In this study the antioxidant activity of natural limonoids from Meliaceae swietenolide (1), 3,6-O,O-diacetylswietenolide (2), swietenine (3), swietemahonin G (4) and 2-hydroxyswietenine (5) were investigated along with the semisynthetic analogues (6-25) of compounds 1, 3-4. Lipid peroxidation (LPO) inhibitory assays revealed 85.6, 13.3, 77.3, 61.2 and 24.6 % inhibition for the natural compounds 1-5. Excellent antioxidant activity was seen for the semisynthetic analogues 10 (98.3 %), 16-17, 21-22 and 25 (100 %), which were more active than the positive controls BHA (91.3 %) and TBHQ (95.7 %).
ItoN., HiroseM. (1989) Antioxidants-carcinogenic and chemopreventive properties. Advances in Cancer Research, 53, 247–302.
2.
HocmanG. (1988) Chemoprevention of cancer: Phenolic antioxidants (BHT, BHA). International Journal of Biochemistry, 20, 639–651.
3.
MannersG.D. (2007) Citrus Limonoids: Analysis, bioactivity, and biomedical prospects. Journal of Agricultural and Food Chemistry, 55, 8285–8294.
4.
YuJ., WangL., WalzemR.L., MillerE.G., PikeL.M., PatilB.S. (2005) Antioxidant activity of citrus limonoids, flavonoids, and coumarins. Journal of Agricultural and Food Chemistry, 53, 2009–2014.
5.
MootooB.S., AliA., MotilalR., PingalR., RamlalA., KhanA., ReynoldsW.F., McleanS. (1999) Limonoids from Swietenia macrophylla and S. aubrevilleana. Journal of Natural Products, 62, 1514–1517.
6.
KadotaS., MarpaungL., KikuchiT., EkimotoH. (1990) Constituents of the seed of Swietenia mahagoni JACQ. I. Isolations, structures and 1H and 13C nuclear magnetic resonance signal assignment of new tetranortriterpenoids related to swietenine and swietenolide. Chemical and Pharmaceutical Bulletin, 38, 639–651.
7.
KadotaS., MarpaungL., KikuchiT., EkimotoH. (1990) Constituents of the seeds Swietenia-Mahagoni JACQ. II. Structures of swietemahonin A B C D E F and G and swietemahonolide. Chemical and Pharmaceutical Bulletin, 38, 894–901.
8.
DailyA., SeligmannO., LotterH., WagnerH. (1985) 2-Hydroxyswietenin, a new limonoid from Swietenia mahagoni DC. Zeitschrift für Naturforschung Section C, Journal of Biosciences, 40, 519–522.
9.
FowlesR., MootooB., RamsewakR., KhanA., RamsubhagA., ReynoldsW., NairM. (2010) Identification of new limonoids from Swietenia and their biological activity against insects. Pest Management Science, 66, 1298–1303.
10.
WangH., NairM.G., StrasburgG.M., BoorenA.M., GrayJ.I. (1999) Novel antioxidant and anti-inflammatory compounds from Tart cherries. Journal of Natural Products, 62, 86–88.