Lee-Yu Huang

Bio: Lee-Yu Huang is an academic researcher from Fooyin University. The author has contributed to research in topics: Michelia & Vanillic acid. The author has an hindex of 6, co-authored 7 publications receiving 184 citations.

Chemical constituents from the leaves of Michelia alba

Abstract: The genus Michelia (Magnoliaceae) consists of about 30 species. Michelia alba is an evergreen tree, especially distributed in Taiwan and China. Michelia species have been used by indigenous peoples for the treatment of cancer. For example, Michelia champaca has been used in India for the treatment of abdominal tumors and M. hypoleuca and M. officinalis for carcinomatous sores and leukemia, respectively, in China [1]. Previous phytochemical studies on this species isolated, from the roots and flowers of M. alba, ushinsunine, oxoushinsunine, salicifoline, michelalbine, limonene, benzyl acetate, linalool, nerol, hydroxycitronellal, benzaldehyde, benzyl benzoate, and methyl eugenol [2, 3]. To further understand the chemotaxonomy and to continue searching for novel agents from Magnoliaceous plants, the leaves of M. albawere chosen for the first time for phytochemical investigation. In this paper, we report the isolation of 21 pure substances. The compounds included four aporphines, (-)-anonaine ( 1) [4], (-)-norushinsunine ( 2) [5], (-)-ushinsunine ( 3) [5], and (-)-N-acetylanonaine ( 4) [6]; two oxoaporphines, liriodenine ( 5) [5] and oxoxylopine ( 6) [7]; three sesquiterpene lactones, michelenolide ( 7) [8], costunolide ( 8) [8], and 11,13-dehydrolanuginolide ( 9) [9]; one amide, N-trans-feruloyltyramine ( 10) [10]; one lignan, (+)-syringaresinol ( 11) [11]; three benzenoids, 4-hydroxybenzaldehyde ( 12) [12], 4-hydroxybenzoic acid ( 13) [12], and methylparaben ( 14) [12]; two steroids, β-sitosterol and stigmasterol [13]; three aliphatic compounds, palmitic acid [14], stearic acid [15], and linoleic acid [16]; and two chlorophylls, pheophorbide a [17] and aristophyll-C [18]. In addition to 3 and 5, all of these compounds were isolated for the first time from this source.

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).

Anonaine induces DNA damage and inhibits growth and migration of human lung carcinoma h1299 cells

Abstract: The anticancer effects of (−)-anonaine were investigated in this current study. (−)-Anonaine at concentration ranges of 50−200 μM exhibited significant inhibition to cell growth and migration activities on human lung cancer H1299 cells at 24 h, albeit cell cycle analyses showed that (−)-anonaine at the above concentration ranges did not cause any significant changes in cell-cycle distributions. Significant nuclear damages of H1299 cells were observed with 10−200 μM (−)-anonaine treatment in a comet assay, whereas higher concentrations (6 and 30 mM) of (−)-anonaine concentrations were required to cause DNA damages in an in vitro plasmid cleavage assay. In summary, our results demonstrated that (−)-anonaine exhibited dose-dependent antiproliferatory, antimigratory, and DNA-damaging effects on H1299 cells. We inferred that (−)-anonaine can cause cell-cycle arrest and DNA damage to hamper the physiological behavior of cancer cells at 72 h, and therefore, it can be useful as one of the potential herbal supplem...

Bioconstituents from stems of Synsepalum dulcificum Daniell (Sapotaceae) inhibit human melanoma proliferation, reduce mushroom tyrosinase activity and have antioxidant properties

Abstract: A new amide, dihydro-feruloyl-5-methoxytyramine ( 1 ), along with 13 known compounds, including (+)-syringaresinol ( 2 ), (+)- epi -syringaresinol ( 3 ), 4-acetonyl-3,5-dimethoxy- p -quinol ( 4 ), cis - p -coumaric acid ( 5 ), trans - p -coumaric acid ( 6 ), p -hydroxybenzoic acid ( 7 ), syringic acid ( 8 ), vanillic acid ( 9 ), veratric acid ( 10 ), N - cis -feruloyltyramine ( 11 ), N - trans -feruloyltyramine ( 12 ) and N - cis -caffeoyltyramine ( 13 ), were isolated from the stems of Synsepalum dulcificum Daniell (Sapotaceae). The structures of these compounds were established on the basis of spectroscopic analysis. One of the purposes of this study was to survey the antioxidant properties of 13 pure constituents. The radical scavenging and antioxidant activities were investigated by: scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals; metal chelating power was completed by ferrous ions; and reducing power was demonstrated by iron ions reduction reaction. In addition, all compounds were evaluated for their cell proliferation inhibition activities on human skin melanoma cells and tyrosinase inhibitions. The anti-tyrosinase effects were to calculate the hydroxylation of l -tyrosine to l -dopa according to in vitro mushroom tyrosinase assay. In sum, the inhibition effects of compounds ( 2 – 3 ) on human melanoma cells were significant. Besides, DPPH, ABTS radical scavenging, metal chelating and reducing power were found to be moderate compared with the positive controls.