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  • Wu, Tung-Ying  (38)
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  • 1
    Language: English
    In: Journal of agricultural and food chemistry, 24 February 2016, Vol.64(7), pp.1540-8
    Description: Cordyceps militaris (bei-chong-chaw, northern worm grass) is a precious and edible entomopathogenic fungus, which is widely used in traditional Chinese medicine (TCM) as a general booster for the nervous system, metabolism, and immunity. Saccharides, nucleosides, mannitol, and sterols were isolated from this fungus. The biological activity of C. militaris was attributed to the saccharide and nucleoside contents. In this study, the aqueous methanolic fraction of C. militaris fruiting bodies exhibited a significant anti-inflammatory activity. Bioactivity-guided fractionation of the active fraction led to the isolation of eight compounds, including one new and two known cerebrosides (ceramide derivatives), two nucleosides, and three sterols. Cordycerebroside A (1), the new cerebroside, along with soyacerebroside I (2) and glucocerebroside (3) inhibited the accumulation of pro-inflammatory iNOS protein and reduced the expression of COX-2 protein in LPS-stimulated RAW264.7 macrophages. This is the first study on the isolation of cerebrosides with anti-inflammatory activity from this TCM.
    Keywords: Cordyceps Militaris ; Lps-Stimulated Raw264.7 Macrophages ; Anti-Inflammatory ; Cerebrosides ; Fungal Fruiting Bodies ; Anti-Inflammatory Agents -- Chemistry ; Cerebrosides -- Chemistry ; Cordyceps -- Chemistry
    ISSN: 00218561
    E-ISSN: 1520-5118
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  • 2
    Language: English
    In: Tetrahedron Letters, 14 September 2016, Vol.57(37), pp.4239-4242
    Description: Two new eunicellin-type diterpenoids, cladieunicellins R ( ) and S ( ), were isolated from the octocoral and their structures were elucidated by spectroscopic methods. Eunicellin was proven to be the first 2,6-hemiketal eunicellin and was found to exhibit moderate cytotoxicity toward the MOLT-4, K562, and SUP-T1 cells.
    Keywords: Cladiella Tuberculosa ; Eunicellin ; Cladieunicellin ; Cytotoxicity ; Chemistry
    ISSN: 0040-4039
    E-ISSN: 1873-3581
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  • 3
    Language: English
    In: Phytochemistry, February 2016, Vol.122, pp.184-192
    Description: 3-Methyl-4,5-dihydro-oxepine ( ), four polyoxygenated seco-cyclohexenes ( – ) and two polyoxygenated cyclohexenes ( – ), along with four known compounds, were isolated from . The phytochemical investigation of the methanolic extract of (Annonaceae) leaves led to the isolation of seven compounds including, 3-methyl-4,5-dihydro-oxepine (flexuvaroxepine A), four polyoxygenated seco-cyclohexene (flexuvarin A–D) and two polyoxygenated cyclohexene (flexuvarol A–B) derivatives, together with four known flavones. The structures of the isolated compounds were elucidated using different spectroscopic techniques. A plausible biogenetic route of the new compounds was discussed. The anti-inflammatory activity of the isolated compounds was evaluated by superoxide anion generation and elastase release assays. Among the tested compounds, flexuvarol B and chrysin showed the most potent anti-inflammatory effect by inhibiting superoxide anion generation and elastase release from human neutrophils in response to fMLP with IC 2.25–5.55 μM. Moreover, 5-hydroxy-6,7-dimethoxy-flavone showed selective inhibitory activity on superoxide anion generation (IC = 1.19 ± 0.34 μM).
    Keywords: Uvaria Flexuosa ; Annonaceae ; 3-Methyl-4,5-Dihydro-Oxepine ; Polyoxygenated Cyclohexenes ; Polyoxygenated Seco-Cyclohexenes ; Anti-Inflammatory ; Botany
    ISSN: 0031-9422
    E-ISSN: 1873-3700
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  • 4
    Language: English
    In: Journal of Ethnopharmacology, 11 October 2011, Vol.137(3), pp.1283-1290
    Description: Tamoxifen resistance is common in estrogen receptor-α (ERα)-positive breast cancers. Pawpaw and soursop are anticancer annonaceous plants in complementary medicine. Thus, we studied the effects of annonacin, an annonaceous acetogenin, in breast cancer cells. Cell growth and ERα-related pathways were studied. The effects of annonacin were tested in MCF-7 xenografts in nude mice. In ERα-positive MCF-7 cells, annonacin (half-effective dose ED = 0.31 μM) and 4-hydroxytamoxifen (ED = 1.13 μM) decreased cell survival whereas annonacin (0.5-1 μM) increased cell death at 48 h. Annonacin and 4-hydroxytamoxifen were additive in inhibiting cell survival. Annonacin (0.1 μM) induced / growth arrest while increasing p21 and p27 and decreasing cyclin D1 protein expression. Annonacin (0.1 μM) decreased cyclin D1 protein expression more than 4-hydroxytamoxifen (1 μM). Annonacin (0.1 μM) increased apoptosis while decreasing Bcl-2 protein expression. The combination of annonacin (0.1 μM) and 4-hydroxytamoxifen (1 μM) decreased Bcl-2 protein expression and ERα transcriptional activity more than annonacin (0.1 μM) did alone. Annonacin, but not 4-hydroxytamoxifen, decreased ERα protein expression. Moreover, annonacin decreased phosphorylation of ERK1/2, JNK and STAT3. In nude mice, annonacin decreased MCF-7 xenograft tumor size at 7–22 days. Moreover, annonacin decreased ERα, cyclin D1 and Bcl-2 protein expression in the xenograft at 22 days. Annonacin induced growth arrest and apoptosis in ERα-related pathways in MCF-7 cells. Annonacin and 4-hydroxytamoxifen were additive in inhibiting cell survival and ERα transcriptional activity. Moreover, annonacin attenuated MCF-7 xenograft tumor growth while inhibiting ERα, cyclin D1 and Bcl-2 protein expressions in nude mice.
    Keywords: Annonacin ; Tamoxifen ; Estrogen Receptor-Α ; Breast Cancer ; Cell Cycle ; Pharmacy, Therapeutics, & Pharmacology
    ISSN: 0378-8741
    E-ISSN: 1872-7573
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  • 5
    Language: English
    In: Progress in the chemistry of organic natural products, 2016, Vol.101, pp.113-230
    Description: In recent decades, annonaceous acetogenins have become highly studied plant secondary metabolites in terms of their isolation, structure elucidation, synthesis, biological evaluation, mechanism of action, and toxicity. The aim of the present contribution is to summarize chemical and biological reports published since 1997 on annonaceous acetogenins and synthetic acetogenin mimics. The compounds are considered biologically in terms of their cytotoxicity for cancer cell lines, neurotoxicity, pesticidal effects, and miscellaneous activities.
    Keywords: Acetogenin Mimics ; Acetogenins ; Annonaceae ; Anti-Cancer Activity ; Apoptosis ; Atypical Parkinsonism ; Ionophores ; Mitochondria Complex I Inhibition ; Neurotoxicity ; Pesticidal Activity ; Acetogenins -- Chemistry ; Annonaceae -- Chemistry ; Plant Extracts -- Chemistry
    ISSN: 2191-7043
    Source: MEDLINE/PubMed (U.S. National Library of Medicine)
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  • 6
    Language: English
    In: Planta medica, 2010, Vol.76(13), pp.1390-1404
    Description: Abstract Studies on the Annonaceous acetogenins began after the first cytotoxic acetogenin, uvaricin, was isolated in 1982. This attractive finding made many medicinal and natural product chemists direct their efforts on the isolation and identification of these classes of compounds. As more Annonaceous acetogenins were isolated, more information about them was uncovered. From their structural identification to the total synthesis of natural product analogues and from cell-based screening and molecular-based targeting to animal testing, the mechanisms of action of the Annonaceous acetogenins became clearer. The purpose of this review is to give an account of recent studies on this class of compounds and their analogues, which will aid us not only in clarifying how the Annonaceous acetogenins act but also in establishing principles for the further development of this class of compounds.
    Keywords: Annonaceae ; Acetogenins ; Mitochondria Complex I Inhibitor ; Pesticidal Activity ; Anticancer Activity ; Apoptosis ; Acetogenin Mimics
    ISSN: 0032-0943
    E-ISSN: 1439-0221
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  • 7
    Language: English
    In: Helvetica Chimica Acta, December 2014, Vol.97(12), pp.1714-1718
    Description: A phytochemical investigation of MeOH extract of var. afforded two new compounds, 1,7‐dihydroxyeudesman‐4‐one () and 5‐megastigm‐7‐ene‐3,4,6,9‐tetrol (), together with nine known terpenoids. The structures of the new compounds were elucidated by 1D‐ and 2D‐NMR spectroscopic analysis. Their relative configurations were assigned by NOESY experiments.
    Keywords: Desmos Cochinchinensis ; Sesquiterpenes ; Cytotoxic Activity ; Anti‐Inflammatory Activity
    ISSN: 0018-019X
    E-ISSN: 1522-2675
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  • 8
    Language: English
    In: Journal of Pharmaceutical and Biomedical Analysis, 10 September 2018, Vol.159, pp.548-566
    Description: In current work, targeted and non-targeted analysis of alkaloids and acetogenins from methanolic extracts of , species and dietary supplements have been performed using UHPLC-QToF in positive ion mode. Thirty-five standard compounds (twelve alkaloids and twenty-three acetogenins) were used for the analysis. The fragment ions produced by collision induced dissociation (CID) revealed the characteristic cleavage and provided structural information. Aporphine alkaloids and acetogenins are the major groups found in and species. An untargeted analysis based on high-resolution mass spectrometry was carried out to profile the alkaloids and acetogenins from species ( , ). Magnoflorine, being a major alkaloid from twigs of samples, was used as an example to discuss the fragmentation patterns. In (+)-ESI-MS, magnoflorine gave [M] ions at 342.1705. The fragment ions at 297.1127 [M-(CH ) NH] , 282.0886 [M-(CH ) NH] , 265.0865 [M-(CH ) NH-CH OH] , 237.0916 [M-(CH ) NH-CH OH-CO] , and 222.0681 [M-(CH ) NH-CH OH-CO-CH ] resulted from the [M] molecular ion. One dietary supplement claiming to contain paw paw ( ) was also analyzed and showed a similar profile to twigs of . A total of 131 compounds including standard compounds were identified from the different parts of and samples. These compounds can be used to distinguish species. However, for definite identification of these unknown components, further investigation is required. This may provide a model for the rapid screening and structural characterization of bioactive constituents from plant extracts in a single analysis.
    Keywords: Asimina Triloba (L.) Dunal ; Annona Species ; Uhplc-Qtof ; Alkaloids ; Acetogenins ; Targeted and Non-Targeted Analysis ; Pharmacy, Therapeutics, & Pharmacology
    ISSN: 0731-7085
    E-ISSN: 1873-264X
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  • 9
    Language: English
    In: ChemInform, May 2015, Vol.46(20), pp.no-no
    Description: isolation and structure of two new compounds, 1β,7α‐dihydroxyeudesman‐4‐one (I) and 5αH‐megastigm‐7‐ene‐3α,4α,6.beta,9‐tetrol (II), along with nine known terpenoids
    Keywords: Terpenes ; Structure Organic Substances
    ISSN: 0931-7597
    E-ISSN: 1522-2667
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  • 10
    Language: English
    In: Journal of Food and Drug Analysis, January 2016, Vol.24(1), pp.29-45
    Description: and its products have been used in Asia for centuries to treat various ailments, including arthritis, gout, cancer, and inflammation. In general, their preparations and dispensing have been restricted to qualified folk medicine healers due to their low safety index and reported toxicity. In the past few decades, official guidelines have been introduced in Asian pharmacopeias to control herbal products. However, these guidelines were based on primitive analytical techniques for the determination of the whole alkaloids and were unable to distinguish between toxic and nontoxic components. Recent advances in analytical techniques, especially high performance liquid chromatography (HPLC) and electrophoresis coupled with highly sensitive detectors, allowed rapid and accurate determination of secondary metabolites. Reports focusing on liquid chromatography/mass spectrometry analysis of and its herbal products are discussed in the current review. This review can be used by the health regulatory authorities for updating pharmacopeial guidelines of and its herbal products.
    Keywords: Aconitum ; Arthritis ; Asia ; Diterpene Alkaloids ; Liquid Chromatography/Mass Spectrometry ; Diet & Clinical Nutrition
    ISSN: 1021-9498
    E-ISSN: 22246614
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