CN: 32-1845/R
ISSN: 2095-6975
Cite this paper:
0
XIONG Lei, CHEN Chang-Fa, MIN Tao-Ling, HU Hai-Feng. Romipeptides A and B, two new romidepsin derivatives isolated from Chromobacterium violaceum No.968 and their antitumor activities in vitro[J]. Chinese Journal of Natural Medicines, 2019, 17(2): 155-160

Romipeptides A and B, two new romidepsin derivatives isolated from Chromobacterium violaceum No.968 and their antitumor activities in vitro

XIONG Lei, CHEN Chang-Fa, MIN Tao-Ling, HU Hai-Feng
State Key Lab of New Drug & Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai 200000, China
Abstract:
Romipeptides A and B (1 and 2), two new romidepsin derivatives, and three known compounds, chromopeptide A (3), romidepsin (4) and valine-leucine dipeptide (5) were isolated from the fermentation broth of Chromobacterium violaceum No. 968. Their structures were elucidated by interpretation of their UV, HR-ESI-MS and NMR spectra. The absolute configuration of compound 1 and 2 were established by single crystal X-ray diffraction analysis. Compounds 1-5 were evaluated for their anti-proliferative activities against three human cancer cell lines, SW620, HL60, and A549. The results showed most of these compounds exhibited antitumor activities in vitro, in which compound 2 displayed potent cytotoxicity to SW620, HL60 and A549 cell lines, with IC50 of 12.5, 6.7 and 5.7 nmol�L-1, respectively.
Key words:    Chromobacterium violaceum    Romidepsin derivatives    Cytotoxicity   
Received: 2018-07-17   Revised:
Tools
PDF (431 KB) Free
Print this page
Email this article to others
Authors
Articles by XIONG Lei
Articles by CHEN Chang-Fa
Articles by MIN Tao-Ling
Articles by HU Hai-Feng
References:
[1] Durán N, Menck CFM. Chromobacterium violaceum:a review of pharmacological and industiral perspectives[J]. Crit Rev Microbiol, 2001, 27(3):201-222.
[2] Ueda H, Nakajima H, Hori Y, et al. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties, and antitumor activity[J]. J Antibiot, 1994, 47(3):301-310.
[3] Vandermolen KM, Mcculloch W, Pearce CJ, et al. Romidepsin (Istodax, NSC 630176, FR901228, FK228, Depsipeptide):anatural product recently approved for cutaneous t-cell lymphoma[J]. J Antibiot, 2011, 64(8):525-531.
[4] Mullard A. 2011 FDA drug approvals[J]. Nat Rev Drug Discov, 2012, 11(2):91-94.
[5] Jonsson KL, Tolstrup M, Vadnielsen J, et al. Histone deacetylase inhibitor romidepsin inhibits De Novo HIV-1 infections[J]. Antimicrob Agents Chemother, 2015, 59(7):3984-3994.
[6] Wang C, Henkes LM, Doughty LB, et al. Thailandepsins:Bacterial products with potent histone deacetylase inhibitory activities and broad-spectrum antiproliferative activities[J]. J Nat Prod, 2011, 74(10):2031-2038.
[7] Masuoka Y, Nagai A, Shin-ya K, et al. Spiruchostatins A and B, novel gene expression-enhancing substances produced by Pseudomonas sp[J]. Tetrahedron Lett, 2001, 42(1):41-44.
[8] Zhou Z, Xin W, Hui Z, et al. Chromopeptide A, a highly cytotoxic depsipeptide from the marine sediment-derived bacterium Chromobacterium sp. Hs-13-94[J]. Acta Pharm Sin B, 2015, 5(1):62-66.
[9] Yang DS, Qiu-Xia HE, Yang YP, et al. Chemical constituents of Euphorbia tibetica and their biological activities[J]. Chin J Nat Med, 2014, 12(1):38-42.
[10] Zhao W, Jian-Xin PU, Xue DU, et al. Cytotoxic diterpenoids from Isodon adenolomus[J]. Chin J Nat Med, 2011, 9(4):253-258.
[11] Shigematsu N, Ueda H, Takase S, et al. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. Ⅱ. Structure determination[J]. J Antibiot, 1994, 47(3):311-314.
[12] Prasad C. Bioactive cyclic dipeptides[J]. Peptides, 1995, 16(1):151-164.
[13] Mohammad-taghi M, Karimi A, Alidadi S, et al. In vitro antiproliferative and apoptosis-inducing activities of crude ethyle alcohole extract of Quercus brantii L. acorn and subsequent fractions[J]. Chin J Nat Med, 2016, 14(3):196-202.
[14] Cheng YQ, Yang M, Matter AM. Characterization of a gene cluster responsible for the biosynthesis of anticancer agent FK228 in Chromobacterium violaceum No. 968[J]. Appl Environ Microb, 2007, 73(11):3460-3469.
[15] Wang C, Wesener SR, Zhang H, et al. An FAD-dependent pyridine nucleotide-disulfide oxidoreductase is involved in disulfide bond formation in FK228 anticancer depsipeptide[J]. Chem Biol, 2009, 16(6):585-593.
[16] Liao CR, Kuo YH, Ho YL, et al. Studies on cytotoxic constituents from the leaves of Elaeagnus oldhamii maxim. In non-small cell lung cancer A549 cells[J]. Molecules, 2014, 19(7):9515-9534.