Abietane Diterpenoids from the Barks of Cryptomeria japonica

Abstract

From the bark of Cryptomeria japonica were isolated sugikurojins I (1) and J (2), and an abietane derivative (3) was obtained for the first time as a natural product. These structures were elucidated primarily through extensive NMR experiments. Sugikurojin I (1) has a unique skeleton incorporating an abietane diterpene and a 1,10-secocadinane sesquiterpene. Sugikurojin J (2) is a peroxyester of hydroxyabietane diterpene and isopimarane acid diterpene. Compound 3 was p-quinone acid, which occurred by cleavage between C-7 and C-8 of sugiol; it was deduced to [4-isopropyl-1(S),3,3-trimethyl-3,6-dioxo-bicyclohexyl-1,4-dien-2(R)-yl]-acetic acid. Also obtained in this investigation were three known diterpenes (4-6).

Novel Abietane Diterpenoids and Aromatic Compounds from Cladonia rangiferina and Their Antimicrobial Activity against Antibiotics Resistant Bacteria

“…20) Among those tested, compounds 1 and 2 showed mild activity. Depside derivatives, (14, 15) and benzofuran derivatives, (16,17) showed good correlation activities against MRSA and VRE strains (Table 2).…”

A Quinone Isolated from the Nest of Vespa simillima and Its Growth-Inhibitory Effect on Rat Liver Cancer Cells

“…18) In these woods, a variety of biologically active abietane-type and two pimarane-type diterpenoids have been isolated. [22][23][24][25][26][27][28][29][30][31] These reports are indicative that yellow hornets utilize these woods not only for building material for the nest but also as a chemical tool to protect the nest from microorganisms.…”

“…[22][23][24][25][26][27][28][29][30][31] However, these molecular mechanisms have not been well examined. Ross reported that an anticancer quinone classified as an abietane terpenoid exhibited apoptosis, based on morphological changes in the cancer cells.…”

Bioactive Dimeric Abietanoid Peroxides from the Bark of Cryptomeria japonica

“…This plant has been cultivated as an important coniferous tree species in Taiwan since 1906. Phytochemical investigations indicated the presence of monoterpenoids, sesquiterpenoids, and diterpenoids [2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24] in the leaves, heartwood, and barks of C. japonica . The crude extracts and secondary metabolites from this species exhibited a wide array of bioactivities including cytotoxic [23], antifungal [24], antibacterial [23], antioxidant [25], anti-inflammatory [26], and insect antifeedant [27] and repellent [18] properties.…”