Six pentacyclic triterpenoid saponins, named antoniosides E-J along with two known alkaloids, were isolated from the leaves of Antonia ovata. Their structures were determined by the extensive use of 1D and 2D-NMR experiments along with HRESIMS analysis and acid hydrolysis. All isolated saponins contained the same pentasaccharide chain: 3-O-[β-D-glucopyranosyl-(1→2)]-[β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl(1→6)]-β-D-glucopyranoside, linked at C-3 of esterified derivatives of polyhydroxyoleanene triterpenoids (theasapogenol A and 15α-hydroxy-theasapogenol A). Isolated compounds were evaluated for their cytotoxic activity against KB cell line by a WST-1 assay, and the IC(50) values ranged from 3.3 to 5.3 μM.
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Triterpene saponins from Antonia ovata leaves.
Phytochemistry
May 2012
Laboratoire de Pharmacognosie, Institut de Chimie Moléculaire de Reims, UMR CNRS 6229, IFR 53 Biomolécules, Bâtiment 18, BP 1039, 51687 Reims cedex 2, France.
Six pentacyclic triterpenoid saponins, named antoniosides E-J along with two known alkaloids, were isolated from the leaves of Antonia ovata. Their structures were determined by the extensive use of 1D and 2D-NMR experiments along with HRESIMS analysis and acid hydrolysis. All isolated saponins contained the same pentasaccharide chain: 3-O-[β-D-glucopyranosyl-(1→2)]-[β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl(1→6)]-β-D-glucopyranoside, linked at C-3 of esterified derivatives of polyhydroxyoleanene triterpenoids (theasapogenol A and 15α-hydroxy-theasapogenol A).
View Article and Find Full Text PDFCytotoxic triterpenoid saponins from the stem bark of Antonia ovata.
Phytochemistry
March 2010
Laboratoire de Pharmacognosie, Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, IFR 53 Biomolécules, Bâtiment 18, BP 1039, 51687 Reims Cedex 2, France.
Phytochemical investigation of the MeOH extract of the stem bark of Antonia ovata led to the isolation of four triterpenoid saponins, along with eleven known compounds. Their structures were established by extensive 1D and 2D NMR, as well as HR-MS analysis and acid hydrolysis. All isolated saponins contained the same tetrasaccharide chain O-beta-d-xylopyranosyl-(1-->2)-O-beta-d-glucopyranosyl-(1-->3)-O-[beta-d-glucopyranosyl-(1-->2)]-beta-d-glucuropyranoside linked to C-3 of esterified derivatives of R(1)-barrigenol, A(1)-barrigenol, barringtogenol C, or camelliagenin.
View Article and Find Full Text PDFPreliminary assays indicate that Antonia ovata (Loganiaceae) and Derris amazonica (Papilionaceae), ichthyotoxic plants used for fishing in Roraima, Brazil, have an insecticide effect on Lutzomyia longipalpis (Diptera: Psychodidae: Phlebotominae).
Mem Inst Oswaldo Cruz
July 2002
Núcleo Avançado de Vetores, Instituto Oswaldo Cruz, Fiocruz, Rio de Janeiro, RJ, Brasil.
Laboratory-reared Lutzomyia longipalpis (Lutz and Neiva 1912) was tested with extracts of two ichthyotoxic plants, known as timbós, used as fishing poison in the Amazon. Phlebotomines, L. longipalpis, and plants, Antonia ovata and Derris amazonica, were collected in the Raposa-Serra do Sol Indian Reserve, a focus of visceral leishmaniasis in the State of Roraima, Brazil.
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