沉香样品中曲霉属真菌菌株 HNWSW-20 的分离鉴定及其次生代谢产物的研究

本文采用平板分离法从沉香样品中分离得到一株真菌 HNWSW-20,从形态学和分子生物学上鉴定其为曲霉菌（Aspergillus sp.）,并利用多种色谱技术对其次生代谢产物进行分离纯化,根据波谱数据和理化性质鉴定其化合物结构为：2?,3?-dihydrosorbicillin（1）,sorbicillin（2）,2,3-二氢-2-(1-丙烯)-6,8-二甲基-7-羟基-色酮（3）,邻苯二甲酸二丁酯（4）,7-羟基-异苯并呋喃-1(3H)-酮（5）二十烷酸甲酯（6）;分别采用 Ellman 比色法和 pNPG 法测定化合物的乙酰胆碱酯酶抑制活性和 α-葡萄糖苷酶抑制活性,结果显示上述化合物 1、2、4 具有乙酰胆碱酯酶抑制活性,而化合物 1、3、5 具有 α-葡萄糖苷酶抑制活性。本文中化合物 1~2 为首次从曲霉属中分离得到,并首次报道具有乙酰胆碱酯酶和 α-葡萄糖苷酶抑制活性。     

海洋放线菌Streptomyces sp. HNWSW-49的次生代谢产物研究

对1株具有抗芒果炭疽病菌活性的海口湾海泥来源放线菌Streptomyces sp.HNWSW-49发酵液的化学成分进行研究。采用多种色谱技术对化合物进行分离纯化,以波谱数据确定化合物的结构。从来源于海口湾海泥的放线菌Streptomyces sp.HNWSW-49发酵液的乙酸乙酯提取物中分离鉴定了7个含氮化合物,分别为:环-(苯丙-丙)二肽(1),环-(亮-甘)二肽(2),环-(苯丙-缬)二肽(3),环-(羟脯-苯丙)二肽(4),N-(2-苯基)乙酰胺(5),β-腺苷(6),和2-哌啶酮(7)。所有化合物均为首次从该放线菌中分离得到,其中化合物6为首次从微生物中分离得到。      

植物次生代谢产物及其在环境胁迫中的抵御作用

次生代谢过程是植物在长期进化中对生态环境适应的结果,它在处理植物与生态环境的关系中充扮着重要的角色.文章简单阐述了植物次生代谢产物的种类,综述了植物次生产物对环境胁迫的防御作用,以期利用植物次生产物保护处于逆境中的植物.     

外源NO对人参愈伤组织次生代谢产物的影响

研究NO供体硝普钠(SNP)在光照胁迫下对人参愈伤组织细胞生长及次生代谢产物积累的影响。利用人参愈伤组织培养体系,给予光强5000 lx,每天8h的光照,通过在不同时期向培养基中添加不同浓度的SNP溶液,测定培养物次生代谢产物及酶的活性。培养基中添加了SNP,使得强光对人参愈伤组织的危害程度降低,酶的活性及次生代谢产物的积累明显增加。     

糖胶树花次生代谢产物及其抗细菌活性

采用水蒸气蒸馏法提取糖胶树花挥发油,通过气相色谱-质谱联用技术(GC-MS)对挥发油进行成分分析,采用薄层层析——生物自显影法测定糖胶树花乙酸乙酯层提取物对供试细菌的抑制活性。结果表明,糖胶树花挥发油得率为0.018%,通过GC-MS分析,从中鉴定出20个成分,占挥发油总量的97.53%,其主要成分为2-莰烯(23.30%),芳樟醇(23.09%),(-)-4-萜品醇(10.54%)。糖胶树花乙酸乙酯层提取物对大肠杆菌表现出较强的抑制活性,其次为黄瓜角斑病菌,对其他供试细菌未表现出抑制活性。     

8株具有生物活性的红树林真菌烟曲霉的分离、鉴定

对海南文昌清澜港红树林和广西北海红树林采集的植物组织和土壤样品进行真菌选择性分离,并对其发酵液进行抗金黄色葡萄球菌、抗白色念珠菌和细胞毒活性筛选。得到具有生物活性的真菌63株,通过培养特征、形态特征、ITS序列测定及其系统发育分析对菌株进行鉴定,发现其中有8株同为烟曲霉,占活性菌株的12.7%。综上表明,分离自红树林的烟曲霉部分菌株,产生了与其它生境烟曲霉菌株不一样的性质,具有了良好的生物活性。     

海洋青霉HN89菌株次生代谢产物抗菌活性的研究

海洋青霉HN89菌株次生代谢产物的抗菌活性与发酵条件对抗生素产量影响的研究结果表明:海洋青霉HN89菌株的次生代谢产物对细菌、酵母、霉菌均有抑制作用;摇瓶发酵产生抗生素(HN89A)的最佳培养基成分为:玉米淀粉20g/L,黄豆粉2g/L,K2HPO41g/L,NaCl0.5g/L,MgSO4 0.5g/L,FeSO4·7H2O0.01g/L,蛋白胨1g/L,用海水配制的海带汁(W/V,2%)1L,最佳发酵条件为28℃下振荡培养(200r/min)96~108h。合适的温度刺激能促进HN89A的合成。      

蝴蝶和蝗虫肠道共生菌次生代谢产物的分离

对分离自健康蝴蝶和蝗虫肠道的共生菌Aspergillus sp. HDf1,Aspergillus sp. HCf2和Amycolatopsis sp. HCa1发酵液的化学成分进行了研究。采用色谱技术对化合物进行分离纯化,以波谱技术确定化合物的结构,结果从蝴蝶肠道共生真菌Aspergillus sp. HDf1,蝗虫肠道共生真菌Aspergillus sp. HCf2和放线菌Amycolatopsis sp. HCa1发酵液的乙酸乙酯提取物中各分离鉴定了1个化合物,分别为N-benzoylphenylalanyl-L-phenylalaninol acetate（1）,bostrycin（2）和2-spirocyclohexyl-2,3-dihydroquinazolin-4（1H）-one（3）;以上化合物均为首次从昆虫来源的共生菌中分离得到,其中化合物3是首次从Amycolatopsis属放线菌中发现。     

放线菌次生代谢产物对不同来源大豆胞囊线虫J2毒性的研究

抗生素是控制植物病害的重要手段之一,而放线菌是抗生素的主要产生菌。针对已筛选到的5株放线菌C25-3、H-4、H-2、C44和C49,利用室内培养法对其发酵液抑制田间大豆胞囊线虫J2混合群体的活性作用进行了比较研究。结果表明：发酵液4×稀释浓度下,处理24h后,C25-3对大豆胞囊线虫J2的毒性最高,其校正死亡率达到95％左右;其他4株菌的次生代谢产物也具有一定的毒杀作用,对J2的校正死亡率均达到60％以上。5株放线菌菌株中,C25-3,H-2和C44对大豆胞囊线虫J2的毒性不因线虫的致病性和活性差异而改变,而C49和H-4表现出因线虫的致病性和活性差异而改变的特性。     

海洋共生菌Aspergillus sp.HDf2新活性次生代谢产物研究(英文)

对紫海胆共生真菌Aspergillus sp.HDf2的次生代谢产物进行分离和鉴定。采用摇瓶液体发酵,运用柱层析等方法对其发酵液成分进行分离纯化,经波谱解析和质谱分析进行结构鉴定,并运用滤纸片法对化合物进行体外抗金黄色葡萄球菌的活性测试。结果从该真菌发酵产物中鉴定出2个secospiculisporic acid新类似物,分别为secospiculisporic acid B(1)和secospiculisporic acid C(2),其中化合物1具有弱抗菌活性,抑菌直径为9.2 mm(20 mg/mL)。首次对化合物1的NMR数据进行了归属,化合物2为secospiculisporic acid类的新化合物。     

New Diterpenoids and Isocoumarin Derivatives from the Mangrove-Derived Fungus Hypoxylon sp.

Two new diterpenoids, hypoxyterpoids A (1) and B (2), and four new isocoumarin derivatives, hypoxymarins A–D (4–7), together, with seven known metabolites (3 and 8–13) were obtained from the crude extract of the mangrove-derived fungus Hypoxylon sp. The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) nuclear magnetic resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of compounds 1, 2, 4, 5, and 7 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, and the absolute configurations of C-4′ in 6 and C-9 in 7 were determined by [Rh₂(OCOCF₃)₄]-induced ECD spectra. Compound 1 showed moderate α-glucosidase inhibitory activities with IC₅₀ values of 741.5 ± 2.83 μM. Compounds 6 and 11 exhibited DPPH scavenging activities with IC₅₀ values of 15.36 ± 0.24 and 3.69 ± 0.07 μM, respectively.     

New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003

Nine new secondary metabolites, including six isocoumarin analogues, 7-hydroxyoospolactone (1), 7-methoxyoospolactone (2), 7-methoxy-9-hydroxyoospolactone (3), 10-acetoxy-9-hydroxyoospolactone (4), 6-dehydroxysescandelin (5), parapholactone (6), and three compounds with a rare skeleton of isocoumarin coupled with phenylethylamine, namely paraphamide A (12), paraphamide B (13), and paraphamide C (14), together with five known compounds, oospolactone (7), 8-O-methyloospolactone (8), 10-hydroxyoospolactone (9), 9,10-dihydroxyoospolactone (10), and oospoglycol (11), were isolated and identified from the marine-derived fungus Paraphoma sp. CUGBMF180003. Their chemical structures were determined using spectroscopic data, including HRESIMS and 1D and 2D NMR techniques. Furthermore, the stereogenic carbons in 5 and 14 were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. The carbon skeleton of 12–14 was identified as the first example of isocoumarin coupled with phenylethylamine derivatives. All of these compounds were examined for antimicrobial activities against Candida albicans and Staphylococcus aureus. Both 1 and 6 showed antibacterial activity against S. aureus with MIC values of 12.5 μg/mL.     

New Andrastin-Type Meroterpenoids from the Marine-Derived Fungus Penicillium sp.

Three new andrastin-type meroterpenoids penimeroterpenoids A–C (1–3) together with two known analogs (4 and 5) were isolated from the cultures of the marine-derived Penicillium species (sp.). The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of 1–3 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed moderate cytotoxicity against A549, HCT116, and SW480 cell lines.     

New Ophiobolins from the Deep-Sea Derived Fungus Aspergillus sp. WHU0154 and Their Anti-Inflammatory Effects

Deep-sea fungi have become a new arsenal for the discovery of leading compounds. Here five new ophiobolins 1–5, together with six known analogues 6–11, obtained from a deep-sea derived fungus WHU0154. Their structures were determined by analyses of IR, HR-ESI-MS, and NMR spectra, along with experimental and calculated electronic circular dichroism (ECD) analysis. Pharmacological studies showed that compounds 4 and 6 exhibited obvious inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine macrophage RAW264.7 cells. Mechanical study revealed that compound 6 could inhibit the inducible nitric oxide synthase (iNOS) level in LPS-stimulated RAW264.7 cells. In addition, compounds 6, 9, and 10 could significantly inhibit the expression of cyclooxygenase 2 (COX 2) in LPS-induced RAW264.7 cells. Preliminary structure-activity relationship (SAR) analyses revealed that the aldehyde group at C-21 and the α, β-unsaturated ketone functionality at A ring in ophiobolins were vital for their anti-inflammatory effects. Together, the results demonstrated that ophiobolins, especially for compound 6, exhibited strong anti-inflammatory effects and shed light on the discovery of ophiobolins as new anti-inflammatory agents.     

Three New Resveratrol Derivatives from the Mangrove Endophytic Fungus Alternaria sp.

Three new resveratrol derivatives, namely, resveratrodehydes A–C (1–3), were isolated from the mangrove endophytic fungus Alternaria sp. R6. The structures of these compounds were elucidated by analysis of their MS, 1D and 2D NMR spectroscopic data. All compounds showed broad-spectrum inhibitory activities against three human cancer cell lines including human breast MDA-MB-435, human liver HepG2, and human colon HCT-116 by MTT assay (IC₅₀ < 50 μM). Among them, compounds 1 and 2 both exhibited marked cytotoxic activities against MDA-MB-435 and HCT-116 cell lines (IC₅₀ < 10 μM). Additionally, compounds 1 and 3 showed moderate antioxidant activity by DPPH radical scavenging assay.     

Pyranodipyran Derivatives with Tyrosyl DNA Phosphodiesterase 1 Inhibitory Activities and Fluorescent Properties from Aspergillus sp. EGF 15-0-3

Four new benzodipyran racemates, namely (±)-aspergiletals A–D (3–6), representing a rare pyrano[4,3-h]chromene scaffold were isolated together with eurotiumide G (1) and eurotiumide F (2) from the soft-coral-derived fungus Aspergillus sp. EGF 15-0-3. All the corresponding optically pure enantiomers were successfully separated by a chiral HPLC column. The structures and configurations of all the compounds were elucidated based on the combination of NMR and HRESIMS data, chiral separation, single-crystal X-ray diffraction, quantum chemical ¹³C NMR, and electronic circular dichroism calculations. Meanwhile, the structure of eurotiumide G was also revised. The TDP1 inhibitor activities and photophysical properties of the obtained compounds were evaluated. In the TDP1 inhibition assay, as a result of synergy between (+)-6 and (−)-6, (±)-6 displayed strong inhibitory activity to TDP1 with IC₅₀ values of 6.50 ± 0.73 μM. All compounds had a large Stokes shift and could be utilized for elucidating the mode of bioactivities by fluorescence imaging.     

Secondary Metabolites from Marine Sponges of the Genus Oceanapia: Chemistry and Biological Activities

In this review, we summarized the distribution of the chemically investigated Oceanapia sponges, including the isolation and biological activities of their secondary metabolites, covering the literature from the first report in 1989 to July 2019. There have been 110 compounds reported during this period, including 59 alkaloids, 33 lipids, 14 sterols and 4 miscellaneous compounds. Besides their unique structures, they exhibited promising bioactivities ranging from insecticidal to antibacterial. Their complex structural characteristics and diverse biological properties have attracted a great deal of attention from chemists and pharmaceuticals seeking to perform their applications in the treatment of disease.     

Metabolites with Anti-Inflammatory Activity from the Mangrove Endophytic Fungus Diaporthe sp. QYM12

One new diterpenoid, diaporpenoid A (1), two new sesquiterpenoids, diaporpenoids B–C (2,3) and three new α-pyrone derivatives, diaporpyrones A–C (4–6) were isolated from an MeOH extract obtained from cultures of the mangrove endophytic fungus Diaporthe sp. QYM12. Their structures were elucidated by extensive analysis of spectroscopic data. The absolute configurations were determined by electronic circular dichroism (ECD) calculations and a comparison of the specific rotation. Compound 1 had an unusual 5/10/5-fused tricyclic ring system. Compounds 1 and 4 showed potent anti-inflammatory activities by inhibiting the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW264.7 cells with IC₅₀ values of 21.5 and 12.5 μM, respectively.     

Anti-Inflammatory Polyketide Derivatives from the Sponge-Derived Fungus Pestalotiopsis sp. SWMU-WZ04-2

Five undescribed polyketide derivatives, pestaloketides A–E (1–5), along with eleven known analogues (6–16), were isolated from the sponge-derived fungus Pestalotiopsis sp. Their structures, including absolute configurations, were elucidated by analyses of NMR spectroscopic HRESIMS data and electronic circular dichroism (ECD) calculations. Compounds 5, 6, 9, and 14 exhibited weak cytotoxicities against four human cancer cell lines, with IC₅₀ values ranging from 22.1 to 100 μM. Pestaloketide A (1) is an unusual polyketide, featuring a rare 5/10/5-fused ring system. Pestaloketides A (1) and B (2) exhibited moderately inhibited LPS-induced NO production activity, with IC₅₀ values of 23.6 and 14.5 μM, respectively, without cytotoxicity observed. Preliminary bioactivity evaluations and molecular docking analysis indicated that pestaloketides A (1) and B (2) had the potential to be developed into anti-inflammatory activity drug leads.