ABSTRACT
Saponins with an aldehyde function bound at C-4 from different plant origins increase the cytotoxicity of the lectin agrostin by enhancing its penetration through the cell membrane. Experiments with different pure saponins in combination with agrostin showed that also the glycosidic part of acidic bisdesmosidic saponins especially the oligosaccharidic ester chain at C-28 plays an important role in the potentiation of agrostin's cytotoxicity as result of an interaction between saponins and lectins at the cell membrane.
Subject(s)
Plant Proteins/toxicity , Saponins/chemistry , Saponins/pharmacology , Antineoplastic Agents/metabolism , Antineoplastic Agents/toxicity , Cell Line, Tumor , Humans , Molecular Structure , Plant Proteins/metabolism , Ribosome Inactivating Proteins, Type 1 , Structure-Activity RelationshipABSTRACT
A novel triterpene saponin, 3-Osulfate-gypsogenic acid-23-O-beta-D-4-O-sulfate-glucopyranoside (junceoside D), has been isolated from the roots of Arenaria juncea. The structure was characterized mainly by a combination of 2D-NMR techniques, mass spectrometry and chemical methods.
Subject(s)
Caryophyllaceae/chemistry , Saponins/chemistry , Triterpenes/chemistry , Magnetic Resonance Spectroscopy , Plant Extracts , Plant Roots/chemistry , Saponins/isolation & purification , Saponins/pharmacology , Spectrometry, Mass, Electrospray Ionization , Spectrometry, Mass, Fast Atom Bombardment , Triterpenes/pharmacologyABSTRACT
Three novel triterpenoid saponins, junceosides A (1), B (2), and C (3), together with two known saponins have been isolated from the roots of Arenaria juncea. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-glucopyranosyl(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (1), 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and 3-O-beta-D-xylopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (3).
Subject(s)
Caryophyllaceae/chemistry , Drugs, Chinese Herbal/isolation & purification , Oleanolic Acid/analogs & derivatives , Plants, Medicinal/chemistry , Saponins/isolation & purification , Triterpenes/isolation & purification , Chemical Phenomena , Chemistry, Physical , Chromatography, Thin Layer , Drugs, Chinese Herbal/chemistry , Hydrolysis , Molecular Structure , Plant Roots/chemistry , Saponins/chemistry , Spectrophotometry, Infrared , Triterpenes/chemistryABSTRACT
Two novel triterpenoid saponins (1 and 2) have been isolated from the roots of Acanthophyllum squarrosum. The structures were established mainly by a combination of 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-be ta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3 )-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L- rhamnopyranosyl-(1-->3)]-beta-D-fucopyranoside (1) and 3-O-beta-D-glucopyranosylgypsogenin-28-O-alpha-L-rhamnopyranosyl-( 1-- >2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6 )]- beta-D-glucopyranoside (2). Compound 1 showed a moderate concentration-dependent immunomodulatory effect in an in vitro lymphocyte proliferation assay.