查看更多>>摘要：? 2021 Elsevier B.V.Eight previously undescribed compounds, two quinones (1–2), one sesquiterpene (3), and five phenol compounds (4–8), including three enantiomers (6a, 7a, and 8a), along with three corresponding known enantiomers (6b–8b) were isolated from the aerial parts of Morinda umbellata L. Their structures were elucidated by 1D and 2D NMR spectroscopy, X-ray diffraction, and experimental and calculated ECD spectra, respectively. Compound 5 was found to have weak cytotoxity, which inhibited the growth of seven human cancer cell lines (A2780, HeLa, MCF-7, BGC-823, H7420, Ketr3 and SW 1990) with IC50 values from 13.3 to 15.1 μM.
查看更多>>摘要：? 2021 Elsevier B.V.The first natural product isolation studies of Nothofagus gunnii (Hook.f.) Oerst and Nothofagus cunninghamii (Hook.f.) Oerst have been undertaken. A previously unreported stilbene derivative, pinosylvin monoacetate, was isolated from the leaves of N. gunnii, in addition to 14 known compounds; including the flavonoids galangin, pinobanksin, catechin and quercetin; sesquiterpenoids such as, ilicol and (+)-β-costol acetate; 2,4-dihydroxy-6-methoxychalcone and pinosylvin. Four known flavonoid natural products, catechin, quercetin, ayanin, and avicularin were isolated from the leaves of N. cunninghamii. This study reveals that N. gunnii is a rich source of flavonoid, chalcone and stilbene compounds, while primarily hydroxyflavonoid compounds are found in N. cunninghamii. The isolated phytochemicals are consistent with the evolutionary relationships suggested to exist among Nothofagus species.
查看更多>>摘要：Eight new compounds (1-8), along with three known related compounds (9-11) were isolated from the leaves of Sauropus spatulifolius Beille. Their structures and configurations were elucidated by means of spectrometric and the modified Mosher's method. Among the new compounds, compounds 1 and 2 were identified as ethyl 3, 6-anhydro-2-deoxy-beta-D-arabino-hexofuranoside (1) and ethyl 3, 6-anhydro-2-deoxy- hexofuranoside (2). Compounds 3-5 were the 2-acetylpyrrole derivatives and identified as 2-(2-acetyl-1H-pyrrol-1-yl)-4-hydroxybutyric acid (3), methyl 4-(2-acetyl-lH-pyrrol- 1-yl) butanoate (4) and 1, 4-bis (2-acetyl-1H-pyrrol-1-yl) butane (5), respectively. Compound 6 was elucidated as 7-megastigmane-3, 8, 9-triol. Compounds 7, 8 were identified as kaempferol-3-O-2-deoxy-beta-D-glucoside (7) and kaempferol-3-O-beta-D- glucopyranosyl-(1-6)-2-deoxy-beta-D-glucoside (8). In addition, the cytotoxic activities of all the compounds were also evaluated, where compounds 3, 5, 7, 910 and 11 exhibited the magnificent inhibition activity on lung fibroblast differentiation induced by TGF-beta 1with low toxicity against the RLE-6TN cell.
查看更多>>摘要：Chemical fractionation of the EtOH extract of a medicinal macro fungus, Inonotus obliquus, afforded an array of lanostane-type triterpenoids (1 11) including two new ones (1 and 8). The structures of these compounds were determined on the basis of spectroscopic analyses, single crystal X-ray crystallography of 3-6 and biosynthetic considerations. With the confirmatory structural information provided by X-ray diffraction analysis in hand, several previously reported 21,24-cyclolanostanes, such as inonotsutriols A-C and (20R,21S,24S)-21,24-cyclo-penta-3 beta,21,25-trihydroxylanosta-8-ene, were structurally corrected. In addition, the NMR data of other types of 21,24-cyclo triterpenoids were also re-examined and structural revisions were thus suggested. Compounds 2, 6 and 8 showed significant cytostatic effects against a panel of tumor cell lines with IC50 values ranging from 7.80 to 18.5 mu M. Further assays established that compound 2 exerted promising in vitro anti-breast cancer potential by inhibiting the proliferation and migration of 4T1 cells.
查看更多>>摘要：Caged-polyprenylated xanthonoids represent a rare class of natural products. This type of compounds is mainly isolated from Genus Garcinia. Phytochemical studies on the leaves and twigs of Garcinia oligantha led to the isolation of four new caged-polyprenylated xanthonoids, oliganthone C-F (1-4), and two new simple xanthones (5-6), oliganthaxanthone D and oliganthaxanthone E. Eight known other polyprenylated xanthones (7-14) including five caged-polyprenylated xanthonoids (7-11) were also isolated. Their structures were elucidated based on the analyses of extensive spectroscopic data. All the isolated compounds except for 5, 6 and 14 showed cell viability reducing effect against human lung cancer A549 cells. Compounds 1-3 were proved to be potential apoptosis inducing agents.
查看更多>>摘要：The biochemical class of the polymethoxylated flavonoids represents uncommon phenolic compounds in plants presenting a more marked lipophilic behavior due to the alkylation of its hydroxylic groups. As a polymethoxylated flavone, which concerns a different bioavailability, artemetin (ART) has been examined in vitro against lipid oxidation and its impact on cancer cells has been explored. Despite this flavone only exerted a slight protection against in vitro fatty acid and cholesterol oxidative degradation, ART significantly reduced viability and modulated lipid profile in cancer Hela cells at the dose range 10-50 mu M after 72 h of incubation. It induced marked changes in the monounsaturated/saturated phospholipid class, significant decreased the levels of palmitic, oleic and palmitoleic acids, maybe involving an inhibitory effect on de novo lipogenesis and desaturation in cancer cells. Moreover, ART compromised normal mitochondrial function, inducing a noteworthy mitochondrial membrane polarization in cancer cells. A dose-dependent absorption of ART was evidenced in HeLa cell pellets (15.2% of the applied amount at 50 mu M), coupled to a marked increase in membrane fluidity, as indicate by the dose-dependent fluorescent Nile Red staining (red emissions). Our results validate the ART role as modulatory agent on cancer cell physiology, especially impacting viability, lipid metabolism, cell fluidity, and mitochondrial potential.
查看更多>>摘要：Three novel alkaloids, identified as (E)-N-((2R)-3-(2,5-dihydroxy-4-((3,4,5-trihydroxy-6-(hydroxymethyl)tetra-hydro-2H-pyran-2-yl)oxy)phenyl)-2-hydroxypropanoyl)-3-(4-hydroxyphenyl)acrylamide (1), named oleracrylimide A, (E)-N-((2R)-3-(2,5-dihydroxy-4-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl) oxy)phenyl)-2-hydroxypropanoyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide (2), named oleracrylimide B, and (E)-N-((2R)-3-(2,5-dihydroxy-4-((3,4,5-trihydroxy-6-(((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H- pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-hydroxypropanoyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide (3), named oleracrylimide C were isolated from Portulaca oleracea L. and the structures of the three novel compounds were determined by 1D and 2D NMR, circular dichroism, and UHPLC-ESI-QTOF/MS spectroscopic methods. Moreover, the bioactivities of anti-inflammation of the three compounds were investigated via testing RAW 264.7 macrophage cell stimulated by Lipopolysaccharide.
查看更多>>摘要：? 2021Adhesion of monocytes to endothelial cells is an important initiating step in atherogenesis. One of the most abundant flavonoids in the diet, quercetin has been reported to inhibit monocyte adhesion to endothelial cells. However, it is poorly absorbed in the upper gastrointestinal tract during oral intake but rather is metabolized by the intestinal microbiota into various phenolic acids. Since the biological properties of the microbial metabolites of quercetin remain largely unknown, herein, we investigated how the microbial metabolite of quercetin, 3-(3-hydroxyphenyl)propionic acid (3HPPA) impact monocyte adhesion to endothelial cells. Direct treatment with 3HPPA for 24 h was not cytotoxic to human aortic endothelial cells (HAECs). Cotreatment with 3HPPA inhibited tumor necrosis factor α (TNFα)-induced adhesion of THP-1 monocytes to HAECs, and suppressed the upregulation of cell adhesion molecule E-selectin but not intercellular adhesion molecule 1 or vascular cell adhesion molecule 1. Furthermore, 3HPPA was found to inhibit TNFα-induced nuclear translocation and phosphorylation of the p65 subunit of nuclear factor κB (NF-κB). We conclude that 3HPPA mitigates the adhesion of monocytes to endothelial cells by suppressing the expression of the cell adhesion molecule E-selectin in HAECs via inhibition of the NF-κB pathway, providing additional evidence for the health benefits of dietary flavonoids and their microbial metabolites as therapeutic agents in atherosclerosis.
查看更多>>摘要：? 2021 Elsevier B.V.Seven new terpenes and its derivatives classified into a p-menthane glycoside (1), a guaianolide glycoside (2), three eudesmane and its glycosides (3–5), and two mono-terpene derivatives (9 and 10) were isolated from Ainsliaea bonatii, together with three known guaianolides (6–8). Their structures were elucidated by spectroscopic data analysis, and absolute configurations were determined by DP4+ probability analysis via calculated 13C NMR data of isomers. Compounds 6 and 9 showed nitric oxide (NO) inhibitory effects in LPS-induced RAW 264.7 macrophage cells with IC50 values of 9.3 and 10.6 μM, respectively.
查看更多>>摘要：? 2021 Elsevier B.V.This review describes the chemical composition and biological properties of essential oils from plants of the Ocotea genus, from different origin. This taxon belongs to the Laureaceae family, which in turn, is best known for medicinal use, often related to the essential oils. The text includes studies about Ocotea species distributed mainly on the South American continent, but also reporting species located in North America and Africa. Brazil, Colombia, Costa Rica and Ecuador are countries with highest number of species mentioned in the review. Also, the major components of each essential oil, its chemical structures, as well as the description and extent of biological activities related to essential oils are detailed in this review. Finally, the text discusses the chemical and biological aspects of these studies in a comparatively way, also informing additional data such as yield, biome of origin and pharmacobotanical location.
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