ABSTRACT
Six new (1-3 and 6-8) and seven known diterpenoids were isolated from the whole plant of Ligularia fischeri. Compound 1 is a new 15,16-dinorerythroxylane-type diterpenoid possessing a C18 skeleton, and 2 is the first example of a 6/6/6/6/5/5-fused hexacyclic ent-kaurane diterpenoid with 19,20-olide and 11,16-epoxy moieties. The structures of the new compounds were elucidated by spectroscopic analysis and chemical methods. The absolute configurations of 1 and 7 were determined by single-crystal X-ray diffraction. Compounds 1-13 were evaluated for their immunosuppressive activity, and 4, 7, and 13 showed moderate inhibitory activities against human B lymphoblast HMy2.CIR cells with IC50 values of 56.3 ± 2.2, 13.3 ± 0.8, and 31.4 ± 0.9 µM, respectively.
Subject(s)
Asteraceae/chemistry , Diterpenes, Kaurane/isolation & purification , Diterpenes, Kaurane/pharmacology , Diterpenes/isolation & purification , Diterpenes/pharmacology , Immunosuppressive Agents/isolation & purification , Immunosuppressive Agents/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Diterpenes/chemistry , Diterpenes, Kaurane/chemistry , Drug Screening Assays, Antitumor , Humans , Inhibitory Concentration 50 , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , X-Ray DiffractionABSTRACT
Two new acylphloroglucinol derivatives, 1-(hexanoyl)phloroglucinol-α-d-arabinopyranoside (1) and 1-(hexanoyl)phloroglucinol-ß-d-glucopyranoside (2), along with two known ones, 1-(acetyl)phloroglucinol-ß-d-glucopyranoside (3) and ethyl 2,4,6-trihydroxybenzoate (4), were isolated from the EtOAc soluble fraction of EtOH extract of Decaspermum gracilentum. The structures of the new compounds were determined by extensive spectroscopic analyses including HRESIMS, 1D and 2D NMR data. Interestingly, all of the compounds showed ABTS(·+) radical scavenging activity with the IC50 values less than 10 µM. Furthermore, compounds 3 and 4 displayed moderate cytotoxicity on human non-small-cell lung carcinoma cell line A549 (IC50 = 50.9 µΜ) and human renal carcinoma cell line 786-O (IC50 = 38.6 µΜ), respectively.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Antioxidants/isolation & purification , Antioxidants/pharmacology , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Myrtaceae/chemistry , Phloroglucinol , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antioxidants/chemistry , Carcinoma, Non-Small-Cell Lung/drug therapy , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Gallic Acid/analogs & derivatives , Gallic Acid/chemistry , Gallic Acid/isolation & purification , Gallic Acid/pharmacology , Glycosides , Humans , Mice , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Phloroglucinol/analogs & derivatives , Phloroglucinol/chemistry , Phloroglucinol/isolation & purification , Phloroglucinol/pharmacology , Plant Roots/chemistryABSTRACT
An unusual aromadendrane-type sesquiterpenoid with a rare hemiketal-containing 10/3 ring system, named vladimuliecin C (1), and one new eudesmane-type sesquiterpenoid, named vladimuliecin D (4), together with four known sesquiterpenoids, were isolated from the roots of Vladimiria muliensis. The structures of these compounds were elucidated by analysis of spectroscopic data. The absolute configuration of 1 was assigned by X-ray diffraction analysis. A possible biosynthetic process for the formation of 1 is proposed. Compound 1 showed moderate cytotoxicity against three human tumor cell lines.
