Furanocoumarins from Dorstenia foetida

• Published in: Phytochemistry (Oxford) 2011-06, Vol.72 (9), p.929-934
• Main Authors: Heinke, Ramona, Franke, Katrin, Porzel, Andrea, Wessjohann, Ludger A., Awadh Ali, Nasser A., Schmidt, Jürgen
• Format: Article
• Language: English
• Subjects: 7-Hydroxy-5-methoxy-6-carboxymethyl-3-[3-( β- d-glucopyranosyloxy)-2-hydroxy-3-methyl-butyl]-coumarin; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Biological and medical sciences; Cell Line, Tumor; Chemical constitution; Dorstenia foetida; Fundamental and applied biological sciences. Psychology; Furanocoumarins; Furocoumarins - chemistry; Furocoumarins - isolation & purification; Humans; Molecular Structure; Moraceae; Moraceae - chemistry; Phytochemistry; Plant Leaves - chemistry; Plant physiology and development
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2011.03.008

Ten prenylated furanocoumarins, including four unknown compounds, and one carboxymethyl coumarin derivative ( 1) were isolated from leaves of Dorstenia foetida (Forssk.) Schweinf. (Moraceae). Further four furanocoumarins were characterized by mass spectral investigations. [Display omitted] ► In this report we describe the structure elucidation of new linear furanocoumarins. ► Furthermore, a new coumarin derivative with a 6-carboxymethyl function was isolated. ► This the first phytochemical report on leaves of Dorstenia foetida (Moraceae). ► The nonpolar extracts exhibit antifungal, antibacterial and cytotoxic activity. The linear furanocoumarins 5-(2,3-epoxy-3-methyl-butoxy)-chalepensin, 5-methoxy-3-(3-methyl-2,3-dihydroxybutyl)-psoralen-diacetate ( 7), 5-methoxy-3-[3-( β- d-glucopyranosyloxy)-2-acetyloxy-3-methyl-butyl]-psoralen and 5-(3-methyl-2,3-dihydroxybutyloxy)-3-[3-( β- d-glucopyranosyloxy)-2-hydroxy-3-methyl-butyl]-psoralen, and the coumarin derivative 7-hydroxy-5-methoxy-6-carboxymethyl-3-[3-( β- d-glucopyranosyloxy)-2-hydroxy-3-methyl-butyl]-coumarin were isolated from the leaves of Dorstenia foetida (Moraceae) along with the known compounds psoralen, bergapten, isopimpinellin, phellopterin, 5-methoxychalepensin and turbinatocoumarin. Further furanocoumarins were characterized by ESI-MS/MS investigations. The nonpolar extracts of D. foetida exhibit antifungal, antibacterial and cytotoxic activity, however, no anthelminthic activity.