Abstract
The first bicyclic megastigmane glycoside rhododendroside A (1) along with four known megastigmane glycosides (2 – 5) were isolated from the Korean endangered plant Rhododendron brachycarpum. For investigation of the absolute configuration of 1, gauge-invariant atomic orbital (GIAO) NMR chemical shift calculation technology were applied and the accurate stereochemical details were improved by application of DP4 analysis. Consequently, the structure of 1 was defined as (3S,5R,6R)-1,1,5,9-tetramethyl-3-β-D-glucopyranosyloxy-2,3,4,5,-tetrahydro-7 H-chromen-6-ol, named as rhododendroside A. Meanwhile, compounds 1, 2, and 5 exerted vascular protective potential via inhibition of HMGB1-induced pro-inflammatory response in vitro, and improved the mice survival rate to 60, 40, and 40%, respectively, 132h after CLP operation in vivo. These results demonstrate that the active molecules are developable anti-septic lead with mitigating HMGB1-induced vascular pro-inflammatory stimuli.
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