Apowalsogynes A and B, Two Highly Oxidized 3,4-Seco-Apotirucallane Triterpenoids from Walsura chrysogyne

Abstract

Two new 3,4-seco-apotirucallane triterpenoids, Apowalsogynes A and B (1 and 2), were isolated from the barks of Walsura chrysogyne, and their structures were determined on the basis of the NMR and CD spectra, and by using the modified Mosher's method. In addition, the cytotoxic activities of 1 and 2 against various cancer cell lines were evaluated.

Chemistry and Biology of Novel Meliaceae Limonoids

“…At 2000 μg/mL, compound (1439) exhibited antifeedant activity against third-instar larvae of Plutella xylostella with antifeedant rate of 28.0 % after 48 hrs with corrected mortality after 6 days is 0.0 465 . Compounds (105,121) exhibited moderate antifeedant activity against tobacco caterpillar (S. litura) with mortality percent LC 50 (95 % FL) value of 22.40, 41.08 % respectively and castor semilooper (A.janata) with mortality percent LC 50 (95 % FL) value of 30.21, 41.35 % respectively, whereas compounds (120,124,125) did not exhibit activity as antifeedant index was <20 109 . Comopound (249) exhibited antifeedant activity against fifth instar larvae of Pieris rapae L. with antifeedant effect AFC 50 value of 1.32 mM 173 ..…”

“…Compounds (130 and 131) isolated from Aphanamixis polystachya were reported as Aphataiwanin C and D respectively. Same compounds were isolated from Walsura chrysogyne by another research group which named them as Apowalsogyne B and A (130 and 131) 120,121 . Aphataiwanin A (132) is a C25 dehydro analog of compound (130).…”

“…Piscidinol I (121) is C11 hydroxyl, C21 acetyl analog of compound (120). 11,25-dideacetyltrichostemonate ( 122) is C7 acetyl analog of compound (121) with oxidation at C23. Trichostemonate (123) is C11, C25 acetyl analog of Compound (122).…”

Walsogynes H–O from Walsura chrysogyne

“…Walsura, a genus belonging to Meliaceae, is composed of about 16 species distributed from Sri Lanka to the Himalaya and Indochina through Malaysia, Indonesia to New Guinea, and Walsura chrysogyne is distributed in Peninsular Malaysia [1]. The plants of this genus have been reported to produce limonoids, dammarane, tirucallane and apotirucallane triterpenoids [2][3][4][5][6][7]. In our search for new bioactive compounds [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27], we have reported the isolation of new limonoids and triterpenoids from plants of this genus [3,4,19], and alkaloids showing antimalarial activity [22,26,27].…”

“…The plants of this genus have been reported to produce limonoids, dammarane, tirucallane and apotirucallane triterpenoids [2][3][4][5][6][7]. In our search for new bioactive compounds [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27], we have reported the isolation of new limonoids and triterpenoids from plants of this genus [3,4,19], and alkaloids showing antimalarial activity [22,26,27]. Continuation of the bioassay-guided investigation on the extract of W. chrysogyne bark led to the isolation of eight new limonoids, walsogynes H-O (1)(2)(3)(4)(5)(6)(7)(8) showing antimalarial activity (Fig.…”