Details of Research Outputs

TitleCircumdatin M, a new benzodiazepine alkaloid with a unique pyrimidone-4-pyrone moiety from a Hawaiian marine fungus Aspergillus sp. FM242
Author (Name in English or Pinyin)
Wang, Fuqian1,2; Hu, Zhenquan3; Li, Chunshun1; Wu, Xiaohua1; Cao, Shugeng1,4
Date Issued2019-06-27
Source PublicationTETRAHEDRON LETTERS
ISSN0040-4039
DOI10.1016/j.tetlet.2019.05.061
Indexed BySCIE
Firstlevel Discipline化学
Education discipline科技类
Published range国外学术期刊
Volume Issue Pages卷: 60 期: 26 页: 1724-1726
References
[1] Li, C., Yang, B., Fenstemacher, R., Turkson, J., Cao, S., Tetrahedron Lett., 56, 2015, 1724.
[2] Li, C., Ding, Y., Yang, B., Miklossy, G., Yin, H., Walker, L.A., Turkson, J., Cao, S., Org. Lett., 17, 2015, 3556.
[3] Li, C., Ding, Y., Yang, B., Yin, G.H.-Q., Turkson, J., Cao, S., Phytochemistry, 126, 2016, 41.
[4] Li, C., Ren, G., Yang, B., Miklossy, G., Turkson, J., Fei, P., Ding, Y., Walker, L.A., Cao, S., Org. Lett., 18, 2016, 2335.
[5] Fei-Zhang, D.J., Li, C., Cao, S., Cancer Biol. Ther., 17, 2016, 709.
[6] Li, C., Yang, B., Turkson, J., Cao, S., Phytochemistry, 140, 2017, 77.
[7] Li, C., Sarotti, A.M., Turkson, J., Cao, S., Tetrahedron Lett., 58, 2017, 2290.
[8] Huang, P., Li, C., Sarotti, A.M., Turkson, J., Cao, S., Tetrahedron Lett., 58, 2017, 1330.
[9] Li, C., Sarotti, A.M., Yang, B., Turkson, J., Cao, S., Molecules, 22, 2017, pii:E1166.
[10] Li, C., Sarotti, A.M., Huang, P., Dang, U.T., Hurdle, J.G., Kondratyuk, T.P., Pezzuto, J.M., Turkson, J., Cao, S., Sci. Rep., 7, 2017, 10424.
[11] Li, C., Sarotti, A.M., Yoshida, W., Cao, S., Tetrahedron Lett., 58, 2018, 42.
[12] Li, C., Hu, Z., Liu, Q., Wu, X., Cao, S., Tetrahedron Lett., 59, 2018, 3381.
[13] Li, C., Sarotti, A.M., Wu, X., Yang, B., Turkson, J., Chen, Y., Liu, Q., Cao, S., Molecules, 24, 2019 pii:E196.
[14] (a) General experimental procedures: Optical rotations were measured with a Rudolph research analytical autoPol automatic polarimeter. UV, CD and FT-IR spectra were recorded on Shimadzu UV-1800, JASCO J-815 CD and Thermo scientific nicolet iS10 IR spectrometer respectively. NMR spectra including 1D and 2D experiments were recorded on a Bruker AM-400 spectrometer. High resolution mass spectra were recorded on a Agilent 6530 accurate-Mass Q-TOF LC-MS spectrometer. Preparative HPLC was carried out on an Ultimate 3000 chromatographic system with a Phenomenex preparative column (Phenyl-Hexyl, 5 µ, 100 × 21.20 mm) and Semi-preparative HPLC on an Ultimate 3000 chromatographic system with an Dionex Ultimate 3000 DAD detector, Dionex Ultimate 3000 automated fraction collector and a Phenomenex semi-preparative column (C18, 5 µ, 250 × 10 mm), and all solvents were HPLC grade. Column chromatography used Diaion HP-20. (b) Strain isolation and cultivation: The strain Aspergillus sp. FM 242 was isolated from a soil sample collected at Waikiki beach of Oahu in May 2014, Hawaii. The rDNA ITS1-4 region sequence of fungus has been submitted to GenBank (Accession number MH879469). The strain was deposited at Daniel K. Inouye College of Pharmacy, University of Hawaii, HI, USA. The strain was grown on PDA plates at 28 °C, then it was cut into pieces (0.5 × 0.5 cm) and inoculated into 30 L autoclaving sterilized liquid medium (mannitol 20 g, glucose 10 g, monosodium glutamate 5 g, KH2PO4 (0.5 g), MgSO4·7H2O 0.3 g, yeast extract 3 g, sea salt 30 g for 1 L distilled water; pH 6.5 prior sterilization.) for fermentation at 25 °C for 21 days. (c) Extraction and isolation: After filtering, the mycelia were extracted with MeOH under ultrasonic (1 L × 3 times), then removed methanol under reduced pressure to afford an aqueous solution. Combined the mycelia extraction and supernatant solution then it was subjected to HP-20 column eluted with MeOH-H2O (10%, 50%, 70%, 100%) to afford four fractions (Fr.1-4). Fraction 4 (9.99 g) was separated by prep-HPLC (Phenyl-Hexyl, 5 µ, 100 × 21.20 mm; 8 mL/min) eluted with 45%-100% MeOH-H2O in 35 minutes to get sub-fractions (SFr. 1-35). SFr 24 was purified by semi-preparative HPLC (10 % - 100% CH3OH with 0.1% formic acid in 35 min; 3 mL/min) to afford compound 1 (2.0 mg, tR 26.3 min). (d) Circumdatin M (1): reddish powder; [α]25 D +18 (c = 0.03, MeOH); UV (MeOH) λmax (log ε) 278 (3.63), 370 (3.04) nm; CD (c 2.98 × 10−5 M, MeOH) λmax(Δε) 249 (+6.9), 281 (−0.9) nm; IR νmax 1672, 1632, 1606, 1578, 1452, 1440 cm−1; 1H (in DMSO-d6 at 400 MHz) and 13C NMR (in DMSO-d6, 100 MHz) data, see Table 1; positive HR-ESIMS m/z 336.0980 [M + H]+ (calcd 336.0984). (e) The viability of A2780 and the cisplatin-resistant, A2780CisR [27], was determined using the CyQuant cell proliferation assay kit, according to the manufacturer's instructions (Life Technologies, Eugene, OR, USA). Briefly, cells in 96-well plates, seeded 24 h prior, were treated with or without compounds for 72 h, and subjected to CyQuant cell viability assay (Life Technologies, Eugene, OR, USA) [28–30]. Each cell line was cultured in 96-well plates at 6,000 cells per well with the following conditions: 0 (no treatment, vehicle (DMSO)) and increasing concentrations of compounds for 72 h. Cisplatin was used as a positive control. Viable cells were analyzed by subjecting the plates to the CyQuant, as previously reported [28–30]. Relative viability of the treated cells was normalized to the DMSO-treated control cells. All experiments were performed in triplicate.
[15] Ookura, R., Kito, K., Ooi, T., Namikoshi, M., Kusumi, T., J. Org. Chem., 73, 2008, 4245.
[16] Rahbaek, L., Breinholt, J., Frisvad, J.C., Christophersen, C., J. Org. Chem., 64, 1999, 1689.
[17] Ma, W.G., Fuzzati, N., Xue, Y., Yang, C.R., Hostettmann, K., Phytochemistry, 41, 1996, 1287.
[18] Willoughby, P.H., Jansma, M.J., Hoye, T.R., Nature Protocol., 9, 2014, 643.
[19] Peng, J., Zhang, X.Y., Tu, Z.C., Xu, X.Y., Qi, S.H., J. Nat. Prod., 76, 2013, 983.
[20] Wang, Q., Hu, Z., Li, X., Wang, A., Wu, H., Liu, J., Cao, S., Liu, Q., J. Nat. Prod., 81, 2018, 2531.
[21] Witt, A., Bergman, J., J. Org. Chem., 66, 2001, 2784.
[22] Rahbaek, L., Breinholt, J., J Nat Prod., 62, 1999, 904.
[23] Dai, J., Carté, B.K., Sidebottom, P.J., Sek Yew, A.L., Ng, S., Huang, Y., Butler, M.S., J. Nat. Prod., 64, 2001, 125.
[24] López-Gresa, M.P., González, M.C., Primo, J., Moya, P., Romero, V., Estornell, E., J. Antibiot., 58, 2005, 416.
[25] Zhang, D., Yang, X., Kang, J.S., Choi, H.D., Son, B.W., J. Antibiot., 61, 2008, 40.
[26] Zhichkin, P.E., Jin, X., Zhang, H., Peterson, L.H., Ramirez, C., Snyder, T.M., Burton, H.S., Org. Biomol. Chem., 8, 2010, 1287.
[27] Yue, P., Zhang, X., Paladino, D., Sengupta, B., Ahmad, S., Holloway, R.W., Ingersoll, S.B., Turkson, J., Oncogene, 31, 2012, 2309.
[28] Lopez-Tapia, F., Brotherton-Pleiss, C., Yue, P., Murakami, H., Costa Araujo, A.C., Reis Dos Santos, B., Ichinotsubo, E., Rabkin, A., Shah, R., Lantz, M., Chen, S., Tius, M.A., Turkson, J., ACS Med. Chem. Lett., 2018, 250.
[29] Yue, P., Lopez-Tapia, F., Paladino, D., Li, Y., Chen, C.-H., Namanja, A.T., Hilliard, T., Chen, Y., Tius, M.A., Turkson, J., Cancer Res., 76, 2016, 652.
[30] Zhang, X., Yue, P., Page, B.D., Li, T., Zhao, W., Namanja, A.T., Paladino, D., Zhao, J., Chen, Y., Gunning, P.T., Turkson, J., Proc. Natl. Acad. Sci. USA, 109, 2012, 9623.
Citation statistics
Cited Times [WOS]:0   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
Identifierhttps://irepository.cuhk.edu.cn/handle/3EPUXD0A/555
CollectionArieh Warshel Institute for Computational Biology
Corresponding AuthorCao, Shugeng
Affiliation
1.Univ Hawaii, Daniel K Inouye Coll Pharm, Dept Pharmaceut Sci, 200 West Kawili St, Hilo, HI 96720 USA
2.Wuhan First Hosp, Dept Pharm, Wuhan 430022, Hubei, Peoples R China
3.Chinese Univ Hong Kong , Sch Life & Hlth Sci, Warshel Inst Computat Biol, Shenzhen 518172, Peoples R China
4.Univ Hawaii, Canc Ctr, Canc Biol Program, Honolulu, HI 96813 USA
Recommended Citation
GB/T 7714
Wang, Fuqian,Hu, Zhenquan,Li, Chunshunet al. Circumdatin M, a new benzodiazepine alkaloid with a unique pyrimidone-4-pyrone moiety from a Hawaiian marine fungus Aspergillus sp. FM242[J]. TETRAHEDRON LETTERS,2019.
APA Wang, Fuqian, Hu, Zhenquan, Li, Chunshun, Wu, Xiaohua, & Cao, Shugeng. (2019). Circumdatin M, a new benzodiazepine alkaloid with a unique pyrimidone-4-pyrone moiety from a Hawaiian marine fungus Aspergillus sp. FM242. TETRAHEDRON LETTERS.
MLA Wang, Fuqian,et al."Circumdatin M, a new benzodiazepine alkaloid with a unique pyrimidone-4-pyrone moiety from a Hawaiian marine fungus Aspergillus sp. FM242".TETRAHEDRON LETTERS (2019).
Files in This Item:
There are no files associated with this item.
Related Services
Usage statistics
Google Scholar
Similar articles in Google Scholar
[Wang, Fuqian]'s Articles
[Hu, Zhenquan]'s Articles
[Li, Chunshun]'s Articles
Baidu academic
Similar articles in Baidu academic
[Wang, Fuqian]'s Articles
[Hu, Zhenquan]'s Articles
[Li, Chunshun]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Wang, Fuqian]'s Articles
[Hu, Zhenquan]'s Articles
[Li, Chunshun]'s Articles
Terms of Use
No data!
Social Bookmark/Share
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.