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Yang, Nam, and Kang: Two New Scalaranes from a Korean Marine Sponge Spongia sp.
Original Article

Natural Product Sciences 2015;21(4):289-292.

Published online: 17 January 2015

DOI: https://doi.org/10.20307/nps.2015.21.4.289

Two New Scalaranes from a Korean Marine Sponge Spongia sp.

Inho Yang1, Sang-Jip Nam2, ∗, Heonjoong Kang∗, 1, 3

1 School of Earth and Environmental Sciences, Seoul National University, NS-80, Seoul 151-747, Korea

2 Department of Chemistry and Nano Science, Global Top5 Program, Ewha Womans University, Seoul 120-750, Korea

3 Research Institute of Oceanography, Seoul National University, NS-80, Seoul 151-747, Korea

∗Author for correspondence Sang-Jip Nam, Department of Chemistry and Nano Science, Global Top5 Program, Ewha Womans University, Seoul 120-750, Korea Tel: +82-2-3277-6805; E-mail: sjnam@ewha.ac.kr

Heonjoong Kang, School of Earth and Environmental Sciences, Seoul National University, NS-80, Seoul 151-747, Korea Tel: +82-2-880-5730; E-mail: hjkang@snu.ac.kr

      Revised 30 June 201514 August 2015       Accepted 17 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

Intensive chemical investigation of Korean marine sponge Spongia sp. has led to the isolation of two new scalaranes. The planar structures of the new compounds 1 and 2 were determined through 1D and 2D NMR spectral data analysis, while the relative stereochemistry of the compounds was determined based on the analysis of 1H-1H coupling constants and NOESY spectroscopic data. Compounds 1 and 2 did not display any significant biological activities on farnesoid X-activated receptor (FXR) in co-transfection assay.

Keywords: Scalarane, Sesterpenoid, Spongia sp., Korean sponge, Marine natural product

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Fig. 1.
Chemical structures of 1 and 2.
nps-21-289f1.tif
Fig. 2.
Key COSY and HMBC correlations of 1.
nps-21-289f2.tif
Table 1.
1H and 13C NMR data of 1 and 2 in CDCl3.
1a 2b
No. δC, mc δH, m, J (Hz) COSY HMBC δC, mc δH, m, J (Hz)
1 40.1, CH2 0.79, m 2 3, 23 40.4, CH2 0.76, m
1.67, m 1.67, m
2 18.8, CH2 1.51, m 1, 3 18.7, CH2 1.38, m
1.55, m 1.48, m
3 42.2, CH2 1.13, dt (9.4, 3.7) 2 5 42.2, CH2 1.15, m
1.39, m 1.38, m
4 33.5, C 33.4, C
5 56.6, CH 0.78, m 56.5, CH 0.76, m
6 18.2, CH2 1.40, m 18.2, CH2 1.33, m
1.51, m 1.48, m
7 41.8, CH2 0.96, dt (13.2, 3.5) 5, 9, 24 41.8, CH2 0.89, m
1.69, d (10.2) 1.69, m
8 37.8, C 37.3, C
9 61.4, CH 0.85, m 58.5, CH 0.83, m
10 37.8, C 37.3, C
11 17.3, CH2 1.42, m 8 26.9, CH2 1.43, m
1.55, m 1.69, m
12 40.7, CH2 1.40, m 9, 18, 25 76.2, CH 3.56, dd (11.8, 4.2)
1.78, d (9.8)
13 37.8, C 44.0, C
14 54.7, CH 1.30, m 15 24, 25 47.7, CH 1.33, m
15 24.2, CH2 2.07, m 14, 16 16, 17 25.9, CH2 2.21, d (11.4)
2.31, dd (20.4, 4.0) 2.36, dt (20.2, 5.2)
16 136.6, CH 6.84, d (3.3) 15, 18 18, 20 143.1, CH 7.28, m
17 127.0, C 125.8, C
18 57.9, CH 2.47, m 19 57.8, CH 3.58, s
19 105.6, CH 5.20, d (5.8) 18 19-OMe 204.0, CH 9.86, d (3.6)
20 171.0, C 167.0, C
21 21.5, CH3 0.78, s 22 21.4, CH3 0.77, s
22 33.5, CH3 0.84, s 21 33.4, CH3 0.84, s
23 16.5, CH3 0.84, s 17.0, CH3 0.88, s
24 16.6, CH3 0.91, s 16.8, CH3 0.89, s
25 15.5, CH3 0.76, s 16.0, CH3 0.90, s
19-OMe 57.9, CH3 3.56, s
20-OMe 52.1, CH3 3.70, s

a 600 MHz for 1H NMR and 150 MHz for 13C NMR.

b 500 MHz for 1H NMR and 125 MHz for 13C NMR

c Multiplicity was determined by the analysis of 2D NMR spectroscopic data.

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