Showing papers on "Michelia published in 2010"

Chemical constituents from the stems of Michelia alba

Abstract: We have continued the study of constituents from Michelia alba 1 . To further understand the chemotaxonomy and to continue searching for novel agents from Magnoliaceous plants, the stems of M. alba were chosen for the first time for phytochemical investigation. In this paper, we report the isolation of 20 pure substances. The compounds, including six aporphines, (–)-anonaine (1), (–)-norushinsunine (2), (–)-ushinsunine (3), (–)-N-formylanonaine (4) [2], (–)-romerine (5) [3], and (–)-asimilobine (6) [4]; two oxoaporphines, liriodenine (7) and oxoxylopine (8); one lignan, (+)-syringaresinol (9); one amide, N-trans-feruloyltyramine (10); seven benzenoids, 4-hydroxybenzaldehyde (11), p-anisaldehyde (12) [5], veratraldehyde (13) [5], 3,4,5-trimethoxybenzoic acid (14) [6], 3,4-dimethoxybenzoic acid (15) [7], eugenol (16) [8], and methyl isoeugenol (17) [8]; one triterpenoid, ficaprenol (18) [9]; two steroids, -sitosterol (19) [10] and stigmasterol (20) [10], are isolated from the stems of Michelia alba. Compounds 4, 5, and 6 and 12–18 were isolated for the first time from this species [2]. The MeOH extract (156.7 g) was obtained from M. alba according to the literature method 1 (89.2 g) and H2O (60.8 g). The CHCl3-soluble fraction was chromatographed over silica gel (800 g, 70–230 mesh) using n-hexane–EtOAc– CHCl3–MeOH mixtures as eluents to produce five fractions. Part of fraction 1 (12.86 g) was subjected to silica gel chromatography by eluting with n-hexane–EtOAc (40:1) and enriched gradually with EtOAc to furnish three fractions (1-1–1-3). Fraction 1-1 (5.32 g) was further purified on a silica gel column using n-hexane–EtOAc mixtures to obtain eugenol (16) (23 mg), methylisoeugenol (17) (18 mg), and ficaprenol (18) (20 mg). Fraction 1-2 (4.63 g) was further purified on a silica gel column using n-hexane–EtOAc mixtures to obtain p-anisaldehyde (12) (19 mg), veratraldehyde (13) (22 mg), 3,4,5-trimethoxybenzoic acid (14) (26 mg), and 3,4-dimethoxybenzoic acid (15) (25 mg). Fraction 1-3 (3.28 g) was further purified on a silica gel column using n-hexane–EtOAc mixtures to obtain -sitosterol (19) (45 mg) and stigmasterol (20) (38 mg). Part of fraction 2 (9.33 g) was subjected to silica gel chromatography by eluting with n-hexane–EtOAc (30:1) and enriched with EtOAc to furnish two further fractions (2-1–2-2). Fraction 2-1 (5.22 g) was further purified on a silica gel column using n-hexane–EtOAc mixtures to obtain liriodenine (7) (62 mg). Part of fraction 2-2 (3.62 g) was further purified on a silica gel column using n-hexane–EtOAc mixtures to obtain (+)-syringaresinol (9) (30 mg). Part of fraction 3 (11.36 g) was subjected to silica gel chromatography by eluting with n-hexane–EtOAc (10:1) and enriched with EtOAc to furnish three further fractions (3-1–3-3). Fraction 3-1 (5.59 g) was further purified on a silica gel column using n-hexane–EtOAc mixtures to obtain oxoxylopine (8) (18 mg). Fraction 3-2 (5.45 g) was further purified on a silica gel column using n-hexane–EtOAc mixtures to obtain 4hydroxybenzaldehyde (11) (28 mg). Part of fraction 4 (25.63 g) was subjected to silica gel chromatography by eluting with CHCl3–MeOH (100:1) and enriched with MeOH to furnish three fractions (4-1 4-3). Fraction 4-1 (11.62 g) was further purified on a silica gel column using CHCl3–MeOH mixtures to obtain (–)-anonaine (1) (68 mg) and (–)-ushinsunine (3) (32 mg). Fraction 4-2 (5.32 g), eluted with CHCl3–MeOH (60:1), was further separated using silica gel column chromatography and preparative TLC (CHCl3–MeOH (100:1) and gave (–)-N-formylanonaine (4) (18 mg) and (–)-romerine (5) (15 mg). Fraction 4-3 (4.58 g), eluted with CHCl3–MeOH (50:1), was further separated using silica gel column chromatography and preparative TLC (CHCl3–MeOH (80:1) and gave N-trans-feruloyltyramine (10) (22 mg). Part of fraction 5 (10.82 g) was subjected to silica gel chromatography by eluting with CHCl3–MeOH (30:1) and enriched with MeOH to furnish two fractions (5-1–5-2).

Chemical constituents from the stems of Michelia compressa VAR. lanyuensis

Abstract: A new taxon of Michelia, M. compressa var. lanyuensis S. Y. Lu, endemic to Lanyu of Taiwan is described and illustrated. It is sporadic from sea level to 500 m elevation in broadleaf forests. It is similar to M. compressa var. compressa of Japan and the Ryukyus but distinguishable by the perianth color. It is also similar to M. compressa var. formosana but differs in leaf texture and leaf shape [1]. To further understand the chemotaxonomy of the Michelia species [2, 3], M. compressa var. lanyuensis was chosen for phytochemical investigation. The chemical constituents of this plant have not yet been reported. The compounds derived from the stem include four aporphines, (–)-anonaine (1) [4], (–)-ushinsunine (2) [5], (–)-N-acetylanonaine (3) [6], and liriodenine (4) [7]; one fatty acid, stearic acid (5) [8]; two steroids, 6 -hydroxystigmast-4-en-3-one (6) [8] and 6 -hydroxystigmast-4,22-dien-3-one (7) [8]; one sesquiterpene lactone, costunolide (8) [8]; one amide, N-trans-feruloyltyramine (9) [9]; one chlorophyl, pheophorbide b [10]; (+)-O-methylarmepavine (10) [9] and 4-acetonyl-3,5-dimethoxy-p-quinol (11) [11]. All of these compounds were found for the first time from this plant.

Research Advance on Michelia Plants

Abstract: The chemical constituents, medicinal effects of Magnoliaceae Michelia plants were summarized, and the direction for development study was pointed out.

Michelia mannii(Magnoliaceae),A Newly Recorded Species from Vietnam

Abstract: Michelia mannii King(Magnoliaceae),a previously known species only in Bristish India,is newly recorded from Vietnam.It was found in primary limestone forest in Cuc Phuong National Park,Northern Vietnam and in Langbiang Plateau,Lam Dong Province,Southern Vietnam.The specimens of this species are being preserved in CHI,CPNP,IBSC,L,and VFU.