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Leutou, Yang, Seong, Ko, and Nam: Violapyrone J, α-Pyrone Derivative from a Marine-derived Actinomycetes, Streptomyces sp.
Original Article

Natural Product Sciences 2015;21(4):248-250.

Published online: 17 January 2015

DOI: https://doi.org/10.20307/nps.2015.21.4.248

Violapyrone J, α-Pyrone Derivative from a Marine-derived Actinomycetes, Streptomyces sp.

Alain S. Leutou1, Inho Yang1, Chi Nam Seong2, Jaeyoung Ko3, Sang-Jip Nam1, ∗

1 Department of Chemistry and Nano Science, Global Top 5 Program, Ewha Womans University, Seoul 120-750, Korea

2 Department of Biology, College of Life Science and Natural Resources, Sunchon National University, Suncheon 540-742, Korea

3 Skin Research Division Amorepacific R&D Unit, Yongin 449-729, Korea

∗Author for correspondence Sang-Jip Nam, Department of Chemistry and Nano Science, Global Top 5 Program, Ewha Womans University, Seoul, 120-750, Korea Tel: +82-2-3277-6805; E-mail: sjnam@ewha.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

A new α-pyrone derivative, violapyrone J (1), and along with the two known violapyrones B (2) and C (3) were isolated from the fermentation broth of a marine actinomycete Streptomyces sp. SC0718. The structure of violapyrone J (1) was elucidated from 1D and 2D NMR spectroscopic analyses.

Keywords: α-Pyrone, Violapyrone, Marine actinomycetes, Streptomyces sp.

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Fig. 1.
The structures of violapyrones J (1), B (2) and C (3).
nps-21-248f1.tif
Fig. 2.
Key HMBC and COSY correlations of violapyrone J (1) in CD3 OD.
nps-21-248f2.tif
Table 1.
NMR data of violapyrone J (1) in CD3 OD. (δ in ppm)a
No. 1
δC, mult.b δH (J in Hz) COSY HMBC
2 181.1, C
3 96.6, C
4 171.4, C
5 108.2, CH 5.77, s 3, 6, 7
6 163.4, C
7 32.3, CH2 2.35-2.45, m 8 5
8 35.3, CH2 1.70, 1.20, m 7, 9
9 35.4, CH 1.45, m 8, 10,12
10 30.6 CH2 1.40, 1.20, m 9, 11 11, 12
11 12.0, CH3 0.91, t (7.0) 10
12 19.6, CH3 0.93 d (6.3) 9 8
3-Me 9.0, CH3 1.81, s 2, 3, 4

a 700 MHz for 1H NMR and 175 MHz for 13C NMR.

b Numbers of attached protons were determined by analysis of 2D spectroscopic data.

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