Yuanhuacin and Related Anti-Inflammatory and Anticancer Daphnane Diterpenes from Genkwa Flos—An Overview
Tóm tắt
Từ khóa
Tài liệu tham khảo
Zhou, 2021, Comprehensive evaluation on anti-inflammatory and anti-angiogenic activities in vitro of fourteen flavonoids from Daphne genkwa based on the combination of efficacy coefficient method and principal component analysis, J. Ethnopharmacol., 268, 113683, 10.1016/j.jep.2020.113683
Chinese Pharmacopoeia Commission (2015). Pharmacopoeia of the People’s Republic of China, China Medical Science Press. [3rd ed.].
Yu, 2017, How impaired efficacy happened between Gancao and Yuanhua: Compounds, targets and pathways, Sci. Rep., 7, 1
Sun, 2020, Anti-rheumatoid arthritis effects of flavonoids from Daphne genkwa, Int. Immunopharmacol., 83, 106384, 10.1016/j.intimp.2020.106384
Li, 2013, Isolation of anticancer constituents from flos genkwa (Daphne genkwa Sieb.et Zucc.) through bioassay-guided procedures, Chem. Central J., 7, 159, 10.1186/1752-153X-7-159
Li, 2013, Daphnane-type diterpenes with inhibitory activities against human cancer cell lines from Daphne genkwa, Bioorganic Med. Chem. Lett., 23, 2500, 10.1016/j.bmcl.2013.03.025
Kwon, 2015, Sibjotang Increases Atrial Natriuretic Peptide Secretion in Beating Rabbit Atria, Evid.-Based Complement. Altern. Med., 2015, 1
Zhang, 2021, Toxicity reduction and water expelling effect preservation of Shizaotang after its toxic members processing with vinegar on rats with malignant pleural effusions, J. Ethnopharmacol., 268, 113583, 10.1016/j.jep.2020.113583
Jiang, 2014, Evaluation of the indicative roles of seven potential biomarkers on hepato-nephrotoxicity induced by Genkwa Flos, J. Ethnopharmacol., 158, 317, 10.1016/j.jep.2014.10.055
Li, 2015, Fingerprint of Vinegar Processed Genkwa Flos Based on Improving Euclidean Distance, Zhong yao cai, 38, 1168
Yun, 2015, Evaluation of subchronic (13week) toxicity and genotoxicity potential of vinegar-processed Genkwa Flos, Regul. Toxicol. Pharmacol., 72, 386, 10.1016/j.yrtph.2015.04.008
Geng, 2012, Metabonomic Study of Genkwa Flos-induced Hepatotoxicity and Effect of Herb-Processing Procedure on Toxicity, Phytother. Res., 27, 521, 10.1002/ptr.4748
Geng, 2013, Discrimination of raw and vinegar-processed Genkwa Flos using metabolomics coupled with multivariate data analysis: A discrimination study with metabolomics coupled with PCA, Fitoterapia, 84, 286, 10.1016/j.fitote.2012.12.003
Tao, 2018, Pharmacokinetic comparisons of six components from raw and vinegar-processed Daphne genkwa aqueous extracts following oral administration in rats by employing UHPLC–MS/MS approaches, J. Chromatogr. B, 1079, 34, 10.1016/j.jchromb.2018.02.005
Guo, 2020, Sesquiterpenoids from the roots of Daphne genkwa Siebold et Zucc. With potential anti-inflammatory activity, Phytochemistry, 174, 112348, 10.1016/j.phytochem.2020.112348
Ren, 2019, Guaiane-Type Sesquiterpenoids from the Roots of Daphne genkwa and Evaluation of Their Neuroprotective Effects, J. Nat. Prod., 82, 1510, 10.1021/acs.jnatprod.8b01049
Wang, 2019, Assignment of the stereostructures of sesquiterpenoids from the roots of Daphne genkwa via quantum chemical calculations, Fitoterapia, 138, 104352, 10.1016/j.fitote.2019.104352
Wang, 2020, Discovery of guaiane-type sesquiterpenoids from the roots of Daphne genkwa with neuroprotective effects, Bioorganic Chem., 95, 103545, 10.1016/j.bioorg.2019.103545
Jin, Y.-X., Shi, L.-L., Zhang, D.-P., Wei, H.-Y., Si, Y., Ma, G.-X., and Zhang, J. (2019). A Review on Daphnane-Type Diterpenoids and Their Bioactive Studies. Molecules, 24.
Nie, Y.-W., Li, Y., Luo, L., Zhang, C.-Y., Fan, W., Gu, W.-Y., Shi, K.-R., Zhai, X.-X., and Zhu, J.-Y. (2021). Phytochemistry and Pharmacological Activities of the Diterpenoids from the Genus Daphne. Molecules, 26.
Han, 2017, Daphnane and Phorbol Diterpenes, Anti-neuroinflammatory Compounds with Nurr1 Activation from the Roots and Stems of Daphne genkwa, Biol. Pharm. Bull., 40, 2205, 10.1248/bpb.b17-00641
Zhang, 2019, Yuanhuatine from Daphne genkwa selectively induces mitochondrial apoptosis in estrogen receptor α-positive breast cancer cells in vitro, Planta Med., 85, 1275, 10.1055/a-1013-1439
Ying, 1977, Studies on the active principles in the root of Yuan-Hua (Daphne gemkwa). I. Isolation and structure of yuanhuacine, Acta Chim. Sin. (Hua Hsueh Hsueh Pao), 35, 103
Zhou, 1993, NMR assignments and conformational analysis of yuanhuacin, Magn. Reson. Chem., 31, 194, 10.1002/mrc.1260310208
Yang, 1981, Mechanism of the action of Yuanhuacine to induce labor during mid pregnancy (author’s transl), Zhonghua yi xue za zhi, 61, 613
Ding, 1987, Important Chinese herbal remedies, Clin. Ther., 9, 345
Liang, 1979, Morphological observations of placenta in 56 cases of mid-term abortion induced by Yuanhua preparations (author’s transl), Zhonghua fu chan ke za zhi, 14, 290
Huang, 1982, Comparison of 4 methods of midterm termination and their maternal influence (author’s transl), Tianjin Yi Yao, 10, 284
Zhang, 1987, The clinical and pathological study of induced abortion by Yuanhuacine film in 12–16 week pregnancy, Sheng zhi yu bi yun, 7, 65
Li, 1989, Yuanhuacin film for menstruation induction and termination of early pregnancy: Analysis of 382, Zhonghua fu chan ke za zhi, 24, 231
Yan, 1993, Preparation of yuanhuacine by low pressure column chromatography, China J. Chin. Mater. Medica, 18, 729
Zhang, 1994, Determination of yuanhuacine in Daphne genkwa Sieb. et Zucc. by HPLC, China J. Chin. Mater. Medica, 19, 551
Hallx, 1982, Antitumor Agents LV: Effects of Genkwadaphnin and Yuanhuacine on Nucleic Acid Synthesis of P-388 Lymphocytic Leukemia Cells, J. Pharm. Sci., 71, 1263, 10.1002/jps.2600711120
Liou, 1982, Antitumor Agents LVI: The Protein Synthesis Inhibition by Genkwadaphnin and Yuanhuacine of P-388 Lymphocytic Leukemia Cells, J. Pharm. Sci., 71, 1340, 10.1002/jps.2600711208
Zhang, 1993, Yuanhuacin A is a selective antagonist of phorbol ester receptor in protein kinase C, Sci. China Ser. B Chem. Life Sci. Earth Sci., 36, 803
Zhang, 2006, Preparation of yuanhuacine and relative daphne diterpene esters from Daphne genkwa and structure–activity relationship of potent inhibitory activity against DNA topoisomerase I, Bioorganic Med. Chem., 14, 3888, 10.1016/j.bmc.2006.01.055
Bailly, 2019, Irinotecan: 25 years of cancer treatment, Pharmacol. Res., 148, 104398, 10.1016/j.phrs.2019.104398
Hall, 1986, The effects of Genkwadaphnin and Gnidilatidin on the growth of P-388, L-1210 leukemia and KB carcinoma cells in Vitro, Eur. J. Cancer Clin. Oncol., 22, 45, 10.1016/0277-5379(86)90341-X
Hong, 2010, Daphnane Diterpene Esters with Anti-proliferative Activities against Human Lung Cancer Cells from Daphne genkwa, Chem. Pharm. Bull., 58, 234, 10.1248/cpb.58.234
Kang, J.I., Hong, J.-Y., Lee, H.-J., Bae, S.Y., Jung, C., Park, H.J., and Lee, S.K. (2015). Anti-Tumor Activity of Yuanhuacine by Regulating AMPK/mTOR Signaling Pathway and Actin Cytoskeleton Organization in Non-Small Cell Lung Cancer Cells. PLoS ONE, 10.
Park, 2007, Daphnane diterpene esters isolated from flower buds of Daphne genkwa induce apoptosis in human myelocytic HL-60 cells and suppress tumor growth in Lewis lung carcinoma (LLC)-inoculated mouse model, J. Ethnopharmacol., 111, 496, 10.1016/j.jep.2006.12.023
Bang, 2013, Melanogenesis inhibitory daphnane diterpenoids from the flower buds of Daphne genkwa, Bioorganic Med. Chem. Lett., 23, 3334, 10.1016/j.bmcl.2013.03.096
Fermaintt, C.S., Peramuna, T., Cai, S., Takahashi-Ruiz, L., Essif, J.N., Grant, C.V., O’Keefe, B.R., Mooberry, S.L., Cichewicz, R.H., and Risinger, A.L. (2021). Yuanhuacine Is a Potent and Selective Inhibitor of the Basal-Like 2 Subtype of Triple Negative Breast Cancer with Immunogenic Potential. Cancers, 13.
Zhang, 2014, The Chinese herb isolate yuanhuacine (YHL-14) induces G2/M arrest in human cancer cells by up-regulating p21 protein expression through an p53 protein-independent cascade, J. Biol. Chem., 289, 6394, 10.1074/jbc.M113.513960
Saraiva, 2001, Differential activation by daphnetoxin and mezerein of PKC-isotypes alpha, beta I., delta and zeta, Planta Med., 67, 787, 10.1055/s-2001-18843
Kogiso, 1976, Odoracin, a nematicidal constituent from Daphne odora, Agric. Biol. Chem., 40, 2119
Ohigashi, 1982, Resiniferonol-related Diterpene Esters from Daphne odora Thunb. and their Ornithine Decarboxylase-inducing Activity in Mouse Skin, Agricult. Biol. Chem., 46, 2605
Kupchan, 1976, Isolation and structural elucidation of new potent antileukemic diterpenoid esters from Gnidia species, J. Org. Chem., 41, 3850, 10.1021/jo00886a016
Fujita, 1977, The Chemistry on Diterpenoids in 1976, Bull. Inst. Chem. Res., 55, 494
Borris, 1984, Studies of the Thymelaeaceae II. Antineoplastic Principles of Gnidia kraussiana, J. Nat. Prod., 47, 270, 10.1021/np50032a006
Shigemori, 2013, Promoting Effects on Hepatocyte Growth Factor Production of Daphnane Diterpenoids from Daphne odora, HETEROCYCLES, 87, 1087, 10.3987/COM-13-12687
Matsuyama, 2009, Effect of Mediterranean Medicinal Plant Extracts on Melanogenesis Regulation, J. Arid. Land Studies, 19, 387
Villareal, M.O., Sato, Y., Matsuyama, K., and Isoda, H. (2018). Daphnane diterpenes inhibit the metastatic potential of B16F10 murine melanoma cells in vitro and in vivo. BMC Cancer., 18.
Qiao, Y., Zhao, Y., Wu, Q., Sun, L., Ruan, Q., Chen, Y., Wang, M., Duan, J., and Wang, D. (2014). Full Toxicity Assessment of Genkwa Flos and the Underlying Mechanism in Nematode Caenorhabditis elegans. PLoS ONE, 9.
Chen, 2013, Toxicity of daphnane-type diterpenoids from Genkwa Flos and their pharmacokinetic profile in rat, Phytomedicine, 21, 82, 10.1016/j.phymed.2013.06.012
Li, 2017, Preparation of dry powder inhalation of yuanhuacine and its tissue distribution in rats, J. China Pharm. Univ., 6, 297
Li, M., Liu, X., Cai, H., Shen, Z., Xu, L., Li, W., Wu, L., Duan, J., and Chen, Z. (2016). Validation and Application of an Ultra High-Performance Liquid Chromatography Tandem Mass Spectrometry Method for Yuanhuacine Determination in Rat Plasma after Pulmonary Administration: Pharmacokinetic Evaluation of a New Drug Delivery System. Molecules, 21.
Zhang, 2009, Evaluation of poly(d,l-lactide-co-glycolide) microspheres for the lung-targeting of yuanhuacine, a novel DNA topoisomerase I inhibitor, J. Drug Target., 17, 286, 10.1080/10611860902737912
Chen, 2017, Hierarchical pulmonary target nanoparticles via inhaled administration for anticancer drug delivery, Drug Deliv., 24, 1191, 10.1080/10717544.2017.1365395
Wang, 1980, Studies on the active principles in the root of Yuan-Hua (Daphne genkwa). II. Isolation and structure of a new antifertile diterpene orthoester, yuanhuadine, Chin. Pharm. Bull., 15, 39
Wang, 1981, Studies on the active principles in the root of Yuan-Hua (Daphne genkwa). II. Isolation and structure of a new antifertile diterpene yuanhuadine, Acta Chim. Sin., 39, 421
Wang, 1982, Isolation and structure of a new diterpene orthester, yuanhuafine, Chin. Pharm. Bull., 17, 174
Wang, 1982, Studies on the active principles in the root of Yuan-Hua (Daphne gemkwa). III. Isolation and structure of yuanhuafine, Acta Chim. Sin., 40, 835
Hu, 1985, Antifertility constituent of the flower Yuan-Hua. Isolation and structure of yuanhuatine, Acta Chim. Sin., 43, 460
Sha, 1986, Constituents of the Yuanhua’s flower buds—isolation and structure of yuanhuapine, Acta Chim. Sin., 44, 843
Wang, 1983, Clinico-pathologic study on the action of yuanhuadine in mid-trimester abortion, Zhonghua fu chan ke za zhi, 18, 154
Zhang, 2006, Evaluation of Daphne genkwa diterpenes: Fingerprint and quantitative analysis by high performance liquid chromatography, Phytochem. Anal., 18, 91, 10.1002/pca.953
Hong, 2011, Growth Inhibition of Human Lung Cancer Cells via Down-regulation of Epidermal Growth Factor Receptor Signaling by Yuanhuadine, a Daphnane Diterpene from Daphne genkwa, J. Nat. Prod., 74, 2102, 10.1021/np2003512
Kim, 2019, AXL degradation in combination with EGFR-TKI can delay and overcome acquired resistance in human non-small cell lung cancer cells, Cell Death Dis., 10, 1, 10.1038/s41419-019-1601-6
Jeong, 2019, Overcoming the Intrinsic Gefitinib-resistance via Downregulation of AXL in Non-small Cell Lung Cancer, J. Cancer Prev., 24, 217, 10.15430/JCP.2019.24.4.217
Bae, 2015, Targeting the degradation of AXL receptor tyrosine kinase to overcome resistance in gefitinib-resistant non-small cell lung cancer, Oncotarget, 6, 10146, 10.18632/oncotarget.3380
Bae, 2016, Down-regulation of SerpinB2 is associated with gefitinib resistance in non-small cell lung cancer and enhances invadopodia-like structure protrusions, Sci. Rep., 6, 32258, 10.1038/srep32258
Bach, 2018, Targeting Nicotinamide N-Methyltransferase and miR-449a in EGFR-TKI-Resistant Non-Small-Cell Lung Cancer Cells, Mol. Ther.—Nucleic Acids, 11, 455, 10.1016/j.omtn.2018.03.011
Bach, 2018, BMP4 Upregulation Is Associated with Acquired Drug Resistance and Fatty Acid Metabolism in EGFR-Mutant Non-Small-Cell Lung Cancer Cells, Mol. Ther.—Nucleic Acids, 12, 817, 10.1016/j.omtn.2018.07.016
Luu, 2020, Overexpression of AGR2 Is Associated with Drug Resistance in Mutant Non-small Cell Lung Cancers, Anticancer Res., 40, 1855, 10.21873/anticanres.14139
Wang, 2018, Anti-inflammatory and anti-angiogenic activities in vitro of eight diterpenes from Daphne genkwa based on hierarchical cluster and principal component analysis, J. Nat. Med., 72, 675, 10.1007/s11418-018-1202-1
Li, 2010, Daphnane-Type Diterpenoids from the Flower Buds of Daphne genkwa, Helvetica Chim. Acta, 93, 1172, 10.1002/hlca.200900359
Chen, 2015, Pharmacokinetic profile and metabolite identification of yuanhuapine, a bioactive component in Daphne genkwa by ultra-high performance liquid chromatography coupled with tandem mass spectrometry, J. Pharm. Biomed. Anal., 112, 60, 10.1016/j.jpba.2015.04.023
Chen, 2016, Yuanhuapine-induced intestinal and hepatotoxicity were correlated with disturbance of amino acids, lipids, carbohydrate metabolism and gut microflora function: A rat urine metabonomic study, J. Chromatogr. B, 1026, 183, 10.1016/j.jchromb.2015.08.024
Wender, 2011, Gateway synthesis of daphnane congeners and their protein kinase C affinities and cell-growth activities, Nat. Chem., 3, 615, 10.1038/nchem.1074
Kuok, 2017, Synergistic antibacterial effects of herbal extracts and antibiotics on methicillin-resistant Staphylococcus aureus: A computational and experimental study, Exp. Biol. Med., 242, 731, 10.1177/1535370216689828
Hayes, 2010, Daphnane- and Tigliane-Type Diterpenoid Esters and Orthoesters from Pimelea elongata, J. Nat. Prod., 73, 1907, 10.1021/np1005746
Jo, 2012, Anticancer Activity of Novel Daphnane Diterpenoids from Daphne genkwa through Cell-Cycle Arrest and Suppression of Akt/STAT/Src Signalings in Human Lung Cancer Cells, Biomol. Ther., 20, 513, 10.4062/biomolther.2012.20.6.513
Zhao, 2019, Rapid Recognition and Targeted Isolation of Anti-HIV Daphnane Diterpenes from Daphne genkwa Guided by UPLC-MSn, J. Nat. Prod., 83, 134, 10.1021/acs.jnatprod.9b00993
Kang, 2016, PRDM1, a Tumor-Suppressor Gene, is Induced by Genkwadaphnin in Human Colon Cancer SW620 Cells, J. Cell. Biochem., 117, 172, 10.1002/jcb.25262
Wu, 2020, Genkwadaphnin inhibits growth and invasion in hepatocellular carcinoma by blocking DHCR24-mediated cholesterol biosynthesis and lipid rafts formation, Br. J. Cancer, 123, 1673, 10.1038/s41416-020-01085-z
Kim, 2013, Protein kinase C-α downregulates estrogen receptor-α by suppressing c-Jun phosphorylation in estrogen receptor-positive breast cancer cells, Oncol. Rep., 31, 1423, 10.3892/or.2013.2936
Yun, 2013, Crosstalk between PKCalpha and Notch-4 in endocrine-resistant breast cancer cells, Oncogenesis, 2, 60, 10.1038/oncsis.2013.26
Li, 1983, Isolation and identification of Yuan Hua (Daphne genkwa) flavonoids, Chin. Tradit. Herb. Drugs, 14, 392
Ji, 1986, Flavonoids in the Yuanhua Leaf (Daphne genkwa), Zhangcaoyao, 17, 487
Tosun, 1994, Türlerinin kimyasal içeriği ve biyolojik aktiviteleri: Chemical constituents and biological activities of Daphne L. Species, Ank. Univ. Eczaci. Fak. Derg., 35, 001
Ulubelen, 1982, Flavone 5-O-glucosides from Daphne sericea, Phytochemistry, 21, 801, 10.1016/0031-9422(82)83199-3
Vankar, 2009, Chemical characterization of extract derived from Daphne papyraceae and sonicator dyeing of cotton, silk and wool with the extract, Pigment Resin Technol., 38, 181, 10.1108/03699420910957042
Xu, 2009, Chemical constituents from Daphne pedunculata, Chem. Nat. Compd., 45, 417, 10.1007/s10600-009-9330-1
Xu, 2011, Phytochemical and Biological Studies of the Plants from the Genus Daphne, Chem. Biodivers., 8, 1215, 10.1002/cbdv.201000117
Frezza, C., Venditti, A., De Vita, D., Sciubba, F., Tomai, P., Franceschin, M., Di Cecco, M., Ciaschetti, G., Di Sotto, A., and Stringaro, A. (2021). Phytochemical Analysis and Biological Activities of the Ethanolic Extract of Daphne sericea Vahl Flowering Aerial Parts Collected in Central Italy. Biomolecules, 11.
Zheng, 2007, Total flavonoids of Daphne genkwa root significantly inhibit the growth and metastasis of Lewis lung carcinoma in C57BL6 mice, Int. Immunopharmacol., 7, 117, 10.1016/j.intimp.2006.07.010
Devkota, 2012, Phenolic Compounds from the Aerial Parts of Diplomorpha canescens, Chem. Pharm. Bull., 60, 554, 10.1248/cpb.60.554
Tewtrakul, 2003, HIV-1 integrase inhibitory substances from Coleus parvifolius, Phytotherapy Res., 17, 232, 10.1002/ptr.1111
Qawoogha, 2020, Identification of potential anticancer phytochemicals against colorectal cancer by structure-based docking studies, J. Recept. Signal Transduct., 40, 67, 10.1080/10799893.2020.1715431
Chen, 2018, Incompatibility assessment of Genkwa Flos and Glycyrrhizae Radix et Rhizoma with biochemical, histopathological and metabonomic approach, J. Ethnopharmacol., 229, 222, 10.1016/j.jep.2018.10.014
Yu, 2020, Licorice-Yuanhua Herbal Pair Induces Ileum Injuries Through Weakening Epithelial and Mucous Barrier Functions: Saponins, Flavonoids, and Di-Terpenes All Involved, Front. Pharmacol., 11, 869, 10.3389/fphar.2020.00869
Yu, 2019, Health risk of Licorice-Yuanhua combination through induction of colonic H2S metabolism, J. Ethnopharmacol., 236, 136, 10.1016/j.jep.2019.01.042
Hou, 2021, Daphnane-type diterpenes from genus Daphne and their anti-tumor activity, Chin. Herb. Med., 13, 145
Pan, 2020, Daphnane Diterpenoids from Daphne genkwa Inhibit PI3K/Akt/mTOR Signaling and Induce Cell Cycle Arrest and Apoptosis in Human Colon Cancer Cells, J. Nat. Prod., 83, 1238, 10.1021/acs.jnatprod.0c00003
Hou, 2018, Neogenkwanine I from the flower buds of Daphne genkwa with its stereostructure confirmation using quantum calculation profiles and antitumor evaluation, Nat. Prod. Res., 34, 405, 10.1080/14786419.2018.1536133