Production of red pigments by the insect pathogenic fungus Cordyceps unilateralis BCC 1869

Production of red pigments (naphthoquinones) by the insect pathogenic fungus Cordyceps unilateralis BCC 1869 was investigated in this study. Cultivation conditions, including temperature, intitial pH of medium, and aeration, were optimised to improve the yield of total naphthoquinones in shake-flask culture of C. unilateralis. The highest yield of total naphthoquinones (3 g L^–1) was obtained from a 28-day culture grown in potato dextrose broth with an initial pH of 7.0, at 28°C with shaking-induced aeration at 200 rpm. An extraction process for isolation of the targeted naphthoquinone, 3,5,8-trihydroxy-6-methoxy-2-(5-oxohexa-1,3-dienyl)-1,4-naphthoquinone (3,5,8-TMON), from a culture of C. unilateralis, was also developed. The yield of 3,5,8-TMON obtained was about 1.2 g L^–1 or 40% of total naphthoquinones. The stability of 3,5,8-TMON was very high, even upon exposure to strong sunlight (70,000 lx), high temperature up to 200°C, and acid and alkali solutions at concentrations of 0.1 M     

Semi-defined Medium for in vitro Cultivation of the Fastidious Insect Pathogenic Fungus Cordyceps unilateralis

Cordyceps unilateralis is a fastidious fungal pathogen affecting ants. Up to now, only the complex and expensive Grace’s insect cell culture medium has been used for in vitro cultivation (as blastospores and mycelium) of this fungus. To obtain an inexpensive and less complicated medium, the effects of carbon and nitrogen sources, salt solution and carbon-to-nitrogen (C:N) ratio on the growth of this fungus were examined. Glucose was the most important factor for blastospore formation, and yeast extract could be used as a nitrogen source for blastospore formation and mycelial growth. A suitable C:N ratio (glucose: yeast extract) was 33.3:1. As a result, a new semi-defined medium was achieved, composed of 26.68 g L⁻¹ glucose, 3.3 g L⁻¹ yeast extract and salt solution. This medium supported blastospore formation and mycelial growth of all tested C. unilateralis isolates.     

New naphthoquinones from Diospyros

7-Methyljuglone (I), isodiospyrin (II), the 2,2′-binaphthyl-1,1′-quinone (III), and a new quinone (IV), hydroxyisodiospyrin, were isolated from the     

Bioactive styryllactones,two new naphthoquinones and one new styryllactone,and other constituents from Goniothalamus scortechinii

Two new naphthoquinones, goniothalaminone A (1) and B (2), and a new styryllactone, (?)-8-epi-9-deoxygoniopypyrone acetate (12) together with one known naphthoquinone (3), one known indolequinone (4), one known 1-azaanthraquinone (5), six known styryllactones (6–11) and one known sesquiterpene (13) were isolated from the roots and leaves of Goniothalamus scortechinii. The structures of the new compounds were elucidated by spectroscopic analysis and of the known compounds by comparison of their physical, UV, IR, ¹H and ¹³C NMR data with those of published compounds. Antiplasmodial, antimycobacterial and cytotoxic activities of the styryllactones were evaluated. Compounds 6–10 exhibited cytotoxic against human cancer cell lines, KB, BC and NCI-H187 with IC₅₀ values ranging from 0.13 to 11.7 μg/ml.     

古尼虫草的生物活性物质I含肽镇痛组分的分离及性质

用理化分离分析和生物检测方法相结合,从古尼虫草(Cordyceps gunnii(Berk.)Berk.)无性型,古尼拟青霉(Paecilomyces gunnii Liang)菌丝体中初步分离纯化得到镇痛物质,该物质经氨基酸组成分析表明是一种酸性氨基酸残基高的肽类物质。经不同温度、pH及蛋白酶的稳定性试验分析观察到这种肽类物质对酸稳定、在酸性条件下抗热,对胃蛋白酶、胰蛋白酶部分敏感,对蛋白酶K不敏感。经小鼠竖尾法和大鼠攻击法测定,无吗啡类药物依赖性。     

Antimicrobial activity of naphthoquinones from Fusaria

Twenty-two naphthoquinone compounds isolated or derived synthetically from culture extracts ofFusarium solani andF. oxysporum were examined for antimicrobial activity. Fifteen exhibited antibiotic activity againstStaphylococcus aureus, and 12 were active againstStreptococcus pyogenes, but none were active at the highest rate of 128 g/ml againstEscherichia coli, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, Serratia marcescens, orPseudomonas aeruginosa. Of 8 plant pathogenic bacteria tested against 11 naphthoquinones,Corynebacterium poinsettiae was inhibited by 6 compounds, andPseudomonas viridiflava was weakly inhibited by one. Only one of a group of 6 fluorescent soil pseudomonads was inhibited by one naphthoquinone. Antifungal activity of 10 compounds against 8 fungal plant pathogens was limited to inhibition ofPhytophthora parasitica by one naphthopyran.South Atlantic, Agricultural Research Service, U.S. Department of Agriculture. Mention of a trademark or proprietary product is for identification only and does not imply a warranty or guarantee of the product by the U.S. Department of Agriculture over other products which may also be suitable.     

Cytotoxic naphthoquinones from roots of Lippia microphylla

A new prenylated naphthoquinone dimer named microphyllaquinone (1), a mixture of 6-methoxy- and 7-methoxy-naphtho[2,3-b]-furan-4,9-quinones (2a/2b) and tecomaquinone I (3), were isolated from roots of Lippia microphylla. The structures were elucidated by spectroscopic methods, including detailed 1D and 2D (COSY, NOESY, HMQC, HMBC) NMR data. Unpublished 13C NMR data of 2a and 2b are reported. The in vitro cytotoxic activity of the isolated compounds was tested against five types of tumor cells.     

Bioactive deoxypreussomerins and dimeric naphthoquinones from Diospyros ehretioides fruits: deoxypreussomerins may not be plant metabolites but may be from fungal epiphytes or endophytes

Deoxypreussomerin derivatives, palmarumycins JC1 (1) and JC2 (2), and two dimeric naphthoquinones, isodiospyrin (3) and its new derivative isodiospyrol A (4), were isolated from dried fruits of Diospyros ehretioides. Structures of the isolated compounds were elucidated by spectroscopic analyses. Palmarumycins were not found in the extract of freshly collected fruits; however, they were present in dried fruit extract. The absence of palmarumycins in fresh fruits of D. ehretioides, together with the chemotaxonomic point of view, we proposed that palmarumycins JC1 (1) and JC2 (2) are more likely to be fungal metabolites, i.e., endophytes or epiphytes. The isolation of palmarumycins 1 and 2 from dried D. ehretioides fruits could be reproducible; both plant samples collected in the years 2002 and 2004 provided the same result, and, therefore, symbiont fungal strains should be specific to the plant host, D. ehretioides, and they can grow on the fruits during drying the sample. Palmarumycin JC1 (1) did not exhibit antimalarial, antifungal, antimycobacterial, and cytotoxic activities. Palmarumycin JC2 (2) exhibited antimalarial (IC50 4.5 microg/ml), antifungal (IC50 12.5 microg/ml), antimycobacterial (MIC 6.25 microg/ml), and cytotoxic (IC50 11.0 microg/ml for NCI-H187 cell line) activities. In our bioassay systems, isodiospyrin (3) did not exhibit antimycobacterial, antifungal, antimalarial, and cytotoxic activities. Isodiospyrol A (4) exhibited antimalarial (IC50 2.7 microg/ml) and antimycobacterial (MIC 50 microg/ml) activities, but was inactive towards Candida albicans. Compound 4 also exhibited cytotoxicity against BC cells (IC50 12.3 microg/ml), but not towards KB and Vero cell lines.     

Naphthalenes and naphthoquinones from Ventilago species

Two new naphthalene derivatives and three naphthoquinones have been found in the root bark of Ventilago maderaspatana. Their structures are 2-acetyl-6,7-dimethoxy-3-methyl-1,8-methylenedioxynaphthalene (ventilaginone) and 1,3-dihydro-6,9-dihydroxy-7,8-dimethoxy-1-methylnaphtho[2,3-c]furan-3-one (ventilagol), 2(2′-acetoxypropyl)-3-hydroxy-5,7,8-trimethoxy-1,4-naphthoquinone (maderone), cordeauxione and isocordeauxione. The root bark of V. calyculata contains 2-methoxystypandrone and 1-hydroxy-6-methoxy-3-methylxanthone-8-carboxylic acid (calyxanthone).     

Cytotoxic naphthoquinones and plumbagic acid glucosides from Plumbago zeylanica

Two plumbagic acid glucosides, 3'-O-beta-glucopyranosyl plumbagic acid and 3'-O-beta-glucopyranosyl plumbagic acid methylester along with five naphthoquinones (plumbagin, chitranone, maritinone, elliptinone and isoshinanolone), and five coumarins (seselin, 5-methoxyseselin, suberosin, xanthyletin and xanthoxyletin) were isolated from the roots of Plumbago zeylanica. All coumarins were not previously found in this plant. Cytotoxicity of these compounds to various tumor cells lines was evaluated, and plumbagin significantly suppressed growth of Raji, Calu-1, HeLa, and Wish tumor cell lines.     

Unusual naphthoquinones, catechin and triterpene from Byrsonima microphylla

The new triterpene Delta1-lupenone (1), together with lupeol, beta-amyrin and betulin were isolated from the wood of Byrsonima microphylla (Malpighiaceae). The new compounds 3-hydroxy-2-methoxy-8,8,10-trimethyl-8H-antracen-1,4,5-trione (2), 3,7-dihydroxy-2-methoxy-8,8,10-trimethyl-7,8-dihydro-6H-antracen-1,4,5-trione (3), (2S*,10aR*)-2,8-dihydroxy-6-methoxy-1,1,7-trimethyl-2,3,10, 10a-tetrahydro-1H-fenantren-9-one (4) and (2S,3S)-3'-hydroxy-4',5,7-trimethoxy-flavan-3-ol (5) were also isolated through monitored TLC using the antioxidant beta-carotene reagent. The antioxidant potential of the compounds 2-5 was measured and none of them showed activity. The structures of these compounds were elucidated by chemical and spectroscopic analysis based on NMR techniques (1H, 13C NMR, COSY, nOe difference, HMQC and HMBC), UV and MS.     

生物磁效应对蛹虫草活性物质含量的影响

利用场强为0.1、0.25、0.4T恒定磁场,以流速为1 m·s^-1,分别对普通水进行9次处理,串联（SC）磁场处理3次的磁处理水,进而用于栽培蛹虫草,并研究了生物磁效应对蛹虫草虫草素、虫草酸、多糖含量及生物学转化效率的影响。结果表明,0.4T处理有利于蛹虫草虫草酸含量及生物学效率的提高,相比对照组分别提高了7.29%和15.37%;0.25T处理组有利于虫草素的积累,比对照组提高了11.31%;0.1T处理有利于多糖的积累,相比对照组提高了14.80%。方差分析表明,经不同场强处理的磁化水对蛹虫草子实体生长和活性物的代谢影响差异显著。但磁处理水对于不同物质含量的影响规律存在一定的差异性。     

Bioactive proteins from mushrooms

Mushrooms have been used as food or medicine for thousands of years. Due to low-fat content and absence of cholesterol, many mushrooms are excellent sources of protein. There are various mushroom proteins with interesting biological activities, such as lectins, fungal immunomodulatory proteins (FIP), ribosome inactivating proteins (RIP), ribonucleases, laccases, and other proteins, which have become popular sources of natural antitumor, antiviral, antimicrobial, antioxidative, and immunomodulatory agents. The aim of this review is to update the present status of bioactive proteins in mushrooms, and to discuss their biomedical potential and future prospectives.     

粘帚霉属真菌代谢物的研究进展

从化合物分类角度综述了国内外学者对粘帚霉属真菌代谢物50多个化学成分及其生物活性的研究,提出了今后可能的研究方向。     

Antiplasmodial activity of naphthoquinones and one anthraquinone from Stereospermum kunthianum

Six new partheniol metabolites were isolated from the biotransformation reaction with Mucor circinelloides ATCC 15242. These metabolites are: humula-1(10), 4, 7-trien-6alpha-ol 2, maali-3-en-8alpha-ol 3, aromadendrane-4alpha, 8alpha, 10alpha-triol 4, maaliane-4alpha, 8alpha, 9alpha-triol 5, maaliane-5alpha, 8alpha, 9alpha-triol 6, 5(9), 6-tricyclohumulane-4alpha, 8alpha, 10alpha-triol 7. The structural assignments of these metabolites were made possible by different spectroscopic means.     

STAT3 inhibitory activity of naphthoquinones isolated from Tabebuia avellanedae

The extract of Tabebuia avellanedae has been used as a folk medicine, and the various biological activities of T. avellanedae have been extensively studied. However, few studies have reported which natural products play a role in their biological effects. In this study, we evaluated representative naphthoquinones isolated from T. avellanedae and found that furanonaphthoquinones were the key structures required to exhibit STAT3 phosphorylation inhibitory activities. Our SAR analysis indicated that removal of a hydroxyl group enhanced the STAT3 phosphorylation inhibitory activity. In addition, the combined results of a mobility shift assay, SH2 domain binding assay, and docking simulation by Autodock 4.2.6 suggested that (S)-5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (1) could directly bind to the hinge region of STAT3.     

Cytotoxic naphthoquinones,molluscicidal saponins and flavonols from Diospyros zombensis

7-Methyljuglone, isodiospyrin and three glucuronides of oleanolic acid were isolated from the lipophilic and the methanol extracts, respectively, of the root bark of Diospyros zombensis. Cytotoxic activities of the naphthoquinones and strong molluscicidal activity of 3-O-[O-α-L-rhamnopyranosyl-(1 → 3)-β-D-glucuronopyranosyl]-oleanolic acid were shown. In addition hyperoside, quercitrin and quercetin-3-O-β-D-glucuronopyranoside were isolated from a methanol extract of the leaves.