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Mar. Drugs 2019, 17(1), 26; https://doi.org/10.3390/md17010026

Capillasterin A, a Novel Pyrano[2,3-f]chromene from the Australian Crinoid Capillaster multiradiatus

1
Griffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia
2
Biodiversity and Geosciences, Queensland Museum, South Brisbane BC, QLD 4101, Australia
3
Faculty of Health Sciences, Simon Fraser University, Burnaby, BC V5A 1S6, Canada
*
Author to whom correspondence should be addressed.
Received: 29 November 2018 / Revised: 21 December 2018 / Accepted: 27 December 2018 / Published: 4 January 2019
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Abstract

Capillasterin A (1), a novel pyrano[2,3-f]chromene, together with seven known naphthopyrones including comaparvin (2), TMC-256C1 (3), 6-methoxycomaparvin-5- methyl ether (4), 5,8-dihydroxy-6-methoxy-2-propyl-4H-naphtho[2,3-b]pyran-4-one (5), 5,8-dihydroxy-6,10-dimethoxy-2-propyl-4H-naphtho[2,3-b]pyran-4-one (6), TMC-256A1 (7) and 6-methoxycomaparvin (8) were isolated from an EtOH/H2O extract from the Australian crinoid Capillaster multiradiatus. The structures of all the compounds were determined by detailed spectroscopic (1D/2D NMR and MS) data analysis. This is the first report of a natural product that contains the pyrano[2,3-f]chromene skeleton. Compounds 26 were observed to display moderate inhibition of in vitro HIV-1 replication in a T cell line with EC50 values ranging from 7.5 to 25.5 µM without concomitant cytotoxicity. View Full-Text
Keywords: Crinoid; feather star; Capillaster multiradiatus; naphthopyrones; pyrano[2,3-f]chromene; capillasterin A; HIV-1 Crinoid; feather star; Capillaster multiradiatus; naphthopyrones; pyrano[2,3-f]chromene; capillasterin A; HIV-1
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Lum, K.Y.; Carroll, A.R.; Ekins, M.G.; Read, S.; Haq, Z.; Tietjen, I.; St John, J.; Davis, R.A. Capillasterin A, a Novel Pyrano[2,3-f]chromene from the Australian Crinoid Capillaster multiradiatus. Mar. Drugs 2019, 17, 26.

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