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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    MAPKK2/4/5/7-MAPK3-JAZs modulate phenolic acid biosynthesis in Salvia miltiorrhiza

    Xie Y.Ding M.Yin X.Wang G....
    10页
    查看更多>>摘要:? 2022Phenolic acids are the major bioactive metabolites produced in Salvia miltiorrhiza, a traditional Chinese medicine called Danshen. Many phytohormone elicitor treatments induce phenolic acid biosynthesis, even though the underlying mechanism remains obscure. Expression pattern analysis showed that SmMAPK3 was highly expressed in leaves, and SmMAPK3 was significantly induced by salicylic acid (SA) and methyl jasmonate (JA). Bioinformatics analysis revealed that SmMAPK3 belongs to group A and contains a TEY motif in the activation loop together with three conserved regions (P-loop, C-loop and CD-domain). A previous study speculated that SmMAPK3 is likely a positive regulator in the biosynthesis of phenolic acids in S. miltiorrhiza. In this study, overexpression of SmMAPK3 increased phenolic acid biosynthetic gene expression and enhanced the accumulation of phenolic acids in S. miltiorrhiza plantlets. Yeast two-hybrid (Y2H) analysis and firefly luciferase complementation imaging (LCI) assays revealed that SmMAPKK2/4/5/7-SmMAPK3-SmJAZs form a cascade that regulates the accumulation of phenolic acids. In summary, this work deepens our understanding of the posttranscriptional regulatory mechanisms of phenolic acid biosynthesis and sheds new light on metabolic engineering in S. miltiorrhiza.

    Polychlorinated cyclopentenes from a marine derived Periconia sp. (strain G1144)

    Cech N.B.Oberlies N.H.Rice C.A.Kyle D.E....
    8页
    查看更多>>摘要:? 2022 Elsevier LtdStudies on an organic extract of a marine fungus, Periconia sp. (strain G1144), led to the isolation of three halogenated cyclopentenes along with the known and recently reported rhytidhyester D; a series of spectrometric and spectroscopic techniques were used to elucidate these structures. Interestingly, two of these compounds represent tri-halogenated cyclopentene derivatives, which have been observed only rarely from Nature. The relative and absolute configurations of the compounds were established via mass spectrometry (MS), nuclear magnetic resonance (NMR) spectroscopy, Mosher's esters method, optical rotation and GIAO NMR calculations, including correlation coefficient calculations and the use of both DP4+ and dJ DP4 analyses. Several of the isolated compounds were tested for activity in anti-parasitic, antimicrobial, quorum sensing inhibition, and cytotoxicity assays and were shown to be inactive.

    Sesquiterpene lactones from Artemisia mongolica

    Zhu Z.Turak A.Aisa H.A.
    10页
    查看更多>>摘要:? 2022 Elsevier LtdTwelve undescribed sesquiterpene lactones and seven known sesquiterpene lactones were isolated from the whole plant of Artemisia mongolica. Their structures were elucidated based on the interpretation of NMR, HRESIMS, and electronic circular dichroism (ECD) data. The absolute configurations of mongolicolide A (1), mongolicolide C (3), 1R, 3S-Dihydroxy-7S, 11R-germacra-4Z.9Z-dien-12, 6S-olide (5), indicumolide E (9), indicumolide F (10), and indicumolide G (11) were determined by single-crystal X-ray crystallography. The X-ray crystal structure of artabsinolide E (15) was reported for the first time. In addition, beibersteneolide-B (13) showed moderate anti-inflammatory activity and marked antitumor activity, artemyriantholide E (18) show moderate antitumor activity.

    Meroterpenoids containing benzopyran or benzofuran motif from Ganoderma cochlear

    Qin F.-Y.Wang D.-W.Xu T.Zhang B.-S....
    9页
    查看更多>>摘要:? Elsevier LtdFive undescribed benzopyran containing meroterpenoids, ganodercins Q-U, two undescribed benzofuran containing meroterpenoids, ganodercins V and W, and two known meroterpenoids were isolated from Ganoderma cochlear. Their structures were elucidated by using HRESIMS, NMR spectroscopy and computational methods. The results of biochemical studies using a palmitic acid (PA) induced insulin resistance (IR) model show that (?)-ganodercin Q, (+)-ganodercins R and W activate phospho-AKT (p-AKT) at 20 μM and improve glucose uptake in a concentration dependent manner. The results of renoprotection studies show that (+)-ganodercin S, cochlearol F, (+)- and (?)-ganodercins V reduce the expression of collagen I.

    Chemical and biological studies of Daphniphyllum oldhamii from Hunan Province, China

    Chen Y.Wang X.-M.Shen S.-M.Yang M....
    8页
    查看更多>>摘要:? 2022 Elsevier LtdThe fruits, twigs and leaves of Daphniphyllum oldhamii (Hemsl.) K. Rosenthal, collected from Longshan County, Hunan Province, China, were chemically investigated. Three undescribed daphniphyllum alkaloids, namely longshanoldhamines A?C, and six known related ones have been isolated from the fruits, whereas two undescribed triterpenoids and one undescribed lignan, along with six known triterpenoids, were found in the twigs and leaves. Their structures were elucidated by extensive spectroscopic analysis, X-ray diffraction analysis and comparison with the reported data.

    Diterpenoids and p-methoxycinnamic acid diol esters from Kaempferia saraburiensis Picheans. (Zingiberaceae): Structural assignment of saraburol and their biological activities

    Mahidol C.Reuk-Ngam N.Khlaychan P.Batsomboon P....
    10页
    查看更多>>摘要:? 2022 Elsevier LtdFive undescribed compounds, including three diterpenoids namely, saraburol, saraburanes A and B, and two p-methoxycinnamic acid monoterpene diol esters, named E/Z-saraburinic esters, together with ten known oxygenated isopimarane diterpenoids, were isolated from the whole plant of Kaempferia saraburiensis Picheans. Among these compounds, saraburol possesses an unusual 6/9/6 tricyclic ring system bearing a 1,3-dioxonane-4-one scaffold, which is rarely found in natural products. The structure of isolated compounds was elucidated by spectroscopic methods, including HRESIMS, FTIR, 1D and 2D-NMR, and by comparison with published data, and their absolute configurations were determined by comparison of experimental with calculated ECD spectra and hydrolysis reaction. Using gauge-independent atomic orbital (GIAO) NMR shift calculations coupled with DP4+ probability analyses, biogenetic considerations, and optical rotation allowed for the complete characterization of saraburol. A plausible biosynthetic pathway for saraburol and saraburane A was proposed. The cytotoxicity result indicated that E-saraburinic ester exhibited the most potent activity with an IC50 value of 12.0 μM against MOLT-3 cells with a selectivity index of 12.5. Saraburane B exhibited the most potent activity against Gram-positive bacteria strain Staphylococcus epidermidis with MIC (MBC) value of 25 (50) μg/mL.

    On the free radical scavenging and metallic ion chelating activities of pyridoxal - Could the pro-oxidant risk be competitive?

    Ngo T.C.Truong D.H.Dao D.Q.Nguyen T.T.N....
    13页
    查看更多>>摘要:? 2022 Elsevier LtdPrimary and secondary antioxidant activities of pyridoxal have been investigated by using density functional theory (DFT) at the M05–2X level combined with 6–311++G(d,p) basis set for non-metallic atoms and LanL2DZ for metallic ions. The former has been examined by its free radical scavenging activity towards HOO●, HO●, and NO2● via different mechanisms including formal hydrogen transfer (FHT), proton transfer (PT), single electron transfer (SET), and radical adduct formation (RAF). The latter has been accomplished through its transition metal-chelating ability with Fe(III)/Fe(II) and Cu(II)/Cu(I) ions. The results show that pyridoxal illustrates as an efficient radical scavenger, especially, for HO● and NO2● in water. The overall rate constants (koverall) for the reactions with HOO●, HO●, and NO2● radicals are 1.30 × 104, 5.76 × 109, and 1.43 × 109 M?1s?1, respectively. The SET from the anionic state is the most dominant for the HOO● and NO2● scavenging reactions, while both RAF and SET contribute largely to the reaction with highly reactive HO● radicals. Moreover, the anionic form of pyridoxal demonstrates a better role as a metal chelator than the neutral. However, the pro-oxidant risks of the formed complexes could be observed if there are superoxide radical anion (O2●–) and ascorbate (Asc–) in aqueous media.

    Six C21 steroidal glycosides from Cynanchum wallichii Wight roots and their multidrug resistance reversal activities

    Liu Z.Lu L.Zhang R.-R.Zhang L....
    10页
    查看更多>>摘要:? 2022 Elsevier LtdSix unidentified C21 steroidal glycosides, cynwallosides A?F, as well as twenty-two known compounds, were isolated from the roots of Cynanchum wallichii Wight. The structures of cynwallosides A?F were determined by spectroscopic analysis and acidic hydrolysis. Most of these twenty-eight compounds were found to significantly reverse drug resistance in both the MCF-7/ADR and HepG2/ADM cell lines by suppressing P-gp protein expression. Further investigation revealed that three compounds suppressed P-gp expression by significantly inactivating the JNK and NF-κB pathways.

    Abietane diterpenes from the twigs and leaves of Cephalotaxus oliveri Mast. with antitumor activity

    Jiang C.Yang M.Zhao C.Liu F....
    8页
    查看更多>>摘要:? 2022 Elsevier LtdTwenty one abietane diterpenes were isolated from Cephalotaxus oliveri Mast. The structures of 7 undescribed diterpenoids, named cephaloliverins A-G, were elucidated via spectroscopic data interpretation and electronic circular dichroism (ECD) analysis. The isolated diterpenoids were evaluated for their cytotoxicity against three kinds of human tumor cell lines (MCF-7, HepG2, and A549). Metaglyptin A was the most active with IC50 values of 16.34, 15.63 and 21.33 μM and was further investigated for colony formation and apoptosis in HepG2 cells.

    Classification of sugarcane genotypes susceptible and resistant to the initial attack of sugarcane borer Diatraea saccharalis using epicuticular wax composition

    Lopes Ribeiro de Queiroz M.E.Teofilo R.F.Wartha C.A.Tomaz A.C....
    9页
    查看更多>>摘要:? 2022 Elsevier LtdIdentifying compounds present in the sugarcane epicuticular wax and using these compounds to classify the genotypes susceptible and resistant to the initial attack of sugarcane borer (Diatraea saccharalis) was the aim of this study. A greenhouse experiment was performed in a factorial scheme with and without borer infestation using genotypes previously characterized as resistant or susceptible in field-based experiments. Sugarcane whorls of six-month-old plants were collected before (BI) and after (AI) 72 h of sugarcane borer infestation. The sugarcane epicuticular wax was extracted in both times, i.e., BI and AI and its chemical composition was assessed by gas chromatography coupled to mass spectrometry (GC-MS). Twenty-five compounds were identified for both BI and AI. Classification models were built using partial least squares for discriminant analysis (PLS-DA) and linear discriminant analysis (LDA). Variable selection methods were used to improve the classification models. Ordered predictors selection for discriminant analysis (OPSDA) selected compounds that correctly classified all the test samples before borer infestation (Error = 0.000), and exhibited the most suitable classification parameters for the test set after borer infestation (Error = 0.111). The C30 pentacyclic triterpene friedelin and a high alcohol/aldehyde ratio were associated with the classification of resistant genotypes. Our findings have applicability in developing a screening methodology for breeding programs interested in identifying genotypes resistant to the initial feeding of sugarcane borer.