New Cyclopeptide Alkaloids from Zizyphus lotus

Abstract

A [1] and B [2], have been isolated from the aerial parts of Ziziphus lotus, together with the known alkaloids sanjoinenine [3], sanjoinine F [4], and frangufoline [51• Ziziphus lotus Lam. (Rhamnaceae) is a small tree that is widely distributed in the Jordan Valley. The genus Ziziphus comprises several species that are used in indigenous medicine for the treatment of various diseases (1-5). We report here the first chemical investigations of Z. lotus, yielding two new 14-membered frangulanine-type (6) cyclopeptide alkaloids from an extract of the aerial pans of Z. lotus. The new compounds, lotusanine A [1} and lotusanine B [2] were isolated along with the known alkaloids, sanjoinenine {31 (7), sanjoinine F [4] (7), and frangufoline [51 (8) (Table 1). Characterization of these compounds was achieved with the help of spectroscopic studies, especially mass spectrometry, which permitted conclusions to be drawn about the structural units (amino acids and styryl moiety) present in the compound and the manner in which they are linked (6,9). RESULTS AND DISCUSSIONCc of an alkaloidal fraction of the C6H6 extract of Z. lotus (see Experimental) gave an amorphous solid, lotusanine A [1]. The uv spectrum of 1 showed only terminal absorption. The ir spectrum exhibited bands for NH-(3260 cm '), amide carbonyls

Antidiabetic activity and toxicity of Zizyphus spina-christi leaves

“…From the different species of the genus Zizyphus, peptide and cyclopeptide alkaloids, flavonoids, sterols, tannins, betulinic acid and triterpenoidal saponin glycosides have been isolated and chemically identified (Ikram et al, 1981;Higuchi et al, 1984;Nawwar et al, 1984;Han et al, 1990;Barboni et al, 1994;Abu-Zarga et al, 1995;Cheng et al, 2000;Shahat et al, 2001;Tripathi et al, 2001).…”

Global identification and quantitative analysis of chemical constituents in traditional Chinese medicinal formula Qi-Fu-Yin by ultra-high performance liquid chromatography coupled with mass spectrometry

“…The fragmentation pattern of cyclopeptide alkaloids was characterized with which presented According to the publication about cyclopeptide alkaloids [28], compound Z17 was tentatively assigned as sanjoinine A (frangufoline). and P31−P50) [29,30].…”

Phytochemical screening of different organic crude extracts from the stem bark of Ziziphus spina-christi (L.)

“…Previous phytochemical studies on the different species of the genus Ziziphus led to the isolation and characterization of peptide, cyclopeptide alkaloids, flavonoids, sterols, tannins, betulinic acid and triterpenoidal saponin glycosides [7,[12][13][14][15]. Ziziphus spina-christi (L.) extracts were evaluated for their phytochemical content in the stem bark as well as the antimicrobial and cytotoxic activities.…”