Diterpenoids from the Wood of Cunninghamia konishii

Abstract

Investigation of the wood of Cunninghamia konishii resulted in the isolation and characterization of one new abietane diterpenoid, (6α,7β)‐7,8‐epoxy‐6‐hydroxyabieta‐9(11),13‐dien‐12‐one (1), and two new labdane diterpenoids, (12R)‐12‐hydroxylabda‐8(17),13(16),14‐trien‐19‐oic acid (2) and (12R)‐12‐hydroxylabda‐8(17),13(16),14‐trien‐18‐oic acid (3). The structures of these new compounds were elucidated by analysis of their spectroscopic data.

Sesquiterpenoids and Diterpenoids from the Wood of Cunninghamia konishii and Their Inhibitory Activities against NO Production

“…Three new sesquiterpenoids, 2α-hydroxy-3,3,6α,9β-tetramethyltricyclo[4,3,2 1,4 ]undecane (1), 11-acetoxyeudesman-4β-ol (4), and 2α,3β-dihydroxy-4β-methyl-6,8,10-cadinatriene (6), four known sesquiterpenoids (2, 3, 5, and 7), together with eight known diterpenoids (8)(9)(10)(11)(12)(13)(14)(15), were isolated from the wood of C. konishii. Among them, four sesquiterpenoids (1, 4, 5, and 6) and eight diterpenoids (8)(9)(10)(11)(12)(13)(14)(15), five of which we reported previously (11)(12)(13)(14)(15), were evaluated for their anti-inflammatory activity and the results showed that compounds 10 and 15 exhibited moderate inhibitory effects on lipopolysaccharides (LPS)-induced nitric oxide production in RAW264.7 cells.…”

“…LPS can significantly increase the level of nitric oxide (NO) in macrophages through activation of iNOS [29]. In this study, the inhibitory activity toward NO production of four sesquiterpenoids (1, 4, 5, and 6) and eight diterpenoids (8)(9)(10)(11)(12)(13)(14)(15) was evaluated by measurement of nitrite/nitrate in LPS-stimulated RAW 264.7 cells. To search for the appropriate concentrations for the above assay, these 12 compounds were first tested their cytotoxic activity against the RAW 264.7 cells, and no significant cytotoxic activities were observed under all tested concentrations (Table 3).…”

“…Among these isolated compounds, four sesquiterpenoids (1, 4, 5, and 6) and eight diterpenoids (8)(9)(10)(11)(12)(13)(14)(15), including five diterpenoids that we reported previously (11)(12)(13)(14)(15), were evaluated for their inhibitory effects on lipopolysaccharides (LPS)-induced nitric oxide production in RAW 264.7 cells. sesquiterpenes, diterpenes, and lignans were found in its wood [2][3][4][5][6][7][8][9][10][11][12], bark [13], leaf [8], and whole plant [14], some of which have been proven to possess anti-inflammatory [10], antifungal [8,9], and cytotoxic [14] activities. As part of our program to search for secondary metabolites from this plant, we had reported the isolation and structure elucidation of 27 diterpenoids and two lignans from the wood of this plant [6,7,[10][11][12]15,16].…”

“…sesquiterpenes, diterpenes, and lignans were found in its wood [2][3][4][5][6][7][8][9][10][11][12], bark [13], leaf [8], and whole plant [14], some of which have been proven to possess anti-inflammatory [10], antifungal [8,9], and cytotoxic [14] activities. As part of our program to search for secondary metabolites from this plant, we had reported the isolation and structure elucidation of 27 diterpenoids and two lignans from the wood of this plant [6,7,[10][11][12]15,16]. In our continuing study of new chemicals from the wood of C. konishii, three new sesquiterpenoids, 2α-hydroxy-3,3,6α,9β-tetramethyltricyclo[4,3,2 1,4 ]undecane (1), 11-acetoxyeudesman-4β-ol (4), and 2α,3β-dihydroxy-4β-methyl-6,8,10-cadinatriene (6), four known sesquiterpenoids (2, 3, 5, and 7), together with three known diterpenoids (8)(9)(10), were isolated ( Figure 1).…”

“…Herein, we reported the extraction, isolation, and structure elucidation of compounds 1, 4, and 6. Among these isolated compounds, four sesquiterpenoids (1, 4, 5, and 6) and eight diterpenoids (8)(9)(10)(11)(12)(13)(14)(15), including five diterpenoids that we reported previously (11)(12)(13)(14)(15), were evaluated for their inhibitory effects on lipopolysaccharides (LPS)-induced nitric oxide production in RAW 264.7 cells. …”