Two new sesquarterpenoids from the bark of Cryptomeria japonica

Terpenoids of the Swamp Cypress Subfamily (Taxodioideae), Cupressaceae, an Overview by GC-MS

“…The diterpenoid constituents of Cryptomeria japonica and Taxodium distichum have been studied more extensively [24,25,26,27,28,29,31,32,33,34,35,38,39,40,41,42,48] and references therein]. However, none of these earlier studies reported the natural product compositions of the total resin/plant extracts, but instead the mixtures were separated by liquid or high-pressure liquid chromatography (LC or HPLC), followed by structure determination of each compound by NMR, HRMS for elemental composition, and sometimes MS (underivatized by direct insertion probe).…”

“…The identification of cymenylferruginol ( a26 ), a triterpenoid like the chamaecydins, in both the extant and fossil resins is of interest because natural product chemists are identifying numerous dimer terpenoids, i.e., mono-to-diterpenoid, sesqui-to-diterpenoid and diterpenoid dimers, in extant plants [25,26,36,41,48]. Therefore, the formation mechanism is for example ferruginol reacting at C-7 with cymene to produce 7-cymenylferruginol, 6-deoxotaxodione reacting at C-7 and C-14 with sabinene or thujene to form chamaecydin, cadinols reacting with ferruginol at C-7 to yield the various sesquaterpenoids, or peroxidation of ferruginol to dimers [26,41,48,72,73]. Some of these natural products, if adequately concentrated in the extant biomass, may become preserved as tracers in the geological record, as for example cymenylferruginol reported here.…”

“…Structure determinations and pharmacological potential studies of resin terpenoids isolated and purified from species of the Taxodioideae subfamily have been reported by numerous chemists and pharmacologists [24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42]. However, the connection of the known natural products isolated from these conifers with their application as tracers in other interdisciplinary sciences has been limited [7,8,14,43].…”

New Abietane-type Diterpenoids from the Bark of Cryptomeria japonica

“…A variety of biological activities including cytotoxic [23], antifungal [24], antibacterial [25], antioxidant [26], anti-inflammatory [27], and insect antifeedant [28] and repellent [29] properties have been reported for the crude extracts or secondary metabolites from this species. While searching for the new chemical ingredients of the bark of C. japonica, we have already reported the isolation of a cytotoxic sesquarterpene (C 35 ), cryptotrione, with an unprecedented skeleton possessing a conjugated abietane and cadinane [30], ten abietane-type diterpenoids [31][32][33], and two sesquarterpenoids [34]. In this report, we describe the isolation and structure elucidation of two new abietane-type diterpenoids (Figure 1).…”

Bioactive Dimeric Abietanoid Peroxides from the Bark of Cryptomeria 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. While searching for bioactive chemical ingredients of the bark of C. japonica , we have already reported the isolation of three sesquarterpenoids [28,29] and ten abietane-type diterpenoids [30,31,32]. Herein, the isolation and structure elucidation of three new dimeric abietane-type diterpenoids are described as well as their inhibitory activity towards xanthine oxidase and angiotensin-converting enzymes.…”