Phytochemical Investigation of Aglaia andamanica

Abstract

Four new compounds, the limonoid 24-epi-melianodiol (8), the tirucallane aglaiodiol (9), and the two cyclopentatetrahydrobenzopyran derivatives pyramidaglain A (11) and B (12) were isolated from the leaves of Aglaia andamanica Hiern (Meliaceae), together with the eleven known constituents beta-sitosterol, beta-sitosterol glucoside, cycloart-23E-ene-3 beta,25-diol (1), three flavonoids 5-hydroxy-3,4',7-trimethoxyflavone (2), retusin (3) and pachypodol (4), the tirucallane 24-epi-piscidinol A (5), the lignan yangambin (6), the limonoid melianodiol (7), the bisamide pyramidatine (10) and the amino acid N-methyl-trans-4-hydroxy-L-proline (13). All structures were established by means of detailed spectroscopic analysis.

Constituents of the leaves and stem bark of Aglaia foveolata

“…To the best of our knowledge, there is only one previous report of the isolation of two other cyclopenta [b]benzopyran-type compounds possessing a benzoyl-1,4-butanediamide moiety, which were obtained from the leaves of A. andamanica Hiern collected in Thailand. 18 The structures of these known compounds, pyramidaglains A and B, are similar to foveoglin A (2), except for the absence of a 10-acetoxy group in the latter compound and differences in the substituents affixed to positions 3 and 4. 13 C NMR spectra of compounds 2 and 3 were comparable, suggesting that compound 3 also possesses a cyclopenta[b]benzopyran skeleton with a benzoyl-1,4-butanediamide moiety.…”

“…or SunFire Preparative (5 μm, 150 × 19 mm i.d.) C 18 OBD column (Waters, Milford, MA). All solvents used from chromatographic separations were purchased from Fisher Scientific (Fair Lawn, NJ).…”

Diamide Derivatives and Cycloartanes from the Leaves of Aglaia elliptica.

“…Several novel amides containing a cyclopenta-[bc]benzopyran moiety (ϭaglain-type) and a cyclopenta- [b]benzofuran moiety (ϭrocaglamide-type) as the acid part have been characterized from this genus, [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] some of which were shown to exhibit cytotoxic 1,3,5,7,10,19,20) insecticidal, 2,6,8,9,[11][12][13][14][15]17) and antifungal 4) activities. In our series of studies of this genus, 16) we have investigated the constituents of the leaves of Aglaia elliptica Bl.…”

Apotirucallane and Tirucallane Triterpenoids from Cedrela sinensis

“…Its molecular formula was determined to be C 31 H 50 O 5 from the [MϩNa] ϩ peak at m/z 525.3531 (Calcd for C 31 H 50 O 5 Na, 525.3556) in the HR-ESI-MS. Its NMR spectra generally resembled those of melianodiol 4) suggesting that 7 had a tiru- callane-type skeleton. Analysis of the HMBC spectrum revealed the presence of a carbonyl group at C-3, a double bond between C-7 and C-8, a tertiary methyl group at C-14, a methoxyl group at C-21, and two hydroxyl groups at C-24 and C-25.…”