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1.
《Bioorganic & medicinal chemistry letters》2020,30(4):126956
Three new pentacyclic triterpenoid saponins (1–3), together with medicagenic acid (4) were isolated and purified from 70% EtOH extract of Medicago sativa L. by different column chromatographic and semi-preparative HPLC. Their structures were established by direct interpretation of their spectral data, mainly HR-ESI-MS, 1D-NMR, 2D-NMR, and chemical methods, as well as comparison with literature data. Additionally, all isolates were evaluated for their neuroprotective activities against H2O2-induced damage in human neuroblastoma SHSY5Y cells. As a results, compounds 1 and 2 (67.14% and 73.05%) exhibited potent neuroprotective activities. These findings provide new insights into developing better treatment of neurodegenerative diseases for M. sativa in the future. 相似文献
2.
《Bioorganic & medicinal chemistry letters》2019,29(15):1909-1912
Thirty-eight chalcone derivatives bearing a chromen or benzo[f]chromen moiety were synthesized and evaluated for their anti-inflammatory and analgesic activities. Using an ear edema model, anti-inflammatory activities were observed for compounds 3a-3s (ear inflammation: 1.75–3.71 mg) and 4a-4s (ear inflammation: 1.71–4.94 mg). All compounds also displayed analgesic effects with inhibition values of 66.7–100% (3a-3s) and 96.2–100% (4a-4s). The 12 compounds that displayed excellent anti-inflammatory and analgesic effects were tested for their inhibitory activity against ovine COX-1 and COX-2. Six compounds bearing a chromen moiety were weak inhibitors of the COX-1 isozyme but showed moderate COX-2 isozyme inhibitory effects (IC50s from 0.37 μM to 0.83 μM) and COX-2 selectivity indexes (SI: 22.49–9.34). Those bearing a benzo[f]chromen moiety were more selective toward COX-2 than those bearing a chromen moiety with IC50s from 0.25 μM to 0.43 μM and COX-2 selectivity indexes from SI: 31.08 to 20.67. 相似文献
3.
Two novel ent-atisane type diterpenoids possessing the extra unusal 2-oxopropyl moiety (1 and 2) and four known analogues have been isolated from the roots of Euphorbia ebracteolata. The structures and absolute configurations of these compounds were determined by extensive spectroscopic data analysis, including 2D NMR, single-crystal X-ray crystallography, 13C NMR calculation, and electronic circular dichroism spectra calculation. Compounds 1 and 2 are the first examples of natural products with ent-atisane type diterpenoids possessing 2-oxopropyl skeleton. Compounds 2, 3, 5, and 6 show antiviral activities against human rhinovirus 3, with IC50 values of 25.27–90.35 μM. Compounds 5 and 6 showed moderate antiviral activities against EV71 at a concentration of 100 μM. 相似文献
4.
Three new cytosporone derivatives dothiorelones K–M (1, 2 and 7), together with six known ones (3–6, 8 and 9) were isolated from the mangrove-derived fungus Dothiorella sp. ML002. Their structures were determined by comprehensive 1D, 2D NMR spectroscopic and HR-ESI-MS spectroscopic data. Compounds 1, 2 and 5 displayed inhibitory activities against α-glucosidase with the IC50 values of 22.0, 77.9 and 5.4 μg/mL, respectively. Additionally, compounds 1, 2, and 5 also exhibited antibacterial activities against Staphylococcus aureus (ATCC 6538) with the same MIC values of 50 μg/mL, respectively. The results indicated that cytosporone derivatives will be useful to as diabetes control agents. 相似文献
5.
In this work six PBN-related indanonitrones 1–6 have been designed, synthesized, and their neuroprotection capacity tested in vitro, under OGD conditions, in SH-SY5Y human neuroblastoma cell cultures. As a result, we have identified indanonitrones 1, 3 and 4 (EC50 = 6.64 ± 0.28 μM) as the most neuroprotective agents, and in particular, among them, indanonitrone 4 was also the most potent and balanced nitrone, showing antioxidant activity in three experiments [LOX (100 μM), APPH (51%), DPPH (36.5%)], being clearly more potent antioxidant agent than nitrone PBN. Consequently, we have identified (Z)-5-hydroxy-N-methyl-2,3-dihydro-1H-inden-1-imine oxide (4) as a hit-molecule for further investigation. 相似文献
6.
Yating Sun Jingtang Liu Lei Li Chi Gong Shuping Wang Fan Yang Huiming Hua Houwen Lin 《Bioorganic & medicinal chemistry letters》2018,28(3):315-318
Two new butenolide derivatives (±)-asperteretal D ((±)-1) and asperteretal E (2) containing rare 2-benzyl-3-phenyl substituted lactone core, together with nine known analogues (3–11) were obtained from a fungus Aspergillus terreus derived from the marine sponge Phakellia fusca. All the structures were elucidated on the basis of extensive NMR spectroscopic data. The chiral chromatography analyses allowed the separation of the (±)-asperteretal D, of which the absolute configurations were determined by comparing the experimental to calculated electronic circular dichroic (ECD) spectra. Compounds (±)-1, 2–5, and 7 exhibited potent inhibitory activities against α-glucosidase with IC50 values ranging from 8.65 to 20.3?µM (positive control acarbose with an IC50 value of 320?µM). In addition, derivatives 5–8 also showed moderate antioxidant activities. 相似文献
7.
Eight new meroterpenoids with different types of monoterpene units, namely, magmenthanes A-H (1–8), were identified from the bark of Magnolia officinalis var. biloba. Magmenthane A (1) possesses a 1,3-dioxabicyclo [4.3.01,5] nonane skeleton, 1–5 possess five pairs of enantiomers and 6 possesses a 1,1′-diallyl-biphenyl fragment. The structures of 1–8 were elucidated on the basis of 1D and 2D NMR, HRESIMS and electronic circular dichroism (ECD) calculations. Compounds 5 and 8 displayed significant PTP1B inhibitory activities with IC50 values of 4.38 and 3.88 μM, respectively. 相似文献
8.
Twenty-five derivatives of 5-chloro-2-aryl benzo[d]thiazole (1–25) were synthesized and evaluated for their α-glucosidase (S. cerevisiae EC 3.2.1.20) inhibitory activity in vitro. Among them eight compounds showed potent activity with IC50 values between 22.1 ± 0.9 and 136.2 ± 5.7 μM, when compared with standard acarbose (IC50 = 840 ± 1.73 μM). The most potent compounds 4, 9, and 10 showed IC50 values in the range of 22.1 ± 0.9 to 25.6 ± 1.5 μM. Compounds 2, 5, 11, and 19 showed IC50 values within the range of 40.2 ± 0.5 to 60.9 ± 2.0 μM. Compounds 1 and 3 were also found to be good inhibitors with IC50 values 136.2 ± 5.7 and 104.8 ± 9.9 μM, respectively. Their activities were compared with α-glucosidase inhibitor drug acarbose (standard) (IC50 = 840 ± 1.73 μM). The remaining compounds were inactive. Structure-activity relationships (SAR) have also been established. Kinetics studies indicated compounds 2, 3, 10, 19, and 25 to be non-competitive, while 1, 5, 9, and 11 as competitive inhibitors of α-glucosidase enzyme. All the active compounds (1–5, 9–11, and 19) were also found to be non-cytotoxic, in comparison to the standard drug i.e., doxorubicin (IC50 = 0.80 ± 0.12 μM) in MTT assay. Furthermore, molecular interactions of active compounds with the enzyme binding sites were predicted through molecular modeling studies. 相似文献
9.
Toshio Morikawa Kiyofumi Ninomiya Fengming Xu Naomichi Okumura Hisashi Matsuda Osamu Muraoka Takao Hayakawa Masayuki Yoshikawa 《Phytochemistry letters》2013,6(2):198-204
Two new acylated dolabellane-type diterpenes, nigellamines B3 (9) and D (10), were isolated from Nigella sativa (Ranunculaceae) seeds using column chromatography and preparative HPLC. Their structures were determined based on chemical and physicochemical evidence, and confirmed using previously isolated related compounds as reference. Of the seed constituents, nigellamines A2 (2), A3 (3), A5 (5), B1 (6), and B2 (7) had in vitro triglyceride metabolism-promoting activities in the high glucose-pretreated human liver carcinoma cell line, HepG2. 相似文献
10.
《Bioorganic & medicinal chemistry letters》2019,29(13):1576-1579
Basing on chromatographic separation techniques, fifteen aglycones (1–15), including two new anthraquinone aglycones (1, 2) and thirteen known compounds (3–15), were isolated from the small polar fraction of Cassia obtusefolia (petroleum ether extract). Structural elucidations were performed by 1D/2D NMR spectroscopy and mass spectrometry. The in vitro antioxidant and α-glucosidase inhibitory activities of these fifteen compounds were determined. Except compounds 12 (IC50 3.03 ± 0.31 μg/mL, stronger than ascorbic acid, which IC50 was 6.48 ± 2.30 μg/mL) and 13 (IC50 78.40 ± 2.39 μg/mL), the free radical scavenging capacities of other compounds were weak. Compounds 4, 5, 6 and 13 exhibited inhibitory activities on α-glucosidase with IC50 values of 50.60 ± 1.10, 22.57 ± 0.07, 60.09 ± 1.40, and 80.01 ± 2.66 μg/mL separately, however, all the α-glucosidase inhibitory activities were weaker than positive control (acarbose). 相似文献
11.
The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A–D (1–4), and 12 known metabolites (5–16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC50 values between 0.05 and 4.28 μM. 相似文献
12.
《Bioorganic & medicinal chemistry letters》2014,24(11):2459-2462
To search for novel cytotoxic constituents against cancer cells as lead structures for drug development, four new 3-phenylpropanoid-triacetyl sucrose esters, named tomensides A–D (1–4), and three known analogs (5–7) were isolated from the leaves of Prunus tomentosa. Their structures were elucidated by spectroscopic analyses (1D, 2D NMR, CD and HRESIMS). The cytotoxic activities of all isolates against four human cancer cell lines (MCF-7, A549, HeLa and HT-29) were assayed, and the results showed that these isolates displayed stronger inhibitory activities compared with positive control 5-fluorouracil. Tomenside A (1) was the most active compound with IC50 values of 0.11–0.62 μM against the four tested cell lines. The structure–activity relationship (SAR) of the isolates was also discussed. The primary screening results indicated that these 3-phenylpropanoid-triacetyl sucrose esters might be valuable source for new potent anticancer drug candidates. 相似文献
13.
Lukuan Hou Shuyao Wang Huiming Huang Huayue Li Wei Wang Wenli Li 《Bioorganic & medicinal chemistry letters》2018,28(17):2865-2868
Heterologous expression of the type III polyketide synthase (PKS) gene vioA in marine-derived Streptomyces youssoufiensis OUC6819 led to production of six violapyrones (VLPs), including four novel compounds VLPs Q–T (1–4) and two known compounds VLPs B and I (5 and 6). The structures of 1–4 were elucidated by a combination of spectroscopic analyses, including HR-ESIMS and 1D and 2D NMR data, demonstrating that 1–4 are novel VLPs which are methylated at 4-OH with their corresponding non-methylated counterparts to be VLP A, 5 and 6 and VLP C, respectively. Anti-influenza A [H1N1 (A/Virginia/ATCC1/2009) and H3N2 (A/Aichi/2/1968)] virus activity of compounds 1–6 as well as VLPs A and C were then evaluated using ribavirin as a positive control (IC50?=?66.7 and 99.6?μM). The results revealed that these VLPs showed considerable anti-H1N1 and anti-H3N2 activities with IC50 values of 30.6–132.4?μM and 45.3–150.0?μM, respectively. Notably, all the methylated VLPs displayed better anti-virus activity than their non-methylated counterparts, among which compound 3 (VLP S) exhibited the best activities. Interestingly, methylation at 4-OH has negative effect on the anti-MRSA (methicillin-resistant Staphylococcus aureus) activity instead, with methylated VLPs displaying decreased (2) or abolished (3 and 4) activities in comparison with each of their non-methylated counterparts. 相似文献
14.
Three new germacrane-type sesquiterpene lactones, koanolides B–D (1-3) have been isolated from the aerial parts of Koanophyllon gibbosum (Asteraceae), along with the previously reported sesquiterpene lactone koanolide A and the flavonoid eupatorin. The structures of the new compounds were elucidated using spectroscopic and spectrometric data analyses, including 1D and 2D NMR, and by comparison with known spectral data. The antiproliferative activities of the new compounds were evaluated in a panel of six representative human solid tumor cell lines and showed GI50 values ranging from 1.3 to 16 μM for the new molecules. 相似文献
15.
Chemical investigation of Paris polyphylla smith var. yunnanensis afforded two new polyhydroxylated steroidal glycosides, named Parisyunnanosides K and L (1–2), together with nine known ones. The chemical structures of the new compounds were elucidated by 1D, 2D NMR and HR-ESI-MS techniques, together with chemical methods. Parisyunnanosides K and L (1–2) are rare C27 steroidal glycosides with two double bonds located at C-5, 6 and C-25, 26 of the aglycone, respectively. The cytotoxic activities of the isolated compounds were evaluated against Caco-2 cells by CCK-8 assay. Among them, compounds 5–11 exhibited potent cytotoxic activity with IC50 values ranging from 1.10 to 14.14 μM compared with the positive control oxaliplatin (1.38 μM). 相似文献
16.
Eighteen secondary metabolites were isolated from the fermentation broth of the endophytic fungus Xylaria sp. SYPF 8246, including four new compounds, xylarianins A-D (1–4), three new natural products, 6-methoxycarbonyl-2′-methyl-3,5,4′,6′-tetramethoxy-diphenyl ether (5), 2-chlor-6-methoxycarbonyl-2′-rnethyl-3,5,4′,6′-tetramethoxy-diphenyl ether (6), and 2-chlor-4′-hydroxy-6-methoxy carbonyl-2′-methyl-3,5,6′-trimethoxy-diphenyl ether (7), and eleven known compounds (8–18). Their structural elucidations were conducted by using 1D and 2D NMR, HRESIMS, and Rh2(OCOCF3)4-induced electronic circular dichroism (ECD) spectra analyses. The integrated 1H and 13C NMR data of three new natural products 5–7 were reported for the first time. All the isolated compounds were assayed for their inhibitory activities against human carboxylesterase 2 (hCE 2). Compounds 1, 5–9, and 18 displayed significant inhibitory activities against hCE 2 with IC50 values of 10.43 ± 0.51, 6.69 ± 0.85, 12.36 ± 1.27, 18.25 ± 1.78, 29.78 ± 0.48, 18.86 ± 1.87, and 20.72 ± 1.51 µM, respectively. The interactions between compounds 1 and 5 with hCE 2 were anaylzed by molecular docking. 相似文献
17.
Two new glycoalkaloids, erianosides A (1) and B (2) along with five known compounds (3–7) were isolated from the leaves of Solanum erianthum. Their structures were elucidated from analyses of spectroscopic data and all isolates were tested for in vitro cytotoxic activity against human breast cancer cell lines (BT-549, MDA-MB-231, T74D, and MCF-7). Solasonine (5) and solamargine (6) were active against the aforementioned four cancer cell lines with IC50 values of 27.26–35.89 and 5.84–10.13 μM, respectively. Erianoside A (1) (T74D: IC50, 56.39 µM) and solasodine (3) (BT-549 and MDA-MB-231: IC50, 59.15 and 75.63 µM, respectively) had moderate cytotoxic effects towards some cell lines in the panel. 相似文献
18.
Three undescribed aporphine alkaloids dasymaroine A (1), 3-methoxyoxoputerine N-oxide (2), and dasymaroine B (3), along with nine known analogues (4–12) were isolated from the stems of Dasymaschalon rostratum Merr. The structures were elucidated using spectroscopic methods and by comparison with published NMR spectroscopic data. Compound 1 is a rarely reported nitro aporphine alkaloid and its absolute configuration was defined based on negative specific rotation and single-crystal X-ray diffraction. Compound 2 represents the first example of oxoaporphine alkaloid N-oxide. All compounds were evaluated for their activities of six pathogenic bacteria, 1 exhibited significant inhibition against Escherichia coli and Saphylococcus aureus with MIC values of 1.2 and 2.5 μM, respectively. As well as compounds 1–5, 7, 10, 12 were evaluated for their anti-HIV activities with EC50 ranged from 1.93 to 9.70 μM. 相似文献
19.
Vishal Sharma Venugopal Singamaneni Nisha Sharma Amit Kumar Divya Arora Manoj Kushwaha Shashi Bhushan Sundeep Jaglan Prasoon Gupta 《Bioorganic & medicinal chemistry letters》2018,28(12):2217-2221
Addition of the valproic acid (histone deacetylases inhibitor) to a culture of an endophytic fungus Diaporthe sp. harbored from Datura inoxia significantly altered its secondary metabolic profile and resulted in the isolation of three novel compounds, identified as xylarolide A (1), diportharine A (2) and xylarolide B (3) along with one known compound xylarolide (4). The structures of all the compounds (1–4) were determined by detailed analysis of 1D and 2D NMR spectroscopic data. The relative configurations of compounds 1–3 were determined with the help of NOESY data and comparison of optical rotations with similar compounds with established stereochemistry. All the isolated compounds were screened for antibacterial, antioxidant and cytotoxic activities. Xylarolide A (1) and xylarolide (4) displayed significant growth inhibition of MIAPaCa-2 with an IC50 of 20 and 32?µM respectively and against PC-3 with an IC50 of 14 and 18?µM respectively. Moreover, compound 1 displayed significant DPPH scavenging activity with EC50 of 10.3?µM using ascorbic acid as a positive control. 相似文献
20.
Jiangtao Feng Haifeng He Yuan Zhou Meng Cai Hao Peng Honglin Liu Lei Liu Lingling Feng Hongwu He 《Bioorganic & medicinal chemistry》2019,27(24):115159
Harmful cyanobacteria bloom (HCB) has occurred frequently in recent years and it is urgent to develop novel algicides to deal with this problem. In this paper, a series of novel thiamin diphosphate (ThDP) analogs 5a?5g were designed and synthesized targeting cyanobacterial pyruvate dehydrogenase complex E1 (Cy-PDHc E1). Our results showed that compounds 5a?5g have higher inhibitory activities against Cy-PDHc E1 (IC50 9.56–3.48 µM) and higher inhibitory activities against two model cyanobacteria strains Synechocystis sp PCC6803 (EC50 2.03–1.58 µM) and Microcystis aeruginosa FACHB905 (EC50 1.86–0.95 µM). Especially, compound 5b displayed highest inhibitory activities (IC50 = 3.48 µM) against Cy-PDHc E1 and powerful inhibitory activities against cyanobacteria Synechocystis sp PCC6803 (EC50 = 1.58 µM) and Microcystis aeruginosa FACHB905 (EC50 = 1.04 µM). Moreover, the inhibitory activities of compound 5b were even higher than those of copper sulfate (EC50 = 2.02 and 1.71 µM separately) which has been widely used as algicide against cyanobacteria PCC6803 and FACHB905. The more important was that compound 5b display much higher inhibitory selectivity between Cy-PDHc E1 (Inhibitory rate 97.4%) and porcine PDHc E1 (Inhibitory rate 11.8%) under the same concentration (100 μM). The inhibition kinetic experiment and molecular docking research showed that compound 5b can inhibit Cy-PDHc E1 by occupying the ThDP-binding pocket and then blocking Cy-PDHc E1 bound to ThDP as competitive inhibitor. The imagines of SEM and TEM showed that cellular microstructures were heavily destroyed under compound 5b stress. Our results demonstrated compound 5b could be taken as a potential lead compound targeting Cy-PDHc E1 to obtain environment-friendly algicide for harmful cyanobacterial blooms control. 相似文献