Yu-Chang Chen

Isobutylamides from the fruit of Zanthoxylum integrifoliolum

Abstract Investigation of the fruit of Zanthoxylum integrifoliolum led to the isolation of three new isobutylamides, lanyuamide I–III and six known isobutylamides, tetrahydrobungeanool, γ-sanshool, hydroxy γ-sanshool, mixture of (2E,4E,8Z,11E)- and (2E,4E,8Z,11Z)-2′-hydroxy-N-isobutyl-2,4,8,11-tetradecatetraenamide and hazaleamide which was mixed with lanyuamide III. These amides were all with a (2E,4E)-dienamide moiety and their structures were elucidated on the basis of spectral analyses.

Anti-inflammatory lanostanoids and lactone derivatives from Antrodia camphorata.

Four new lanostanoids, ethyl lucidenate A (1), ethyl lucidenate F (2), 15-O-acetylganolucidate A (3), and 3,11,15,23-tetraoxo-27ξ-lanosta-8,16-dien-26-oic acid (4), and two new lactone derivatives, 5-hydroxy-5-(methoxymethyl)-4-methylfuran-2(5H)-one (5) and 3-(4-methoxy-2-oxo-2H-pyran-6-yl)propanoic acid (6), together with four known compounds, 11α-hydroxy-3,7-dioxolanost-8,24(E)-dien-26- oic acid (7), 3,7,11-trioxo-5α-lanosta-8,24(E)-dien-26-oic acid (8), methyl 3,7,11,12,15,23-hexaoxo-5α-lanost-8-en-26-oate (9), and ethyl 3,7,11,12,15,23-hexaoxo-5α-lanost-8-en-26-oate (10), were characterized from Antrodia camphorata. The structures of these new compounds were determined by analysis of their spectroscopic data, including 1D and 2D NMR experiments. Ten components were evaluated for anti-inflammatory activity by examining their effect on LPS-iNOS-dependent NO production in murine macrophage (RAW 264.7) cells. Among them, compounds 1, 3, 7, 8, 9, and 10 significantly suppressed the NO concentration in LPS-treated RAW 264.7 cells with IC50 values ≤ 10 μM.

Diterpenoids with Anti-Inflammatory Activity from the Wood of Cunninghamia konishii

Two new diterpenoids, konishone (1) and 3β-hydroxy-5,6-dehydrosugiol (2), along with three known diterpenoids—hinokiol (3), sugiol (4), and 12-hydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial (5)—were isolated from the wood of Cunninghamia konishii. Compound 1 is a novel skeleton of the 7,20-dinorabietane-type diterpene. In addition, when RAW264.7 macrophages were treated with different concentrations of compounds 1, 3, and 5 together with LPS, a significant concentration-dependent inhibition of NO production was detected. The IC50 values for inhibition of nitrite production of compounds 1, 3, and 5 were about 9.8 ± 0.7, 7.9 ± 0.9, and 9.3 ± 1.3 μg/mL, respectively. This study presents the potential utilization of compounds 1, 3, and 5, as lead compounds for the development of anti-inflammatory drugs.

A New Butanolide Compound from the Aerial Part of Lindera akoensis with Anti-inflammatory Activity

A new butanolide, 3β-((E)-dodec-1-enyl)-4β-hydroxy-5β-methyldihydrofuran-2-one (1) and four known butanolides: Akolactone A (2), (3Z,4α,5β)-3-(dodec-11-enylidene)-4-hydroxy-5-methylbutalactone (3), (3E,4α,5β)-3-(dodec-11-enylidene)-4-hydroxy-5-methylbutalactone (4) and dihydroisoobtusilactone (5), were isolated from the aerial parts of Lindera akoensis. These butanolides showed in vitro anti-inflammatory activity decrease the LPS-stimulated production of nitrite in RAW264.7 cell, with IC50 values of 1.4–179.9 μM.