T. J. Hsieh

Bio: T. J. Hsieh is an academic researcher from Fooyin University. The author has contributed to research in topics: Propidium iodide & Cinnamomum subavenium. The author has an hindex of 4, co-authored 5 publications receiving 173 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.

Cytotoxic constituents from the leaves of Cinnamomum subavenium.

Abstract: Two new butanolides, subamolide D (1) and subamolide E (2), and a new secobutanolide, secosubamolide A (3), along with 21 known compounds were isolated from the leaves of Cinnamomum subavenium. The structures of 1-3 were determined by spectroscopic analysis. Propidium iodide staining and cytometry analysis were used to evaluate the cell cycle progression of the treated SW480 cells and it was found that 1 and 2 caused DNA damage in a dose- and time-dependent manner.

Chemical constituents from the stems of Cinnamomum insulari-montanum

Abstract: Cinnamomum insulari-montanum Hayata (Lauraceae) is an endemic tree that grows in Taiwan s natural hardwood forest at elevations between 400 and 1500 m [1] In the course of screening for biologically and chemically novel agents from Formosan Lauraceous plants [2–15], C insulari-montanum Hayata was chosen for further phytochemical investigation In this paper, we reinvestigated the constituents in the stems of C insulari-montanum Hayata [16–21] The MeOH extract of its stems was subjected to solvent partitioning and chromatographic separation to afford eight pure substances The chemical constituents in the stems of C insulari-montanum Hayata were separated with column chromatography Seven compounds, including a mixture of -sitosterol (1) and stigmasterol (2) [22], coumarin (3) [14], cinnamyl alcohol (4) [14], cinnamic acid (5) [14], p-hydroxybenzoic acid (6) [14], kaempferol (7) [15], and kaempferitrin (8) [15], were isolated from the stems of C insulari-montanum Hayata All of these compounds were found for the first time in this plant The specimen of C insulari-montanum Hayata was collected from Pingtung County, Taiwan, March 2003 A voucher specimen (Cinnamo 3) was identified by Dr Fu-Yuan Lu (Department of Forestry and Natural Resources College of Agriculture, National Chiayi University) and was deposited in the School of Medical and Health Science, The Fooyin University, Kaohsiung County, Taiwan The stems (70 kg) of C insulari-montanum Hayata were extracted repeatedly with MeOH at room temperature for 24–48 h The MeOH extract was dried and evaporated to leave a viscous residue (824 g) The residue was placed on a silica gel column and eluted with CHCl3 gradually enriched with MeOH to afford 17 fractions Fraction 3 was rechromatographed on silica gel (n-hexane–EtOAc, (18:1)) and recrystallized from EtOAc to give coumarin (3) and a mixture of -sitosterol (1) and stigmasterol (2) (2000 mg) Fraction 6, eluted from n-hexane–EtOAc (1:2), was further chromatographed on silica gel eluting with EtOAc–MeOH (15:1) and recrystallized from acetone to give cinnamic acid (5) (50 mg) and cinnamyl alcohol (4) (50 mg), respectively Fraction 11 was purified by silica gel chromatography (EtOAc–MeOH, 10:1) to give colorless needles of kaempferol (7) Fraction 14 was purified by silica gel chromatography (EtOAc–MeOH, 8:1) to give colorless needles of p-hydroxybenzoic acid (6) (520 mg) Fraction 18 was rechromatographed on silica gel (EtOAc–MeOH, (5:1)) and recrystallized from MeOH to give kaempferitrin (8) (7800 mg)

Lignans from the Stem of Cinnamomum camphora

Abstract: (+)-Diasesamin (1), (+)-sesamin (2), (+)-episesamin, stearic acid, palmitic acid, a mixture of β-sitosterol and stigmasterol, and a mixture of β-sitosterol-D-glucoside and stigmasterol-D-glucoside

Cytotoxic Constituents from the Leaves of Cinnamomum subavenium

Abstract: Two new butanolides, subamolide D (1) and subamolide E (2), and a new secobutanolide, secosubamolide A (3), along with 21 known compounds were isolated from the leaves of Cinnamomum subavenium. The structures of 1-3 were determined by spectroscopic analysis. Propidium iodide staining and cytometry analysis were used to evaluate the cell cycle progression of the treated SW480 cells and it was found that 1 and 2 caused DNA damage in a dose- and time-dependent manner.

The Renaissance of α‐Methylene‐γ‐butyrolactones: New Synthetic Approaches

Abstract: The amount of research activity concerning alpha-methylene-gamma-butyrolactones and alpha-alkylidene-gamma-butyrolactones has increased dramatically in recent years. This Review summarizes the structural types, biological activities, and biosynthesis of these compounds, concentrating on publications from the past 10 years. Traditional approaches to alpha-methylene-gamma-butyrolactones and alpha-alkylidene-gamma-butyrolactones are then reviewed together with novel approaches, including those from our own research group, reported more recently.

Identifying melanogenesis inhibitors from Cinnamomum subavenium with in vitro and in vivo screening systems by targeting the human tyrosinase.

Abstract: Tyrosinase is known to be the first two and rate-limiting enzyme in the synthesis of melanin pigments responsible for colouring skin, hair and eyes. Tyrosinase inhibition is one major strategy used to treat hyperpigmentation. In human skin melanocytes, the cellular tyrosinase inhibition was examined by the conversion of l-tyrosine and oxidation of l-DOPA to dopaquinone. We evaluated the skin pigmentation inhibitor effects with both in vitro and in vivo systems to find skin-whitening agents without cytotoxic concerns. First, linderanolide B and subamolide A were isolated from the stems of Cinnamomum subavenium and exhibited mushroom tyrosinase inhibition. Then, these two herbal compounds were proved to have good pigmentation inhibitory abilities at low doses and demonstrated free cytotoxicities to normal human skin cells and zebrafish system. With molecular docking, in a virtual model of human tyrosinase, linderanolide B and subamolide A displayed meta(l) -coordinating interactions with Cu(2+) ions. The results obtained from biological assays showed that linderanolide B and subamolide A possessed anti-tyrosinase properties, which exhibited potential for application in medical cosmetology.

Cytotoxic compounds from the stems of Cinnamomum tenuifolium.

Abstract: Three new butanolides, tenuifolide A (1), isotenuifolide A (2), and tenuifolide B (3), a new secobutanolide, secotenuifolide A (4), and one new sesquiterpenoid, tenuifolin (5), along with 16 known compounds were isolated from the stems of Cinnamomum tenuifolium. Their structures were determined by spectroscopic analyses. Compound 4 was found to induce apoptotic-related DNA damage, increase sub-G1 cells, and inhibit the growth of human prostate cancer cells, DU145. In addition, treatment with 4 significantly increased intracellular H2O2 and/or peroxide. The results show that 4 induced (a) noticeable reduction of mitochondrial transmembrane potential (DeltaPsim); (b) significant increase in the ratio of cytochrome c concentration (cytosol/mitochondria); and (c) subsequent activation of caspase-9/caspase-3. Antiproliferation caused by 4 was found to markedly decrease when pretreated with caspase-9/caspase-3 inhibitor. In ROS scavenging, antioxidant, NADPH oxidase, and NO inhibitor studies, pretreatment of DU145 cells with either DPI, dexamethasone, L-NAME, or mannitol decreased 4-induced intracellular DCF fluorescence of ROS. These results suggest that an increase of H2O2 and/or peroxide by 4 is the initial apoptotic event and 4 has anticancer effects on DU145 cells.