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Kim, Son, Kim, Jeon, Ko, Ryoo, Shin, Hirota, Takahashi, Osada, Jang, and Ahn: Penidioxolanes A and B, 1,3-Dioxolane Containing Azaphilone Derivatives from Marine-derived Penicillium sp. KCB12C078
Original Article

Natural Product Sciences 2015;21(4):231-236.

Published online: 17 January 2015

DOI: https://doi.org/10.20307/nps.2015.21.4.231

Penidioxolanes A and B, 1,3-Dioxolane Containing Azaphilone Derivatives from Marine-derived Penicillium sp. KCB12C078

Seung Min Kim1, Sangkeun Son1, 2, Jong Won Kim1, Eun Soo Jeon1, Sung-Kyun Ko1, In-Ja Ryoo1, Kee-Sun Shin5, Hiroshi Hirota3, Shunji Takahashi3, 4, Hiroyuki Osada4, Jae-Hyuk Jang1, 2, , Jong Seog Ahn1, 2,

1 Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, Chungbuk 363-883, Korea

2 Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea

3 RIKEN-KRIBB Joint Research Unit, Global Research Cluster, RIKEN, Saitama 351-0198, Japan

4 Chemical Biology Research Group, RIKEN CSRS, Saitama 351-0198, Japan

5 Microbial Resources Center, KRIBB, Daejeon 306-809, Korea

∗Author for correspondence Jong Seog Ahn, Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, Chungbuk 363-883, Korea Tel: +82-43-240-6160; E-mail: jsahn@kribb.re.kr

Jae-Hyuk Jang, Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, Chungbuk 363-883, Korea Tel: +82-43-240-6164; E-mail: jangjh@kribb.re.kr

      Revised 5 June 201517 June 2015       Accepted 17 June 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

Two new azaphilone derivatives containing 1,3-dioxolane moiety, penidioxolanes A (1) and B (2), were isolated from marine-derived fungus Penicillium sp. KCB12C078, together with four known compounds (3-6) by chemical investigation. Compounds 1 - 6 were isolated by combination of silica gel, ODS column chromatography and preparative HPLC. Their structures were determined by analysis of spectroscopic data including 1D-, 2D-NMR, and MS techniques. The isolates were evaluated against cancer cell growth inhibition effects and antimicrobial activity.

Keywords: azaphilone derivatives, 1,3-Dioxolane, Marine-derived fungus, Penicillium

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Fig. 1.
Structures of isolated compounds 1 - 6.
nps-21-231f1.tif
Fig. 2.
Key COSY and HMBC correlations for 1 and 2.
nps-21-231f2.tif
Fig. 3.
NOESY correlations for 1 and 2.
nps-21-231f3.tif
Table 1.
1H (900 MHz) and 13C (225 MHz) NMR data of 1 and 2 in DMSO-d6
No. 1 2
δH (mult., J in Hz) δC δH (mult., J in Hz) δC
1 4.01 (dd, 14.0, 10.8)4.53 (dd, 10.8, 5.5) 68.7 3.80 (dd, 14.0, 11.0)4.49 (dd, 11.0, 5.0) 67.8
3 160.3 161.2
4 6.14 (s) 103.2 6.19 (s) 102.3
4a 144.0 144.9
5 117.3 119.5
6 194.0 188.0
7 78.3 74.5
7-CH3 1.22 (s) 23.6 1.19 (s) 20.0
8 3.91 (d, 3.0) 74.6 4.93 (d, 10.0) 73.3
8a 3.16 (ddd, 14.0, 5.5, 3.0) 37.4 3.26 (ddd, 14.0, 10.0, 5.0) 35.9
9 6.43 (d, 16.0) 123.9 6.49 (d, 15) 123.6
10 6.43 (d, 16.0) 140.6 6.43 (d, 15) 141.1
11 80.7 80.8
11-CH3 1.23 (s) 21.0 1.22 (s) 21.4
12 3.40 (d, 10.0) 88.0 3.37 (d, 9.0) 88.3
13 1.55 (m) 34.4 1.61 (m) 34.2
13-CH3 0.99 (d, 6.5) 16.7 0.99 (d, 6.0) 16.6
14 0.92 (m) 25.0 0.96 (m) 25.0
1.35 (m) 1.36 (m)
14-CH3 0.84 (t, 7.0) 11.2 0.85 (t, 7.0) 11.1
1’ 170.7
1’-CH3 2.16 (s) 21.0
2’ 4.94 (t, 5.5) 102.2 4.94 (t, 5.0) 102.3
3’ 1.55 (m) 36.6 1.56 (m) 36.6
4’ 1.39 (m) 17.3 1.39 (m) 17.3
4’- CH3 0.91 (t, 7.0) 14.4 0.91 (t, 7.0) 14.4
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