Suppr超能文献

巨大芽孢杆菌ATCC 13368对抗黑色素瘤药物桦木酸的生物转化

Biotransformation of the antimelanoma agent betulinic acid by Bacillus megaterium ATCC 13368.

作者信息

Chatterjee P, Kouzi S A, Pezzuto J M, Hamann M T

机构信息

Department of Basic Pharmaceutical Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, Louisiana 71209, USA.

出版信息

Appl Environ Microbiol. 2000 Sep;66(9):3850-5. doi: 10.1128/AEM.66.9.3850-3855.2000.

Abstract

Microbial transformation of the antimelanoma agent betulinic acid was studied. The main objective of this study was to utilize microorganisms as in vitro models to predict and prepare potential mammalian metabolites of this compound. Preparative-scale biotransformation with resting-cell suspensions of Bacillus megaterium ATCC 13368 resulted in the production of four metabolites, which were identified as 3-oxo-lup-20(29)-en-28-oic acid, 3-oxo-11alpha-hydroxy-lup-20(29)-en-28-oic acid, 1beta-hydroxy-3-oxo-lup-20(29)-en-28-oic acid, and 3beta,7beta, 15alpha-trihydroxy-lup-20(29)-en-28-oic acid based on nuclear magnetic resonance and high-resolution mass spectral analyses. In addition, the antimelanoma activities of these metabolites were evaluated with two human melanoma cell lines, Mel-1 (lymph node) and Mel-2 (pleural fluid).

摘要

研究了抗黑素瘤药物桦木酸的微生物转化。本研究的主要目的是利用微生物作为体外模型来预测和制备该化合物潜在的哺乳动物代谢产物。用巨大芽孢杆菌ATCC 13368的静息细胞悬浮液进行制备规模的生物转化,产生了四种代谢产物,基于核磁共振和高分辨率质谱分析,它们被鉴定为3-氧代羽扇-20(29)-烯-28-酸、3-氧代-11α-羟基羽扇-20(29)-烯-28-酸、1β-羟基-3-氧代羽扇-20(29)-烯-28-酸和3β,7β,15α-三羟基羽扇-20(29)-烯-28-酸。此外,用两种人黑素瘤细胞系Mel-1(淋巴结)和Mel-2(胸水)评估了这些代谢产物的抗黑素瘤活性。

相似文献

1
Biotransformation of the antimelanoma agent betulinic acid by Bacillus megaterium ATCC 13368.
Appl Environ Microbiol. 2000 Sep;66(9):3850-5. doi: 10.1128/AEM.66.9.3850-3855.2000.
2
Microbial transformations of the antimelanoma agent betulinic acid.
J Nat Prod. 2000 Dec;63(12):1653-7. doi: 10.1021/np000343a.
3
Glucosidation of betulinic acid by Cunninghamella species.
J Nat Prod. 1999 May;62(5):761-3. doi: 10.1021/np980432b.
4
New derivatives of ursolic acid through the biotransformation by Bacillus megaterium CGMCC 1.1741 as inhibitors on nitric oxide production.
Bioorg Med Chem Lett. 2017 Jun 1;27(11):2575-2578. doi: 10.1016/j.bmcl.2017.03.076. Epub 2017 Mar 27.
5
Biotransformation of betulinic and betulonic acids by fungi.
Phytochemistry. 2007 Mar;68(6):834-9. doi: 10.1016/j.phytochem.2006.12.007. Epub 2007 Jan 26.
7
Biotransformation of ursolic acid by Syncephalastrum racemosum CGMCC 3.2500 and anti-HCV activity.
Fitoterapia. 2013 Apr;86:123-8. doi: 10.1016/j.fitote.2013.02.007. Epub 2013 Feb 17.
8
Cytotoxic lupane-type triterpenoids from Acacia mellifera.
Phytochemistry. 2004 Apr;65(8):1159-64. doi: 10.1016/j.phytochem.2004.03.002.
10
Microbial transformation of the anti-diabetic agent corosolic acid by Cunninghamella echinulata.
J Asian Nat Prod Res. 2017 Jul;19(7):645-650. doi: 10.1080/10286020.2016.1187140. Epub 2016 May 30.

引用本文的文献

1
Transformation of the drug ibuprofen by Priestia megaterium: reversible glycosylation and generation of hydroxylated metabolites.
Environ Sci Pollut Res Int. 2025 Apr;32(19):11981-11995. doi: 10.1007/s11356-025-36393-5. Epub 2025 Apr 21.
5
Structural Investigation of Betulinic Acid Plasma Metabolites by Tandem Mass Spectrometry.
Molecules. 2022 Oct 29;27(21):7359. doi: 10.3390/molecules27217359.
6
Biocatalysis in the Chemistry of Lupane Triterpenoids.
Molecules. 2021 Apr 14;26(8):2271. doi: 10.3390/molecules26082271.
8
The Constituents of the Stems of and Their Bioactivities.
Molecules. 2018 Oct 28;23(11):2799. doi: 10.3390/molecules23112799.
9
An efficient process for the transformation of betulin to betulinic acid by a strain of Bacillus megaterium.
3 Biotech. 2017 Jul;7(3):157. doi: 10.1007/s13205-017-0759-9. Epub 2017 Jun 16.
10
Microbial biotransformation of gentiopicroside by the endophytic fungus Penicillium crustosum 2T01Y01.
Appl Environ Microbiol. 2014 Jan;80(1):184-92. doi: 10.1128/AEM.02309-13. Epub 2013 Oct 18.

本文引用的文献

1
DNA polymerase beta inhibitors from Tetracera boiviniana.
J Nat Prod. 1999 Dec;62(12):1660-3. doi: 10.1021/np990326p.
2
Glucosidation of betulinic acid by Cunninghamella species.
J Nat Prod. 1999 May;62(5):761-3. doi: 10.1021/np980432b.
4
Synthesis of betulinic acid derivatives with activity against human melanoma.
Bioorg Med Chem Lett. 1998 Jul 7;8(13):1707-12. doi: 10.1016/s0960-894x(98)00295-9.
6
Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents.
J Med Chem. 1996 Mar 1;39(5):1016-7. doi: 10.1021/jm950922q.
7
Identification of four biliary metabolites of the diterpene sclareol in the laboratory rat.
Xenobiotica. 1993 Jun;23(6):621-32. doi: 10.3109/00498259309059400.
9
Triterpene derivatives that block entry of human immunodeficiency virus type 1 into cells.
Proc Natl Acad Sci U S A. 1994 Apr 26;91(9):3564-8. doi: 10.1073/pnas.91.9.3564.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验