cis-Martynoside

Bioactive constituents of Lindernia crustacea and its anti-EBV effect via Rta expression inhibition in the viral lytic cycle.[Pubmed:31863859]

J Ethnopharmacol. 2020 Mar 25;250:112493.

ETHNOPHARMACOLOGICAL RELEVANCE: Lindernia crustacea (L.) F.Muell. (Scrophulariaceae) was selected for phytochemical investigation owing to its traditional use against human herpes virus infection and its anti-Epstein-Barr virus (EBV) effect. AIMS OF THE STUDY: The present study focused on the phytochemical investigation of L. crustacea including the isolation and structure determination of its biologically active compounds. Compounds with anti-EBV effects were also investigated. MATERIALS AND METHODS: The EtOH extract of L. crustacea was subsequently partitioned using different solvents. The EtOAc fraction was subjected to several chromatographic methods to obtain pure compounds. The structures of all isolates were established by spectroscopic analysis and compared with previously reported physical data. The anti-EBV effect was evaluated in an EBV-containing Burkitt's lymphoma cell line (P3HR1) to study the expression of EBV lytic proteins. RESULTS: Thirty-three compounds, including one diterpene (1), four anthraquinones (2-5), two ionones (6 and 7), fourteen phenylpropanoid glycosides (8-21), five flavonoids (22-26), one lignan glycoside (27), one phenethyl alcohol glycoside (28), one phenylpropene glycoside (29), one glucosyl glycerol derivative (30), one furanone (31), and two cinnamic acid derivatives (32 and 33), were isolated from the ethanolic extract of the plant. All isolated compounds were obtained for the first time from Lindernia sp. The evaluation of the anti-EBV activity of L. crustacea crude extract, partitioned fractions, and constituents was performed for the first time. Phytol (1), aloe-emodin (2), byzantionoside B (7), a mixture of trans-martynoside (8) and cis-Martynoside (9), a mixture of trans-isomartynoside (10) and cis-isomartynoside (11), luteolin-7-O-beta-D-glucopyranoside (24), and apigenin-7-O-[beta-D-apiofuranosyl (1-->6)-beta-D-glucopyranoside] (25) exhibited significant inhibitory effects on the EBV lytic cycle at 20 mug/mL in the immunoblot analysis. On the other hand, (6R,7E,9R)-3-oxo-alpha-ionol-beta-D-glucopyranoside (6) and a mixture of trans-dolichandroside A (12) and cis-dolichandroside A (13) showed moderate anti-EBV activity at 20 mug/mL. CONCLUSIONS: L. crustacea and its active isolates could be developed as potential candidates against EBV. Our findings provide scientific evidence for the traditional use of L. crustacea for its antiviral effects.

Chemical constituents and HRESI-MS analysis of an Algerian endemic plant - Verbascum atlanticum batt. - extracts and their antioxidant activity.[Pubmed:31009247]

Nat Prod Res. 2019 Apr 22:1-5.

This is the first report on the phytochemistry and antioxidant activity of ethyl acetate and n- butanol extracts from an Algerian endemic plant Verbascum atlanticum Batt. (Scrophulariaceae). Both extracts were subjected to a phytochemical study by semi-preparative HPLC, which led to the isolation and identification of nine compounds: methyl linolenate (1), methyl linoleate (2), Phytol-1(3), Martynoside (4), Isomartynoside (5), cis-Martynoside (6), Ilwensisaponin C (7), Ilwensisaponin B (8), Ilwensisaponin A (9). In addition, the fractions from both extracts were analysed by LC-UV-MS and HRESI-MS. This later revealed the presence of eight other metabolites by using a comparison with known microbial metabolites data. Finally, both extracts were estimated for their phenolic and flavonoid contents as well as the evaluation of their antioxidant activity using five different assays DPPH, CUPRAC, reducing power, beta-carotene bleaching and superoxide DMSO alkaline. The results showed that the ethyl acetate extract had the most antioxidant effect.

Phenylpropanoid glycosides from Penstemon serrulatus.[Pubmed:9917298]

J Nat Prod. 1999 Jan;62(1):127-9.

Two new phenylpropanoid glycosides named cis-Martynoside (1) and cis-leucosceptoside A (3) were recognized in cell suspension cultures of Penstemon serrulatus Menz. The structures of these compounds were determined on the basis of 1H NMR spectral data.