ABSTRACT
Twenty-four aromatic metabolites belonging to cyanogenins, lignans, flavonoids, and phenolic glycosides were obtained from Sambucus nigra. Structures were determined on the basis of their spectroscopic features. Two compounds have been isolated and identified as (2S)-2-O-beta-D-glucopyranosyl-2-hydroxyphenylacetic acid and benzyl 2-O-beta-D-glucopyranosyl-2,6-dihydroxybenzoate. All the compounds have been assayed on dicotyledons Lactuca sativa (lettuce) and Raphanus sativus (radish) and monocotyledon Allium cepa (onion) to test their stimulatory or inhibitory effects on seed germination and radicle elongation. Cyanogenins have a mainly inhibiting effect while lignans stimulate the growth. Some compounds show different effects on dicotyledons and monocotyledons.
Subject(s)
Glucosides/isolation & purification , Hydroxybenzoates/isolation & purification , Magnoliopsida/chemistry , Phenylacetates/isolation & purification , Glucosides/chemistry , Hydroxybenzoates/chemistry , Molecular Structure , Phenylacetates/chemistry , Plant Leaves/chemistry , Spectrum AnalysisABSTRACT
Ten flavone glycosides have been isolated and identified in aerial parts of alfalfa. These included six tricin, one 3'-O-methyltricetin, and three chrysoeriol glycosides. Most of these compounds were acylated with ferulic, coumaric, or sinapic acids, and acylation occurred on the terminal glucuronic acid. Eight of these compounds, including 7-O-beta-D-glucuronopyranosyl-3'-O-methyltricetin, 7-O-beta-D-glucuronopyranosyl-4'-O-beta-D-glucuronopyranosidechrysoeriol, 7-O-[2'-O-feruloyl-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]chrysoeriol, 7-O-[2'-O-feruloyl-[beta-D-glucuronopyranosyl(1-->3)]-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]chrysoeriol, 7-O-[2'-O-sinapoyl-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, 7-O-[2'-O- feruloyl-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, 7-O-[2'-O-p-coumaroyl-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, and 7-O-[2'-O-feruloyl-[beta-D-glucuronopyranosyl(1-->3)]-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, have not been reported previously in the plant kingdom. Two previously identified alfalfa flavones, 7-O-beta-D-glucuronopyranosidetricin and 7-O-[beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, were also isolated.
Subject(s)
Flavonoids/isolation & purification , Glycosides/isolation & purification , Medicago/chemistry , Carbohydrate Conformation , Flavones , Flavonoids/chemistry , Glycosides/chemistry , Spectrum AnalysisABSTRACT
Three flavones, including 4'-O-[2'-O-E-feruloyl-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]apigenin, 7-O-beta-D-glucuronopyranosyl-4'-O-[2'-O-E-feruloyl-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]apigenin and 7-O-beta-D-glucuronopyranosyl-4'-O-[2'-O-p-E-coumaroyl-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]apigenin have been identified in alfalfa var. Artal. The known flavone 7-O-[2-O-E-feruloyl-[beta-D-glucuronopyranosyl(1-->3)]-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucurono-pyranoside] apigenin was also isolated. The structures of these compounds were deduced on the basis of their spectral data.
Subject(s)
Flavonoids/isolation & purification , Glycosides/isolation & purification , Medicago sativa/chemistry , Acylation , Apigenin , Chromatography, High Pressure Liquid , Flavonoids/chemistry , Glycosides/chemistry , Magnetic Resonance Spectroscopy , Spectrometry, Mass, Fast Atom BombardmentABSTRACT
Four new metabolites with carotane skeletons, trichocaranes A (1), B (2), C (3), and D (4), were isolated from Trichoderma virens and their structures established by the interpretation of NMR and mass spectroscopic data. The trichocaranes significantly inhibited the growth of etiolated wheat coleoptiles: 40% at 10(-4) M with 1 and 2 and 86% at 10(-3) M with 3.
Subject(s)
Sesquiterpenes/pharmacology , Trichoderma/chemistry , Triticum/drug effects , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Triticum/growth & developmentABSTRACT
A collection of 11 natural and synthetic podolactones have been tested as allelochemicals in a range between 10(-4) and 10(-9) M, and their potential use as natural herbicide models is discussed. Their effects on the germination and growth of the dicots Lactuca sativa (cv. Nigra and cv. Roman), Lepidium sativum, and Lycopersicon esculentum and the monocots Allium cepa, Hordeum vulgare, and Triticum aestivum as standard target species have been studied. An important inhibitory effect on the germination and growth of all tested species (average = 90%) was produced by compounds 9-11 at 10(-4) M. The specific structural requirements related to their activities are studied. On the basis of these results, their use as potential natural herbicide models is proposed.
Subject(s)
Insecticides/chemistry , Terpenes/chemistry , Herbicides/pharmacology , Insecticides/pharmacology , Models, Chemical , Plants/drug effects , Structure-Activity Relationship , Sulfonylurea Compounds/pharmacology , Terpenes/pharmacologyABSTRACT
The structures of four new, naturally occurring bioactive spiroditerpenoids, (+)-breviones B, C, D, and E, potential allelopathic agents, have been determined from extracts of semisolid fermented Penicillium brevicompactum Dierckx. The structures display the novel breviane spiroditerpenoid skeleton. Structure elucidation was performed by chemical transformations and by homo- and heteronuclear 2D-NMR spectral data. On the basis of combined studies of the theoretical conformations and NOEDIFF data, their relative stereochemistry is proposed. A mixed biogenesis for this novel family of spiroditerpenoids is tendered. The levels of activity shown by breviones B, C, and E in the etiolated wheat coleoptiles bioassay, especially breviones E (100% inhibition) and C (80% inhibition) both at 10(-4) M, suggest them as lead compounds for new agrochemicals.
