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A New Diketopiperazine, Cyclo-(4-S-hydroxy-R-proline-R-isoleucine), from an Australian Specimen of the Sponge Stelletta sp.†
Australian Institute of Marine Science, PMB no. 3, Townsville MC, Townsville 4810, Australia
Defence Science & Technology Organisation, 506 Lorimer St. Fishermans Bend, Victoria 3207, Australia
ACD Labs UK, Building A, Trinity Court, Wokingham Road, Bracknell, Berkshire RG42 1PL, UK
Advanced Analytical Centre, James Cook University, Townsville, QLD 4811, Australia
College of Pharmacy, University of Hawaii, 34 Rainbow Drive, Hilo, HI 96720, USA
† Dedication: We dedicate this paper to the memory of Dr. Peter Murphy (Townsville, Australia), a former AIMS colleague and dear friend, for his passionate contributions to the field of natural products chemistry and marine biodiversity, in particular recognising the need for access and benefit sharing arrangements between scientific organisations and local communities.
* Author to whom correspondence should be addressed.
Received: 29 August 2011; in revised form: 11 November 2011 / Accepted: 16 November 2011 / Published: 22 November 2011
Abstract: While investigating the cytotoxic activity of the methanol extract of an Australian marine sponge Stelletta sp. (Demospongiae), a new diketopiperazine, cyclo-(4-S-hydroxy-R-proline-R-isoleucine) (1), was isolated together with the known bengamides; A (2), F (3), N (4), Y (5), and bengazoles; Z (6), C4 (7) and C6 (8). The isolation and structure elucidation of the diketopiperazine (1), together with the activity of 1–8 against a panel of human and mammalian cell lines are discussed.
Keywords: Stelletta; diketopiperazine (DKP); cyclo-(4-S-hydroxy-R-proline-R-isoleucine); bengamide; bengazole; anti-cancer activity
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Ovenden, S.P.B.; Nielson, J.L.; Liptrot, C.H.; Willis, R.H.; Tapiolas, D.M.; Wright, A.D.; Motti, C.A. A New Diketopiperazine, Cyclo-(4-S-hydroxy-R-proline-R-isoleucine), from an Australian Specimen of the Sponge Stelletta sp.. Mar. Drugs 2011, 9, 2469-2478.
Ovenden SPB, Nielson JL, Liptrot CH, Willis RH, Tapiolas DM, Wright AD, Motti CA. A New Diketopiperazine, Cyclo-(4-S-hydroxy-R-proline-R-isoleucine), from an Australian Specimen of the Sponge Stelletta sp.. Marine Drugs. 2011; 9(11):2469-2478.
Ovenden, Simon P. B.; Nielson, Jonathan L.; Liptrot, Catherine H.; Willis, Richard H.; Tapiolas, Dianne M.; Wright, Anthony D.; Motti, Cherie A. 2011. "A New Diketopiperazine, Cyclo-(4-S-hydroxy-R-proline-R-isoleucine), from an Australian Specimen of the Sponge Stelletta sp.." Mar. Drugs 9, no. 11: 2469-2478.