Abstract
Stauntonia hexaphylla (Lardizabalaceae) has been used as a traditional herbal medicine in Korea and China for its anti-inflammatory and analgesic properties. As part of a bioprospecting program aimed at the discovery of new bioactive compounds from Korean medicinal plants, a phytochemical study of S. hexaphylla leaves was carried out leading to isolation of two oleanane-type triterpene saponins, 3-O-[β-d-glucopyranosyl (1→2)-α-l-arabinopyranosyl] oleanolic acid-28-O-[β-d-glucopyranosyl (1→6)-β-d-glucopyranosyl] ester (1) and 3-O-α-l-arabinopyranosyl oleanolic acid-28-O-[β-d-glucopyranosyl (1→6)-β-d-glucopyranosyl] ester (2). Their structures were established unambiguously by spectroscopic methods such as one- and two-dimensional nuclear magnetic resonance and infrared spectroscopies, high-resolution electrospray ionization mass spectrometry and chemical reactions. Their anti-inflammatory activities were examined for the first time with an animal model for the macrophage-mediated inflammatory response as well as a cell-based assay using an established macrophage cell line (RAW 264.7) in vitro. Together, it was concluded that the saponin constituents, when they were orally administered, exerted much more potent activities in vivo than their sapogenin core even though both the saponins and the sapogenin molecule inhibited the RAW 264.7 cell activation comparably well in vitro. These results imply that saponins from S. hexaphylla leaves have a definite advantage in the development of oral medications for the control of inflammatory responses.
Highlights
Immunity is the body’s defense system against infectious agents or tumor formation.Proper magnitudes and durations of the responses are, critical for the health of the body as unnecessarily overactive or long-lasting immune responses can cause various immunological disorders compromising the quality of life
Diverse proinflammatory cytokines and mediators such as nitric oxide (NO), and tumor necrosis factor α (TNF-α) are mainly released by activated macrophages, which emerge in response to exogenous stress or endogenous signals such as external pathogen and damage-associated molecular patterns (DAMPs) [3]
The molecular formula of compound 1 was deduced as C53 H86 O22 based on the electrospray ionization mass spectrometry (ESI MS) ion peak at m/z 1092.5 [M + NH4 ]+
Summary
Immunity is the body’s defense system against infectious agents or tumor formation.Proper magnitudes and durations of the responses are, critical for the health of the body as unnecessarily overactive or long-lasting immune responses can cause various immunological disorders compromising the quality of life. While macrophages play a critical role in defense against bacterial infections, they can cause inflammatory disorders when their responses persist. Diverse proinflammatory cytokines and mediators such as nitric oxide (NO), and tumor necrosis factor α (TNF-α) are mainly released by activated macrophages, which emerge in response to exogenous stress or endogenous signals such as external pathogen and damage-associated molecular patterns (DAMPs) [3]. These are key mediators to induce inflammatory disorders and may have potential as the therapeutic targets [4]
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