Bruceines D, E and H

Abstract

The absolute stereochemistry of bruceines D, E and H has been confirmed to be 1S, 5S, 7R, 8R, 9R, 10S, 11R, 12S, 13R, 14R, 15R and additionally 2S for bruceine E by a combination of 2D nmr [1H‐1H and 1H‐13C (one‐bond and long‐range) COSY] nOe and cd spectroscopic analyses.

A new triterpenoid from Brucea javanica

“…13 C NMR (125 MHz, DMSO-d 6 ) δ: 132.4 (C-1), 149.6 (C-2), 198.1 (C-3), 41.9 (C-4), 44.9 (C-5), 30.4 (C-6), 84.6 (C-7), 47.1 (C-8), 41.0 (C-9), 40.5 (C-10), 72.9 (C-11), 76.7 (C-12), 82.9 (C-13), 49.5 (C-14), 68.6 (C-15), 169.8 (C-16), 74.6 (C-17), 12.4 (C-18), 17.5 (C-19), 172.0 (C-20), 165.5 (C-1'), 115.9 (C-2'), 160.5 (C-3'), 26.8 (C-4'), 20.5 (C-5'), 102.9 (C-1''), 74.9 (C-2''), 78.4 (C-3''), 71.5 (C-4''), 77.6 (C-5''), 62.7 (C-6''), 53.1 (OCH 3 ) (Ohnishi et al, 1995). C NMR (125 MHz, CD 3 OD) δ: 80.7 (C-1), 71.9 (C-2), 125.2 (C-3), 133.6 (C-4), 41.8 (C-5), 27.2 (C-6), 79.3 (C-7), 48.9 (C-8), 44.6 (C-9), 43.8 (C-10), 73.9 (C-11), 79.6 (C-12), 82.8 (C-13), 81.2 (C-14), 68.8 (C-15), 173.7 (C-16), 68.8 (C-17), 20.7 (C-18), 11.6 (C-19), 18.2 (C-20) (Li et al, 1989). (Ohnishi et al, 1995).…”

“…Recently we examined the aerial parts of this plant, and isolated a new triterpenoid. In this paper we describe the isolation and structure elucidation of this new compound from B. javanica, together with eight known compounds, bruceoside A (2) (Ohnishi et al, 1995), bruceoside B (3) (Fukamiya et al, 1992), bruceine D (4) (Shen et al, 2008), bruceine E (5) (Li et al, 1989), yadanzioside A (6) (Ohnishi et al, 1995), yadanzioside G (7) (Ohnishi et al, 1995), (20R)-O-(3)-α-L-arabinopyranosyl-pregn-5-ene-3β,20-diol (8) (Kamperdick et al, 1995), and α-D-glucopyranoside, (3β, 20R)-3-hydroxypregn-5-en-20-yl (9) (Thompson et al, 1985). Among the known compounds, compound 9 was isolated firstly from this plant.…”

Delaumonones A and B, New Antiplasmodial Quassinoids from Laumoniera bruceadelpha

“…15) A fraction eluted by CHCl 3 /MeOH (0 : 1) was further purified on ODS HPLC with 55% MeOH containing 0.1% TFA to afford delaumonone A (1, 11.9 mg). n-BuOH-soluble materials were subjected to an HP-20 column (H 2 O/MeOH, 1 : 0→0 : 1), in which a fraction eluted 80% MeOH was further purified on a silica gel column (CHCl 3 /MeOH, 1 : 0→0 : 1) and ODS HPLC (55% MeOH containing 0.1% TFA) to afford delaumonone A (1, 15.0 mg) together with brucein D (5, 1.2 mg) 16) and yadanziolide A (6, 3.7 mg). 17) These compounds could also be isolated from EtOH extract of the same plant.…”

“…15) n-BuOH-soluble materials were subjected to an HP-20 column, and then a silica gel column (CHCl 3 /MeOH), followed by ODS HPLC to afford delaumonone A (1, 15.0 mg) together with brucein D (5, 1.2 mg) 16) and yadanziolide A (6, 3.7 mg). laumonone A was elucidated to be 1.…”

Isolation, chemotaxonomic significance and cytotoxic effects of quassinoids from Brucea javanica

“…The structures of other sixteen known compounds were identified by comparing their spectroscopic data (UV, MS, 1 H and 13 C NMR) with those of reported values and found to be bruceine D (3) [19], yadanzioside E (4) [20], brusatol (5) [21], bruceoside B (6) [22], bruceantinol (7) [23], yadanzioside K (8) [23], P (9) [24], bruceine A (10) [20], yadanzioside B (11) [20], bruceantarin (12) [25], bruceoside A (13) [26], yadanzioside C (14) [20], G (15) [20], F (16) [27], A (17) [20], and M (18) [23].…”