ABSTRACT
Investigation of the dried whole plants of Artemisia annua led to the isolation of two new sesquiterpenes, artemanins A (1) and B (2), along with twenty-nine known compounds. The structures of the new compounds were elucidated by spectroscopic and chemical means.
Subject(s)
Artemisia annua/chemistry , Magnetic Resonance Spectroscopy/methods , Plants/chemistry , Sesquiterpenes/chemistry , Molecular StructureABSTRACT
Phytochemical investigation of the dried leaves and twigs of Ligustrum vulgare has led to the isolation of the secoiridoid glucosides, (2''R)- and (2''S)-10-hydroxy-2''-methoxyoleuropeins (1 and 2), and the secoiridoid aglycones, ligustrohemiacetals A (3) and B (4). Their structures were elucidated by spectroscopic and chemical means. Enzymatic hydrolysis of 10-hydroxyoleuropein to the analog of ligustrohemiacetals A and B led to the structural revision of jasmolactones.
Subject(s)
Ligustrum/chemistry , Plant Extracts/chemistry , Hydrolysis , Iridoids/chemistry , Iridoids/isolation & purification , Molecular Structure , Plant Leaves , Plant StemsABSTRACT
Five phenolic glycosides 1-5 and an iridoid glucoside 6 were isolated, together with 22 known compounds, from the dried barks and woods of Strychnosaxillaris. Their structures were determined by application of spectroscopic (NMR, MS) and chemical methodologies.
Subject(s)
Glycosides/chemistry , Iridoids/chemistry , Phenols/chemistry , Strychnos/chemistry , Glycosides/isolation & purification , Iridoids/isolation & purification , Magnetic Resonance Spectroscopy/methods , Magnetic Resonance Spectroscopy/standards , Mass Spectrometry/methods , Molecular Structure , Phenols/isolation & purification , Reference Standards , Species Specificity , StereoisomerismABSTRACT
Three new secoiridoid glucosides, stryspinoside (1) and strychosides A (2) and B (3), were isolated, together with 23 known compounds, from the dried branches of Strychnos spinosa. The structures of the new compounds were determined by spectroscopic means.
Subject(s)
Glucosides/isolation & purification , Iridoids/isolation & purification , Plants, Medicinal/chemistry , Strychnos/chemistry , Glucosides/chemistry , Iridoid Glucosides , Iridoids/chemistry , Japan , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
From the dried roots of Rauwolfia serpentina were isolated five new indole alkaloids, N(b)-methylajmaline (1), N(b)-methylisoajmaline (2), 3-hydroxysarpagine (3), yohimbinic acid (4), isorauhimbinic acid (5), a new iridoid glucoside, 7-epiloganin (6), and a new sucrose derivative, 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (7), together with 20 known compounds. The structures of the new compounds were determined by spectroscopic and chemical means. The inhibitory activities of the selected alkaloids on topoisomerase I and II and their cytotoxicity against the human promyelocytic leukemia (HL-60) cell lines were assessed.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Indole Alkaloids/isolation & purification , Plants, Medicinal/chemistry , Rauwolfia/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Indole Alkaloids/chemistry , Indole Alkaloids/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Roots/chemistry , ThailandABSTRACT
From the dried roots of Neonauclea sessilifolia (Rubiaceae), two new triterpenoid saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-quinovopyranosyl quinovic acid (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-quinovopyranosyl pyrocincholic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (2), were isolated, together with five known saponins. The structures of the new saponins were determined by spectroscopic and chemical means.
Subject(s)
Rubiaceae/chemistry , Saponins/chemistry , Triterpenes/chemistry , Hydrolysis , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Conformation , Plant Roots/chemistry , Saponins/isolation & purification , Spectrophotometry, Infrared , Triterpenes/isolation & purificationABSTRACT
From the dried roots of Neonauclea sessilifolia, two new chromone-secoiridoid glycosides, sessilifoside and 7"-O-beta-D-glucopyranosylsessilifoside, and three novel indole alkaloid glycosides, neonaucleosides A, B, and C, were isolated along with the main known glycosides, 5-hydroxy-2-methylchromone-7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, sweroside, loganin, grandifloroside, and quinovic acid 3 beta-O-beta-D-quinovopyranoside-28-O-beta-D-glucopyranoside. The structures of these new glycosides were determined by spectroscopic and chemical means. Neonaucleoside A and its C-3 epimer were prepared from secologanin and tryptamine.
Subject(s)
Indole Alkaloids/chemistry , Iridoids/chemistry , Rubiaceae/chemistry , Glycosides/chemistry , Glycosides/isolation & purification , Iridoid Glucosides , Iridoids/isolation & purification , Nuclear Magnetic Resonance, Biomolecular , Plant Roots/chemistry , Rubiaceae/classification , Spectrophotometry, Ultraviolet , Stereoisomerism , Tryptamines/chemistryABSTRACT
The effect of a revised Linsmaier-Skoog (LS) medium on betacyanin production was investigated in suspension cultures of table beet (Beta vulgaris L.). The effects of a high iron concentration and low concentration of zinc on betacyanin production were not cumulative. The composition of the new revised medium for high betacyanin production was established by reducing the concentration of inorganic nitrogen (30 mM), modifying the ratio of ammonium to nitrate (1:14), reducing the concentration of zinc (0.0003 mM), and removing copper and cobalt. The revised LS medium enabled the maximum betacyanin yield of 550 mg/l to be obtained from a 14-day culture. This medium promoted the betacyanin production in three types of cell line differing in the betacyanin productivity. The betacyanin productivity (40 mg/l x day) was higher than that quoted in any other previous reports.
Subject(s)
Beta vulgaris/metabolism , Flavonoids/metabolism , Beta vulgaris/drug effects , Bromodeoxyuridine/pharmacology , Cells, Cultured , Cobalt/pharmacology , Copper/pharmacology , Culture Media , Iron/pharmacology , Kinetics , Nitrates/pharmacology , Nitrogen/metabolism , Thymidine/pharmacology , Zinc/pharmacologyABSTRACT
Phytochemical investigation of the dried leaves of Syringa afghanica, has led to the isolation of nine secoiridoid glucosides, safghanosides A-H and 2"-epi-frameroside, as well as an iridoid glucoside, syringafghanoside along with nineteen known compounds. The structures were elucidated by spectroscopic and chemical means.
Subject(s)
Glucosides/chemistry , Oleaceae/chemistry , Pyrans/chemistry , Glucosides/isolation & purification , Iridoids , Magnetic Resonance Spectroscopy , Plant Leaves/chemistry , Pyrans/isolation & purificationABSTRACT
Six new flavonoid glycosides, quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (1), quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (2), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (3), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (4), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-cis-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (5), and isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-feruloyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (6), were isolated from the dried aerial parts of Rhazya orientalis. The structures of 1-6 were determined by spectroscopic and chemical means.