Substrate Specificity in the Fungal Metabolism of Prenylated Flavonoids

نویسندگان

  • Satoshi Tahara
  • John L. Ingham
  • Junya Mizutani
چکیده

The prenylated flavonoids, topazolin [5,7,4'-trihydroxy-3-methoxy-6-(3,3-dimethylaIlyl)flavone], piscerythrone [5,7,2',4'-tetrahydroxy-5'-methoxy-3'-(3,3-dimethylallyl)isoflavone] and piscidone [5,7,4',5'-tetrahydroxy-2'-methoxy-6'-(3,3-dimethylallyl)isoflavone] were meta­ bolized by Aspergillus flavus and Botrytis cinerea to give a variety of products. Topazolin and piscerythrone were converted by both fungi to compounds similar to those previously ob­ tained from luteone (6-prenyl) and licoisoflavone A (3'-prenyl) respectively. The 6'-prenylated isoflavone piscidone was metabolized only by B. cinerea to give the corresponding dihydropyrano-isoflavone as a major product. Neither fungus was found to metabolize the 8-prenylated pyranoflavanonol lupinifolinol.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Two New Prenylated Flavonoids From Paracalyx Scariosa

Two new prenylated flavonoids, named scariosin (1) and isorhynchospermin (2) were isolated from the leaves of paracalyx scariosa together with kaempferol, quercetin, kaempferol 3-O- rutinoside and rutin. The structures of (1) and (2) were characterized as 8-C- prenyl- taxifolin 7,3'-dimethylether and 6-C-prenylquercetin 7,4'-dimethylether by their chemical and spectra data, respectively.

متن کامل

Structural basis for non-genuine phenolic acceptor substrate specificity of Streptomyces roseochromogenes prenyltransferase CloQ from the ABBA/PT-barrel superfamily

Acceptor substrate specificity of Streptomyces roseochromogenes prenyltransferase SrCloQ was investigated using different non-genuine phenolic compounds. RP-UHPLC-UV-MSn was used for the tentative annotation and quantification of the prenylated products. Flavonoids, isoflavonoids and stilbenoids with different types of substitution were prenylated by SrCloQ, although with less efficiency than t...

متن کامل

Prenylated Flavonoids from Pongamia pinnata

Pongamia pinnata (Leguminosae) is widely distributed along southeastern Asia to the west Pacific and north Australia. All parts of the plant have been used as crude drug for the treatment of tumors, piles, skin diseases, wounds, ulcers, etc. [1]. Extracts of the plant possess significant anti-diarrhoeal, anti-fungal, anti-plasmodial, anti-ulcerogenic, anti-inflammatory, analgesic activities [2 ...

متن کامل

Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens.

Prenylated flavonoids are natural compounds that often represent the active components in various medicinal plants and exhibit beneficial effects on human health. Prenylated flavonoids are hybrid products composed of a flavonoid core mainly attached to either 5-carbon (dimethylallyl) or 10-carbon (geranyl) prenyl groups derived from isoprenoid (terpenoid) metabolism, and the prenyl groups are c...

متن کامل

Metabolism of the Prenylated Pterocarpan Edunol by Aspergillus flavus

In our previous papers, we reported that isoflavones with a 3,3-dimethylallyl (prenyl) substituent at C-6, C-8 (ring A) or C-3' (ring B) were variously metabolized by the fungus Aspergillus flavus to give hydrates (luteone [1] and wighteone [2]), and deri­ vatives possessing dihydrofurano, dihydropyrano or 2,3-dihydrodihydroxyprenyl side-attachments (luteone [1], wighteone [2], 2,3-dehydrokievi...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2013