Staminane- and Isopimarane-Type Diterpenes from Orthosiphon stamineus of Taiwan and Their Nitric Oxide Inhibitory Activity

From the MeOH extract of Taiwanese Orthosiphon stamineus, two new staminane-type diterpenes, staminols C (1) and D (2), and three new isopimarane-type diterpenes, orthosiphonone C (3) and D (4) and 14-deoxo-14-O-acetylorthosiphol Y (5), have been isolated together with 16 known diterpenes, orthosiphols A, B, D, K, M, N, O, X, and Y, nororthosiphonolide A, neoorthosiphol B, orthosiphonone A, secoorthosiphols B and C, 3-O-deacetylorthosiphol I, and 2-O-deacetylorthosiphol J. Their structures were determined on the basis of the spectroscopic data. All the newly isolated diterpenes exhibited dose-dependent inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophage-like J774.1 cells, and 2-O-deacetylorthosiphonone A showed the most potent activity, with an IC₅₀ value of 35.0 μM, comparable to that of the positive control N^G-monomethyl-L-arginine (L-NMMA; IC₅₀, 35.7 μM).