Novel ent-beyeran-19-oic acids from biotransformations of isosteviol metabolites by Mortierella isabellina

Planta Medica

Volumn 73, Issue 15, 2007, Pages 1581-1587

  Lin, Che Ling ^a,b   Lin, Shwu Jiuan ^b   Huang, Wei Jan ^b,c   Ku, Yuan Ling ^d   Tsai, Tung Hu ^a   Hsu, Feng Lin ^b  

^a NATIONAL YANG MING UNIVERSITY   (Taiwan)

^b TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^c CHANG GUNG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

^d Medical and Pharmaceutical Industry Technology and Development Center   (Taiwan)

Author keywords

ent 16 Hydroxybeyeran 19 oic acid; Hydroxylation; Isoteviol; Microbial biotransformations; Mortierella isabellina; MTT formazan exocytosis; Stevioside

Indexed keywords

14BETA,16BETA DIHYDROXYBEYERAN 19 OIC ACID; 16BETA HYDROXYBEYERAN 19 OIC ACID; 7ALPHA,12BETA DIHYDROXY 16 OXOBEYERAN 19 OIC ACID; 7ALPHA,16BETA DIHYDROXYBEYERAN 19 OIC ACID; DITERPENE; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS NIGER; BACILLUS MEGATERIUM; BACTERIAL METABOLISM; BIOASSAY; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL ASSAY; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG TRANSFORMATION; EXOCYTOSIS; FUNGAL METABOLISM; FUNGUS; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; HYDROXYLATION; LIQUID CHROMATOGRAPHY; LIVER CELL CULTURE; MASS SPECTROMETRY; METABOLITE; MICROBIAL METABOLISM; MORTIERELLA ISABELLINA; NONHUMAN; OXIDATION; STRUCTURE ACTIVITY RELATION;

AGARICALES; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIOTRANSFORMATION; CELL LINE, TUMOR; CELL SURVIVAL; CHROMATOGRAPHY, LIQUID; DITERPENES; DITERPENES, KAURANE; GLUCOSIDES; HUMANS; MASS SPECTROMETRY;

UMBELOPSIS ISABELLINA;

EID: 38149053013     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-993756     Document Type: Article

References (19)

1. Oliveira BH, Santos MC, Leal PC. Biotransformation of the diterpenoid, isosteviol, by Aspergillus niger, Penicillium chrysogenum and Rhizopus arrhizus. Phytochemistry 1999; 51: 737-41.
2. Hanson JR. The microbiological transformation of diterpenoids. Nat Prod Rep 1992; 9: 139-52.
3. Atta-ur-Rahman , Farooq A, Choudhary MI. Microbial transformation of sclareolide. J Nat Prod 1997; 60: 1038-40.
4. Yang LM, Hsu FL, Cheng JT, Chang CH, Liu PC, Lin SJ. Hydroxylation and glucosidation of ent-16β-hydroxybeyeran-19-oic acid by Bacillus megaterium and Aspergillus niger. Planta Med 2004; 70: 359-6.
5. Hou CC. Studies on the active compounds from Bacopa monniera, Lactuca indica, and Stevia rebaudiana. [dissertation]. Taipei: Taipei Medical University; 2003.
6. Lee CN, Wong KL, Liu JC, Chen YJ, Cheng JT, Chan P. Inhibitory effect of stevioside on calcium influx to produce antihypertension. Planta Med 2001; 67: 796-9.
7. Ali HS, Hanson JR, de Oliveira BH. The biotransformation of some ent-beyeran-19-oic acids by Gibberella fujikuroi. Phytochemistry 1992; 31: 507-10.
8. Abourashed EA, Clark AM, Hufford CD. Microbial models of mammalian metabolism of xenobiotics: An updated review. Curr Med Chem 1999; 6: 359-74.
9. Diana J, Govaerts C, Hoogmartens J, VanSchepdael A, Adams E. Charaterization of impurities in dirithromycin by liquid chromatography/ion trap mass spectrometry. J Chromatogr A 2006; 1125: 52-66.
10. Wan ECH, Yu JZ. Determination of sugar compounds in atmospheric aerosols by liquid chromatography combined with positive electrospray ionization mass spectrometry. J Chromatogr A 2006; 1107: 175-81.
11. Hsu FL, Hou CC, Yang LM. Microbial transformations of isosteviol. J Nat Prod 2002; 65: 273-7.
12. Chang CH, Lin SJ. Microbial transformations of steviol and ent-16β-hydroxybeyeran-19-oic acid. [dissertation]. Taipei: Taipei Medical University; 2002.
13. Huang SX, Zhao QS, Xu G, Wiao WL, Li RT, Hou AJ et al. ent-Kaurane diterpenoids from Isodon albopilosus. J Nat Prod 2005; 68: 1758-62.
14. Xian M, Kang Y, Yan J, Liu J, Bi Y, Zhen K. Production of linolenic acid by Mortierella isabellina grown on octadecanol. Curr Microbiol 2002; 44: 141-4.
15. Liu Y, Peterson DA, Schubert D. Amyloid β peptide alters intracellular vesicle trafficking and cholesterol homeostasis. Proc Natl Acad Sci USA 1998; 95: 13266-71.
16. Slater TF, Sawyer B, Strauli U. Studies on succinate-tetrazolium reductase system III: points of coupling of four tetrazolium salts. Biochim Biophys Acta 1963; 77: 383-93.
17. Liu Y, Peterson DA, Kimura H, Schubert D. Mechanism of cellular 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction. J Neurochem 1997; 69: 581-93.
18. Hertel C, Hauser N, Schubenel R, Seilheimer B, Kemp J. A β-amyloid-induced cell toxicity: enhancement of 3-(4,5-dimethylthiazol-2- yl)-2,5-diphenyltetrazolium bromide-dependent cell death. J Neurochem 1996; 67: 272-6.
19. Abe K, Saito H. Cholesterol does not affect the toxicity of amyloid β fragment but mimics it effect on MTT formazan exocytosis in cultured rat hippocampal neurons. Neurosci Res 1999; 35: 165-74.