Microbial Transformation of Protopanaxadiol and Protopanaxatriol Derivatives with <i>Mycobacterium</i> sp. (NRRL B-3805)

Wang, K. C.; Wang, Perng-Haur; Lee, Shoei‐Sheng

doi:10.1021/np970331y

Cited by 9 publications

(5 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This has been observed using 25-hydroxylated cholesterol as the substrate (36), concluding that C-25 hydroxylation must be a distinct reaction from that of the usual cholesterol side chain degradation pathway. Indeed, the authors do not consider that steroid metabolism is a specific function of UPOs, not as much as it is the oxidation of alkanes, alkenes, ethers, or aromatics.…”

Section: Discussionmentioning

confidence: 74%

Steroid Hydroxylation by Basidiomycete Peroxygenases: a Combined Experimental and Computational Study

Babot

Río

Cañellas

et al. 2015

Appl Environ Microbiol

View full text Add to dashboard Cite

The goal of this study is the selective oxyfunctionalization of steroids under mild and environmentally friendly conditions using fungal enzymes. With this purpose, peroxygenases from three basidiomycete species were tested for the hydroxylation of a variety of steroidal compounds, using H 2 O 2 as the only cosubstrate. Two of them are wild-type enzymes from Agrocybe aegerita and Marasmius rotula, and the third one is a recombinant enzyme from Coprinopsis cinerea. The enzymatic reactions on free and esterified sterols, steroid hydrocarbons, and ketones were monitored by gas chromatography, and the products were identified by mass spectrometry. Hydroxylation at the side chain over the steroidal rings was preferred, with the 25-hydroxyderivatives predominating. Interestingly, antiviral and other biological activities of 25-hydroxycholesterol have been reported recently (M. Blanc et al., Immunity 38:106 -118, 2013, http://dx.doi.org/10.1016/j.immuni.2012.11.004). However, hydroxylation in the ring moiety and terminal hydroxylation at the side chain also was observed in some steroids, the former favored by the absence of oxygenated groups at C-3 and by the presence of conjugated double bonds in the rings. To understand the yield and selectivity differences between the different steroids, a computational study was performed using Protein Energy Landscape Exploration (PELE) software for dynamic ligand diffusion. These simulations showed that the active-site geometry and hydrophobicity favors the entrance of the steroid side chain, while the entrance of the ring is energetically penalized. Also, a direct correlation between the conversion rate and the side chain entrance ratio could be established that explains the various reaction yields observed.

show abstract

Section: Discussionmentioning

confidence: 74%

Steroid Hydroxylation by Basidiomycete Peroxygenases: a Combined Experimental and Computational Study

Babot

Río

Cañellas

et al. 2015

Appl Environ Microbiol

View full text Add to dashboard Cite

show abstract

“…Additionally, Mycobacterium sp. selectively catalyzed the specific C-3 dehydrogenation of ginsenosides (Wang et al, 1997). These regiospecific hydroxylation reactions may be important to increase bioactivity (Li et al, 2009b; Tian et al, 2005).…”

Section: Structural Diversitymentioning

confidence: 99%

Ginsenosides from American ginseng: Chemical and pharmacological diversity

2011

View full text Add to dashboard Cite

Ginseng occupies a prominent position in the list of best-selling natural products in the world. Compared to the long history of use and widespread research on Asian ginseng, the study of American ginseng is relatively limited. In the past decade, some promising advances have been achieved in understanding the chemistry, pharmacology and structure-function relationship of American ginseng. To date, there is no systematic review of American ginseng. In this review, we present the different structures of the ginsenosides in American ginseng, including naturally occurring compounds and those resulting from steaming or biotransformation. Preclinical and clinical studies published in the past decade will also be discussed. We highlight the chemical and pharmacological diversity and potential structural-activity relationship of ginsenosides. Our hope is that this article is a useful reference to chemists and biologists researching American ginseng, and will open the door to novel agents in drug discovery.

show abstract

“…In addition to the triterpenoids from A. cinnamomea, many biotransformations of triterpenoids from other sources have been reported [11][12][13][14][15][16][17][18][19][20][21][22][26][27][28][29]. In the present study, Psychrobacillus sp.…”

Section: Discussionmentioning

confidence: 48%

“…Among these bacteria, three Actinobacteria (Mycobacterium sp. [27], Nocardia coralline [28], and Rhodococcus rhodochrous [29]) have been demonstrated to catalyze the oxidation of the 3-hydroxyl group on the tetracyclic triterpenoid 20R-dihydroprotopanaxadiol and the pentacyclic triterpenoids echinocystic acid and betulin, respectively, to form the corresponding 3-oxo-triterpenoid derivatives. In addition, the Bacillus megaterium ATCC (American Type Culture Collection) 14581 and CGMCC (China General Microbiological Culture Collection Center) 1.1741 strains were found to catalyze the oxidation of the 3-hydroxyl group on the pentacyclic triterpenoids betulinic acid [26] and ursolic acid [18], respectively, to form the corresponding 3-oxo-triterpenoid derivatives.…”

Section: Discussionmentioning

confidence: 99%

Biotransformation of Ergostane Triterpenoid Antcin K from Antrodia cinnamomea by Soil-Isolated Psychrobacillus sp. AK 1817

Chiang

Wang

et al. 2017

Catalysts

View full text Add to dashboard Cite

Antcin K is one of the major ergostane triterpenoids from the fruiting bodies of Antrodia cinnamomea, a parasitic fungus that grows only on the inner heartwood wall of the aromatic tree Cinnamomum kanehirai Hay (Lauraceae). To search for strains that have the ability to biotransform antcin K, a total of 4311 strains of soil bacteria were isolated, and their abilities to catalyze antcin K were determined by ultra-performance liquid chromatography analysis. One positive strain, AK 1817, was selected for functional studies. The strain was identified as Psychrobacillus sp., based on the DNA sequences of the 16S rRNA gene. The biotransformation metabolites were purified with the preparative high-performance liquid chromatography method and identified as antcamphin E and antcamphin F, respectively, based on the mass and nuclear magnetic resonance spectral data. The present study is the first to report the biotransformation of triterpenoids from A. cinnamomea (Antrodia cinnamomea).

show abstract

Microbial Transformation of Protopanaxadiol and Protopanaxatriol Derivatives with Mycobacterium sp. (NRRL B-3805)

Cited by 9 publications

References 11 publications

Steroid Hydroxylation by Basidiomycete Peroxygenases: a Combined Experimental and Computational Study

Steroid Hydroxylation by Basidiomycete Peroxygenases: a Combined Experimental and Computational Study

Ginsenosides from American ginseng: Chemical and pharmacological diversity

Biotransformation of Ergostane Triterpenoid Antcin K from Antrodia cinnamomea by Soil-Isolated Psychrobacillus sp. AK 1817

Contact Info

Product

Resources

About