ABSTRACT
Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC(50) value of 113.1 µM. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC(50) values of 0.9, 4.2, and 2.0 µM, respectively. (23R,25R)-3,4-seco-9ßH-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC(50)=14.7 µM).
Subject(s)
Abies/chemistry , Anti-Inflammatory Agents/isolation & purification , Antineoplastic Agents, Phytogenic/isolation & purification , Nitric Oxide/biosynthesis , Plant Extracts/pharmacology , Sesquiterpenes/pharmacology , Triterpenes/pharmacology , Animals , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/therapeutic use , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/therapeutic use , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Inhibitory Concentration 50 , Lipopolysaccharides , Macrophages/drug effects , Macrophages/metabolism , Mice , Molecular Structure , Phytotherapy , Plant Extracts/chemistry , Plant Extracts/therapeutic use , Sesquiterpenes/isolation & purification , Sesquiterpenes/therapeutic use , Triterpenes/isolation & purification , Triterpenes/therapeutic useABSTRACT
Two new, i.e., 1 and 2, and 69 known phenolics were isolated from the aerial parts of Abies nephrolepis. These chemical constituents included 22 lignans, 30 flavonoids, and 19 other phenols. Their structures were determined mainly by analysis of the 1D- and 2D-NMR spectroscopic data. All the 71 isolates were evaluated for their inhibitory activities against lipopolysaccharide (LPS)-induced NO production in RAW 264.7 macrophages. Compound 1 exhibited a potent effect with an IC(50) value of 13.7 µg/ml.
Subject(s)
Abies/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Nitric Oxide/antagonists & inhibitors , Phenols/isolation & purification , Plant Extracts/isolation & purification , Animals , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/toxicity , Cell Line , Cell Survival/drug effects , Macrophages/drug effects , Macrophages/metabolism , Mice , Molecular Structure , Phenols/pharmacology , Phenols/toxicity , Plant Components, Aerial/chemistry , Plant Extracts/pharmacologyABSTRACT
Systematical phytochemical investigations on Abies spectabilis afforded 72 chemical constituents. On the basis of physical and spectroscopic data, including 1D and 2D homo- and heteronuclear NMR experiments (heteronuclear single quantum coherence (HSQC), (1)H-(1)H correlation spectroscopy (COSY), heteronuclear multiple bond connectivity (HMBC), and nuclear Overhauser effect spectroscopy (NOESY)), and by comparison with the literature references, they were identified as 3 triterpenoids, 23 diterpenoids, 1 sesquiterpenoid, 13 flavonoids, 12 lignans, and 20 other components. Among these compounds, three were identified as new including abieta-7,13-diene-12α-methoxy-18-oic acid (1), 7α-methoxy-dehydroabietic acid (2), and 5-hydroxy-6-methyl-7,4'-dimethoxyflavone-8-O-ß-D-glucopyranoside (3). These three new compounds (1-3) and all the known terpenoids (4-28) were tested for cytotoxic activities against four tumor cell lines: A549, COLO-25, QGY-25, and THP-1. However, none of them showed a positive effect (IC50>100 µM).
