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Biotransformation of neoruscogenin (NR, 1, spirosta-5,25(27)-diene-1β,3β-diol), the major bioactive sapogenin of Ruscus preparations, was carried out with the endophytic fungus Alternaria eureka. Fourteen new biotransformation products (2-15) were isolated, and their structures were elucidated by NMR and HRESIMS data analyses. A. eureka affected mainly oxygenation, oxidation, and epoxidation reactions on the B and C rings of the sapogenin to afford compounds 8-15. In addition to these, cleavage of the spiroketal system as in compounds 2-7 and subsequent transformations provided unusual metabolites. This is the first study reporting conversion of the spirostanol skeleton to cholestane-type metabolites 2-5. Additionally, the cleavage of the C-22/C-26 oxygen bridge yielding a furostanol-type steroidal framework and subsequent formation of the epoxy bridge between C-18 and C-22 in 7 was encountered for the first time in steroid chemistry.

Biotransformation of steroidal ruscogenins (neoruscogenin and ruscogenin) was carried out with Cunninghamella blakesleeana NRRL 1369 and endophytic fungus Neosartorya hiratsukae yielding mainly P450 monooxygenase products together with a glycosylated compound. Fermentation of ruscogenins (75:25, neoruscogenin-ruscogenin mixture) with C. blakesleeana yielded 8 previously undescribed hydroxylated compounds. Furthermore, microbial transformation of neoruscogenin by endophytic fungus N. hiratsukae afforded three previously undescribed neoruscogenin derivatives. While hydroxylation at C-7, C-12, C-14, C-21 with further oxidation at C-1 and C-7 were observed with C. blakesleeana, N. hiratsukae biotransformation provided C-7 and C-12 hydroxylated compounds along with C-12 oxidized and C-1(O) glycosylated derivatives. The structures of the metabolites were elucidated by 1-D (H, C and DEPT135) and 2-D NMR (COSY, HMBC, HMQC, NOESY, ROESY) as well as HR-MS analyses.

A b s t r a c t Introduction: Traditionally, Anthemis genus has been used for the treatment of gastrointestinal disorders, haemorrhoid and stomach ache in Europe. There are several in-vitro and in-vivo studies that showed the pharmacological properties of Anthemis species such as antibacterial, anti-inflammatory, antiedemic and hepatoprotective properties. Aim: Our study referred to the model of inflammation formed in rats; we aimed to evaluate anti-inflammatory properties of A. tricolor extracts. Material and methods: Five different extracts of A. tricolor were tested against the negative control and 2 different topical corticosteroids (betamethasone and hydrocortisone); n-hexane and sesquiterpene extracts of A. tricolor Bois showed significantly reduced erythema compared to the negative control. Results: Only n-hexane and sesquiterpene extracts of A. tricolor have the anti-inflammatory effect. Conclusions: This is the first report on anti-inflammatory activity of A. tricolor and we showed an anti-inflammatory effect of n-hexane and sesquiterpene extract of A. tricolor with UV erythema test as a result, hence A. tricolor extracts can be used for the treatment of inflammatory skin diseases due to anti-inflammatory activity.