ABSTRACT
Two new 19-norbufadienolides (1 and 2) and one new 14,15-epoxy bufadienolide (3) alongside 16 known bufadienolides (4-19) were isolated from Bufonis Venenum that originated from the skin and parotid venom glands of an Asiatic toad (Bufo bufo gargarizans Cantor). The structures of these bufadienolides were elucidated based on the interpretation of their HRESIMS and NMR data. Compound 1, which had a unique peroxide, was established through extensive single-crystal X-ray diffraction. The two 19-norbufadienolides exhibited more potent cardiotonic activity in the isolated toad heart model and lower cytotoxicity against U87, U251, and LN-18 cell lines than other bufadienolides, such as bufalin and bufotalin. The results suggested that 19-norbufadienolides might be more suitable for developing cardiotonic agents with low cytotoxicity.
Subject(s)
Amphibian Venoms/chemistry , Bufanolides/chemistry , Bufo bufo , Cardiotonic Agents/pharmacology , Animals , Bufanolides/isolation & purification , Bufanolides/pharmacology , Cardiotonic Agents/isolation & purification , Cell Line, Tumor , Heart/drug effects , Humans , In Vitro Techniques , Molecular StructureABSTRACT
One new neolignan identified as 2, 3-( trans) -dihydro-2-(4-hydroxy-3-methoxyphenyl) -3-[(beta-D-glucopyranosyloxy) methyl]-7-methoxybenzofuran-5-propenoic acid (1) and five known steroidal glycosides namely torvoside A(2), torvoside C(3), torvoside H(4), solanolactoside A (5), (25S)-6alpha-hydroxy-5alpha-spirostan-3-one-6-0-[alpha-L-rhamnopyranosyl-(1-->3-beta3)-beta-D-D-quinovopyr-anoside] (6) were isolated from the fruits of Solanum torvum. Their structures were elucidated on the basis of 1D, 2D NMR and MS spectroscopic analysis.
Subject(s)
Fruit/chemistry , Lignans/chemistry , Lignans/isolation & purification , Solanum/chemistry , IsomerismABSTRACT
Pterocenoids A-E (1-4), which Pterocenoids A(1) is one novel dimer containing a pyridine monoterpene alkaloid; and Pterocenoids B-E (2-4) are rare arranged non-glycosidic bis-iridoids were isolated from Pterocephlus hookeri. The structures of the compounds were established by 1D and 2D NMR spectroscopy and mass spectrometry. All bis-iridoids isolated from P. hookeri were found to possess secoiridoid/iridoid subtype skeletons. Hence, bis-iridoids can be regarded as the chemotaxonomic markers of P. hookeri. The origins of the new bis-iridoids (1-4) were postulated and their activities of inhibition of the NF-κB pathway were assayed and compounds 1-3 showed moderate activity in inhibiting NF-κB.
Subject(s)
Caprifoliaceae/chemistry , Iridoids/chemistry , NF-kappa B/antagonists & inhibitors , HEK293 Cells , Humans , Iridoids/isolation & purification , Molecular StructureABSTRACT
Two new sulfated sesquiterpenoids, megastigman-7-ene-3, 5, 6, 9-tetrol-3-O-ß-D-6'-sulfonated-glucopyranoside (1) and 3-O-ß-D-6'-sulfonated-glucopyranosyl-6-(3-oxo-2-butenylidenyl)-1, 1, 5-trimethylcyclohexan-5-ol (2), along with one known sesquitepenoid compound icariside B1 (3) were isolated from the whole herb of Petasites tricholobus Franch. Their structures were identified by their chemical and spectroscopic characters. All obtained compounds were tested for their cytotoxicity against four cancer cell lines.
Subject(s)
Petasites/chemistry , Sesquiterpenes/pharmacology , Cell Line, Tumor , Glycosides/isolation & purification , Glycosides/pharmacology , Humans , Norisoprenoids/isolation & purification , Norisoprenoids/pharmacology , Sesquiterpenes/isolation & purificationABSTRACT
To study the chemical constituents of Lysimachia patungensis Hand.-Mazz., silica gel column chromatography, reverse phase ODS column chromatography, MCI and Sephadex LH-20, were used to separate the 95% EtOH extract of the whole plant of Lysimachia patungensis Hand.-Mazz.. The structures of the isolated compounds have been established on the basis of chemical and NMR spectroscopic evidence as well as ESI-MS in some cases. Twelve phenolic compounds were obtained and identified as quercetin-3, 3'-di- O-alpha-L-rhamnoside (1), myricetrin (2), quercitrin (3), rutin (4), 2-hydroxynaringenin-4'-O-glucopyranoside (5), naringenin 7-O-glucopyranoside (6), liquiritin apioside (7), licochalcone B (8), tetrahydroxymethoxy chalcone (9), methyl-p-coumarate (10), 2, 4, 6-trihydroxy acetophenone-2-O-glucopyranoside (11) and vaccihein A (12). Among them, compound 1 is a new compound, and compounds 5, 11 and 12 are isolated from the genus Lysimachia L. for the first time, and the others are isolated from the plant for the first time.
Subject(s)
Phenols/isolation & purification , Plants, Medicinal/chemistry , Primulaceae/chemistry , Quercetin/analogs & derivatives , Chalcones/chemistry , Chalcones/isolation & purification , Cinnamates/chemistry , Cinnamates/isolation & purification , Molecular Structure , Phenols/chemistry , Quercetin/chemistry , Quercetin/isolation & purification , Rutin/chemistry , Rutin/isolation & purificationABSTRACT
Two new lignans (R-biar)-12-angeloyloxy-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7-dibenzo[a,c]cyclooctenol (1) and (R-biar)-12-benzoyloxy-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7-dibenzo[a,c]cyclooctenol (2) were isolated from the stems of Celastrus flagellaris Rupr. Their structures were elucidated on the basis of spectroscopic methods including HR-EI-MS, 1D and 2D NMR, HMQC, NOESY, and CD.
Subject(s)
Celastrus/chemistry , Drugs, Chinese Herbal/isolation & purification , Lignans/isolation & purification , Drugs, Chinese Herbal/chemistry , Lignans/chemistry , Molecular Structure , Plant Stems/chemistryABSTRACT
A new oleanane-type triterpenoid glycoside, 3beta-O-(f-D-xylopyranosyl-(1-->2)-[beta-D-glucopyranosyl (1-->4)-beta-D-glucopyranosyl-(1 -->3)]-beta-D-fucopyranosyl-11, 13(18) diene-olean-23alpha, 28 diol (1), along with three known phenylethyl glycosides (2-4), was isolated from the root of traditional Chinese medicine Scrophularia ningpoensis. Among them, compounds 2 and 3 were obtained from Scrophularia genus for the first time. The structure of compound 1 was elucidated on the basis of spectroscopic method including 1D, 2D NMR and HR-ESI-MS.
