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

Abstract

A methanol extract of the dried leaves of Lansium domesticum showed antimutagenic effects against 3-amino-1,4dimethyl-5H-pyrido [4,3-b]indole (Trp-P-1) and 2-amino-1-methyl-6-phenylimidazo[4,5-bI]pyridine (PhIP) using the Ames assay. Nine new onoceranoid-type triterpenoids, lansium acids I−IX (1−9), and nine known compounds (10−16) were isolated from the extract. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence. The absolute stereostructures of the new compounds were determined via their electronic circular dichroism spectra. Several isolated onoceranoid-type triterpeneoids showed antimutagenic effects in an in vitro Ames assay. Moreover, oral intake of a major constituent, lansionic acid (10), showed antimutagenic effects against PhIP in an in vivo micronucleus test.

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

“…As a result, limonin (19) and lansionic acid (53) significantly decreased the frequency of micronucleated reticulocytes (MNRETs) treated with PhIP at 24 h and 48 h after the administration ( Fig. 4) [4,7].…”

“…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.…”

“…We used nobiletin as the positive control that have been reported to have antimutagenic effects using the Ames test [44]. As shown in Tables 2 and 4, among the compounds isolated from the peels of C. limon, furanocoumarins, (+)-tert-O-methyloxypeucedanin hydrate [7,8]. The antibacterial (19) at low or high dose (0.02% or 0.04%, w/w) were given ad libitum.…”

“…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].…”

“…Chemical structures of the constituents isolated from L. domesticum[7,8] From the MeOH extract of Lansium domesticum dried leaves, twelve new compounds, namely, lansium acids I (35), II(36), III (37), IV(38), V (39), VI (40), VII (41), VIII (42), IX (43), X (44), XI…”