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1.
Wenjun Zhang Guangtao Zhang Liping Zhang Wei Liu Xiaodong Jiang Hongbo Jin Zhiwen Liu Haibo Zhang Aihua Zhou Changsheng Zhang 《Tetrahedron》2018,74(47):6839-6845
Polycyclic tetramate macrolactams (PTMs) are widely distributed in nature and are generated from a compact biosynthetic pathway. Bioinformatics analysis of the draft genome sequence of marine-derived Streptomyces sp. SCSIO 40060 revealed the presence of a putative PTM-encoding biosynthetic gene cluster (BGC). Comparison of this PTM BGC with those from the databank by genome mining suggests that Streptomyces sp. SCSIO 40060 should produce PTMs with a 5/6/5 type of carbocyclic ring. Subsequently, a 40-L scale of cultivation of Streptomyces sp. SCSIO 40060 led to the isolation and characterization of four known PTMS, ikarugamycin (1), epoxyikarugamycin (2), capsimycin (3), capsimycin C (4), and three new PTMs, hydroxyikarugamycins A–C (5–7). The planar structures of 5–7 were assigned by comprehensive spectroscopic analysis and the absolute configurations of 5 and 6 were unequivocally determined by X-ray diffraction analysis. The absolute structure of 7 was deduced by comparing ECD spectra of 5–7. Capsimycin (3) showed antimicrobial activity against methicillin-resistant Staphylococcus aureus with a MIC value of 16?μg/mL and displayed cytotoxicity against several cancer cell lines with IC50 values ranging from 2.62 to 6.87?μM. 相似文献
2.
Mohamed S. Abdelfattah Kazufumi Toume Midori A. Arai Hyuma Masu Masami Ishibashi 《Tetrahedron letters》2012,53(26):3346-3348
An unusual alkaloid with a 2-azaquinone-phenylhydrazone structure, katorazone (1), and other metabolites were isolated from the ethyl acetate extract of Streptomyces sp. IFM 11299. The chemical structure of katorazone (1) was elucidated by 1D and 2D NMR analyses together with HR-ESI mass spectrometry. Katorazone (1) showed a synergistic effect in combination with TRAIL and decreased the viability of human gastric adenocarcinoma (AGS) cells. 相似文献
3.
Lin Guo Ze-ping Xie Qin Yang Ling-ling Feng Lu Zhang Yue-zhi Zhang Xiao-nian Li Gennaro Pescitelli Shu-min Zhang 《Tetrahedron letters》2018,59(22):2176-2180
Kiamycins B (1) and C (2), two unusual angucyclinones bearing a novel 6,12-epoxybenz[a]anthracene ring system, were isolated from the cultures of a marine sediment-derived Streptomyces sp. along with one structurally related derivative 3. Their structures and stereochemistries were determined by spectroscopic analyses, single-crystal X-ray diffraction and electronic circular dichroism (ECD) calculations. 相似文献
4.
Ritesh Raju Oleksandr Gromyko Viktor Fedorenko Andriy Luzhetskyy Rolf Müller 《Tetrahedron letters》2012,53(24):3009-3011
A Streptomyces sp. Lv3-13, isolated from the rhizosphere soil of the plant Mespilus germanica, has yielded three new pimprinine derivatives, named pimprinols A–C (1–3) and the unknown (2-aminophenyl)(2-ethyloxazol-5-yl) methanone (4) along with the known compounds 2-ethyl oxazole pimprinine and 2-propyl oxazole pimprinine. The structures of the compounds were elucidated based on spectroscopic methods including UV, HR-ESIMS and 1D, 2D NMR data. Compounds 1–4 were screened for antimicrobial and cytotoxic activities. 相似文献
5.
Li Zhang Jing Shi Cheng Li Liu Lang Xiang Shi Ying Ma Wei Li Rui Hua Jiao Ren Xiang Tan Hui Ming Ge 《Tetrahedron letters》2018,59(51):4517-4520
Three new borrelidin-type macrolactones, designated as borrelidins J?L (4–6), together with borrelidin A (1), borrelidin E (2), and 12-desnitrile-12-carboxyl-borrelidin (3) were isolated from a plant endophytic Streptomyces sp. NA06554. Their structures were determined by extensive spectroscopic analysis including HRESIMS, 1D and 2D NMR data. The antibacterial activities for compounds 1–6 were examined. Borrelidins A (1) and L (6) showed potent and moderate antibacterial activity against Micrococcus luteus, respectively, whereas other derivatives (2–5) are almost inactive, which allows us to propose a plausible structure-activity relationship. 相似文献
6.
Ping Cheng Kuang Xu Yan Chi Chen Ting Ting Wang Yu Chen Cheng Long Yang Shi Ying Ma Yong Liang Hui Ming Ge Rui Hua Jiao 《Tetrahedron letters》2019,60(26):1706-1709
Chemical study of the insect-derived bacterium, Streptomyces sp. NA4286, led to the discovery of four new polyketides, murayaquinones B-E (1–4), together with a known compound, murayaquinone (5). The structures of new compounds (1–4) were determined by extensive analysis of their NMR and HRESIMS data. The absolute configuration of (+)-1 and (?)-1 was assigned through comparison of experimental and calculated ECD spectra. Murayaquinone D (3) exhibited potent cytotoxic activities against six human cancer cell lines with IC50 values ranging from 1.03 to 9.99 μM. 相似文献
7.
Mengxuan Chen Weiyun Chai Rongyao Zhu Tengfei Song Zhizhen Zhang Xiao-Yuan Lian 《Tetrahedron》2018,74(16):2100-2106
Secondary metabolites from marine-associated actinomycetes are important source for the discovery of novel bioactive compounds. In this study, an actinomycete Streptomyces sp. ZZ446 was isolated from coastal soils and different media were used to culture this isolated marine actinomycete. It has been found that this actinomycete in the liquid medium of 2216?E with sea salt produced five new compounds of streptopyrazinones A?D (1–4) and N-acetyl-l-isoleucine-l-leucinamide (5) as well as six known diketopiperazines (6–11) and one alkaloid (12). Structures of the new compounds were determined by extensive NMR analyses, HRESIMS data, electronic circular dichroism (ECD) calculation, chemical degradation, Marfey's method, and X-ray diffraction analysis. This type of streptopyrazinones A?D (1–4) is rarely found in the natural resources. New compounds 1–5 showed activity in inhibiting the growth of Candida albicans and methicillin-resistant Staphylococcus aureus. 相似文献
8.
Vera A. Alferova Maxim V. Shuvalov Roman A. Novikov Alexey S. Trenin Lubov G. Dezhenkova Elena G. Gladkikh Olda A. Lapchinskaya Valeriya V. Kulyaeva Olga P. Bychkova Elena P. Mirchink Pavel N. Solyev Gulnara Kh. Kudryakova Vladimir A. Korshun Anton P. Tyurin 《Tetrahedron letters》2019,60(21):1448-1451
Three natural glycosylated macrolide compounds, known irumamycin 1 and X-14952B 2, as well as new isoirumamycin 3, were isolated from ethyl acetate mycelium extract of Streptomyces sp. INA-Ac-5812. Structures of the compounds were elucidated using 1D and 2D NMR. Isoirumamycin 3 was found to be an isomer of irumamycin with an 18-membered macrolactone ring instead of 20-membered macrolide in irumamycin. A previously unknown stereo configuration of irumamycin epoxide (C23, C24) and hemiketal (C3, C7) fragments was deduced from NMR data (ROESY/NOESY and HSQMBC). Cytotoxic, antifungal and antibacterial activities were studied for all isolated compounds. Comparison of the collected data showed crucial importance of 20-membered macrolactone ring for antimicrobial properties of this antibiotic family. 相似文献
9.
Two new angucyclic quinones, angumycinones A (1) and B (2) and six known angucyclinone analogues (3–8) were isolated from a liquid culture extract of the Streptomyces sp. KMC004 strain from acidic coal mine drainage. The structures of these compounds were established using extensive spectroscopic data analyses, including NMR, HRFABMS, UV, CD, and X-ray crystallography. Compounds 1–8 were tested for antimicrobial activity against ten pathogenic microbial or fungal strains. Angumycinone B (2) exhibited antimicrobial activity against Micrococcus luteus, Enterococcus hirae, and methicillin-resistant Staphylococcus aureus (MRSA) with minimum inhibitory concentration values of 0.78, 1.56, and 12.5 μg/mL, respectively. 相似文献
10.
Shwu-Jen Wu Tsong-Long Hwang Susan Morris-Natschke Tian-Shung Wu 《Tetrahedron letters》2010,51(32):4287-12161
Salviatalin A (1) and salvitrijudin A (2), two diterpenes with novel skeletons, were isolated from the roots of Salvia digitaloides. Their structures were determined using 1D, 2D NMR, and HRESI-MS spectroscopic analyses. Salviatalin A (1) from bioassay-guided fractionation showed a potent inhibitory effect on superoxide anion production in GMLP/CB-activated human neutrophils as well as other anti-inflammatory effects. A plausible biosynthetic pathway is also discussed. 相似文献
11.
Wenwen Yi Qiao Li Tengfei Song Lei Chen Xing-Cong Li Zhizhen Zhang Xiao-Yuan Lian 《Tetrahedron》2019,75(9):1186-1193
New indole alkaloids streptoprenylindoles A–C (1–3) and diterpenoids 18-acetyl-cyclooctatin (8), 5,18-dedihydroxy-cyclooctatin (9), and 5-dehydroxy-cyclooctatin (10) were isolated from the culture of marine-derived Streptomyces sp. ZZ820, along with known 3-cyanomethyl-6-[3-methyl-2-butenyl]indole (4), N-(2-(1H-indol-3-yl)ethylacetamide (5), 1-acetyl-β-carboline (6), indole-3-methylethanoate (7), cyclooctatin (11), and chromomycin A3 (12). Their structures were elucidated by a combination of extensive spectroscopic analyses, ECD calculation, and the Mosher's method. Streptoprenylindoles A (1) and B (2) are enantiomers that were separated through the preparation of their Mosher esters. Three new diterpenoids (8–10) showed antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli with MIC values of 24.11–55.12?μM, while chromomycin A3 (12) showed potent antibacterial activities against MRSA (MIC: 0.59?μM) and E. coli (MIC 0.04?μM). 相似文献
12.
Li-Hua Zhang Jian Bai Dao-Jiang Yan Ya-Nan Wang Ya-Long Zhang Li Li Bing-Yu Liu You-Cai Hu 《Tetrahedron letters》2019,60(4):375-377
Two unique polyketides, pleosporalesones A–B (1–2), bearing an unusual 6/6/7/6 tetracyclic ring system consisting of a chromone ring and a benzoannulated cycloheptanone ring, were isolated from the solid cultures of Pleosporales sp.. The chemical structures were elucidated by analyses of their extensive spectroscopic data, including 1D/2D NMR, ORD, CD and HR-ESI-MS, and the absolute configurations were established by comparison of their experimental circular dichroism data with those calculated. A plausible biosynthetic pathway for pleosporalesones A–B was proposed. 相似文献
13.
Three new macrocyclic peptides, diazonamides C-E (1-3), were isolated together with the previously reported diazonamides A (4) and B (5) from samples of the marine ascidian Diazona sp. collected in Indonesia. Their structures were assigned on the basis of detailed analysis of the 1D and 2D NMR and mass spectral data as well as Marfey’s analysis of the aminoacid residues. All the new compounds isolated displayed moderate cytotoxicity against a panel of three human tumor cell lines. 相似文献
14.
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
15.
Jing Shi Jia-Qi Ma Yong-Chao Wang Zi-Fei Xu Bo Zhang Rui-Hua Jiao Ren-Xiang Tan Hui-Ming Ge 《中国化学快报》2022,33(1):511-515
Lanthipeptides are one of the largest groups of ribosomally synthesized and post-translationally modified peptides(RiPPs) and are characterized by the presence of lanthionine(Lan) or methyllanthionine residues(MeLan). Only very few lanthipeptides contain a C-terminal 2-aminovinyl-cysteine(AviCys) motif, but all of them show potent antibacterial activities. Recent advances of genome sequencing led to the rapid accumulation of new biosynthetic gene clusters(BGCs) for lanthipeptides. In this study,... 相似文献
16.
《Chemistry & biology》1998,5(10):573-586
Background: Virulence in the pathogenic bacterium Yersinia pestis, causative agent of bubonic plague, has been correlated with the biosynthesis and transport of an iron-chelating siderophore, yersiniabactin, which is induced under iron-starvation conditions. Initial DNA sequencing suggested that this system is highly conserved among the pathogenic Yersinia. Yersiniabactin contains a phenolic group and three five-membered thiazole heterocycles that serve as iron ligands.Results: The entire Y. pestis yersiniabactin region has been sequenced. Sequence analysis of yersiniabactin biosynthetic regions (irp2-ybtE and ybtS) reveals a strategy for siderophore production using a mixed polyketide synthase/nonribosomal peptide synthetase complex formed between HMWP1 and HMWP2 (encoded by irp1 and irp2). The complex contains 16 domains, five of them variants of phosphopantetheine-modified peptidyl carrier protein or acyl carrier protein domains. HMWP1 and HMWP2 also contain methyltransferase and heterocyclization domains. Mutating ybtS revealed that this gene encodes a protein essential for yersiniabactin synthesis.Conclusions: The HMWP1 and HMWP2 domain organization suggests that the yersiniabactin siderophore is assembled in a modular fashion, in which a series of covalent intermediates are passed from the amino terminus of HMWP2 to the carboxyl terminus of HMWP1. Biosynthetic labeling studies indicate that the three yersiniabactin methyl moieties are donated by S-adenosylmethionine and that the linker between the thiazoline and thiazolidine rings is derived from malonyl-CoA. The salicylate moiety is probably synthesized using the aromatic amino-acid biosynthetic pathway, the final step of which converts chorismate to salicylate. YbtS might be necessary for converting chorismate to salicylate. 相似文献
17.
Zhi-Jun Zhang Jing Yang Juan He Xing-De Wu Li-Dong Shao Yan Li Sheng-Xiong Huang Rong-Tao Li Qin-Shi Zhao 《Tetrahedron letters》2014
Two new monoterpenoid indole alkaloids, vincamajorines A (1) and B (2), were isolated from Vinca major. Their structures were elucidated by means of 1D and 2D NMR, and HREIMS spectroscopic data. The relative and absolute configurations were deduced by comparing the experimental 13C NMR, ECD spectra, and OR data with those theoretically calculated. Vincamajorine A (1) represents a new C20 carbon skeleton arranged compactly in seven rings, and vincamajorine B (2) is an alkaloid with an unprecedented 6/5/7/5/6 pentacyclic ring system. A possible biosynthetic pathway was also proposed for the formation of 1 and 2. 相似文献
18.
Yong-Jun Jiang Li-She Gan Wan-Jing Ding Zhe Chen Zhong-Jun Ma 《Tetrahedron letters》2017,58(38):3747-3750
Two new gephyromycins (1–2), belonging to angucyclinones, were identified from Streptomyces sp. SS13I. Their structures were elucidated by analysis of HRESIMS, 1D and 2D NMR spectroscopic data, and the structure of 1 was further elucidated by X-ray diffraction data. The absolute configurations of compounds 1–2 were evidenced by ECD calculations. To our best knowledge, Compounds 1–2 were the second reported gephyromycin-type angucyclinones. Compound 2 exhibited significant cytotoxicity against PC3 cell lines with IC50 values of 1.38 ± 0.47 μM. 相似文献
19.
Dashan Zhang Yongjun Jiang Jiaqi Li Haojian Zhang Wanjing Ding Zhongjun Ma 《Tetrahedron》2018,74(46):6667-6672
Alokicenones A-H (1–8), eight new tetrahydroanthracenes and one known okicenone (9) were identified from the secondary metabolites of mangrove-derived Streptomyces sp. HN-A101. Their structures were elucidated by HRESIMS and NMR spectroscopic data. The absolute configurations of them were determined by the calculated and experimental ECD curves. Compounds 1–2 and 9 showed moderate cytotoxicity against HCT116 and SW620 cancer cell lines with IC50 values from 0.63 to 7.73?μM. In addition, compounds 1–3 and 7–9 also exhibited inhibitory activities against ROCK2 or BRD4. 相似文献
20.
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