查看更多>>摘要：? 2022 Elsevier LtdSaltmarsh plants have several defense mechanisms against threatening abiotic conditions, such as salinity, inundation, or exposure to intense radiation, less is known regarding response to insect pests attack. Salicornia europaea L. plant stands are produced as cash crops in Portuguese coastal areas. In 2017, these crops suffered significant attacks from a gall midge fly (Baldratia salicorniae Kieffer), reducing its economic value. To understand how this attack influenced S. europaea chemical composition, infested and non-infested branches were collected, and their extracts were analysed by GS-MS and UHPLC-MS. Results revealed that different degrees of infestations displayed different chemical composition. Several compounds were for the first time identified in S. europaea, such as, arachidic acid, alpha-tocopherol, henicos-1-ene, and squalene. Most evident results were the reduced amount of alkanes in the infested conditions, which seems to be a direct consequence of insect infestation. Several compounds identified in the infested branches are known to have negative effects on insect larvae by reducing larval growth (linoleic acid) or increasing insect mortality (oleic acid). Halophyte plants production is increasing and it is accompanied by the urge to develop early control strategies against potential pests. These strategies may include ecological friendly solutions such as endogenous production of specialized metabolites to retrieve plant self-defences. Further, our results showed that B. salicorniae herbivory also induced the production of higher number of specialized metabolites with important known biological activities. In years in which high infestations reduce organoleptic qualities for fresh consumption plants can be used in biorefinery industries for metabolite extraction.
查看更多>>摘要：? 2022 Elsevier LtdDivinyl ether synthases (DESs) are the enzymes occurring in numerous plant species and catalysing the dehydration of fatty acid hydroperoxides to divinyl ether oxylipins, playing self-defensive and antipathogenic roles in plants. Previously, the DES activities and divinyl ethers were detected in some monocotyledonous plants, including the asparagus (Asparagus officinalis L.). The cloning of the open reading frame of the CYP74H2 gene of asparagus and catalytic properties of the recombinant CYP74H2 protein are described in the present work. The CYP74H2 utilized the 13(S)-hydroperoxide of linoleic acid (13(S)-HPOD) as a preferred substrate and specifically converted it to the divinyl ether, (9Z,11Z)-12-[(1?E)-hexenyloxy]-9,11-dodecadienoic acid, (11Z)-etheroleic acid. The second most efficient substrate after the 13(S)-HPOD was the 9(S)-hydroperoxide of α?linolenic acid (9(S)-HPOT), which was converted to the previously undescribed product, (1?Z)-colnelenic acid. The 13(S)-hydroperoxide of α?linolenic acid (13(S)-HPOT) and 9(S)-hydroperoxide of linoleic acid (9(S)-HPOD) were less efficient substrates for CYP74H2. Both 13(S)-HPOT and 9(S)-HPOD were transformed to divinyl ethers, (11Z)-etherolenic and (1?Z)-colneleic acids, respectively. The CYP74H2 is a second cloned monocotyledonous DES after the garlic CYP74H1 and the first DES biosynthesizing the (1?Z)-colneleic and (1?Z)-colnelenic acids.
查看更多>>摘要：? 2022 Elsevier LtdThymoquinone (TQ), a natural phytochemical predominantly found in Nigella sativa, has been investigated for its numerous health benefits. TQ showed anti-cancer, anti-oxidant, and anti-inflammatory properties, validated in various disease models. The anti-cancer potential of TQ is goverened by anti-proliferation, cell cycle arrest, apoptosis induction, ROS production, anti-metastasis and anti-angiogenesis, inhibition of cell migration and invasion action. Additionally, TQ exhibited antitumor activity via the modulation of multiple pathways and molecular targets, including Akt, ERK1/2, STAT3, and NF-κB. The present review highlighted the anticancer potential of TQ. We summarize the anti-cancer, anti-oxidant, and anti-inflammatory properties of TQ, focusing on its molecular targets and its promising action in cancer therapy. We further described the molecular mechanisms by which TQ prevents signaling pathways that mediate cancer progression, invasion, and metastasis.
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.
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.
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.
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.
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.
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.
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.
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