Biotransformation of l‐menthol by twelve isolates of soil‐borne plant pathogenic fungi (Rhizoctonia solani) and classification of fungi

The microbial transformation of l‐menthol ( 1 ) was investigated by using 12 isolates of soil‐borne plant pathogenic fungi, Rhizoctonia solani (AG‐1‐IA Rs24, Joichi‐2, RRG97‐1; AG‐1‐IB TR22, R147, 110.4; AG‐1‐IC F‐1, F‐4, P‐1; AG‐1‐ID RCP‐1, RCP‐3, and RCP‐7) as a biocatalyst. Rhizoctonia solani F‐1, F‐4 and P‐1 showed 89.7–99.9% yields of converted product from 1 , RCP‐1, RCP‐3, and RCP‐7 26.0–26.9% and the other isolates 0.1–12.0%. In the cases of F‐1, F‐4 and P‐1, substrate 1 was converted to (?)‐(1S,3R,4S,6S)‐6‐hydroxymenthol ( 2 ), (?)‐(1S,3R,4S)‐1‐hydroxymenthol ( 3 ) and (+)‐(1S,3R,4R,6S)‐6,8‐dihydroxymenthol ( 4 ), which was a new compound. Substrate 1 was converted to 2 and/or 3 by RRG97‐1, 110.4, RCP‐1, RCP‐3 and RCP‐7. The structures of the metabolic products were elucidated on the basis of their spectral data. In addition, metabolic pathways of the biotransformation of 1 by Rhizoctonia solani are discussed. Finally, from the main component analysis and the differences in the yields of converted product from 1 , the 12 isolates of Rhizoctonia solani were divided into three groups based on an analysis of the metabolites. Copyright © 2003 Society of Chemical Industry     

Biotransformation of three aromadendrane‐type sesquiterpenoids by Aspergillus wentii

BACKGROUND: The biotransformation of sesquiterpenoids, which are a large class of naturally occurring compounds, using microorganisms as a biocatalyst to produce useful novel organic compounds was investigated. The biotransformation of sesquiterpenoids, (+)‐aromadendrene ( 1 ), (−)‐alloaromadendrene ( 2 ) and (+)‐ledene ( 3 ) has been investigated using Aspergillus wentii as a biocatalyst. Results: Compound 1 was converted to (−)‐(10S,11S)‐10,13,14‐trihydroxyaromadendrane ( 4 ). Compound 2 was converted to (+)‐(1S,11S)‐1,13‐dihydroxyaromadendrene ( 5 ) and (−)‐5,11‐epoxycadin‐1(10)‐en‐14‐ol ( 6 ). Compound 3 was converted to compound 6 , (+)‐(10R,11S)‐10,13‐dihydroxyaromadendr‐1‐ene ( 7 ) and (+)‐(10S,11S)‐10,13‐dihydroxyaromadendr‐1‐ene ( 8 ). The structure of the metabolic products has been elucidated on the basis of their spectral data. CONCLUSION: Compound 1 gave only one product that was hydroxylated at C‐10, C‐13 and C‐14. By contrast, compounds 2 and 3 gave a number of products, one of which was common. The differences in oxidation of 1–3 are due to the configuration of the C‐1 position. Compounds 4–8 were new compounds. Copyright © 2008 Society of Chemical Industry     

Aplysia sea hare assimilation of secondary metabolites from brown seaweed,Stypopodium zonale

JuvenileAplysia dactylomela were found feeding in abundance on the tropical brown algaStypopodium zonale, a seaweed previously shown to contain numerous unique terpene-quinone natural products. Lipid extracts of these herbivorous mollusks were shown by TLC and HPLC-NMR analyses to contain appreciable quantities of twoS. zonale metabolites as well as one new but closely related compound. Spectroscopic analyses of the new compound in concert with functional group modifications identified this new compound as 3-keto epitaondiol. A careful analysis of the seaweed extract failed to locate this ketone, and thus, it most likely represents anAplysia-biotransformed compound. This is the first clear reported observation of metabolite transfer between an alga of the phylum Phaeophyta and a sea hare.     

酶反应产物中人参稀有皂苷F2与C-Mc的分离

原人参二醇类皂苷混合物经人参皂苷酶生物转化后可生成F2、C-Mc等7~10种稀有人参皂苷。天然人参中不含人参皂苷C-Mc,且F2的含量极低。在生物转化所得的人参二醇类皂苷酶反应产物中,分离纯化得到稀有人参皂苷F2与C-Mc,并进行HPLC检测。反应后得到粗产品40g,经脱糖脱色和硅胶柱分离后,成功得到稀有人参皂苷F23.49g,纯度为98.2%,得率8.72%;得到C-Mc 0.70g,纯度为82.2%,得率为1.80%。成功分离出了F2和C-Mc制品,建立了初步的分离制备方法。     

人参皂苷生物转化及固体发酵工艺研究进展

研究表明,人参皂苷在体外可以转化成多种稀有皂苷,它们是在生物体内发挥药理活性的关键物质。微生物转化法及固体发酵技术是工业化生产稀有人参皂苷的基础。文中针对皂苷生物转化研究概况进行综述,探讨了固体发酵工艺条件,并对目前人参皂苷生物转化研究中存在的问题及今后的主要发展方向进行了展望。      

Hydroxylation of Progesterone and Its Derivatives by the Entomopathogenic Strain Isaria farinosa KCh KW1.1

Progesterone biotransformation is worth studying because of the high industrial value of its derivatives. This study investigated the catalytic ability of the entomopathogenic filamentous fungus strain Isaria farinosa KCh KW1.1 to transform progesterone derivatives: 11α-hydroxyprogesterone, 17α-hydroxyprogesterone, 16α,17α-epoxyprogesterone and pregnenolone. In the culture of Isaria farinosa KCh KW1.1, 11α-hydroxyprogesterone was effectively transformed into only one product: 6β,11α-dihydroxyprogesterone. Transformation of 17α-hydroxyprogesterone gave three hydroxy derivatives: 6β,17α-dihydroxyprogesterone, 12β,17α-dihydroxyprogesterone and 6β,12β,17α-trihydroxyprogesterone. Two products: 6β-hydroxy-16α,17α-epoxyprogesterone and 6β,11α-dihydroxy-16α,17α-epoxyprogesterone, were obtained from the 16α,17α-epoxyprogesterone transformation. We isolated two compounds from the biotransformation medium with pregnenolone: 11α-hydroxy-7-oxopregnenolone and 5α,6α-epoxy-3β,11α-dihydroxypregnan-7,20-dione. In this study, we observed only mono- and dihydroxy derivatives of the tested substrates, and the number of obtained products for each biotransformation did not exceed three.     

D-阿洛酮糖酶法生产的研究进展

稀有单糖D-阿洛酮糖是D-果糖的C-3差向异构体,主要通过D-塔格糖3-差向异构酶或D-阿洛酮糖-3-差向异构酶对D-果糖进行异构化获得。D-阿洛酮糖不仅可以作为食品添加剂和膳食补充剂,而且具有改善胰岛素抵抗、增强抗氧化和降血糖控制等多种生理功能。因此,D-阿洛酮糖作为传统高能量糖如蔗糖、果糖等的健康替代品,具有重要的研究价值。作者综述了D-阿洛酮糖的理化性质、来源、体内代谢、生理功能、应用和最新生产技术,讨论了D-阿洛酮糖生产中存在的问题及解决方案。针对低废物生成、低能耗、高糖产量等特点,提出了一种绿色、可循环利用的D-阿洛酮糖生产工艺技术。     

Effect of lactulose on biotransformation of isoflavone glycosides to aglycones in soymilk by lactobacilli

ABSTRACT:  Lactobacillus acidophilus 4461, L. acidophilus 4962, L. casei 290, and L. casei 2607 were used to hydrolyze isoflavone glycosides (IG) to biologically active forms—isoflavone aglycones (IA)—in soymilk (SM) prepared from soy protein isolate (SPI) and soymilk supplemented with 0.5% (w/v) of lactulose (SML). L. acidophilus 4461 utilized the highest level of lactulose (3.01 mg/mL) and L. acidophilus 4962 utilized the least (0.86 mg/mL) at 24 h of incubation. The pH values decreased to 4.00 to 5.00 in SML, while they remained relatively high (6.15 to 6.36) in SM. Supplementation with lactulose significantly ( P < 0.05) enhanced the viable counts of all the 4 Lactobacillus strains. At the end of incubation, the viable counts of Lactobacillus ranged from 8.08 to 8.25 log CFU/mL in SML compared to 6.99 to 7.11 log CFU/mL in SM. Supplementation with lactulose increased the biotransformation of IG to IA after 6 h of incubation. The presence of lactulose in the medium enhanced the biotransformation level of IG to IA by Lactobacillus up to 21.9%. The hydrolysis level of malonyl genistin and acetyl genistin in SML was much higher than in SM by all the 4 probiotic organisms. The biotransformation of IG to IA occurred rapidly during the 1st 12 h of incubation in both SML and SM. Among the 4 Lactobacillus strains, L. acidophilus 4461 biotransformed the highest level (88.8%) of IG to IA in SML compared to 68.2% in SM after 24 h of incubation.     

采用生物转化技术富集大豆制品γ-氨基丁酸研究进展

大豆中含有多种活性成分,具有很高的营养价值及保健功能,开发富含γ-氨基丁酸(GABA)的功能性大豆食品前景广阔。文中综述了大豆富集GABA的方法、途径及采用生物转化技术富集大豆GABA的最新研究进展。     

大豆乳清废水的回收利用研究进展

大豆乳清废水（SWW）是豆腐和大豆分离蛋白生产过程产生的废水。该废水排放量大,且富含大豆乳清蛋白、低聚糖和大豆异黄酮等有机物。目前,大部分企业将该废水排放至污水处理厂进行生化处理,不仅造成豆腐和大豆分离蛋白生产成本的增加,还导致大量有机物的流失。因此,资源化大豆乳清废水成为企业亟待解决的难题。鉴于此,本文从回收大豆乳清废水中的活性成分和生物转化大豆乳清废水两个角度,综述了近年来大豆乳清废水资源化的相关研究报道,并指出了两种策略的优缺点。研究发现,大部分大豆乳清废水资源化方法尚处于实验阶段,仅在废水中大豆乳清蛋白的回收并用于动物饲料与生物转化为沼气两个方面实现了工业化生产。针对上述现状,提出在未来应从以下三个方面进行研究以促进大豆乳清废水资源化的大规模资源化:降低大豆乳清废水中活性成分的分离成本并提高其利用价值;提高大豆乳清废水生物转化效率、转化率和产品附加值;对资源化方法进行经济效益核算,评估其工业化的可能性。