Microbial conversion of ruscogenin by Gliocladium deliquescens NRRL1086: Glycosylation at C-1

Applied Microbiology and Biotechnology

Volumn 86, Issue 2, 2010, Pages 491-497

  Chen, Nai Dong ^a   Zhang, Jian ^a   Liu, Ji Hua ^a   Yu, Bo Yang ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Biotransformation; Gliocladium deliquescens NRRL1086; Microbial glycosylation; Ruscogenin

Indexed keywords

BIOTRANSFORMATION; GLUCOPYRANOSIDE; GLYCOSIDASE INHIBITORS; GLYCOSYL TRANSFERASE; GLYCOSYLATED PRODUCTS; MICROBIAL CONVERSIONS; MICROBIAL TRANSFORMATION; SODIUM DODECYL SULFATE; STEROIDAL SAPONINS;

GLYCOSYLATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE; SODIUM; SODIUM SULFATE; SUGARS;

ESTERIFICATION;

AGLYCONE; IMIDAZOLE; RUSCOGENIN; UNCLASSIFIED DRUG;

BIOTRANSFORMATION; FUNGUS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL ACTIVITY; NUCLEAR MAGNETIC RESONANCE; POLYSACCHARIDE; STEROID;

ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; GLIOCLADIUM; GLIOCLADIUM DELIQUESCENS; GLYCOSYLATION; INFRARED SPECTROMETRY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

CARBON; GLIOCLADIUM; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; SPIROSTANS; STEREOISOMERISM;

GLIOCLADIUM DELIQUESCENS;

EID: 77249170200     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-009-2315-y     Document Type: Article

References (39)

1. E Bouskela FZ Cyrino G Marcelon 1994 Possible mechanisms for the inhibitory effect of Ruscus extract on increased microvascular permeability induced by histamine in hamster cheek pouch J Cardiol Pharm 24 281 285 1:STN:280:DyaK2M%2FlslWgtw%3D%3D
2. C Capra 1972 Pharmacology and toxicology of some components of Ruscus aculeatus L Fitoterapia 43 99 113 1:CAS:528:DyaE3sXltlejsLY%3D
3. LC Chang TR Tsai JJ Wang 1998 The rhamnose moiety of solamargine plays a crucial role in triggering cell death by apoptosis Biochem Biophys Res Commun 242 21 25 10.1006/bbrc.1997.7903 1:CAS:528:DyaK1cXjtl2quw%3D%3D (Pubitemid 28412370)
4. Charney W, Herzog HL (1967) Microbial transformations of steroids. Academic Press, Inc., New York
5. X Chen J Zhang JH Liu BY Yu 2008 Biotransformation of p-, m-, and o-hydroxybenzoic acids by Panax ginseng hairy root cultures J Mol Catal, B Enzym 54 72 75 10.1016/j.molcatb.2007.12.015 1:CAS:528:DC%2BD1cXovF2htrw%3D
6. HD Chludil AM Seldes MS Maier 2002 Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: structure-activity correlations J Nat Prod 65 153 157 10.1021/np010332x 1:CAS:528:DC%2BD38XhsVWltQ%3D%3D (Pubitemid 34171173)
7. E Cundliffee 1992 Glycosylation of macrolide antibiotics in extracts of Streptomyces lividans Antimicrob Agents Chemother 36 348 352
8. RM Facino M Carini R Stefani G Aldini L Saibene 1995 Antielastase and anti-hyaluronidase activities of saponins and sapogenins from Hedera helix, Aesculus hippocastanum, and Ruscus aculeatus: factors contributing to their efficacy in the treatment of venous insufficiency Arch Pharm 328 720 724 10.1002/ardp.19953281006 1:CAS:528:DyaK2MXpsVGrtb4%3D
9. WS Hays DJ Vanderjagt B Bose AS Serianni RH Glew 1998 Catalytic mechanism and specificity for hydrolysis and transglycosylation reactions of cytosolic β-glucosidase from guinea pig liver J Biol Chem 273 34941 34948 10.1074/jbc.273.52.34941 1:CAS:528:DyaK1MXisFWqug%3D%3D (Pubitemid 29028191)
10. M Hosny K Dhar JP Rosazza 2001 Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus J Nat Prod 64 462 465 10.1021/np000457m 1:CAS:528:DC%2BD3MXit1Gjtb4%3D (Pubitemid 32423871)
11. K Hu XS Yao 2002 The cytotoxicity of protoneodioscin(NSC-698789), a furostanol saponin from the rhizomes of Dioscorea collettii var.hypoglauca, against human cancer cells in vitro Phytomedicine 9 560 565 10.1078/ 09447110260573218 1:CAS:528:DC%2BD38XovFKmu7g%3D
12. ARS Ibrahim AM Galal JS Mossa FS Feraly 1997 Glucose-conjugation of the flavones of Psiadia Arabica by Cunninghamella elegans Phytochemistry 46 1193 1195 1:CAS:528:DyaK1cXhs1ylug%3D%3D
13. Iizuka H, Naito A (1981) Microbial transformations of steroids and alkaloids, 2nd edn. University Park Press, Baltimore
14. KM Koeller CH Wong 2000 Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies Chem Rev 100 4465 4493 10.1021/cr990297n 1:CAS:528:DC%2BD3cXmvFGiu7Y%3D (Pubitemid 32090356)
15. JP Kou Y Sun YW Lin ZH Cheng W Zheng BY Yu Q Xu 2005 Antiinflammatory activities of aqueous extract from Radix Ophiopogon japonicus and its two constituents Biol Pharm Bull 28 1234 1238 10.1248/bpb.28.1234 1:CAS:528:DC%2BD2MXpsFahsrk%3D (Pubitemid 41327593)
16. JP Kou YQ Tian YK Tang J Yan BY Yu 2006 Antithrombotic activities of aqueous extract from Radix Ophiopogon japonicus and its two constituents Biol Pharm Bull 29 1267 1270 10.1248/bpb.29.1267 1:CAS:528:DC%2BD28XnslOmu7Y%3D (Pubitemid 43845497)
17. JP Kou L Ma BY Yu 2007 Possible mechanism of anti-adhesive activity of ruscogenin, a major sapogenin from Radix Ophiopogonis japonici Chin J Pharmacol Toxicol 21 323 324
18. KR Lee N Kozukue JS Han 2004 Glycoalkaloids and metabolites inhibit the growth of Human Colon (HT29) and Liver (HepG2) cancer cells J Agric Food Chem 52 2833 2389
19. W Li K Koike Y Asada T Yoshikawa T Nikaido 2002 Biotransformation of umbelliferone by Panax ginseng root cultures Tetrahedron Lett 43 5633 5635 10.1016/S0040-4039(02)01138-3 1:CAS:528:DC%2BD38XlsVels7Y%3D (Pubitemid 34786528)
20. MZ Liu B Yu HZ Hui 1998 First Total synthesis of 25(R)-ruseogenin-l-yl[3- D-xylopyranosyl-(1∈→∈3)-[3-D-glucopyranosyl- (1∈→∈2)]-[3-D-fucopyranoside], an ophiopogonis saponin from the Tuber of Liriope muscari (Decne.) Tetrahedron Lett 39 415 418 10.1016/S0040-4039(97)10536-6 1:CAS:528:DyaK1cXltVSlsw%3D%3D (Pubitemid 28018261)
21. L Ma JP Kou Y Huang BY Yu 2006 Effects of ruscogenin on adhesion of HL-60 cells to ECV304 cells Chin Pharmacol Bull 22 706 709 1:CAS:528: DC%2BD2sXptVClur4%3D
22. Y Mimaki O Nakamura Y Sashida 1994 Steroidal saponins from the bulbs of Lilium longiflorum and their antitumour-promoter activity Phytochemistry 37 227 232 10.1016/0031-9422(94)85030-5 1:CAS:528:DyaK2MXhsleqtrw%3D (Pubitemid 2148870)
23. Y Mimaki A Yokosuka M Kuroda Y Sashida 2001 Cytotoxic activities and structure-cytotoxic relationships of steroidal saponins Biol Pharm Bull 24 1286 1289 10.1248/bpb.24.1286 1:CAS:528:DC%2BD3MXotFansro%3D (Pubitemid 33049106)
24. SK Ming GC Daniel DA Alexander CA Joyce JH Coats VP Marshall 1989 Microbial glycosylation of erythromycin A Antimicrob Agents Chemother 33 2089 2091
25. S Moalic B Liagre C Corbiere 2001 A plant steroid, diosgenin, induces apoptosis, cell cycle arrest and COX activity in osteosarcoma cells FEBS Lett 506 225 230 10.1016/S0014-5793(01)02924-6 1:CAS:528:DC%2BD3MXnsF2gu74%3D (Pubitemid 32964818)
26. BD MyszkaH M Najder W Kaca 2003 Synthesis and induction of apoptosis in B cell chronic leukemia by diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride and its derivatives Carbohydr Res 338 133 141 10.1016/S0008- 6215(02)00407-X (Pubitemid 36078334)
27. F Rantwijk MW Oosterom RA Sheldon 1999 Glycosidase-catalysed synthesis of alkyl glycosides J Mol Catal, B Enzym 6 511 532 10.1016/S1381-1177(99)00042-9 (Pubitemid 29232612)
28. KV Rao NT Weisner 1981 Microbial transformation of quercetin by Bacillus cereus Appl Environ Microbiol 42 450 452 1:CAS:528:DyaL3MXlsVKrsbY%3D
29. GE Ritchie BE Moffatt RB Sim BP Morgan RA Dwek PM Rudd 2002 Glycosylation and the complement system Chem Rev 102 305 319 10.1021/cr990294a 1:CAS:528:DC%2BD38XotVyqtA%3D%3D (Pubitemid 35377618)
30. J Sasaki K Mizoue S Morimoto S Omura 1996 Microbial glycosylation of macrolide antibiotics by Streptomyces hygroscopicus ATCC31080 and distribution of a macrolide glycosyl transferase in several streptomyces strains J Antibiot 49 1110 1118 1:CAS:528:DyaK28XntlSksrk%3D
31. M Schulman P Doherty B Arison 1993 Microbial conversion of avermectins by Saccharopolyspora erythraea: glycosylation at C-4′ and C-4″ Antimicrob Agents Chemother 37 1737 1741 1:CAS:528:DyaK2cXislWguw%3D%3D (Pubitemid 23265522)
32. M Shibazaki H Yamaguchi T Sugawara K Suzuki T Yamamoto 2003 Microbial glycosylation and acetylation of brefeldin A J Biosci Bioeng 96 344 348 1:CAS:528:DC%2BD2cXhsFertg%3D%3D
33. LL Smith 1973 Microbiological reactions with steroids Spec. Period. Rep. Terpenoids Steroids 4 394 530 10.1039/9781847557032-00394
34. SG Sparg ME Light J Staden 2004 Biological activities and distribution of plant saponins J Ethnopharmacol 94 219 243 10.1016/j.jep.2004.05.016 1:CAS:528:DC%2BD2cXmvFWktrc%3D (Pubitemid 39119924)
35. HX Sun ZG Yang YP Ye 2006 Structure and biological activity of rotopanaxatriol-type saponins from the roots of Panax notoginseng Int Immunopharmaco 6 14 25 10.1016/j.intimp.2005.07.003 1:CAS:528:DC%2BD2MXht12qtLjJ (Pubitemid 41739775)
36. C Vilches C Hernandez C Mendez JA Salas 1992 Role of glycosylation and deglycosylation in biosynthesis of and resistance to oleandomycin in the producer organism, Streptomyces antibiotics J Bacteriol 174 161 165 1:CAS:528:DyaK38XotVWnug%3D%3D
37. G Yang ZM Zhang HJ Bai 2008 Biotransformation of β-amyrin acetate by Rhodobacter sphaeroides J Biosci Bioeng 105 558 561 10.1263/jbb.105.558 1:CAS:528:DC%2BD1cXpt1Wjtr8%3D (Pubitemid 351815039)
38. Yuan YJ, Ge ZQ (2004) Plant cell culture engineering. Chemical Industry Press, Beijing
39. XF Zhang Y Cui JJ Huang 2007 Immuno-stimulating properties of diosgenyl saponins isolated from Paris polyphylla Bioorg Med Chem Lett 17 2408 2413 10.1016/j.bmcl.2007.02.039 1:CAS:528:DC%2BD2sXktVentr4%3D (Pubitemid 46507798)