Jezananals A and B: two novel skeletal triterpene aldehydes from the stem bark of Picea jezoensis var. jezoensis

Hybrids of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) and various anti-oxidants as cancer chemopreventive agents

“…Compounds 15 and 16 are conjugates of one molecule of 1 or 2 and one molecule of quercetin using succinic acid as linker, and 17 (IC 50 ¼ 370) and 18 (IC 50 ¼ 375) are conjugates of one molecule of 1 or 2 and one molecule of baicalein using succinic acid as linker. Compounds In our past work, we found that the inhibitory effects on EBV-EA induction by TPA correlated well with the anti-tumor promoting activity in vivo [5][6][7][8]. Among the 22 conjugates, we selected 15 and 16 to examine their effects on the in vivo two-stage mouse skin carcinogenesis using mouse skin papillomas induced by DMBA as an initiator and TPA as a promoter.…”

“…In our fervent search for biologically active constituents from natural sources, we previously reported several serratane-type triterpenoids that show significant anti-tumor promoting activities in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and 12-O-tetradecanoylphorbol-13-acetate (TPA) as a promoter. These include 3a-methoxyserrat-14-en-21b-ol (1) [5], 13a,14a-epoxy-3b-methoxyserratan-21b-ol and 21a-hydroxy-3b-methoxyserrat-14-en-29-al [6], serrat-14-en-3b,21b-diol [7], and 14b,15b-epoxy-3b-methoxyserratan-21b-ol [8], which were isolated from the bark of Picea jezoensis (Sieb. et Zucc) Carr.…”

“…3a-Methoxyserrat-14-en-21b-ol (1) and 3b-methoxyserrat-14-en-21b-ol (2) and their curcumin, kojic acid, quercetin, and baicalein conjugates(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18).…”

Cancer Chemopreventive Activity of Oleanane‐Type Triterpenoids from the Stem Bark of Betula ermanii

“…Natural products from plants and their synthetic analogs are expected to play an important role in creating new chemopreventive agents [1] [2]. In the course of our search for biologically active constituents from the cones, bark, and leaves of trees that are treated as waste in the forestry industry, we found that several triterpenoids and diterpenoids, such as abiesenonic acid methyl ester, a chemical derivative of abieslactone [3], 13a,14a-epoxy-3b-methoxyserratan-21b-ol [4], serrat-14-ene3b,21b-diol [5], 14b,15b-epoxy-3b-methoxyserratan-21b-ol [6], 15,16-bisnor-13-oxolabd-8(17)-en-19-oic acid [7], and (11E,13E)-15-oxolabda-8(17),11,13-trien-19-oic acid [8], which were isolated from the stem bark of Picea jezoensis Carr. var.…”

“…In our search for antitumor-promoting activity of triterpenoids from natural sources, we examined the constituents of the stem bark of B. ermanii and isolated three known oleanane-type triterpenoids, i.e., 3b-acetoxy-12a-hydroxyoleanan-13b,28-olide (1), 3b-acetoxy-11a,12a-epoxyoleanan-13b,28-olide (2), and b-amyrin acetate (3), four known lupane-type triterpenoids, i.e., 3-oxolup-20(29)-en-28-oic acid (4), lupeol (5), betulin (6), and betulinic acid (7), and a known phytosterol, b-sitosterol (8).…”