ABSTRACT
Two new cerebrosides, ferocerebrosides A (1) [(2S,3R,4E,8E,2'R)-1-O-(beta-glucopyranosyl)-N-(2'-hydroxydocosanoyl)-4,8-sphingadienine] and B (2) [(2S,3R,4E,8E,2'R)-1-O-(beta-glucopyranosyl)-N-(2'-hydroxytetracosanoyl)-4,8-sphingadienine], two new tocopherol trimers, ferotocotrimers C (5) and D (6), and two known tocopherol trimers, IVb (3) and IVa (4), were isolated from the seeds of Euryale ferox. Their structures were determined on the basis of spectroscopic data, especially 1D and 2D NMR experiments. Compounds 1 and 2 showed cytotoxicity in the brine shrimp lethality bioassay, with LC50 values of 0.17 and 0.20 mM, respectively.
Subject(s)
Artemia/drug effects , Cerebrosides/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Nymphaeaceae/chemistry , Plants, Medicinal/chemistry , Tocopherols/isolation & purification , Animals , Cerebrosides/chemistry , Cerebrosides/pharmacology , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Molecular Structure , Seeds/chemistry , Tocopherols/chemistry , Tocopherols/pharmacologyABSTRACT
Four oleanane-type triterpenes, 3alpha,21beta,22alpha-trihydroxy-11,13(18)-oleanadien-28-oic acid (1), 3-epi-papyriogenin C (2), 21-O-acetyl-21-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid (3) and 3beta-hydroxy-21-oxo-11,13(18)-oleanadien-28-oic acid methyl ester (4), together with four known triterpenes, were isolated from Tetrapanax papyriferus (Hook) K. Koch. Papyriogenin A (8) exhibited anti-HIV activity and low cytotoxicity in acutely infected H9 lymphocytes. Their structures were determined by analysis of spectroscopic data, including by 1D and 2D NMR.
Subject(s)
Apiaceae/chemistry , Flowers/chemistry , Oleanolic Acid/analogs & derivatives , Plant Leaves/chemistry , Seeds/chemistry , Animals , Anti-HIV Agents/chemistry , Anti-HIV Agents/isolation & purification , Anti-HIV Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Artemia/drug effects , Humans , Lymphocytes/drug effects , Magnetic Resonance Spectroscopy , Medicine, Chinese Traditional , Oleanolic Acid/chemistry , Oleanolic Acid/isolation & purification , Oleanolic Acid/pharmacology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , TaiwanABSTRACT
Two new flavonoids, kaempferol 7-O-(2-E-p-coumaroyl-alpha-l-rhamnoside) (1) and kaempferol 7-O-(2,3-di-E-p-coumaroyl-alpha-l-rhamnoside) (2), together with 10 known compounds were isolated from the flowers and fruit of Tetrapanax papyriferus. Compounds 1 and 2 showed cytotoxicity by brine shrimp lethality bioassay with LC(50) values of 0.57 and 0.40 mM, respectively.
Subject(s)
Araliaceae/chemistry , Artemia/drug effects , Benzene Derivatives/isolation & purification , Flavonoids/isolation & purification , Plants, Medicinal/chemistry , Animals , Benzene Derivatives/chemistry , Benzene Derivatives/toxicity , Flavonoids/chemistry , Flavonoids/toxicity , Flowers/chemistry , Fruit/chemistry , Kaempferols , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , TaiwanABSTRACT
Four flavonoids including (2S)-3',4'-methylenedioxy-5,7-dimethoxyflavan and hispidulin 7-(6-E-p-coumaroyl-beta-D-glucopyranoside), and one tocopherol were isolated from the capitulum of Eriocaulon buergerianum KOERN. Their structures were established by spectral and chemical evidence.
