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Marine Drugs
Volume 17
Issue 1
10.3390/md17010026
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Article

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

by
Kah Yean Lum
1,
Anthony R. Carroll
1,
Merrick G. Ekins
2,
Silven Read
3,
Zahra Haq
3,
Ian Tietjen
3,
James St John
1 and
Rohan A. Davis
1,*
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.
Mar. Drugs 2019, 17(1), 26; https://doi.org/10.3390/md17010026
Submission 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 2–6 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.
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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MDPI and ACS Style

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. https://doi.org/10.3390/md17010026

AMA Style

Lum KY, Carroll AR, Ekins MG, Read S, Haq Z, Tietjen I, St John J, Davis RA. Capillasterin A, a Novel Pyrano[2,3-f]chromene from the Australian Crinoid Capillaster multiradiatus. Marine Drugs. 2019; 17(1):26. https://doi.org/10.3390/md17010026

Chicago/Turabian Style

Lum, Kah Yean, Anthony R. Carroll, Merrick G. Ekins, Silven Read, Zahra Haq, Ian Tietjen, James St John, and Rohan A. Davis. 2019. "Capillasterin A, a Novel Pyrano[2,3-f]chromene from the Australian Crinoid Capillaster multiradiatus" Marine Drugs 17, no. 1: 26. https://doi.org/10.3390/md17010026

APA Style

Lum, K. Y., Carroll, A. R., Ekins, M. G., Read, S., Haq, Z., Tietjen, I., St John, J., & Davis, R. A. (2019). Capillasterin A, a Novel Pyrano[2,3-f]chromene from the Australian Crinoid Capillaster multiradiatus. Marine Drugs, 17(1), 26. https://doi.org/10.3390/md17010026

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