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Detailed NMR, Including 1,1-ADEQUATE, and Anticancer Studies of Compounds from the Echinoderm Colobometra perspinosa
Australian Institute of Marine Science, PMB No. 3, Townsville MC, Townsville, 4810, Australia
Present address: University of Hawaii, College of Pharmacy, 34 Rainbow Drive, Hilo, HI 96720, USA
Present address: ACD Labs UK, Building A, Trinity Court, Wokingham Road, Bracknell, Berkshire, RG42 1PL, UK
Present address: Defense Science and Technology Organisation, 506 Lorimer Street, Fishermans Bend, Port Melbourne, Victoria 3207, Australia
* Author to whom correspondence should be addressed.
Received: 6 November 2009; in revised form: 10 November 2009 / Accepted: 11 November 2009 / Published: 12 November 2009
Abstract: From the dichloromethane/methanol extract of the crinoid Colobometra perspinosa, collected south east of Richards Island (Bedara), Family Islands, Central Great Barrier Reef, Australia, 3-(1'-hydroxypropyl)-1,6,8-trihydroxy-9,10-anthraquinone [one of the two stereoisomers of rhodoptilometrin, (1)], 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone (3), 2-[(phenylacetyl)amino]ethanesulfonic acid (4), and 4-hydroxybutanoic acid (5) were isolated. Comparison of 1H- and 13C-NMR data for rhodoptilometrin (1) with those reported in the literature showed significant differences for some resonances associated with rings A and C. In an attempt to provide accurately assigned 1H- and 13C-NMR data, as well as to confirm the structure of 1, a thorough NMR investigation of this compound was undertaken. Measurements included: concentration dependent 13C, 1D selective NOE, HSQC, HMBC and 1,1-ADEQUATE. The NMR data for 4 and 5 are reported here for the first time, as is their occurrence from the marine environment. The in vitro anticancer activity of the original extract was found to be associated with 1, 3 and 5.
Keywords: 1,1-ADEQUATE; NMR; marine natural products; echinoderm; Colobometra perspinosa; anticancer
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Wright, A.D.; Nielson, J.L.; Tapiolas, D.M.; Motti, C.A.; Ovenden, S.P.B.; Kearns, P.S.; Liptrot, C.H. Detailed NMR, Including 1,1-ADEQUATE, and Anticancer Studies of Compounds from the Echinoderm Colobometra perspinosa. Mar. Drugs 2009, 7, 565-575.
Wright AD, Nielson JL, Tapiolas DM, Motti CA, Ovenden SPB, Kearns PS, Liptrot CH. Detailed NMR, Including 1,1-ADEQUATE, and Anticancer Studies of Compounds from the Echinoderm Colobometra perspinosa. Marine Drugs. 2009; 7(4):565-575.
Wright, Anthony D.; Nielson, Jonathan L.; Tapiolas, Dianne M.; Motti, Cherie A.; Ovenden, Simon P. B.; Kearns, Philip S.; Liptrot, Catherine H. 2009. "Detailed NMR, Including 1,1-ADEQUATE, and Anticancer Studies of Compounds from the Echinoderm Colobometra perspinosa." Mar. Drugs 7, no. 4: 565-575.