真菌萨氏曲霉D 2-6抗肿瘤活性代谢产物

 目的 阐明真菌萨氏曲霉（Aspergillus sydowi D2-6具抗肿瘤活性的次级代谢产物。方法 摇床发酵培养生产菌D 2-6,活性跟踪分离纯化D 2-6发酵液中的活性单体化合物,并根据理化性质和光谱分析(ESI-MS、UV、IR、NMR等鉴定单体化合物结构;采用细胞形态镜检、MTT方法评价单体化合物对人类慢性髓性白血病K562细胞、人肺癌A549细胞、人肝癌BEL7402细胞、人白血病HL60细胞和小鼠白血病P388细胞的抑制活性。结果 从真菌萨氏曲霉Aspergillus sydowi D 2-6发酵液中分离并鉴定了8个单体化合物,分别为5个二酮哌嗪类化合物fumitremorgin B(1、dihydroxy-fumitremorgin C(2、demethoxy-fumitremorgin C(3、fumitremorgin C(4和gliotoxin(5,1个喹啉类化合物fumiquinazoline C(6,2个杂螺环-γ-内酰胺类化合物azaspirofuran A(7和azaspirofuran B(8。化合物1～7的抗肿瘤活性检测结果显示,5对实验用肿瘤细胞的增殖抑制活性较强,对P388、A549、K562细胞的IC₅₀分别为1.47、0.10、0.57 nmol·L-1,7对P388、A549、BEL7402的IC₅₀分别为31.43、0.01、28.71 μmol·L-1,6对A549细胞的IC₅₀为42.10 μmol·L-1,而1、2、3、4对实验用肿瘤细胞无明显抑制活性(IC₅₀>100 μmol·L-1。结论 真菌萨氏曲霉Aspergillus sydowi D 2-6的主要抗肿瘤活性次级代谢物是含硫二酮哌嗪类、杂螺环-γ-内酰胺类和喹啉类化合物,其中,含硫哌嗪类化合物5对P388、A549、K562细胞的生长具有较强抑制作用,杂螺环-γ-内酰胺类化合物7对A549细胞具有选择性增殖抑制活性。     

海藻真菌菌株 Aspergillus sp. AF044 中的两个新天然产物

目的：研究海藻真菌 Aspergillus sp. AF044 的化学成分。方法：通过色谱层析柱对提取物进行分离纯化, 并通过波谱解析（一维、二维的核磁共振谱和质谱）确定化合物的结构。结果：分离纯化得到3个化合物, 分别鉴定为6-hydroxy-5-methoxy- 3-methyl-3, 6-dihydro-2H-pyran-4-carboxylic acid （1）, 8, 9-dihydroxy-8, 9-deoxyaspyrone（2） and penicillic acid（3）。结论：化合物 1和 2 是首次发现的新化合物。化合物 3 在多种真菌菌株中分离得到。     

Protuboxepins A and B and protubonines A and B from the marine-derived fungus Aspergillus sp. SF-5044

Two new oxepin-containing (1 and 2) and two diketopiperazine-type alkaloids (3 and 4) have been isolated from an EtOAc extract of the marine-derived fungus Aspergillus sp. SF-5044. The structures of these metabolites were determined through analysis of NMR and MS data, along with Marfey's method. Compound 1 showed weak growth inhibitory activity against a small panel of cell lines.     

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??OBJECTIVE To study the secondary metabolites of endophytic fungus Aspergillus TQ67 isolated from Suaeda glauca. METHODS The compounds were isolated and purified by ODS reversed-phase column, preparative HPLC and HPLC techniques.And their structures were identified by the physicochemical properties and spectral analysis. RESULTS The compounds were identified as aspermutarubrol (1), sydowiols D (2), sydowiol E (3), L-tenuazonic acid (4), (E)-5-(hydroxymethyl)-2-(6′-methylhept-2′-en-2′-yl)phenol (5), sydonol (6), (7S)-(+)-7-O-methylsydonol (7), and hydroxysydonic acid (8). Compounds 2/3 and compound 1 were different from other compounds with IC₅₀ values of (9.79±0.33) and (32.30±1.02) μg·mL^-1 by DPPH assay and (230.55±2.50) and (278.99±8.32) μg·mL^-1 by FRAP assay, respectively. CONCLUSION Compounds 2/3 and compound 1 isolated from endophytic fungus Aspergillus TQ67 isolated from Suaeda glauca show strong antioxidant activity.     

环带拟盘多毛孢发酵液中一个新的联苯类化合物(英文)

目的:研究分离于海南红槟榔中环带拟盘多毛孢发酵液的化学成分。方法:利用硅胶柱层析和凝胶柱层析分离纯化得到4个化合物(1~4),借助光谱学手段鉴定其结构。测试了化合物1对大肠埃希氏菌、金黄色葡萄球菌、铜绿假单胞菌、肺炎克来伯氏菌、MRSA耐甲氧西林金黄色葡萄球菌、鲍曼不动杆菌和VRE耐万古霉素屎肠球菌的抑制活性。结果:分离鉴定了4个化合物包括1个新化合物(2'-乙酰基-4',4-二甲氧基联苯-2-醛基),该化合物对7种细菌株有较弱抑制活性,IC50分别为0.75,0.75,0.82,0.81,0.84,0.90和0.87μm·mL-1.结论:化合物1为新的联苯类化合物,对7种细菌株表现出比较弱的抑制活性。化合物2~4为首次从该种中分离得到。     

Irisones A and B: two new isoflavones from Iris missouriensis

Two new isoflavones, irisones A and B, together with the known compound, 5,7-dihydroxy-2',6-dimethoxy isoflavone, were isolated from the roots of Iris missouriensis. With the help of 2D-homonuclear-J-correlation and 2D-nOe experiments the structure of irisone A was deduced to be 5-hydroxy-2'-methoxy-6,7-methylenedioxy isoflavone. The structure of irisone B was elucidated by spectral analyses as 2',5-dihydroxy-6,7-methylenedioxy isoflavone and was confirmed by chemical conversion to irisone A.     

Camganoids A and B, two new sesquiterpenes with different carbon skeletons isolated from fruits of Cinnamomum migao

Objective: To isolate and identify the undescribed compounds from the fruits of Cinnamomum migao and evaluate its nitric oxide inhibition potential. Methods: The chromatographic techniques of silica gel, sephadex, and HPLC were used for isolation and purification of the compounds, while HR-ESI-MS, 1D-NMR, 2D-NMR, ECD, and X-ray diffraction techniques were used to characterize and confirm the isolated compounds. Moreover, the anti-inflammatory activity of the isolated compounds was carried out to check inhibitory potential against the production of nitric oxide with RAW264.7 cells stimulated by LPS. Results: Camganoid A (1), a novel sesquiterpene possessing an unprecedented skeleton, and camganoid B (2), containing a unique eight-membered sesquiterpene moiety with a new carbon skeleton, were isolated and identified from the fruits of C. migao. The absolute configurations of 1 and 2 were confirmed by single crystal X-ray diffraction and electronic circular dichroism (ECD) calculations. Among these compounds, compound 1 exhibited potent inhibitory activity against the production of nitric oxide with IC50 value of 4.59 μmol/L in RAW264.7 cells stimulated by LPS. Conclusion: The isolation of two new skeletons from the fruits part of C. migao possessed unique skeletons which have not been reported before.     

海洋来源真菌Aspergillus sydowi PFW-13中的吲哚-喹唑啉类生物碱及其抗肿瘤活性

 目的研究海洋来源真菌萨氏曲霉(Aspergillus sydowi)PFW-13发酵产物中的抗肿瘤活性次级代谢产物。方法采用活性追踪的方法、利用色谱手段分离获得单体化合物,根据波谱分析及其理化性质确定其结构,利用SRB法评价单体化合物的细胞毒活性。结果获得6个吲哚-喹唑啉类生物碱,其结构分别鉴定为fumiquinazolines A(1)、fumiquinazolines C(2)、fu-miquinazolines D(3)、fumiquinazolines F(4)、fumiquinazolines G(5)、fumiquinazolines J(6),其中化合物6为新天然产物。化合物2和6对肿瘤细胞tsFT210、A549、BEL-7402、HL60和P388的半数抑制浓度(IC₅₀)在1×10^-5～1×10^-4mol·L^-1之间。结论以上化合物均为首次从该种真菌中分离得到。     

Polycitone B and prepolycitrin A: two novel alkaloids from the marine ascidian Polycitor africanus

Two novel compounds, polycitone B (4) and prepolycitrin A (3), were isolated from the marine ascidian Polycitor africanus. The structures of these new dibromotyrosine metabolites were established mainly on the basis of NMR spectroscopic data. Isolation of compound 3 supports the earlier suggestion that it is the bioprecursor of polycitrin A (2).     

Novel chromone derivatives from the fungus Aspergillus versicolor isolated from the marine sponge Xestospongia exigua

From the marine sponge Xestospongia exigua collected in Indonesia the fungus Aspergillus versicolor was isolated. Following cultivation in a seawater-based medium seven new angular tricyclic chromone derivatives (1-7) were obtained from the mycelia and culture filtrate. Compounds 2-7 contain an additional dihydropyran ring system which is replaced by a pyridine ring in 1. The structures of the new natural products were established on the basis of extensive one- and two-dimensional NMR spectroscopic studies (1H, 13C, COSY, HMQC, HMBC, NOE difference spectra) as well as on mass spectral analysis.     

Apakaochtodenes A and B: two tetrahalogenated monoterpenes from the red marine alga Portieria hornemannii.

The structure of apakaochtodene A, the minor isomer of two tetrahalogenated ochtodene monoterpenes, isolated from the red marine alga Portieria hornemannii (Lyngbye) Silva has been identified as 6(S)-bromo-1,4(S),8(R)-trichloro-2(Z)-ochtodene (1) by NMR spectral and X-ray crystallographic analysis. Its geometrical isomer, apakaochtodene B (2), which could not be separated from 1 and thus characterized as a 95:5 mixture of 2:1 had (1)H and (13)C NMR spectral characteristics similar to previously known ochtodene (3) and the related tetrahalogenated monoterpene 4.     

Dantaxusins A and B, two new taxoids from Taxus yunnanensis

Two new taxane diterpenes, dantaxusin A [5 alpha-cinnamoyloxy-2 alpha,7 beta,13 alpha-triacetoxy-2(3-->20)abeo-taxa-4(20),11-diene-9,10-dione (1)] and dantaxusin B [5 alpha-cinnamoyloxy-9 alpha-hydroxy-10 beta,13 alpha-diacetoxytaxa-4(20),11-diene (2)], were isolated from an ethanol extract of the aerial parts of Taxus yunnanensis along with taxuspine B, 2-deacetoxytaxinine J, taxuyunnanine C, taxinine B, taxuspine C, and taxinine NN-4. The structures of 1 and 2 were established on the basis of 1D and 2D NMR and HRMS spectroscopic methods.     

Cernuosides A and B, two sucrase inhibitors from Pulsatilla cernua

Two oleanane-type oligoglycosides, cernuosides A (1) and B (2), were isolated from the roots of Pulsatilla cernua (Ranunculaceae). Structure elucidation was accomplished by 1D and 2D NMR (DQF-COSY, TOCSY, HMQC, HMBC, and ROESY) methods, FABMS, and hydrolysis. Both compounds showed moderate activity against sucrase.     

Auranticins A and B: two new depsidones from a mangrove isolate of the fungus Preussia aurantiaca

Auranticins A and B, two new antimicrobial depsidones, have been obtained from a mangrove isolate of the fungus Preussia aurantiaca. The structures were determined through analysis of selective INEPT, decoupling, COSY, and NOESY experiments.     

Lorneamides A and B: two new aromatic amides from a southern Australian marine actinomycete

A marine actinomycete (MST-MA190) isolated from a sample of beach sand collected near Lorne on the southwest coast of Victoria, Australia, has yielded two new aromatic amides, lorneamide A (1) and lorneamide B (2). The lorneamides belong to a novel class of tri-alkyl-substituted benzenes, and their structures were determined by spectroscopic methods.     

Kalopanaxsaponins A and B isolated from Kalopanax pictus ameliorate memory deficits in mice

The stem-bark of Kalopanax pictus (KP, family Araliaceae), which contains triterpenoid saponins, has been shown to exhibit anticarcinogenic, antiinflammatory, antirheumatoid and antidiabetic activities. In a preliminary study, a KP methanol extract demonstrated acetylcholinesterase activity in vitro and memory enhancement in scopolamine-treated mice. Therefore, we isolated acetylcholinesterase inhibitors, kalopanaxsaponins A and B, from a KP butanol (BuOH) fraction, measured acetylcholinesterase activity in vitro, and investigated their memory-enhancing effects in a passive avoidance test, Y-maze test and Morris water maze test. These constituents inhibited acetylcholinesterase activity and significantly reversed scopolamine-induced deficits. They also increased brain-derived neurotrophic factor (BDNF) and phosphorylated cAMP response element binding (p-CREB) protein expression but reduced TNF-α increased by scopolamine. Based on these findings, kalopanaxsaponins A and B may ameliorate memory deficits by inhibiting acetylcholinesterase activity and inducing BDNF and p-CREB expression.     

Flavimycins A and B, dimeric 1,3-dihydroisobenzofurans with peptide deformylase inhibitory activity from Aspergillus flavipes

Flavimycins A (1) and B (2), novel dimeric 1,3-dihydroisobenzofurans, were isolated as inhibitors of peptide deformylase from cultures of Aspergillus flavipes. Their chemical structures were established by NMR and MS data analysis. Compounds 1 and 2 exist as epimeric mixtures at C-1 through fast hemiacetal-aldehyde tautomerism. Compounds 1 and 2 inhibited Staphylococcus aureus peptide deformylase with IC?? values of 35.8 and 100.1 μM, respectively. Consistent with their PDF inhibition, 1 showed two times stronger antibacterial activity than 2 on S. aureus including MRSA, with MIC values of 32-64 μg/mL.     

Roxburghiadiol A and roxburghiadiol B, two 14 alpha-methylsterols from Aglaia roxburghiana

Two new 14 alpha-methylsterols, roxburghiadiol A and roxburghiadiol B, were isolated from the leaves and fruits of Aglaia roxburghiana. Previously their structures were tentatively assigned as 4-bisnormethyl-24-methylene-cycloarta-3 beta, 7 alpha-diol and 4-bisnormethyl-24-methylene-cycloarta-3 beta, 6 alpha-diol, respectively. A reinvestigation using 2D-nmr technique has confirmed the structure 2 for roxburghiadiol B as previously reported, and roxburghiadiol A is now found to be the corresponding 6 beta epimer 1.     

Microsphaerones A and B,two novel gamma-pyrone derivatives from the sponge-derived fungus Microsphaeropsis sp

Two new metabolites, microsphaerones A (1) and B (2), were identified from the EtOAc extract of the culture of an undescribed fungus of the genus Microsphaeropsis, isolated from the Mediterranean sponge Aplysina aerophoba. Compounds 1 and 2 represent the first examples of gamma-pyrone derivatives of the fungal genus Microsphaeropsis. The structures of the compounds were elucidated on the basis of comprehensive spectral analysis ((1)H, (13)C, (1)H-(1)H COSY, HMQC, and HMBC NMR, as well as low- and high-resolution ESI and EIMS experiments). The (S)-2-methylsuccinic acid moiety present in 1 was established by GC-MS analysis of a hydrolysis product.     

Haligramides A and B, two new cytotoxic hexapeptides from the marine sponge Haliclona nigra

Bioassay-guided fractionation of a cytotoxic aqueous extract of the sponge Haliclona nigra provided two new cyclic hexapeptides, haligramides A (1) and B (2), in addition to the known peptide, waiakeamide (3). The structures of peptides 1 and 2 were elucidated by extensive NMR analyses and by comparison of their spectral data with those of waiakeamide (3). The identity of haligramide A (1) was confirmed by its oxidative conversion to waiakeamide (3). Further structural confirmation was provided by oxidation of peptides 1, 2, and 3 to the common bis-sulfone derivative 4.