Constituents of Some Species of Beilschmiedia and Endiandra (Lauraceae): New Endiandric Acid and Benzopyran Derivatives Isolated From B. oligandra

Abstract

On the basis of a preliminary u.v. assay of the dried leaf of nine species of Beilschmiedia and 26 species of Endiandra, several were selected for closer examination. Magnolol (9) was found in B.volckii and (+)-sesamin (10) was isolated from E. xanthocarpa. Endiandric acid B (2) and endiandric acid C (3) were obtained from both E. jonesii and B. tooram, and endiandric acid A (1) was found in B. obtusifolia. The new endiandric acid derivative (1′RS,3′RS,6′SR,7′SR,10′SR,11′ RS,12′RS,13′RS)-2-[6′-(3″,4″-methylenedioxyphenyl) tetracyclo [5.4.2.03,13.010,12]trideca-4′,8′-dien-11′ -yl ]acetic acid (3″,4″-methylenedioxyendiandric acid A) (4) was extracted from B. oligandra which also yielded the new phenolic benzopyran derivative (-)-(E)-2-(4′,8′-dimethylnona-3′,7′-dienyl)-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-6-ol ( oligandrol ) (12a). Several known hydrocarbon derivatives and terpenoids were isolated from the leaf of E. palmerstonii and E. baillonii, both of which were devoid of endiandric acids.

Antibacterial endiandric acid derivatives from Beilschmiedia anacardioides

“…One signal corresponding to an oxymethylene group appeared at d 4.36 (H-4), together with several methine protons between d 1.43 and 3.3 and one terminal methyl at d 0.92 (t, J = 6.9 Hz, H-8'). These data were partially similar to some previously reported endiandric acid derivatives (Banfield et al, 1994). The basic tetracyclic skeleton was confirmed by correlations observed in the HMBC and COSY spectra of compound 1 ( Table 3).…”

“…B. mannii is also used as appetite stimulant (Iwu, 1993). Previous phytochemical investigations of plants of the genus Beilschmiedia reported the presence of bio-active lignans (Chen et al, 2006;, flavonoids (Harborne and Mendez, 1969), triterpenoids (Chen et al, 2006); tetracyclic endiandric acids (Bandaranayake and Banfield, 1981;Banfield et al, 1994) and alkaloids (Clezy et al, 1966;Kitagawa et al, 1993). To the best of our knowledge, no phytochemical investigation has been carried out on B. anacardioides.…”

Cytotoxic and antibacterial beilschmiedic acids from a gabonese species of Beilschmiedia

“…Specifically, the chemical shifts for H-4 (δ H 4.14, d 10 Hz) and H-5 (δ H 6.91, brs) indicated the presence of an α-OH and an α/β-unsaturated carbonyl. 9 The 1 H NMR spectrum also indicated that the tail portion of compound 6.91), COSY correlations could be followed through the entirety of compound 1 (Figure 1) with the only exceptions being the three quaternary carbons. Those were assigned based on HMBC correlations ( Figure 1).…”

“…[1][2][3][4][5][6][7][8][9][10][11][12][13] These complex fatty acids, typically isolated as racemic mixtures, were proposed by Black to be the result of a series of consecutive nonenzymatic cyclizations (8πe, 6πe, and DielsAlder) of a polyunsaturated fatty acid precurser. 14 Support for such a mode of biosynthesis was provided by a biomimetic synthesis carried out by Nicolaou.…”

Beilschmiedic Acids F and G, Further Endiandric Acid Derivatives from Beilschmiedia anacardioides

“…The resonances of the CH groups at d(C) 39.5 (C(1')), 47.5 (C(3')), 35.7 (C(7')), 33.8 (C(10')), 41.5 (C(11')), 33.5 (C(12')), and 42.4 (C(13')) and of a CH 2 group at d(C) 29.8 (C(2')) in the DEPT spectrum were in part characteristics for the tetracyclic endiandric acid skeleton [6] (1)) and 199.5 (C(4')), of three olefinic CH groups at d(C) 124.4 (C(5')), 122.2 (C(8')), and 130.3 (C(9')), of six aromatic C-atoms at d(C) 130.6 (C(1'')), 107.3 (C(2'')), 148.9 (C(3'')), 148.0 (C(4'')), 108.4 (C(5'')), and 122.0 (C(6'')), and of an OCH 2 O moiety at d(C) 101.6 (C(7'')). The latter, together with the aromatic signals, suggested the presence of the (methylenedioxy)phenyl (¼ 1,3-benzodioxolyl) moiety [11]. The 1 H-NMR spectrum of 1 ( Table 1) showed signals of three olefinic H-atoms at d(H) 6.26 (br.…”