Sophora flavonoids

The formation of phytoalexins such as glyceollins and phaseollins requires C-prenylation by a range of pterocarpan prenyltransferase (PTP) activities, with dimethylallyl pyrophosphate (DMAPP) as the prenyl donor. For glyceollins and phaseollins, prenylation occurs at position C-2 or C-4 of glycinol or C-10 of 3,9-dihydroxypterocarpan. ° ° However, there are differing activities in other species. For example, in Lupinus albus (white lupin) a prenyltransferase acting at the C-6, -8, and -3 positions of isoflavones has been identified.PTPs have also been characterized in detail for the formation of prenylated flavanones in Sophora flavescens (see, e.g., Ref. 207). However, no cDNA clones for flavonoid-related prenyltransferases have been published to date. 

Tanaka, T. et al., Flavonoids from the root and stem of Sophora tomentosa. Phytochemistry, 46, 1431, 1997. 

Kuroyanagi, M. et al.. Antibacterial and antiandrogen flavonoids from Sophora flavescens. Journal of Natural Products, 62, 1595, 1999. 

Prenylated flavonoids contain one or two isoprenyl, geranyl, dimethylallyl, and lavandulyl on the skeleton. They have limited distribution and are mostly isolated from the Moraceae family. Chi et al. isolated 19 prenylated flavonoids from six different genera of Chinese medicinal plants and evaluated inhibition activities on eicosanoid metabolisms with multiple cell line models [189]. Two 8-lavandulylated flavanones, kurarinone and sophoraflavanone G, were discovered to be dual inhibitors. They possessed the most potent COX-1 inhibitory activities with IC50 less than 1 pM comparable with that of indomethacin. Sophoraflavanone G isolated from the roots of Sophora flavescense Art (Fabaceae) also had potent 5-LOX inhibition activity with an IC50 below 0.25 pM. 

Sophora falvescens (Ku shen) contains a variety of matrine alkaloids, such as aloperine, cytosine, lehman-nine, matrine, oxymartine, oxysophocarpine, sophocar-pine, sophoramine, and sophoridine, the flavonoid kushenol, and the saponin sophoraflavoside. Ku shen is a Chinese herbal remedy made from the root of S. falvescens. And Qing luo yin, a Chinese herbal remedy for rheumatoid arthritis, is a combination of extracts of Dioscorea hypoglauca, Phellodendron amurense, Sinomenium acutum, and S. flavescens. 

Keywords Enzyme inhibitory activity Flavonoids Radical scavengers Sophora species... 

A new pterocarpan, (-)-maackiain 3-sulfate (58) was isolated from the methanol extract of roots of Sophora subprostarata together with (-)-maack-iain (6), trifolirhizin (2), lupeol (59), ononin (60), 7,4/-dihydroxyflavone (61), and (+)-syringaresinol (62). Three flavonoids (60-62) were isolated from this plant for the first time (Fig. 11) [9]. 

Fig. 12 Flavonoids for test of estrogen receptor binding from Sophora flavescens...

Fig. 22 Sophoflavescenol (110), flavonoids, and their anti-HIV activity from roots of Sophora flavescens...

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