Chemical Constituents from Annona Glabra III

Abstract

Twenty compounds including a dioxoaporphine, annobraine (1); two oxoaporphines, liriodenine (2) and lysicamine (3); five aporphines, (‐)‐nornuciferine (4), (‐)‐anonaine (5), (‐)‐N‐formylanonaine (6), (‐)‐asimilobine (7) and (+)‐nordomesticine (8); one proaporphine, (+)‐stepharine (9); two protoberberines, (‐)‐kikemanine (10) and dehydrocorydalmine (11); one azaanthraquinone, 1‐aza‐4‐methyl‐2‐oxo‐1,2‐dihydro‐9,10‐anthracenedione (12); two amides, N‐trans‐feruloyltyramine (13) and N‐p‐coumaroyltyramine (14); one ionone, blumenol A (15); and five steroids, β‐sitosterol (16), stigmasterol (17), β‐sitosteryl‐D‐glucoside (18), stigmasteryl‐D‐glucoside (19) and 6‐O‐palmitoyl‐β‐sitosteryl‐D‐glucoside (20), were isolated from the fruits and stems of Annona glabra. Among them, 1 is a novel dioxoaporphine alkaloid and 12 was obtained for the first time from natural sources. These compounds were characterized and identified by physical and spectral evidence.

Anti-Inflammatory and Cytotoxic Diterpenes from FormosanPolyalthia longifoliavar.pendula

“…This indicated that a tworing system remains to be accommodated. Thus, a trans-decalin system of rings A and B was deduced from the 13 Abstract A new clerodane diterpenoid 16-hydroxycleroda-13-ene-15,16olide-3-one (1) was isolated from the bark of Polyalthia longifolia var. The 13 C-and DEPT NMR analyses indicated twenty carbon resonances attributed to five quaternary, three methine, six methylene, and four methyl carbons.…”

The Constituents of Michelia compressa var. formosana and Their Bioactivities

“…The crude extract was suspended into water and partitioned with CHCl 3 to afford CHCl 3 layer and water solubles, respectively. Purification of the CHCl 3 soluble fraction by column chromatography yielded roemerine ( 1 , 13.7 mg) [13], cyathisterol ( 2 , 10.8 mg) [14], liriodenine ( 3 , 379 mg) [10], oliveroline ( 4 , 2.1 mg) [15], ushisurine ( 5 , 230 mg) [10], dihydrocostunolide ( 6 , 3.6 mg) [16], (−)- N -formylanonaline ( 7 , 7.9 mg) [15], 6α-hydroxy-β-sitostenone ( 8 , 4.7 mg) [15], ferulic acid ( 9 , 5.9 mg) [17], β-sitosterone ( 10 , 10.3 mg) [18], β-stigmastenone ( 11 , 11.5 mg) [18], costunolide ( 12 , 1.2 mg) [19], β-sitostanone ( 13 , 1.6 mg) [18], dehydroroemerine ( 14 , 1.9 mg) [20], ferruginol ( 15 , 1.2 mg) [21], sugiol ( 16 , 1.3 mg) [22], ( 11 S )-1-oxoedudesm-4(14)-eno-13, 6α-lactone ( 17 , 1.1 mg) [23], dihydroreynosin ( 18 , 1.2 mg) [23], romucosine ( 19 , 1.6 mg) [24], 11,13-dihydrosantamarin ( 20 , 0.8 mg) [25], 2-methylanthraquinone ( 21 , 1.5 mg) [26], methyl 22-feruloyloxydocosanoate ( 22 , 1.9 mg) [27], annonbraine ( 23 , 1.1 mg) [28], ferulic aldehyde ( 24 , 0.7 mg) [29], secoroemerine ( 25 , 0.6 mg) [30], blumenol A ( 26 , 1.3 mg) [31], (−)- N -formyldehydroanonaline ( 27 , 1.7 mg) [32], 6α,7-dehydroanonaline ( 28 , 0.9 mg) [33], N - trans -feruloyltyramine ( 29 , 1.0 mg) [27], N - trans -feruloylmethoxytyramine ( 30 , 1.1 mg) [17], syringaresinol ( 31 , 1.7 mg) [34], cepharadione-A ( 32 , 0.9 mg) [35], aristolic acid II ( 33 , 0.8 mg) [17], O -acetyl-ushinsunin ( 34 , 0.9 mg) [10], (+)-isolaricirensinol ( 35 , 1.6 mg) [34], northalifoline ( 36 , 1.5 mg) [35], cassyformin ( 37 , 2.0 mg) [36], 3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propan-1-ol ( 38 , 1.7 mg) [37], dehydrodiconiferyl alcohol ( 39 , 0.8 mg) [38], divanillyl tetrahydrofuran ( 40 , 1.9 mg) [39], methyl vanillate ( 41 , 0.7 mg) [24], noroliveroline ( 42 , 0.7 mg) [40], 1-acetyl-β...…”

Crystal structure of N-formylanonaine, C18H15NO3, at 103 K

“…We also reported the crystal structures of several alkaloid from the mother liquor [9][10][11][12][13]. N-formylanonaine, the very common alkaloids with Nformylaporphine skeletons was discovered in families of Annonaceae [14][15][16], Menispermaceae [17,18], and Magnoliaceae [19]. However, it is reported from the species of Sinomenium acutum for the first time.…”