Chemical structures and antimutagenic effects of unusual oximes from the peels of Citrus limon

Isolation and structure elucidation of constituents of Citrus limon, Isodon japonicus, and Lansium domesticum as the cancer prevention agents

“…Based on these studies, we searched for antimutagenic materials derived from foods. In the course of this study, we found using the Ames test that the methanolic (MeOH) extracts of C. limon [4,5], aerial parts of I. japonicus [6], and leaves of L. domesticum [7,8] showed antimutagenic effects against Trp-P-1 and PhIP. Therefore, we directed our efforts toward the isolation of their constituents and evaluation of the antimutagenic effects of the isolated constituents using the Ames test and in vivo micronucleus test.…”

“…The absolute stereochemistries of wakayamalimonol A (1) and B (2) were determined by the modified Mosher's method. In addition, for the identification of the chemical structure and bioassay, wakayamalimonols A (1), B (2) and limonoxime I (21) were synthesized (Scheme 1) [4,5].…”

“…The antibacterial (19) at low or high dose (0.02% or 0.04%, w/w) were given ad libitum. b Normal or sample feeds that included lansionic acid (53) at low or high dose (0.03% or 0.06%, w/w) were given ad libitum [4,8] activity of tested compounds against the S. typhimurium TA98 strain were tested using nutrient agar containing NaCl and all compounds showed weak [44: 23.2% inhibition at 400 nmol/plate, 54: 23.0% inhibition at 400 nmol/plate] or no (other compounds: < 5.0% inhibition at highest concentration in Table 1) antibacterial activities [4][5][6][7][8].…”

“…Antimutagenic activity of coumarins (1 and 2), limonoids(19 and 20), oxime and synthetic intermediates (21, 21a, and 21b), ent-kaurane diterpenoids(25, 26, 29, 30, and 33), and onoceranoid-type triterpenoids(44,(46)(47)(48)(49) 53, and 54) against Trp-P-1 (0.04 μg/plate) using the Ames test[4][5][6][7][8] a Inhibition % (Based on number of revertant colonies)…”

Structures and Antimutagenic Effects of Onoceranoid-Type Triterpenoids from the Leaves of Lansium domesticum

“…A number of onoceranoid-type triterpenoids have been reported from L. domesticum peels. − Previous reports have described the bioactivities of these triterpenoids, such as toxicity against brine shrimp, inhibition of leukotriene D4-induced contraction of guinea pig ileum, cytotoxic activity, and antibacterial activity against Gram-positive bacteria . As part of an ongoing research program for the discovery of new antimutagenic agents, our group has reported the structures and antimutagenic effects of ent -kaurane diterpenoids, coumarins, and oximes . As a continuation of these studies, we found that the MeOH extract of L. domesticum leaves showed antimutagenic effects against 3-amino-1,4-dimethyl-5 H -pyrido­[4,3- b ]­indole (Trp-P-1) [inhibition: 80.8% at 125 μg/plate] and 2-amino-1-methyl-6-phenylimidazo­[4,5- b ]­pyridine (PhIP) [inhibition: 75.7% at 125 μg/plate], using the Ames test.…”