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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Long-chain fatty acid acylated derivatives of isoflavone glycosides from the rhizomes of Iris domestica

    Liu, YanfeiWang, RenzhongYu, DequanLi, Jiayuan...
    7页
    查看更多>>摘要：Six undescribed long-chain fatty acid esters of isoflavone glycosides were obtained from the rhizomes of Iris domestica (L.). Their structures were elucidated by comprehensive spectroscopic data, alkaline hydrolysis, and acid hydrolysis. This is the first report of the long-chain (C14-C18) fatty acid derivatives of isoflavone glycosides from natural products. Belamcandnoate B and D exhibited moderate cytotoxic activities against HCT-116, HepG2, and BGC823 cell lines with IC50 values of 1.69-6.86 mu M. Belamcandnoate B and E exhibited 72.27 and 58.98% inhibitory activities, respectively, against Fe2+/cysteine-induced liver microsomal lipid peroxidation at a concentration of 10 mu M.
      原文链接:
    • NSTL
    • Elsevier

    Pentacyclic and hexacyclic cucurbitacins from Elaeocarpus petiolatus

    Cho, Eun-SeonKrishnan, PremanandLoh, Hwei-SanDaly, Janet M....
    9页
    查看更多>>摘要：Four undescribed cucurbitacins, designated as petiolaticins A-D, and four known cucurbitacins were isolated from the bark and leaves of Elaeocarpus petiolatus (Jack) Wall. Their chemical structures were elucidated based on detailed analyses of the NMR and MS data. The absolute configuration of petiolaticin A was also determined by X-ray diffraction analysis. Petiolaticin A represents a cucurbitacin derivative incorporating a 3,4-epoxyfuranylbearing side chain, while petiolaticin B possesses a furopyranyl unit fused to the tetracyclic cucurbitane core structure. Petiolaticins A, B, and D were evaluated in vitro against a panel of human breast, pancreatic, and colorectal cancer cell lines. Petiolaticin A exhibited the greatest cytotoxicity against the MDA-MB-468, MDA-MB-231, MCF-7, and SW48 cell lines (IC50 7.4, 9.2, 9.3, and 4.6 mu M, respectively). Additionally, petiolaticin D, 16 alpha,23 alpha-epoxy-3 beta,20 beta-dihydroxy-10 alpha H,23 beta H-cucurbit-5,24-dien-11-one, and 16 alpha,23 alpha-epoxy-3 beta,20 beta-dihydroxy-10 alpha H,23 beta H-cucurbit-5,24-dien-11-one 3-O-beta-D-glucopyranoside were tested for their ability to inhibit cell entry of a pseudotyped virus bearing the hemagglutinin envelope protein of a highly pathogenic avian influenza virus. Petiolaticin D showed the highest inhibition (44.3%), followed by 16 alpha,23 alpha-epoxy-3 beta,20 beta-dihydroxy-10 alpha H,23 beta H-cucurbit-5,24-dien-11-one (21.0%), and 16 alpha,23 alpha-epoxy-3 beta,20 beta-dihydroxy-10 alpha H,23 beta H-cucurbit-5,24-dien-11-one 3-O-beta-D-glucopyranoside showed limited inhibition (9.0%). These preliminary biological assays have demonstrated that petiolaticins A and D possess anticancer and antiviral properties, respectively, which warrant for further investigations.
      原文链接:
    • NSTL
    • Elsevier

    Chemical constituents from the flowers of Hypericum monogynum L. with COX-2 inhibitory activity

    Li, Ya-NanZeng, Yan-RongYang, JueHe, Wenwen...
    8页
    查看更多>>摘要：Hypericum monogynum L. (Hypericaceae) has been used as a folk Chinese medicine for the treatment of in-flammatory related diseases. Cyclooxygenase-2 (COX-2) is a crucial target for the development of agents to treat inflammation. To search for anti-inflammatory compounds from traditional Chinese medicines, a chemical constituent study along with COX-2 inhibitory activity analysis was performed for this plant. In this study, sixteen chemical monomers, including three undescribed oxidative degradation polycyclic polyprenylated acylphloroglucinols (PPAPs, hypemoins C-E), two undescribed PPAPs (hypemoins A and B), and 11 known compounds, were identified from the flowers of H. monogynum. Their structures were characterized by HRESIMS, NMR techniques, ECD, and single crystal X-ray diffraction. Four flavonoid derivatives showed remarkable COX-2 inhibitory activities, with IC50 values ranging from 0.220 +/- 0.006 to 1.655 +/- 0.098 mu M. Among these compounds, the possible recognition mechanism between quercetin 3-(6"-O-caffeoyl)-beta-3-D-galactoside and COX-2 was predicted by molecular docking analysis. Moreover, the multidrug resistance reversal activities for the selected compounds were evaluated.
      原文链接:
    • NSTL
    • Elsevier

    Chlomultiols A-L, sesquiterpenoids from Chloranthus multistachys and their anti-inflammatory activities

    Zhu, Zhi-yingChen, Zhi-chaoLuo, Yong-mingChen, Fang-you...
    9页
    查看更多>>摘要：Twelve undescribed sesquiterpenoids, named chlomultiols A-L, involving three lindenane sesquiterpenoid dimers, three eudesmane sesquiterpenoids, three guaiane sesquiterpenoids, and three cadinane sesquiterpenoids, along with four known compounds, were obtained from the whole plant of Chloranthus multistachys. Their structures were determined through spectroscopic techniques (HRESIMS, 1D and 2D NMR). In addition, the absolute and relative configurations of the undescribed compounds were established by using single crystal X-ray crystallography, NOESY and CD spectroscopy. The inhibitory effects of chlomultiols A-M on the production of nitric oxide in RAW 264.7 cells induced by lipopolysaccharide were evaluated. Chlomultiols A-C, and chlomultiols K-L showed moderate anti-inflammatory activities with IC50 values of 3.34 +/- 0.73, 15.06 +/- 1.08, 13.13 +/- 3.99, 6.63 +/- 1.11, and 16.16 +/- 1.88 mu M, respectively.
      原文链接:
    • NSTL
    • Elsevier

    Recent studies on terpenoids in Aspergillus fungi: Chemical diversity, biosynthesis, and bioactivity

    Zhao, Wen-YuYi, JingChang, Yi-BoSun, Cheng-Peng...
    25页
    查看更多>>摘要：Metabolites from fungi are a major source of natural small molecule drugs in addition to plants, while fungal derived terpenoids have been confirmed to have great potentials in many diseases. Aspergillus fungi are distributed in every corner of the earth, and their terpenoid metabolites exhibit promising diversity in term of both their chemistry and bioactivity. This review attempted to provide timely and comprehensive coverage of chemical, biosynthesis, and biological studies on terpenoids discovered from the genus Aspergillus, including mono-, sesqui-, di-, sester-, tri-, and meroterpenoids, in the last decade. The structural characteristics, biosynthesis, and pharmacological activities of 288 terpenoids were introduced.
      原文链接:
    • NSTL
    • Elsevier

    Characterized constituents of insect herbivore oral secretions and their influence on the regulation of plant defenses

    Kallure, Gopal S.Kumari, ArchanaShinde, Balkrishna A.Giri, Ashok P....
    15页
    查看更多>>摘要：For more than 350 million years, there have been ongoing dynamic interactions between plants and insects. In several cases, insects cause-specific feeding damage with ensuing herbivore-associated molecular patterns that invoke characteristic defense responses. During feeding on plant tissue, insects release oral secretions (OSs) containing a repertoire of molecules affecting plant defense (effectors). Some of these OS components might elicit a defense response to combat insect attacks (elicitors), while some might curb the plant defenses (suppressors). Few reports suggest that the synthesis and function of OS components might depend on the host plant and associated microorganisms. We review these intricate plant-insect interactions, during which there is a continuous exchange of molecules between plants and feeding insects along with the associated microorganisms. We further provide a list of commonly identified inducible plant produced defensive molecules released upon insect attack as well as in response to OS treatments of the plants. Thus, we describe how plants specialized and defense-related metabolism is modulated at innumerable phases by OS during plant-insect interactions. A molecular understanding of these complex interactions will provide a means to design eco-friendly crop protection strategies.
      原文链接:
    • NSTL
    • Elsevier

    Lignans from the seeds of Herpetospermum pedunculosum and their farnesoid X receptor-activating effect

    Meng, FanChengMa, YingXiongZhan, HongHongZong, Wei...
    16页
    查看更多>>摘要：The seeds of Herpetospermum pedunculosum (Ser.) C.B. Clarke, a well-known Tibetan medicine in China, are rich in kinds of bioactive lignans. In this phytochemical investigation on H. pedunculosum, sixteen undescribed lignans, named as herpedulins A - P together with 24 known ones were isolated from the ethyl acetate extract of its seeds. Their structures including the absolute configurations were determined by HR MS, 1D and 2D NMR experiments, and comparison of their experimental ECD spectra with calculated ones or literature data. High content screening experiments revealed that 9 compounds could promote the expression of farnesoid X receptor in guggulsterone-induced human normal liver cells L02 cells significantly. Further molecular docking results demonstrated that herpedulin E, J and K exhibited best docking scores (9.70, 9.28 and 10.31, respectively). Hydrogen bonding and hydrophobic interactions might contribute to the main interaction of active compounds with FXR.
      原文链接:
    • NSTL
    • Elsevier

    The complemented mutant (compl)Delta Bcstc7(niaD), in the STC7 of Botrytis cinerea led to the characterization of 11,12,13-tri-nor-eremophilenols derivatives

    Pinedo, CristinaAleu, JosefinaDuran-Patron, RosaSuarez, Ivonne...
    7页
    查看更多>>摘要：Botrytis cinerea has high potential for the production of specialized metabolites. The recent resequencing of the genome of the B05.10 strain using PacBio technology and the resulting update of the Ensembl Fungi (2017) database in the genome sequence have been instrumental in identifying new genes that could be involved in secondary metabolism. Thus, a new sesquiterpene cyclase (STC) coding gene (Bcstc7) has been included in the gene list from this phytopathogenic fungus. We recently constructed the null and complement transformants in STC7 which enabled us to functionally characterize this STC. Deletion of the Bcstc7 gene abolished (+)-4-epi-eremophilenol biosynthesis, and could then be re-established by complementing the null mutant with the Bcstc7 gene. Chemical analysis of the complemented transformant suggests that STC7 is the principal enzyme responsible for the key cyclization step of farnesyl diphosphate (FDP) to (+)-4-epi-eremophil-9-en-11-ols. A thorough analysis of the metabolites produced by two wild-type strains, B05.10 and UCA992, and the complemented mutant (compl)Delta Bcstc7(niaD), revealed the isolation and structural characterization of six 11,12,13-tri-nor-eremophilene derivatives, in addition to a large number of known eremophilen-11-ol derivatives. The structural characterization was carried out by extensive spectroscopic techniques. The biosynthesis of these compounds is explained by a retroaldol reaction or by dehydration and oxidative cleavage of C11-C13 carbons. This is the first time that this interesting family of degraded eremophilenols has been isolated from the phytopathogenous fungus B. cinerea.
      原文链接:
    • NSTL
    • Elsevier

    Alkaloids from Picrasma quassioides: An overview of their NMR data, biosynthetic pathways and pharmacological effects

    Chen Qian-wenYe XiaoLiu Xiao-qianLiang Yao-hua...
    13页
    查看更多>>摘要：Picrasma quassioides, a member of the Simaroubaceae family, is the subject of research in numerous pharmacological and chemical studies. This plant mainly contains alkaloids, quassinoids and terpenoids. These molecules exhibit various pharmacological benefits, such as anti-inflammatory, anticancer, and anti-viral effects, on the cardiovascular system. Alkaloids make up the majority of these molecules. This review describes 127 alkaloid substances from P. quassioides. These alkaloids can be divided into the following classes: beta-carbolines, canthinones and alkaloid dimers. A compilation of their nuclear magnetic resonance spectroscopy data and possible biosynthetic pathways of these compounds and the pharmacological effects of P. quassioides are also included.
      原文链接:
    • NSTL
    • Elsevier

    Sesquiterpenoids and their glycosides from Dobinea delavayi (Baill.) Baill

    Wu, Xiu-RongShen, YiDiao, Hong-MeiDong, Xiang...
    7页
    查看更多>>摘要：Eight undescribed sesquiterpenoids, including two eudesmane glycosides dobinosides A and B, five eudesmane aglycones dobinins Q-U, and one germacrane dobinin P, were isolated from the 80% ethanol extract of roots of Dobinea delavayi. Their structures were elucidated by extensive spectroscopic data (1D and 2D NMR, HR-ESI-MS) and single-crystal X-ray diffraction analysis. Dobinoside A, dobinins Q and R, as well as six reported eudesmane sesquiterpenoids, were evaluated for their in vivo antimalarial activities against Plasmodium yoelii BY265RFP in mice. A summary of preliminary structure-activity relationship of eudesmane sesquiterpenoids for in vivo antimalarial activity was described.
      原文链接:
    • NSTL
    • Elsevier