate from a natural source. Among the isolated compounds, falcarindiol and caffeoyltryptophan showed significant PTP1B inhibition with IC50 values of 7.32 and 16.99 mu M, respectively, compared to those of the positive controls [sodium orthovanadate (IC50 = 17.96 mu M) and ursolic acid (IC50 = 4.53 mu M)]. These two compounds along with several other compounds displayed significant a-glucosidase inhibitions with IC50 values ranging from 12.88 to 91.89 mu M, stronger than that of the positive control (acarbose, IC50 = 298.07 mu M). Enzyme kinetic analysis indicated that caffeoyltryptophan and falcarindiol displayed competitive and mixed-type PTP1B inhibition, respectively, whereas the alpha-glucosidase inhibition type was mixed-type for caffeoyltryptophan and uncompetitive (rarely reported for alpha-glucosidase inhibitors) for falcarindiol. In addition, molecular docking results showed that these active compounds exhibited good binding affinities toward both PTP1B and a-glucosidase with negative binding energies. The results of the present study demonstrate that these active compounds might be beneficial in the treatment of type 2 diabetes.
      原文链接:
    • NSTL
    • Elsevier

    Decalintetracids A and B, two pairs of unusual 3-decalinoyltetramic acid derivatives with phytotoxicity from Fusarium equiseti D39

    Zhao, Dong-LinLiu, JingHan, Xiao-BinWang, Mei...
    8页
    查看更多>>摘要：The filamentous fungi Fusarium sp. are well-known for their ability to produce abundant specialised metabolites with attractive chemical structures and bioactivities. In this study, chemical analyses of the endophyte F. equiseti D39 led to the isolation and identification of two pairs of undescribed 3-decalinoyltetramic acids (3DTAs) E/Z diastereomers, decalintetracids A and B. Their structures were elucidated by comprehensive spectroscopic analysis and quantum-chemical calculations. Although 3DTAs were commonly reported from fungi, decalintetracid A possessed an unprecedented tricyclo [7.2.1.0(2,7)] dodecane skeleton, which added the diversity of these fungal metabolites. In addition, decalintetracid B was featured by a unique 6/6/5 ring system core. A plausible biosynthetic pathway for decalintetracids A and B was proposed. Both compounds exhibited phytotoxicity toward Amaranthus retroflexus L. and Amaranthus hybrid, indicating their potential as natural herbicides.
      原文链接:
    • NSTL
    • Elsevier

    Stilbenes: Source plants, chemistry, biosynthesis, pharmacology, application and problems related to their clinical Application-A comprehensive review

    Teka, TekleabZhang, LeleGe, XiaoyanLi, Yanjie...
    28页
    查看更多>>摘要：Stilbenes are some of the important phenolic compounds originating from plant families like Vitaceae, Leguminaceae, Gnetaceae, and Dipterocarpaceae. Structurally, they have a C6-C2-C6 skeleton, usually with two isomeric forms. Stilbenes are biosynthesized due to biotic and abiotic stresses such as microbial infections, high temperatures, and oxidation. This review aims to provide a comprehensive overview of stilbenes' botanical sources, chemistry, biosynthetic pathways, pharmacology, and clinical applications and challenges based on upto-date data. All included studies were collected from PubMed, ScienceDirect, Google Scholar, and CNKI, and the presented data from these indexed studies were analyzed and summarized. A total of 459 natural stilbene compounds from 45 plant families and 196 plant species were identified. Pharmacological studies also show that stilbenes have various activities such as anticancer, antimicrobial, antioxidant, anti-inflammatory, anti -degenerative diseases, anti-diabetic, neuroprotective, anti-aging, and cardioprotective effects. Stilbene synthase (STS) is the key enzyme involved in stilbene biosynthetic pathways. Studies on the therapeutic application of stilbenes pinpoint that challenges such as low bioavailability and isomerization are the major bottlenecks for their development as therapeutic drugs. Although the medicinal uses of several stilbenes have been demonstrated in vivo and in vitro, studies on the development of stilbenes deserve more attention in the future.
      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

    Bioactive terpenoids derived from plant endophytic fungi: An updated review (2011-2020)

    Amirzakariya, Bahman ZamaniShakeri, Abolfazl
    36页
    查看更多>>摘要：Plant endophytes have been considered as novel sources of naturally occurring compounds with various bio-logical activities, including cytotoxic, antimicrobial, anti-inflammatory, anticancer, herbicides, antileishmanial and antioxidant. A variety of specialised products, comprising terpenoids, alkaloids, polyketides, phenolic compounds, coumarins, and quinone derivatives have been reported from various strains. An increasing number of products, especially terpenoids, are being isolated from endophytes. Herein, the isolated new terpenoids from plant endophytic fungi, their hosts, as well as biological activities, from January 2011 until the end of 2020 are reviewed. In this period, 516 terpenoids are classified into monoterpenes (5), sesquiterpenes (299), diterpenes (76), sesterterpens (22), meroterpenes (83), triterpenes (29), and other terpenoids (2), were isolated from different plant endophytic fungi species.
      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

    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

    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%.
      原文链接:
    • NSTL
    • Elsevier