Abstract
Nine new derivatives of oleanane triterpenoids isolated from Fatsia polycarpa Hayata were synthesized through chemical transformations. Acetylation was effected by reaction with acetic anhydride in pyridine to afford compounds 1–5, while compound 6 was obtained using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) in CH2Cl2. The others derivatives 7–9 were obtained in reactions of the corresponding triterpenoids with EDC·HCl, 4-N,N-dimethylaminopyridine hydrochloride and 4-N,N-dimethylaminopyridine in CH2Cl2. The structures of 1–9 were elucidated from extensive spectroscopic and HRESIMS data, while the structure of 9 was further confirmed by X-ray diffraction analysis. The cytotoxic, anti-hepatitis B virus (HBV), antibacterial, hypoglycaemic and Wnt signaling activities of these derivatives were evaluated in vitro.
Highlights
Numerous oleananoids have gererated tremendous interest from the standpoint of their biological activities, such as antigiardial, anti-HIV, antihyperglycemia, anti-inflammatory, antimycobacterial, antioxidative, antitumor and cardiovascular properties [1,2,3,4,5,6,7,8,9,10]
The carbonyl signal was attributed to the acetate moiety linked to C-3, as further confirmed through the crucial HMBC
After varying its structure at C-3 and C-28 positions, we found 1–6 to be more potent than the parent compounds (Table 1), and these findings are in accordance with the available literature data concering structure−activity relationship [13,14]
Summary
Numerous oleananoids have gererated tremendous interest from the standpoint of their biological activities, such as antigiardial, anti-HIV, antihyperglycemia, anti-inflammatory, antimycobacterial, antioxidative, antitumor and cardiovascular properties [1,2,3,4,5,6,7,8,9,10]. Some of them are known to have anticarcinogenic activity in experimental animals [11]. It has been well recognized to possess anti-inflammatory and antihyperlipidemic activities in animals [12]. In our previous paper we reported the isolation and characterization of seven oleananoids, named fatsicarpains A–G, with moderate cytotoxic and antibacterial activities [2]. In view of the bioactive potential of these isolated compounds, the goal of this study was to modify the two active portions of them, namely, the C-3 hydroxy group and the carboxyl group at C-28. We have prepared nine new derivatives 1–9, as shown in Scheme 1
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