Microbial transformation of xanthohumol

Herath, Wimal; Ferreira, Daneel; Khan, Ikhlas A.

doi:10.1016/s0031-9422(02)00615-5

Cited by 39 publications

(34 citation statements)

References 10 publications

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“…32 Microbial transformation of chalcone xanthohumol, using the culture broth of Pichia membranifaciens afforded three metabolites, one isomeric prenylflavanone in 3.3% yield, and two modified prenylchalcones in 0.55 and 0.58% yield. 33 The yields obtained in the biotransformation reactions of chalcones to dihydrochalcones in this work are higher (15.6-75.5% yield) than those reported in the literature, although no reaction can be directly compared, because none of them performed this type of bioreduction (direct formation of dihydrochalcones from chalcone).…”

Section: Resultsmentioning

confidence: 53%

Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum trin

Corrêa¹,

Nunes²,

Bitencourt³

et al. 2011

J. Braz. Chem. Soc.

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O fungo Aspergillus flavus isolado como endofítico da planta Paspalum maritimum Trin. foi avaliado quanto ao seu potencial de aplicação em reações de biotransformações. Os compostos chalcona (1), 3,4,5-trimetoxichalcona (2) e 2,3,4,4'-tetrametoxichalcona (3) foram biotransformados, respectivamente, na diidrochalcona (4), 3,4,5-trimetoxidiidrochalcona (5) e 2,3,4,4'-tetrametoxidiidrochalcona (6). As estruturas destes compostos foram determinadas por análises de RMN uni e bidimensionais e por espectrometria de massas. As diidrochalconas 5 e 6 são substâncias inéditas. The fungus Aspergillus flavus isolated as endophytic of the plant Paspalum maritimumTrin. was evaluated for its potential application in biotransformation reactions. The compounds chalcone (1), 3,4,5-trimethoxychalcone (2) and 2,3,4,4'-tetramethoxychalcone (3) were biotransformed, respectively, in dihydrochalcone (4), 3,4,5-trimethoxydihydrochalcone (5) and 2,3,4,4'-tetramethoxydihydrochalcone (6). The structures were elucidated by spectroscopic methods including 1D and 2D NMR techniques, and MS analysis. The dihydrochalcones 5 and 6 are new compounds.

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Section: Resultsmentioning

confidence: 53%

Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum trin

Corrêa¹,

Nunes²,

Bitencourt³

et al. 2011

J. Braz. Chem. Soc.

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“…1) were isolated and characterized. 12) We selected Cunninghamella echinulata NRRL 3655 for scale-up studies as it gave different metabolites than those obtained with the former organism. This transformation afforded the new ( Table 1).…”

Section: Resultsmentioning

confidence: 99%

Identification and Biological Activity of Microbial Metabolites of Xanthohumol

Herath

Ferreira

Khan

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Both analytical and preparative fermentation experiments were conducted by using standard two-stage fermentation experiments. [12][13][14] For the preparation of stage I liquid culture, ten 250 ml flasks (each containing 50 ml of liquid culture media) were inoculated with microorganisms to be screened and incubated on a shaker for 24 h. Stage II cultures was prepared by adding sclareolide (1) (500 mg) as a solution in ethanol having a concentration of 0.33 mg/ml to each flask having five different microorganisms. These fermentation experiments were also monitored by including two controls, a "culture control" and a "substrate control" to eliminate the possibility that metabolic products are not microbial secondary metabolites and that the culture media has not done any chemical transformation on the substrate.…”

Section: Methodsmentioning

confidence: 99%

Novel Microbial Transformations of Sclareolide

Ata

Conci

Betteridge

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Microorganisms such as bacteria and fungi are capable to perform regio-and stereo-selective reactions on organic compounds. The different possible microbial reactions include oxidation, reduction, and degradative reactions.1) Many of these reactions allow the production of new compounds that would be extremely difficult to synthesize chemically. 2)For instance hydroxylation at inactivated methylene is a very common microbial reaction.3) The results obtained from microbial transformations are quite often similar to those obtained from mammal biotransformations.4) The parallel relationship between mammals and microbial transformations is due to the fact that many fungi, such as the filamentous fungus Cunninghamella, utilize the enzyme cytochrome P-450 monoxygenase in the metabolism of xenobiotics.5) This enzyme system is analogous to the enzyme system used by mammals, allowing microbial transformations to be used successfully as in vitro models for mammalian drug metabolism.6) A lead bioactive compounds can also be generated through microbial transformations of natural products. The metabolic products often have improved bioactivity with minimal toxicity compared to the parent natural product. 7)In our continuing effort to discover new bioactive natural products, we decided to do biotransformation studies of sclareolide (1) using whole cell cultures of different fungi. Sclareolide (1) is a minor constituent of the vascular plant Arnica angustifolia and is commercially available.8) Compound 1 has shown modest cytotoxcity against breast (MCF-7), colon (CKCO-1), lung (H-1299) and skin (HT-144) human cancer cell lines. 8) For this project, we screened five different fungi, namely Mucor plumbeus (ATCC 4740), Cunninghamella blakesleeana (ATCC 9245), Cunninghamella echinulata (ATCC 9244), Curvularia lunata (ATCC 12017) and Aspergillus niger (ATCC 1004), for their capability to metabolize compound 1. During these biotransformation experiments, we discovered that Cunninghamella blakesleeana (ATCC 9245) metabolized compound 1 into O 6 -sclareolide (2), 3b,6a-dihydroxysclareolide (3) and 9-hydroxysclareolide (4), along with three known metabolites, 1b,3b-dihydroxysclareolide (5), 3-oxosclareolide (6) and 3b-hydroxysclareolide (7). Biotransformation experiments of compound 1 with Cunninghamella echinulata (ATCC 9244) also yielded two new compounds, 5-hydroxysclareolide (8), and 7b-hydroxysclareolide (9) along with two known compounds 5 and 7. NMR spectroscopic methods were used to establish the structures of compounds 2-9. Compounds 2-9 were found to exhibit modest acetylcholinesterase inhibitory activity. To the best of our knowledge, biotransformation of 1 into 2 is a novel ether-forming microbial reaction. In this paper we report the biotransformations of 1 and structure elucidation of compounds 2-9 as well as their bioactivity data. Results and DiscussionOur first biotransformed product, O 6-sclareolide was obtained as a colorless gum. Its UV spectrum showed terminal absorption indicating the lack of a conjugated p system...

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Microbial transformation of xanthohumol

Cited by 39 publications

References 10 publications

Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum trin

Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum trin

Identification and Biological Activity of Microbial Metabolites of Xanthohumol

Novel Microbial Transformations of Sclareolide

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