RESUMO
BACKGROUND: Tobacco mosaic virus (TMV) is a disreputable plant pathogen that causes a decline in the quality and yield of various economic crops. Natural products are important potential sources of biopesticides to control TMV. This study focuses on the discovery of anti-TMV active flavonoid glycosides and their mode of action on TMV particles from Clematis lasiandra Maxim. RESULTS: A new benzoyl acylated flavonoid glycoside, kaempferol 3-O-(2''-benzoyl)-ß-d-glucopyranosyl-7-O-α-l-rhamnopyranoside (1), and nine known flavonoids (2-10) were identified first from C. lasiandra. The hydroxyl group at C-7, E-p-coumarate at C-6'' in the Glc of C-6, and the glucuronic acid at C-3 were functional groups for the antiviral flavonoid glycosides. Flavonoids 2, 5, and 6 showed higher inactivation efficacies of 64.62% to 82.54% compared with ningnanmycin at 500 µg ml-1 . The protective and curative efficacies for 2 and 5 were 57.44-59.00% and 41.17-43.92% at 500 µg ml-1 , respectively. Compound 5 showed higher TMV systemic resistance with control efficacies of 41.64%, 36.56% and 27.62% at concentrations of 500, 250 and 125 µg ml-1 compared with ningnanmycin in K326 tobaccos, respectively. Compound 5 can directly fracture TMV particles into small fragments combining with the fusion phenomena, and TMV-CP was an important target for 5 to break TMV particles. CONCLUSION: Flavonoid glycosides from C. lasiandra showed potent antiviral activities against TMV with multiple modes of action including inactivation, protective and curative effects, and inducing systemic resistance. TMV-CP was an important target for active flavonoid glycosides to fracture TMV particles. The results provided evidence that flavonoid glycosides from C. lasiandra have the potential to control TMV.
Assuntos
Clematis , Vírus do Mosaico do Tabaco , Antivirais/farmacologia , Flavonoides/farmacologia , Glicosídeos/farmacologia , VírionRESUMO
Four new oleanane type triterpenoid saponins (1-4) and three known saponins (5-7) were isolated from the whole plant of Clematis lasiandra Maxim. The structures of the four new compounds were elucidated as 3-O-ß-D-ribopyranosyl-(1 â 3)-α-L-rhamnopyranosyl-(1 â 2)-[ß-D-glucopyranosyl-(1 â 4)]-ß-D-xylopyranosyl hederagenin (1), 3-O-ß-D-ribopyranosyl-(1 â 3)-α-L-rhamnopyranosyl-(1â2)-ß-D-xylopyranosyl oleanolic acid 28-O-ß-D-glucopyranosyl ester (2), 3-O-ß-D-ribopyranosyl-(1 â 3)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-xylopyranosyl hederagenin (3) and 3-O-ß-D-ribopyranosyl-(1 â 3)-α-L-rhamnopyranosyl-(1 â 2)-[ß-D-glucopyranosyl-(1â4)]-α-L-arabinopyranosyl hederagenin (4) on the basis of extensive spectroscopic analysis and chemical evidence. Compounds 1-7 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, and all of the evaluated saponins showed significant cytotoxicity to those three tumor cell lines with IC50 in the range from 1.40 to 19.50 µmol/L except for compounds 2 and 6.