ent-kaurane diterpenoids from Chinese liverworts and their antitumor activities through Michael addition as detected in situ by a fluorescence probe

Journal of Medicinal Chemistry

Volumn 58, Issue 9, 2015, Pages 3944-3956

  Lin, Zhaomin ^a   Guo, Yanxia ^a   Gao, Yanhui ^a   Wang, Shuqi ^a   Wang, Xiaoning ^a   Xie, Zhiyu ^a   Niu, Huanmin ^a   Chang, Wenqiang ^a   Liu, Lei ^a   Yuan, Huiqing ^a   Lou, Hongxiang ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

13 HYDROXY ENT 9(11) KAUREN 15 ONE; 13 HYDROXY ENT 9(11) KAUREN 18 AL 15 ONE; 13 HYDROXY ENT 9(11),16 KAURADIEN 15 ONE; 13 HYDROXYJUNGERMANNENONE B; 13,18 DIHYDROXY ENT 9(11) KAUREN 15 ONE; 13,18 DIHYDROXY ENT 9(11),16 KAURADIEN 15 ONE; 13,18 DIHYDROXY ENT 9(11),16 KAURADIEN 18 AL 15 ONE; 13,18 DIHYDROXYJUNGERMANNENONE B; 13,19 DIHYDROXY ENT 9(11) KAUREN 15 ONE; 13,19 DIHYDROXY ENT 9(11),16 KAURADIEN 15 ONE; 15BETA HYDROXY ENT 16 KAUREN 11 ONE; 16ALPH,17 DIHYDRO 13,19 DIHYDROXYJUNGERMANNENONE B; 16ALPHA,17 DIHYDRO 13 HYDROXYJUNGERMANNENONE B; 16ALPHA,17 DIHYDRO 13,18 DIHYDROXYJUNGERMANNENONE B; 18 FORMYL 16ALPHA,17 DIHYDRO 13 HYDROXYJUNGERMANNENONE B; 18 HYDROXY ENT 9(11),16 KAURADIEN 15 ONE; 18 HYDROXYJUNGERMANNENONE B; 1ALPHA,15BETA DIHYDROXY ENT 16 KAURENE; 3ALPHA,11BETA DIHYDROXY ENT KAURAN 15 ONE; 6ALPHA,13,18 TRIHYDROXY ENT 9(11) KAUREN 15 ONE; 6ALPHA,15BETA DIHYDROXY ENT 16 KAUREN 11 ONE; 6ALPHA,7APHA,15BETA TRIHYDROXY ENT 16 KAUREN 11 ONE; 7ALPHA,15BETA DIHYDROXY ENT 16 KAUREN 11 ONE; ANTINEOPLASTIC AGENT; ANTIOXIDANT; CISPLATIN; DITERPENOID; FLUORESCENT DYE; KAURANE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; AZIDE; COUMARIN DERIVATIVE; REACTIVE OXYGEN METABOLITE;

ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL LINE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG ISOLATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; FLUORESCENCE IN SITU HYBRIDIZATION; FREE RADICAL SCAVENGING ASSAY; HUMAN; HUMAN CELL; IC50; JUNGERMANNIA FAURIANA; JUNGERMANNIA HYALINA; LIVERWORT; MALE; MICHAEL ADDITION; OXIDATIVE STRESS; PROTEIN DEPLETION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; CELL DEATH; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; METABOLISM; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; AZIDES; CELL DEATH; CELL LINE, TUMOR; COUMARINS; DITERPENES, KAURANE; DRUG SCREENING ASSAYS, ANTITUMOR; FLUORESCENT DYES; HEPATOPHYTA; HUMANS; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84929376647     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00208     Document Type: Article

References (50)

1. Newman, D. J. Natural products as leads to potential drugs: an old process or the new hope for drug discovery? J. Med. Chem. 2008, 51, 2589-2599
2. Lee, K. H. Discovery and Development of Natural Product-Derived Chemotherapeutic Agents Based on a Medicinal Chemistry Approach J. Nat. Prod. 2010, 73, 500-516
3. Newman, D. J.; Cragg, G. M. Natural products as sources of new drugs over the 30 years from 1981 to 2010 J. Nat. Prod. 2012, 75, 311-335
4. Asakawa, Y. Chemosystematics of the Hepaticae Phytochemistry 2004, 65, 623-669
5. Asakawa, Y. Liverworts-potential source of medicinal compounds Curr. Pharm. Des. 2009, 14, 3067-3088
6. Asakawa, Y.; Ludwiczuk, A.; Nagashima, F. Phytochemical and biological studies of bryophytes Phytochemistry 2013, 91, 52-80
7. Asakawa, Y.; Ludwiczuk, A.; Nagashima, F. Chemical Constituents of Bryophytes: Bio- and Chemical Diversity, Biological Activity, and Chemosystematics; Progress in the Chemistry of Organic Natural Products, Vol. 95; Springer: Berlin, 2013.
8. Nagashima, F.; Kondoh, M.; Uematsu, T.; Nishiyama, A.; Saito, S.; Sato, M.; Asakawa, Y. Cytotoxic and apoptosis-inducing ent-kaurane-type diterpenoids from the Japanese liverwort Jungermannia truncata NEES Chem. Pharm. Bull. 2002, 50, 808-813
9. Zheng, H.; Chen, Q.; Zhang, M.; Lai, Y.; Lei, L.; Shu, P.; Zhang, J.; Xue, Y.; Luo, Z.; Li, Y.; Yao, G.; Zhang, Y. Cytotoxic ent-Kaurane Diterpenoids from Salvia cavaleriei J. Nat. Prod. 2013, 76, 2253-2262
10. Zhan, R.; Li, X. N.; Du, X.; Wang, W. G.; Dong, K.; Su, J.; Li, Y.; Pu, J. X.; Sun, H. D. Bioactive ent-Kaurane diterpenoids from Isodon rosthornii J. Nat. Prod. 2013, 76, 1267-1277
11. Sun, H. D.; Huang, S. X.; Han, Q. B. Diterpenoids from Isodon species and their biological activities Nat. Prod. Rep. 2006, 23, 673-698
12. Luo, X.; Pu, J. X.; Xiao, W. L.; Zhao, Y.; Gao, X. M.; Li, X. N.; Zhang, H. B.; Wang, Y. Y.; Li, Y.; Sun, H. D. Cytotoxic ent-Kaurane diterpenoids from Isodon rubescens var. lushiensis J. Nat. Prod. 2010, 73, 1112-1116
13. Aquila, S.; Weng, Z. Y.; Zeng, Y. Q.; Sun, H. D.; Ríos, J. L. Inhibition of NF-κB activation and iNOS induction by ent-kaurane diterpenoids in LPS-stimulated RAW264.7 murine macrophages J. Nat. Prod. 2009, 72, 1269-1272
14. Zhou, G. B.; Kang, H.; Wang, L.; Gao, L.; Liu, P.; Xie, J.; Zhang, F. X.; Weng, X. Q.; Shen, Z. X.; Chen, J.; Gu, L. J.; Yan, M.; Zhang, D. E.; Chen, S. J.; Wang, Z. Y.; Chen, Z. Oridonin, a diterpenoid extracted from medicinal herbs, targets AML1-ETO fusion protein and shows potent antitumor activity with low adverse effects on t(8;21) leukemia in vitro and in vivo Blood 2007, 109, 3441-3456
15. Gu, Z. M.; Wu, Y. L.; Zhou, M. Y.; Liu, C. X.; Xu, H. Z.; Yan, H.; Zhao, Y.; Huang, Y.; Sun, H. D.; Chen, G. Q. Pharicin B stabilizes retinoic acid receptor-α and presents synergistic differentiation induction with ATRA in myeloid leukemic cells Blood 2010, 116, 5289-5297
16. Santagata, S.; Xu, Y.; Wijeratne, E. M. K.; Kontnik, R.; Rooney, C.; Perley, C. C.; Kwon, H.; Clardy, J.; Kesari, S.; Whitesell, L.; Lindquist, S.; Gunatilaka, A. A. L. Using the heat-shock response to discover anticancer compounds that target protein homeostasis ACS Chem. Biol. 2012, 7, 340-349
17. Wijeratne, E. M. K.; Bashyal, B. P.; Liu, M. X.; Rocha, D. D.; Gunaherath, G. M. K. B.; U'Ren, J. M.; Gunatilaka, M. K.; Arnold, A. E.; Whitesell, L.; Gunatilaka, A. A. L. Geopyxins A-E, ent-Kaurane Diterpenoids from Endolichenic Fungal Strains Geopyxis aff. majalis and Geopyxis sp. AZ0066: Structure-Activity Relationships of Geopyxins and Their Analogues J. Nat. Prod. 2012, 75, 361-369
18. Liu, C. X.; Yin, Q. Q.; Zhou, H. C.; Wu, Y. L.; Pu, J. X.; Xia, L.; Liu, W.; Huang, X.; Jiang, T.; Wu, M. X.; He, L. C.; Zhao, Y. X.; Wang, X. L.; Xiao, W. L.; Chen, H. Z.; Zhao, Q.; Zhou, A. W.; Wang, L. S.; Sun, H. D.; Chen, G. Q. Adenanthin targets peroxiredoxin I and II to induce differentiation of leukemic cells Nat. Chem. Biol. 2012, 8, 486-493
19. Guo, D. X.; Zhu, R. X.; Wang, X. N.; Wang, L. N.; Wang, S. Q.; Lin, Z. M.; Lou, H. X. Scaparvin A, a novel caged cis -clerodane with an unprecedented C-6/C-11 bond, and related diterpenoids from the liverwort Scapania parva Org. Lett. 2010, 12, 4404-4407
20. Wang, L. N.; Zhang, J. Z.; Li, X.; Wang, X. N.; Xie, C. F.; Zhou, J. C.; Lou, H. X. Pallambins A and B, unprecedented hexacyclic 19-nor-secolabdane diterpenoids from the Chinese liverwort Pallavicinia ambigua Org. Lett. 2012, 14, 1102-1105
21. Liu, N.; Li, R. J.; Wang, X. N.; Zhu, R. X.; Wang, L.; Lin, Z. M.; Zhao, Y.; Lou, H. X. Highly oxygenated ent-pimarane-type diterpenoids from the Chinese liverwort Pedinophyllum interruptum and their allelopathic activities J. Nat. Prod. 2013, 76, 1647-1653
22. Lin, Z. M.; Guo, Y. X.; Wang, S. Q.; Wang, X. N.; Chang, W. Q.; Zhou, J. C.; Yuan, H.; Lou, H. Diterpenoids from the Chinese liverwort Heteroscyphus tener and their antiproliferative effects J. Nat. Prod. 2014, 77, 1336-1344
23. Zhang, D. Y.; Tang, Y.; Wang, K.; Wu, X. M.; Hua, W. Y. Synthesis and antitumor activity of ent-kaurane diterpenoids J. China Pharm. Univ. 2010, 41, 20-25
24. Nagashima, F.; Kasai, W.; Kondoh, M.; Fujii, M.; Watanabe, Y.; Braggins, J. E.; Asakawa, Y. New ent-kaurene-type diterpenoids possessing cytotoxicity from the New Zealand liverwort Jungermannia species Chem. Pharm. Bull. 2003, 51, 1189-1192
25. Nagashima, F.; Kondoh, M.; Fujii, M.; Takaoka, S.; Watanabe, Y.; Asakawa, Y. Novel cytotoxic kaurane-type diterpenoids from the New Zealand liverwort Jungermannia species Tetrahedron 2005, 61, 4531-4544
26. Qu, J. B.; Zhu, R. L.; Zhang, Y. L.; Guo, H. F.; Wang, X. N.; Xie, C. F.; Yu, W. T.; Ji, M.; Lou, H. X. ent-Kaurane diterpenoids from the liverwort Jungermannia atrobrunnea J. Nat. Prod. 2008, 71, 1418-1422
27. Trachootham, D.; Lu, W.; Ogasawara, M. A.; Nilsa, R. D.; Huang, P. Redox regulation of cell survival Antioxid. Redox Signaling 2008, 10, 1343-1374
28. Rhee, S. G. H2O2, a necessary evil for cell signaling Science 2006, 312, 1882-1883
29. Dickinson, B. C.; Chang, C. J. Chemistry and biology of reactive oxygen species in signaling or stress responses Nat. Chem. Biol. 2011, 7, 504-511
30. Alexandre, J.; Batteux, F.; Nicco, C.; Chéreau, C.; Laurent, A.; Guillevin, L.; Weill, B.; Goldwasser, F. Accumulation of hydrogen peroxide is an early and crucial step for paclitaxel-induced cancer cell death both in vitro and in vivo Int. J. Cancer 2006, 119, 41-48
31. Trachootham, D.; Zhou, Y.; Zhang, H.; Demizu, Y.; Chen, Z.; Pelicano, H.; Chiao, P. J.; Achanta, G.; Arlinghaus, R. B.; Liu, J.; Huang, P. Selective killing of oncogenically transformed cells through a ROS-mediated mechanism by β-phenylethyl isothiocyanate Cancer Cell 2006, 10, 241-252
32. Trachootham, D.; Alexandre, J.; Huang, P. Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? Nat. Rev. Drug Discovery 2009, 8, 579-591
33. Gorrini, C.; Harris, I. S.; Mak, T. W. Modulation of oxidative stress as an anticancer strategy Nat. Rev. Drug Discovery 2013, 12, 931-947
34. Zhen, T.; Wu, C. F.; Liu, P.; Wu, H. Y.; Zhou, G. B.; Lu, Y.; Liu, J. X.; Liang, Y.; Li, K. K.; Wang, Y. Y.; Xie, Y. Y.; He, M. M.; Cao, H. M.; Zhang, W. N.; Chen, L. M.; Petrie, K.; Chen, S. J.; Chen, Z. Targeting of AML1-ETO in t(8;21) leukemia by oridonin generates a tumor suppressor-like protein Sci. Transl. Med. 2012, 4 127ra38
35. Huang, J.; Wu, L.; Tashiro, S.; Onodera, S.; Ikejima, T. Reactive oxygen species mediate oridonin-induced HepG2 apoptosis through p53, MAPK, and mitochondrial signaling pathways J. Pharmacol. Sci. 2008, 107, 370-379
36. Yu, Z. Y.; Liang, Y. G.; Xiao, H.; Shan, Y. J.; Dong, B.; Huang, R.; Fu, Y. L.; Zhao, Z. H.; Liu, Z. Y.; Zhao, Q. S.; Wang, S. Q.; Chen, J. P.; Mao, B. Z.; Cong, Y. W. Melissoidesin G, a diterpenoid purified from Isodon melissoides, induces leukemic-cell apoptosis through induction of redox imbalance and exhibits synergy with other anticancer agents Int. J. Cancer 2007, 121, 2084-2094
37. Liao, Y. J.; Bai, H. Y.; Li, Z. H.; Zou, J.; Chen, J. W.; Zheng, F.; Zhang, J. X.; Mai, S. J.; Zeng, M. S.; Sun, H. D.; Pu, J. X.; Xie, D. Longikaurin A, a natural ent-kaurane, induces G2/M phase arrest via downregulation of Skp2 and apoptosis induction through ROS/JNK/c-Jun pathway in hepatocellular carcinoma cells Cell Death Dis. 2014, 5 e1137
38. Dickinson, D. A.; Forman, H. J. Cellular glutathione and thiols metabolism Biochem. Pharmacol. 2002, 64, 1019-1026
39. Chatterjee, A. Reduced glutathione: a radioprotector or a modulator of DNA-repair activity? Nutrients 2013, 5, 525-542
40. Lu, S. C. Regulation of glutathione synthesis Mol. Aspects Med. 2009, 30, 42-59
41. Li, W.; Sun, W.; Yu, X.; Du, L.; Li, M. Coumarin-based fluorescent probes for H2S detection J. Fluoresc. 2013, 23, 181-186
42. Yuan, L.; Jian, W.; Zhang, D.; Aubry, A. F.; Arnold, M. E. Application of a stabilizer cocktail of N -ethylmaleimide and phenylmethanesulfonyl fluoride to concurrently stabilize the disulfide and ester containing compounds in a plasma LC-MS/MS assay J. Pharm. Biomed. Anal. 2014, 88, 552-561
43. Kim, J. A.; Kang, Y. S.; Park, S. H.; Kim, H. W.; Cho, S. Y.; Lee, Y. S. Role of reactive oxygen species in apoptosis induced by N -ethylmaleimide in HepG2 human hepatoblastoma cells Eur. J. Pharmacol. 2001, 433, 1-6
44. Yellaturu, C. R.; Bhanoori, M.; Neeli, I.; Rao, G. N. N -Ethylmaleimide Inhibits Platelet-Derived Growth Factor BB-Stimulated Akt Phosphorylation via Activation of Protein Phosphatase 2A J. Biol. Chem. 2002, 277, 40148-40155
45. Rajendran, L.; Knölker, H. J.; Simons, K. Subcellular targeting strategies for drug design and delivery Nat. Rev. Drug Discovery 2010, 9, 29-42
46. Mohamed, M. M.; Sloane, B. F. Cysteine cathepsins: multifunctional enzymes in cancer Nat. Rev. Cancer 2006, 6, 764-775
47. Mizushima, N.; Levine, B.; Cuervo, A. M.; Klionsky, D. J. Autophagy fights disease through cellular self-digestion Nature 2008, 451, 1069-1075
48. Boya, P.; Kroemer, G. Lysosomal membrane permeabilization in cell death Oncogene 2008, 27, 6434-6451
49. Sheldrick, G. M.; Schneider, T. R. Methods Enzymol. 1997, 277, 319-343
50. Griffith, O. W. Determination of glutathione and glutathione disulfide using glutathione reductase and 2-vinylpyridine Anal. Biochem. 1980, 106, 207-212