查看更多>>摘要：? 2022 Elsevier LtdFourteen undescribed phloroglucinol-meroterpenoids, namely eucalypcamals A–N, were isolated from a CH2Cl2 extract of the leaves of Eucalyptus camaldulensis Dehnh. In addition, from the same extract, twelve known phloroglucinols, three known flavonoids, and four known phenolic compounds were also isolated. The structures of the undescribed compounds were analyzed by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and high resolution electrospray ionization mass spectrometry (HRESIMS). The assignments of the absolute configurations were performed by comparing the experimental electronic circular dichroism (ECD) data with the calculated values. Eucalyprobusal E was found to be cytotoxic against HCT116, Jurkat, and MDA-MB-231 cell lines with IC50 values of 17.6, 9.44, and 17.9 μM, respectively. Eucalrobusone F exhibited antibacterial activity against methicillin-resistant S. aureus (MRSA) and S. aureus with minimum inhibitory concentration/minimum bactericidal concentration (MIC/MBC) values of 4/4 μg/mL while euglobal Ia1 showed antifungal activity with MIC/MFC values of 16/16 μg/mL.
查看更多>>摘要：? 2022 Elsevier LtdEleven undescribed and three known pterocarpans were isolated and identified from the traditional Chinese medicine “Huang-qi”, Astragali Radix (the root of Astragalus membranaceus var. mongholicus (Bunge) P.K.Hsiao). The structures of these pterocarpans were determined using spectroscopic, X-ray crystallographic, quantum chemical calculation, and chemical methods. Pterocarpans, almost exclusively distributed in the family of Leguminosae, are the second largest subgroup of isoflavanoids. However, pterocarpan glycoside number is limited, most of which are glucosides, and only one pterocarpan apioside was isolated from nature. Notably, nine rare apiosyl-containing pterocarpan glycosides were isolated and identified. The hypoglycemic activities of all these compounds were evaluated using α-glucosidase and DPP-IV inhibitory assays respectively, and some isolates displayed the α-glucosidase inhibitory function. The antioxidant activities of all compounds were evaluated using the ORAC and DPPH radical scavenging assays, respectively. All compounds exhibited varying degrees of oxygen radical absorbance capacity, and some compounds displayed DPPH radical scavenging ability.
查看更多>>摘要：? 2022 Elsevier LtdEleven undescribed limonoids, cipacinerasins A–K, involving of four diverse carbon skeletal types, along with fifteen known analogues, were isolated from the branches and leaves of Cipadessa baccifera. Within them, cipacinerasins A and B feature a rearranged tetrahydropyranyl ring B formed between C-8 and C-30, are unusual miscellaneous-type limonoids. Cipacinerasins E and F are rare trijugin-type limonoids, of which the D-ring δ-lactone is cleaved. Their structures were elucidated on the basis of extensive spectroscopic data (HRESIMS, NMR, UV and IR), electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. All compounds were evaluated in vitro cytotoxicity against five human tumor cell lines (K562, HeLa, PC3, LN-Cap and Hell), and cipacinerasin E showed moderate antitumor activity with IC50 values ranging from 8.0 to 24.8 μM.
查看更多>>摘要：? 2022 Elsevier LtdIdentify the botanical origins of a certain type of propolis may be challenging and time demanding, since it involves bee's behavior observation, plant resins collection and chemical analysis. Thus, this study aimed to determine the plant genetic materials in propolis from southern Brazil using the DNA barcoding to investigate their botanical origins, as well as to compare it with the phytochemical composition determined by ultra-high-performance liquid chromatography coupled with high-resolution mass spectrometry (UHPLC-HRMS) and with the pollinic profile. As principal results, non-native Populus carolinensis Moench (Salicaceae) was almost the only DNA source in some propolis samples, which coincided with the presence of flavonoids typical from poplar exudates. Conversely, other propolis samples had DNA material coming mainly from native plant species, most of them characterized to the species level, although no specific chemical markers from those plants could be identified by UHPLC-HRMS. However, pollen from several plants identified by the DNA barcoding were extracted from some propolis samples. Despite the identification of typical diterpenes, DNA material from Araucaria angustifolia (Bertol.) Kuntze (Araucariaceae), which have been indicated as a major resin source for propolis from preservation areas in southern Brazil, was found in very small abundancies, likely because bees do not drag tissue material containing DNA when collecting resin from this native species. In conclusion, DNA barcoding analysis successfully provided information about the provenance of propolis, although, depending on the plant resin sources, this information is likely to come from pollen.
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.
查看更多>>摘要：? 2022 Elsevier LtdEighteen linear triquinane sesquiterpenoids (LTSs), including seventeen previously undescribed ones (hirsutuminoids A-Q), were isolated from the fermentation of the fungus Stereum hirsutum (Willd.) Pers. The structures and absolute configurations of the isolates were characterized by extensive spectroscopic analysis (1D, 2D NMR, and HRMS data), together with comparing the experimental and calculated data of both electronic circular dichroism and NMR data, as well as X-ray crystallography. Based on the literature survey and efforts on constructing the absolute configurations of these LTSs in this study, one empirical rule about the orientations of substitutions at C-2/C-3/C-7/C-9 was summarized. Anti-inflammatory and cytotoxic bioassays showed that only hirsutuminoid B inhibited the nitric oxide (NO) production in RAW 264.7 macrophages with an IC50 value, 18.9 μM.
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.
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