Nat Prod Sci.  2015 Dec;21(4):255-260. 10.20307/nps.2015.21.4.255.

Graphiumins I and J, New Thiodiketopiperazines from the Marine-derived Fungus Graphium sp. OPMF00224

• Fukuda T
• Nagai K
• Kurihara Y
• Kanamoto A
• Tomoda H

• KMID: 2312906
• DOI: http://doi.org/10.20307/nps.2015.21.4.255

Abstract

Two new thiodiketopiperazines (TDKPs), designated graphiumins I (1) and J (2), were isolated from the culture broth of the marine-derived fungus Graphium sp. OPMF00224 by solvent extraction, silica gel column chromatography, and HPLC. Their absolute structures were elucidated by spectroscopic analyses (1D and 2D NMR data, ROESY correlations, and CD data) and chemical methods. They were found to be structurally rare TDKPs with a phenylalanine-derived indolin substructure. Compounds 1 and 2 inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus (MRSA) with IC50 values of 63.5 and 76.5 microg/ml, respectively, without inhibiting its growth, even at 250 microg/ml.

Keyword

Thiodiketopiperazines; Marine-derived fungus; MRSA; Yellow pigment inhibitor

MeSH Terms

Chromatography
Chromatography, High Pressure Liquid
Fungi*
Inhibitory Concentration 50
Methicillin-Resistant Staphylococcus aureus
Silica Gel
Silica Gel

Figure

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  Fig. 1. Structures of graphiumins I (1), J (2) and A (3).

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  Fig. 2. 1H-1H COSY (a), Key HMBC (a), NOE (b) correlations, and H-H coupling (c) of 1.

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  Fig. 3. 1H-1H COSY and Key HMBC correlations of 2.

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  Fig. 4. Proposed biosynthetic pathway of graphiumins I (1) and J (2).

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