Biotransformation of 11-keto-β-boswellic acid by Cunninghamella blakesleana

被引：18
|
作者：
Wang, Yue [1 ]
Sun, Yan [2 ]
Wang, Chao [2 ]
Huo, Xiaokui [2 ]
Liu, Pinduan [1 ]
Wang, Changyuan [2 ]
Zhang, Baojing [2 ]
Zhan, Libin [3 ]
Zhang, Houli [2 ]
Deng, Sa [2 ]
Zhao, Yanyan [2 ]
Ma, Xiaochi [1 ,2 ,3 ]
机构：
[1] Liaoning Med Univ, Affiliated Hosp 1, Jinzhou 121001, Peoples R China
[2] Dalian Med Univ, Coll Pharm, Dalian 116044, Peoples R China
[3] Dalian Med Univ, Res Inst Integrated Tradit & Western Med, Dalian 116044, Peoples R China
来源：
PHYTOCHEMISTRY | 2013年 / 96卷
基金：
中国国家自然科学基金;
关键词：
Cunninghamella blakesleana AS 3.970; Boswellia serrata; Biotransformation; 11-Keto-beta-boswellic acid; Burseraceae; NO inhibition; BOSWELLIC ACIDS; MICROBIAL TRANSFORMATION; LEUKOTRIENE INHIBITOR; MUCOR-SPINOSUS; DEOXYANDROGRAPHOLIDE; METABOLISM; CINOBUFAGIN; PRODUCTS; CELLS;
D O I：
10.1016/j.phytochem.2013.07.018
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
11-Keto-beta-boswellic acid (KBA), as one of the active constituents in the gum resin of Boswellia serrata, possesses significant biological activities including anti-inflammatory activity. However, its extensive metabolism and low polarity has limited the systemic availability of KBA. The present research was aimed to obtain and explore the various possible derivatives of KBA through biotransformation by Cunninghamella blakesleana AS 3.970. A total of ten transformed compounds were isolated and purified, and their chemical structures were characterized as 7 beta-hydroxy-11-keto-beta-boswellic acid; 7 beta, 15 alpha-dihydroxy-11-keto-beta-boswellic acid; 7 beta, 16 beta-dihydroxy-11-keto-beta-boswellic acid; 7 beta, 16 alpha-dihydroxy-11-keto-beta-boswellic acid; 7 beta, 22 beta-dihydroxy-11-keto-beta-boswellic acid; 7 beta, 21 beta-dihydroxy-11-keto-beta-boswellic acid; 7 beta, 20 beta-dihydroxy-11-keto-beta-boswellic acid; 7 beta, 30-dihydroxy-11-keto-beta-boswellic acid; 3 alpha, 7 beta-dihydroxy-11-oxours-12-ene-24, 30-dioic acid and 3 alpha, 7 beta-dihydroxy-30-(2-hydroxypropanoyloxy)-11-oxours-12-en-24-oic acid by various spectroscopic methods. The biotransformation processes include hydroxylation, oxidation and esterification. Primary structure-activity relationships (SAR) of inhibitory effects on NO production in RAW 264.7 macrophage cells are discussed. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：330 / 336
页数：7
相关论文
共 50 条
  • [1] Oxidative and reductive transformations of 11-keto-β-boswellic acid
    Csuk, Rene
    Barthel-Niesen, Anja
    Stroehl, Dieter
    Kluge, Ralph
    Wagner, Christoph
    Al-Harrasi, Ahmed
    TETRAHEDRON, 2015, 71 (13) : 2025 - 2034
  • [2] Biotransformation of triptolide by Cunninghamella blakesleana
    Ning, LL
    Zhan, JX
    Qu, GQ
    Zhong, L
    Guo, HZ
    Bi, KS
    Guo, D
    TETRAHEDRON, 2003, 59 (23) : 4209 - 4213
  • [3] Synthesis of an antitumor active endoperoxide from 11-keto-β-boswellic acid
    Csuk, Rene
    Niesen-Barthel, Anja
    Barthel, Alexander
    Kluge, Ralph
    Stroehl, Dieter
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) : 3840 - 3843
  • [4] Influence of organic supplements on accumulation of β-boswellic acid, acetyl-β-boswellic acid, 11-keto-β-boswellic acid and acetyl-11-keto-β-boswellic acid in callus culture of Boswellia serrata Roxb.
    Ghorpade, Ravi
    Chopra, Arvind
    Nikam, Tukaram
    ACTA PHYSIOLOGIAE PLANTARUM, 2012, 34 (06) : 2275 - 2283
  • [5] Influence of organic supplements on accumulation of β-boswellic acid, acetyl-β-boswellic acid, 11-keto-β-boswellic acid and acetyl-11-keto-β-boswellic acid in callus culture of Boswellia serrata Roxb.
    Ravi Ghorpade
    Arvind Chopra
    Tukaram Nikam
    Acta Physiologiae Plantarum, 2012, 34 : 2275 - 2283
  • [6] Biotransformation of isoimperatorin by Cunninghamella blakesleana AS 3.970
    Yang, XiaoBo
    Hou, Jie
    Liu, Dan
    Deng, Sa
    Wang, Zhi Bin
    Kuang, Hai Xue
    Wang, ChangYuan
    Yao, Ji Hong
    Liu, Ke Xin
    Ma, Xiao Chi
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 88 : 1 - 6
  • [7] Synthesis and antitumor activity of ring A modified 11-keto-β-boswellic acid derivatives
    Csuk, Rene
    Niesen-Barthel, Anja
    Schaefer, Renate
    Barthel, Alexander
    Al-Harrasi, Ahmed
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 : 700 - 711
  • [8] Investigating permeability related hurdles in oral delivery of 11-keto-β-boswellic acid
    Bagul, Pravin
    Khomane, Kailas S.
    Bansal, Arvind K.
    INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2014, 464 (1-2) : 104 - 110
  • [9] 11-Keto-β-boswellic acid prevents development of insulitis in NOD-mice
    Ammon, H. P. T.
    Shehata, A. M.
    Jauch, J.
    Quintanilla-Martinez, L.
    DIABETOLOGIA, 2012, 55 : S193 - S193
  • [10] Metabolic Profile of 3-Acetyl-11-Keto-β-Boswellic Acid and 11-Keto-β-Boswellic Acid in Human Preparations In Vitro, Species Differences, and Bioactivity Variation
    Yonglei Cui
    Xiangge Tian
    Jing Ning
    Chao Wang
    Zhenlong Yu
    Yan Wang
    Xiaokui Huo
    Lingling Jin
    Sa Deng
    Baojing Zhang
    Xiaochi Ma
    The AAPS Journal, 2016, 18 : 1273 - 1288
12345