ABSTRACT
Volvalerine A (1), a novel N-containing bisesquiterpenoid derivative with a dihydroisoxazole ring, and its possible biosynthetic precursor, 1-hydroxy-1,11,11-trimethyldecahydrocyclopropane azulene-10-one (2), were isolated from the roots of Valeriana officinalis var. latifolia. Their structures and relative configurations were identified using spectroscopic data and X-ray crystallography. A plausible biosynthetic pathway for 1 is also presented.
Subject(s)
Isoxazoles/chemistry , Sesquiterpenes/chemistry , Triterpenes/chemistry , Valerian/chemistry , Acetylcholinesterase/metabolism , Animals , Isoxazoles/isolation & purification , Molecular Structure , PC12 Cells , Plant Roots/chemistry , Rats , Sesquiterpenes/isolation & purification , Triterpenes/isolation & purificationABSTRACT
Volvalerenol A (1), an unprecedented type of triterpenoid with a 7/12/7 tricyclic ring system, was obtained from the ethanol extracts of the roots of Valeriana hardwickii. The structure and relative configurations were established by comprehensive analysis of MS and NMR spectroscopic data. The possible biogenetic pathway of 1 was also deduced.
Subject(s)
Plant Roots/chemistry , Triterpenes/chemistry , Valerian/chemistry , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
An 8,9-seco-lindenane disesquiterpenoid, chloramultiol G, four eudesmane sesquiterpenoids, ent-(3R)-3-hydroxyatractylenolide III and multistalactones A-C, and four guaiane sesquiterpenoids, (1R,4S,5R,8S,10S)-zedoalactone A and multistalactones D-F, along with 14 known compounds, were isolated from whole plant tissues of Chloranthus multistachys. Their structures were established by extensive NMR experiments in conjunction with mass spectrometry. Except for chloramultiol G, the absolute stereochemistries of the other eight were confirmed by single-crystal X-ray crystallography and CD spectra. Nine compounds were tested for cytotoxicity against five human tumor cell lines and for antifungal activity against four microorganisms in vitro, but all were inactive.
Subject(s)
Magnoliopsida/chemistry , Terpenes/chemistry , Terpenes/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , China , Crystallography, X-Ray , Humans , Magnetic Resonance Spectroscopy , Plant Structures/chemistryABSTRACT
Two new guaiane-type sesquiterpenoids, valerol A (1) and kessyl 3-acetate (2), together with nine known compounds, valeracetate (3), anismol A (4), orientalol C (5), spatulenol (6), 4α,10α-epoxyaromadendrane (7), (+)-8-hydroxypinoresinol (8), pinorespiol (9), pinoresinol 4-O-ß-D-glucopyranoside (10), and 8-hydroxypinoresinol 4'-O-ß-D-glucopyranoside (11) were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1 and 2 were elucidated on the basis of spectroscopic methods (1D- and 2D-NMR, MS, UV, and IR). These compounds were evaluated for inhibitory activity on acetylcholinesterase (AChE) and enhancing activity on nerve growth factor (NGF)-mediated neurite outgrowth in PC12 cells.
Subject(s)
Lignans/chemistry , Lignans/pharmacology , Plants, Medicinal/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Valerian/chemistry , Animals , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/pharmacology , Drug Evaluation, Preclinical , Glucosides/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Nerve Growth Factor/physiology , Neurites/drug effects , PC12 Cells , Plant Roots/chemistry , Rats , Sesquiterpenes, Guaiane/chemistryABSTRACT
Volvalerelactones A and B (1 and 2), two new sesquiterpenoid lactones with an unprecedented 3/7/6 tricyclic ring system, were isolated from the roots of Valeriana officinalis var. latifolia. Their structures and relative configurations were elucidated by spectroscopic data and single-crystal X-ray diffraction crystallography, and the absolute configuration was assigned by computational methods. The possible biosynthetic pathways of 1 and 2 were also proposed.
Subject(s)
Cholinesterase Inhibitors/isolation & purification , Lactones/chemistry , Lactones/isolation & purification , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Valerian/chemistry , Animals , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/pharmacology , Crystallography, X-Ray , Dose-Response Relationship, Drug , Lactones/pharmacology , Molecular Conformation , Molecular Structure , Nerve Growth Factor/drug effects , Nerve Growth Factor/metabolism , Neurites/drug effects , Nuclear Magnetic Resonance, Biomolecular , PC12 Cells , Plant Roots/chemistry , Rats , Sesquiterpenes/pharmacologyABSTRACT
Eight new germacrane-type sesquiterpenoids, volvalerenals A-E (2-6) and volvalerenic acids A-C (7-9), along with four known compounds, were isolated from a chloroform extract of the roots of Valeriana officinalis var. latifolia. The structures and relative configurations of 2-9 were elucidated on the basis of spectroscopic data interpretation. The effects of all compounds isolated on acetylcholinesterase were evaluated.
Subject(s)
Cholinesterase Inhibitors/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Sesquiterpenes, Germacrane/isolation & purification , Valerian/chemistry , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/pharmacology , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Roots/chemistry , Sesquiterpenes, Germacrane/chemistry , Sesquiterpenes, Germacrane/pharmacology , Tacrine/pharmacologyABSTRACT
Six new highly complex lindenane-type sesquiterpenoid dimers, chloramultiols A-F (1-6), along with six known analogues, were isolated from the whole plant of Chloranthus multistachys. The structures of 1-6 were elucidated on the basis of mass spectrometry (MS) and 1D and 2D NMR spectroscopic analysis. Among them, compounds 1 and 6 contain a unique 18-membered macrocyclic triester ring. All compounds isolated were evaluated for the inhibition of the growth of five tumor cell lines.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Magnoliopsida/chemistry , Plants, Medicinal/chemistry , Sesquiterpenes/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Female , HL-60 Cells , Humans , Inhibitory Concentration 50 , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacologyABSTRACT
Two new iridoids, volvaltrates A and B (1 and 2), and three new sesquiterpenoids, E-(-)-3beta,4beta-epoxyvalerenal (3), E-(-)-3beta,4beta-epoxyvalerenyl acetate (4), and mononorvalerenone (5), together with five known iridoids and two known sesquiterpenoids were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1-5 were elucidated by spectroscopic evidence. Compound 1 was an unusual iridoid with an oxygen bridge connecting C-3 and C-10, forming a cage-like structure, and compound 5 was a mononorsesquiterpenoid.
