Triterpenoids from the Bark of Avicennia marina

Abstract

Avicennia marina, commonly known as the grey mangrove, is distributed widely along the coast of New South Wales. It is used as a source of tannin in some countries and the very hard timber is used occasionally in boat-building. The bark has now been examined for neutral and acid constituents and was found to contain betulic acid (0 -3 %), taraxerol (0 -06 %), and taraxerone (0.05 %).A minute amount of a hydrocarbon, probably triacontane, was also isolated. ExperimentalMelting points are uncorrected and were determined in evacuated capillaries. Analyses were carried out by the C.S.I.R.O. Microanalytical Laboratory. Light petroleum refers to the fraction, b.p. 60-80 'C.Chopped, dried bark (3 k g ; collected along the Hunter River, Newcastle, N.S.W.) was extracted continuously with ether for 2 days. The extract (5 1.) was reduced to 11. and shaken with N NaOH. The precipitated sodium salt was filtered off and, without drying, purified by treatment of a solution in 50% alcohol (200 ml) with charcoal followed by acidification. The crude acid was dissolved in a 5% solution of KOH in 50% alcohol (200 ml), the solution treated with charcoal and then acidified. Recrystallization from methanol gave 8 . 5 g of betulic acid, m.p. 308-310 OC,

Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant Avicennia lanata

“…Other biological activities showed that 6 and 7 were also allelopathic [46] and displayed anti-fungal activity [47]. Meanwhile, the only difference between compound 8 and 9 is the presence of a double bond on the side chain at ∆ 22,23 . Compound 8 which possessed a saturated side chain was inactive against T. b. brucei with an MIC value of 142.30 µM.…”

“…revealed lapachol, a naphthofuranquinone compound which has been isolated from Indian and West African A. tomentosa [ 6 ]. Later, various classes of chemical components have been isolated from the Avicennia genus, including naphthoquinones [ 7 , 8 , 9 , 10 , 11 ], iridoid glucosides [ 12 , 13 , 14 , 15 , 16 , 17 ], sterols [ 18 , 19 ], flavones [ 16 , 20 ], diterpenes [ 21 ] and triterpenes [ 18 , 19 , 22 , 23 ] from leaves, roots, twigs and stem bark.…”

Antioxidant, Hypoglycemic, and Neurobehavioral Effects of a Leaf Extract of Avicennia marina on Autoimmune Diabetic Mice

“…Avicennia marina is one of the most important mangrove plants that have gained more attention because of its medical importance [3, 4]. Indeed, the study of the medical importance of A. marina started early when Bell and Duewel [5] isolated triterpenoids from the bark of A. marina . These terpenoids were later identified as lupeol, taraxerol, and betulinic acid [6].…”

Autophagy Inhibition Enhances the Mitochondrial-Mediated Apoptosis Induced by Mangrove (Avicennia marina) Extract in Human Breast Cancer Cells

“…Since Bell et al [5] first reported the isolation of triterpenoids from different parts of AM, more than sixty compounds have been isolated from this plant species [6]. The versatility and adeptness to grow in conditions of high salinity, high temperatures, anaerobic soil, strong winds and changing ocean tides allow mangroves to produce a rich source of interesting metabolites.…”