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1.
Ubonta SommartVatcharin Rukachaisirikul Kwanruthai TadpetchYaowapa Sukpondma Souwalak PhongpaichitNongporn Hutadilok-Towatana Jariya Sakayaroj 《Tetrahedron》2012,68(48):10005-10010
One new modiolin, microsphaerodiolin (1), and seven new phthalides, microsphaerophthalides A-G (2-8), together with 12 known compounds were isolated from the endophytic fungus Microsphaeropsis arundinis PSU-G18. Their structures were elucidated by spectroscopic methods. The new 3-oxygenated phthalides are rare natural products. The known 1-(2,5-dihydroxyphenyl)-2-buten-1-one exhibited significant antifungal activity against Microsporum gypseum SH-MU-4 with an MIC value of 8 μg/mL, moderate antimalarial activity with an IC50 value of 9.63 μg/mL and strong radical scavenging potency with the IC50 value of 0.018 mg/mL. The new compounds 2 and 6 showed moderately antifungal activity against M. gypseum SH-MU-4 and Cryptococcus neoformans, respectively, with equal MIC values of 64 μg/mL. 相似文献
2.
Chakapong IntaraudomPranee Rachtawee Rapheephat SuvannakadPattama Pittayakhajonwut 《Tetrahedron》2011,67(39):7593-7597
Two new carbazomycin dimers (6 and 7) and 3-hydroxy-1,2-dimethyl-2,3-dihydro-1H-carbazol-4-one (9) together with six known compounds, carbazomycins A-D, cyclomarin C, and pimprinine have been isolated from Streptomyces sp. BCC26924. Carbazomycins B, C, and cyclomarin C exhibited antimalarial activity (against Plasmodium falciparum, K1 multi-drug resistant strain) with IC50 in a range of 0.24-2.37 μg/mL. Cyclomarin C exhibited anti-TB activity with a minimum inhibitory concentration value of 0.10 μg/mL, while carbazomycin D, compound 7, and pimprinine displayed MIC values in a range of 12.5-25.0 μg/mL. In addition, compounds 2, 5, 6, and 7 showed weak cytotoxicity against cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells. 相似文献
3.
Aibrohim Dramae Sutichai Nithithanasilp Wilunda Choowong Pranee Rachtawee Samran Prabpai Palangpon Kongsaeree Pattama Pittayakhajonwut 《Tetrahedron》2013
Two new natural products, samroiyotmycins A (1) and B (2), along with two naturally new novclobiocin 101 (3) and 4-hydroxy-3-(3-methylbut-2-enyl)benzamide (5), and five known substances including neoantimycin, clorobiocin (4), 29-O-methylabierixin, daidzein, and 1-(3-indolyl)-2,3-dihydroxypropan-1-one have been isolated from Streptomyces sp. BCC33756. Their chemical structures were determined based on NMR spectral information and the relative stereochemistry of compound 1 was determined by X-ray crystallographic data. Both samroiyotmycins A and B exhibited antimalarial activity against Plasmodium falciparum K1—multi-drug resistant strain, with IC50 values of 3.65 and 3.16 μg/mL, respectively. Compound 1 was inactive against both cancerous (MCF-7, KB) and non-cancerous (Vero) cells, while compound 2 displayed cytotoxicity against Vero cell with IC50 value of 29.57 μg/mL. 相似文献
4.
Jittra Kornsakulkarn Siriporn SaepuaSomjit Komwijit Pranee RachtaweeChawanee Thongpanchang 《Tetrahedron》2014
Five new compounds, phthalide 1, dihydroisocoumarin 2, and 3, pyrone 4, and benzophenone 5, together with nine known compounds, 3,4-dihydro-4,5,8-trihydroxy-3-methylisocoumarin, sclerotinin A, methyl-8-hydroxy-6-methylxanthone-1-carboxylate, sydowinin A, conioxanthone A, 1,3,8-trihydroxy-6-methylxanthone, 1,8-dihydroxy-3-methoxy-6-methylxanthone, coniochaetone B, and xylaranol B, were isolated from the fungus Astrocystis sp. BCC 22166. Structures of these compounds were elucidated using NMR spectroscopic and MS spectrometric analyses. Compound 1 exhibited antibacterial activity against Bacillus cereus (IC50=12.5 μg/mL) while compound 2 showed cytotoxicity to KB and Vero cells (IC50=22.6 and 48.2 μg/mL). 相似文献
5.
Four new compounds, two lignans; lucidenal and lucidanin (1 and 2), one alkaloid (3), and one flavanone (4) together with 26 known compounds (5–30), were isolated from the twigs of Feroniella lucida. The structures of the new compounds were determined on the basis of spectroscopic analyses. Lucidenal 1 showed cytotoxicity against HuCCA-1, A549, MOLT-3 and HepG2 cancer cell lines with IC50 values of 4.27, 9.59, 2.31, and 6.50 μg/mL, respectively. A plausible biosynthetic pathway of 1 was proposed. 相似文献
6.
Jittra KornsakulkarnKulvadee Dolsophon Nattawut BoonyuenTanapong Boonruangprapa Pranee RachtaweeSamran Prabpai Palangpon Kongsaeree Chawanee Thongpanchang 《Tetrahedron》2011,67(39):7540-7547
Eleven new dihydronaphthalenones 1-11, together with five known compounds; 5-hydroxydihydrofusarubin C (12), javanicin, bostrycoidin, anhydrofusarubin, and 3-O-methylfusarubin, were isolated from the endophytic fungus Fusarium sp. BCC14842. Structures were elucidated by analyses of the NMR spectroscopic and mass spectrometry data. Javanicin, 3-O-methylfusarubin, compounds 3 and 7 exhibited antimycobacterial and cytotoxic activities. Javanicin also displayed antifungal activity with IC50 of 6.16 μg/mL, while compounds 2, 4, 5, 8, and 12 showed only cytotoxic activity. 相似文献
7.
Kehokorins A (1)-C (3), three novel dibenzofurans, have been isolated from field-collected fruit bodies of the myxomycete, Trichia favoginea var. persimilis, and their structures were elucidated by spectral data. Kehokorin A (1) was a α-l-rhamnopyranoside of kehokorin B (2), while kehokorin C (3) was a 1-demethoxy analog of 2. Kehokorin A (1) was cytotoxic against HeLa cells with an IC50 value of 1.5 μg/mL. 相似文献
8.
Chakapong Intaraudom Aibrohim DramaeSumalee Supothina Somjit KomwijitPattama Pittayakhajonwut 《Tetrahedron》2014
Eight new compounds including 9′-[2-amino-3-(4″-O-methyl-α-rhamnopyranosyloxy) phenyl]nonanoic acid (1), 9′-[2-amino-3-(4″-O-methyl-α-ribopyranosyloxy)phenyl] nonanoic acid (2), 11′-[2-amino-3-(4″-O-methyl-α-rhamnopyranosyloxy)phenyl]undecanoic acid (3), 11′-[2-amino-3-(4″-O-methyl-α-ribopyranosyloxy)phenyl]undecanoic acid (4), 8-(4′-O-methyl-α-rhamnopyranosyloxy)-3,4-dihydroquinolin-2(1H)-one (5), 8-(4′-O-methyl-α-ribopyranosyloxy)-3,4-dihydroquinolin-2(1H)-one (6), 8-(4′-O-methyl-α-rhamnopyranosyloxy)-2-methyquinoline (7), and 8-(4′-O-methyl-α-ribopyranosyloxy)-2-methylquinoline (8) were isolated from Actinomadura sp. BCC27169. The chemical structures of these compounds were determined based on NMR and high-resolution mass spectroscopy. The absolute configurations of these monosaccharides were revealed by the hydrolysis of compounds 7 and 8. Compounds 3 and 8 exhibited antitubercular activity at MIC 50 μg/mL. Only compound 3 showed cytotoxicity against KB cell at IC50 18.63 μg/mL, while other isolated compounds were inactive at tested maximum concentration (50 μg/mL). 相似文献
9.
Lena Hammerschmidt Abdessamad Debbab Tu Duong Ngoc Victor Wray Catalina Perèz Hemphil WenHan Lin Heike Broetz-Oesterhelt Matthias U. Kassack Peter Proksch Amal H. Aly 《Tetrahedron letters》2014
Five new polyketide derivatives, 6′-hydroxypestalotiopsone C (1), acropyrone (2), bicytosporone D (3), waol acid (4), and pestalotiopene C (5), together with seven known metabolites (6–12), were obtained from extracts of the endophytic fungus Acremonium strictum, isolated from the mangrove tree Rhizophora apiculata. The structures of the isolated compounds were elucidated on the basis of comprehensive NMR and MS analysis. Compounds 6, 7, and 9 showed moderate cytotoxic activity against human cisplatin-sensitive (IC50 values 27.1, 76.2, and 8.3 μM, respectively) and resistant A2780 cell lines (IC50 values 12.6, 30.1, and 19.0 μM, respectively), whereas only 9 exhibited antibacterial activity against Staphylococcus aureus (MIC value 14.3 μM). 相似文献
10.
Pattama Pittayakhajonwut Rapheephat Suvannakad Samran Prabpai Morakot Tanticharoen 《Tetrahedron letters》2005,46(8):1341-1344
A structurally unique polyketide, mellisol (1) and 1,8-dihydroxynaphthol 1-O-α-glucopyranoside (3), were isolated from the fungus Xylaria mellisii (BCC 1005). The relative stereostructure of 1 was determined on the basis of X-ray crystallographic data. Compounds 1 and 3 exhibited activity against herpes simplex virus-type 1 with IC50 values of 10.50 and 8.40 μg/mL, respectively. They also showed cytotoxic activity against vero cells at the concentration of 40-50 μg/mL. 相似文献
11.
Masahiko Isaka Somporn PalasarnSomjit Komwijit Sayanh SomrithipolSujinda Sommai 《Tetrahedron letters》2014
Cyclodepsipeptides SCH 217048 (1), SCH 218157 (2), and a new analog, pleosporin A (3), were isolated from cultures of an unidentified elephant dung fungus of the family Pleosporaceae. The structure of 3 was elucidated on the basis of detailed spectroscopic interpretation. The absolute configurations of 1–3 were determined by chiral column HPLC analysis and Marfey’s method. Cyclodepsipeptides 1–3 exhibited antimalarial activity against Plasmodium falciparum K1 with respective IC50 values of 1.6, 6.4, and 1.6 μg/mL, while they did not show cytotoxicity against KB, MCF-7 and NCI-H187 cell-lines or non-cancerous Vero cells at 50 μg/mL. 相似文献
12.
Masahiko Isaka Panida Chinthanom Sukitaya Veeranondha Sumalee Supothina J. Jennifer Luangsa-ard 《Tetrahedron》2008,64(49):11028-11033
Two novel cyclopropyl diketones, hamavellone A (1) and B (2), and two new 14-membered nonaketide macrolactones, hamigeromycin A (3) and B (4), together with six known compounds, 89-250904-F1 (radicicol analogue A, 5), pseurotin A (6), emodin (7), ω-hydroxyemodin (8), and emodin bianthrones (9 and 10) were isolated from the soil fungus Hamigera avellanea BCC 17816. The structures of the new compounds were defined by analysis of NMR and MS data. The absolute stereochemistry of 3 was addressed by chemical correlation to 5. Hamavellone B (2) exhibited antimalarial activity with an IC50 of 5.2 μg/mL, whereas it also showed comparable cytotoxicity. 相似文献
13.
Fourteen new norditerpenoids (abiesanordines A-N, 1-14), including a novel podocarpene bearing a rare enolic structure (abiesanordine A, 1), were isolated from Abies georgei together with eight known ones. Their structures were determined mainly by detailed analysis of 1D and 2D NMR spectroscopic data including HSQC, DQF COSY, HMBC, and NOESY. All the isolates were tested for inhibitory activities against LPS-induced NO production in RAW264.7 macrophages, abiesanordine I (9) showed the strongest activity with the IC50 value of 17.0 μg/mL. Furthermore, it exhibited no cytotoxicity against RAW264.7 macrophages under the concentration of 50 μg/mL. 相似文献
14.
Chemical investigation of a southern Australian deep-water marine sponge, Fasciospongia sp., returned the new meroterpene sulfate fascioquinol A (1) together with a series of acid mediated hydrolysis/cyclization products, fascioquinols B (2), C (3) and D (4), and strongylophorine-22 (5). Additional co-metabolites include the new meroterpenes fascioquinol E (6) and fascioquinol F (8), together with the known sponge metabolite geranylgeranyl 1,4-hydroquinone (7). Structures were assigned to 1-8 on the basis of detailed spectroscopic analysis, chemical interconversion, mechanistic and biosynthetic considerations, and literature comparisons. The known 1,4-hydroquinone 7 was identified as the dominant cytotoxic principle in the Fasciospongia sp. extract, with selective inhibitory activity against gastric adenocarcinoma (AGS, IC50 8 μM) and neuroblastoma (SH-SY5Y, IC50 4 μM) cell lines. By contrast, while the fascioquinols displayed little or no inhibitory activity towards human cell lines, 1 and 2 displayed promising Gram-positive selective antibacterial activity towards Staphylococcus aureus (IC50 0.9-2.5 μM) and Bacillus subtilis (IC50 0.3-7.0 μM). 相似文献
15.
Natalia K. Utkina Aleksandra E. Makarchenko Pavel S. Dmitrenok 《Tetrahedron letters》2004,45(40):7491-7494
A new dipyrroloquinone, zyzzyanone A 1, having a pyrrolo[3,2-f]indole-4,8(1H,7H)-dione skeleton, was isolated from the Australian marine sponge Zyzzya fuliginosa, along with the known pyrroloquinoline alkaloids, makaluvamines C, E, G, H, and L, and damirones A and B. The structure of 1 was determined by spectroscopic data. Zyzzyanone A 1 shows moderate cytotoxic activity against mouse Ehrlich carcinoma cells (IC50 25 μg/mL), inhibits the cell division of fertilized sea urchin eggs at a concentration of 25 μg/mL, and exhibits UV-A and UV-B absorbing activity. 相似文献
16.
Dehai Li Li ChenTianjiao Zhu Tibor Kurtán Attila MándiZhimin Zhao Jing Li Qianqun Gu 《Tetrahedron》2011,67(41):7913-7918
Two novel chlorinated sorbicillinoids named chloctanspirones A (1) and B (2), possessing an unprecedented bicyclo[2.2.2]octane-2-spiro cyclohexane skeleton, together with their quasi-precursors terrestrols K (3) and L (4), two additional new chlorinated compounds, were isolated from a marine sediment derived fungus Penicillium terrestre. Their structures including absolute stereochemistries were elucidated by analysis of NMR, MS data, and TDDFT CD calculations. The cytotoxic effects of 1-4 were preliminarily evaluated in HL-60 and A-549 cells. Compound 1 was active against both HL-60 and A-549 cells with IC50s 9.2 and 39.7 μM, respectively, while 2 showed weaker activity only against HL-60 cells (IC50 37.8 μM). 相似文献
17.
Gui-Jie Zhang Yu-Huan Li Jian-Dong Jiang Shi-Shan Yu Xiao-Jing Wang Peng-Yu Zhuang Yan Zhang Jing Qu Shuang-Gang Ma Yong Li Yun-Bao Liu De-Quan Yu 《Tetrahedron》2014
Seven new diterpenes, jiadifenoic acids J–P (1–7), two new sesquicarane sesquiterpenes, sesquicaranoic acids A and B (8 and 9), and four known compounds, were isolated from the stems of Illicium jiadifengpi. The trans-fused A/B ring junction in diterpenes was deduced from NMR data analysis and confirmed by single-crystal X-ray crystallography of 3. The absolute configurations of compounds 1 and 5 were determined using the Mo2(OAc)4-induced circular dichroism (ICD) method. Compounds 8 and 9 are a pair of C-10 epimers, and their absolute configurations were confirmed by analyzing their CD and ICD data. All of the isolated compounds were evaluated in vitro for their antiviral activities against Coxsackie virus B3 (CVB3). Among the isolated compounds, 4, 5, 7, 10, and 11 exhibited reasonable activity against CVB3, with IC50 values of 7.0–22.2 μmol/mL and selective index values (SI=TC50/IC50) of 49.3, 37.1, 31.3, 45.6 and 40.9, respectively. 相似文献
18.
Shreyans K. Jain Samdarshi Meena Asif K. Qazi Aashiq Hussain Sunil K. Bhola Rajendra Kshirsagar Koteppa Pari Anamika Khajuria Abid Hamid R. Uma Shaanker Sandip B. Bharate Ram A. Vishwakarma 《Tetrahedron letters》2013
The chromone alkaloid dysoline (1), a new regioisomer of rohitukine (2) along with rohitukine and rohitukine-N-oxide (3) were isolated from the stem barks of Dysoxylum binectariferum. The structure of dysoline (1) was determined by extensive 2D-NMR studies and the absolute configuration was established by NOESY and CD spectra. Dysoline (1) consisted of a 5,7-dihydroxy-2-methylchromone nucleus substituted with a 2′-hydroxylated N-Me piperidine ring at the C-6 position. Dysoline differs from rohitukine by the position of the piperidine ring on the chromone nucleus. Dysoline displayed promising cytotoxicity in HT1080 fibrosarcoma cells with an IC50 of 0.21 μM, and also displayed significant inhibition of proinflammatory cytokines TNF-α and IL-6. 相似文献
19.
Pattama Pittayakhajonwut Atit Usuwan Chakapong Intaraudom Punsa Khoyaiklang Sumalee Supothina 《Tetrahedron》2009,65(31):6069-789
Investigation of the insect pathogenic fungus Torrubiella luteorostrata led to the isolation of three new macrocyclic torrubiellutins A-C (1-3) and the known pyrone diterpene 4. Structures were elucidated by spectroscopic data including 1D, 2D NMR, and MS spectral data. The absolute stereochemistry was determined by chemical means using Mosher reactions and Marfey's reagent, together with NOESY spectral data. Torrubiellutin C showed biological activities against KB, MCF-7, NCI-H187, and Vero cell lines with IC50 varying from 0.78 to 4.36 μg/mL, while compound 4 exhibited antimalaria and anti-inflammatory activity with IC50 values of 3.49 and 1.21 μg/mL, respectively. 相似文献