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Journal List > Nat Prod Sci > v.21(4) > 1060595

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Kim, Shin, Lee, Shin, and Oh: Salternamide E from a Saltern-derived Marine Actinomycete Streptomyces sp.
Original Article

Natural Product Sciences 2015;21(4):273-277.

Published online: 17 January 2015

DOI: https://doi.org/10.20307/nps.2015.21.4.273

Salternamide E from a Saltern-derived Marine Actinomycete Streptomyces sp.

Seong-Hwan Kim, Yoonho Shin, Sang Kook Lee, Jongheon Shin, Dong-Chan Oh∗

Natural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea

∗Author for correspondence Dong-Chan Oh, Natural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea Tel: +82-2-880-2491; E-mail: dongchanoh@snu.ac.kr

      Revised 18 July 20154 August 2015       Accepted 7 August 2015

Copyright © 2015 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Comprehensive chemical analysis of extracts and fractions of marine actinomycete strains led to the discovery of a new minor secondary metabolite, salternamide E (1), from a saltern-derived halophilic Streptomyces strain. The planar structure of salternamide E (1) was elucidated by a combinational analysis of spectroscopic data including NMR, MS, UV, and IR. The absolute configuration of salternamide E (1) was determined by circular dichroism spectroscopic analysis. Salternamide E displayed weak cytotoxicity against various human carcinoma cell lines.

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Keywords: Marine actinomycete, Saltern, LC/MS analysis, Salternamide E, Cytotoxicity

REFERENCES

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(2). Moon K., Chung B., Shin Y., Rheingold A. L., Moore C. E., Park S. J., Park S., Lee S. K., Oh K.-B., Shin J., Oh D.-C. J.Nat. Prod. 2015; 78:524–529.
(3). Hou Y., Braun D. R., Michel C. R., Klassen J. L., Adnani N., Wyche T. P., Bugni T. S.Anal. Chem. 2012; 84:4277–4283.
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(5). Yang J. Y., Sanchez L. M., Rath C. M., Liu X., Boudreau P. D., Bruns N., Glukhov E., Wodtke A., de Felicio R., Fenner A., Wong W. R., Linington R. G., Zhang L., Debonsi H. M., Gerwick W. H., Dorrestein P. C. J.Nat. Prod. 2013; 76:1686–1699.
(6). Um S., Kim Y.-J., Kwon H., Wen H., Kim S.-H., Kwon H. C., Park S., Shin J., Oh D.-C. J.Nat. Prod. 2013; 76:873–879.
(7). Um S., Choi T. J., Kim H., Kim B. Y., Kim S.-H., Lee S. K., Oh K.-B., Shin J., Oh D.-C. J.Org. Chem. 2013; 78:12321–12329.
(8). Kwon Y., Kim S.-H., Shin Y., Bae M., Kim B.-Y., Lee S.K.; Oh, K.-B.; Shin, J.; Oh, D.-C. Mar. Drugs. 2014; 12:2326–2340.
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nps-21-273f1.tif
Fig. 1.
The structure of salternamide E (1).
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nps-21-273f2.tif
Fig. 2.
Key COSY () and HMBC (→) correlations of 1.
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nps-21-273f3.tif
Fig. 3.
1H-1H coupling constants (J values) and key NOESY () correlations of 1.
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nps-21-273f4.tif
Fig. 4.
The experimental ECD spectra of 1 and salternamide C.
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Table 1.
1H and 13C NMR data of 1 in CD3 OD. (δ in ppm, 500 MHz for 1H and 125 MHz for 13C)a
Position 1
δH mult. (J in Hz) δC
1 194.2 C
2 133.8 C
3 7.58 s 133.1 CH
4 73.5 C
5 3.98 dd (8.0, 4.0) 70.9 CH
6a 2.82 dd (16.5, 8.0) 42.4 CH2
6b 2.73 dd (16.5, 4.0)
7a 1.87 m 39.4 CH2
7b 1.71 m
8a 1.52 m 24.6 CH2
8b 1.50 m
9a 1.67 m 26.9 CH2
9b 1.65 m
10 2.31 t (7.5) 35.4 CH2
11 178.3 C
1' 167.2 C
2' 6.15 dd (15.5, 1.0) 123.5 CH
3' 6.71 dd (15.5, 8.0) 153.2 CH
4' 2.48 m 35.5 CH
5'a 1.37 m 45.5 CH2
5'b 1.12 m
6' 1.49 m 29.2 CH
7'a 1.09 m 48.5 CH2
7'b 1.01 m
8' 1.66 m 26.3 CH
9' 0.86 d (6.5) 23.7 CH3
10' 0.85 d (6.5) 22.7 CH3
11' 0.87 d (6.5) 20.0 CH3
12' 1.05 d (6.5) 20.9 CH3

a The assignments were based on 1H-1H COSY, HSQC, and HMBC experiments.

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