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. 2019 Jan 4;17(1):26.
doi: 10.3390/md17010026.

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

Kah Yean Lum  1 , Anthony R Carroll  2 , Merrick G Ekins  3 , Silven Read  4 , Zahra Haq  5 , Ian Tietjen  6 , James St John  7 , Rohan A Davis  8
Affiliations

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

Kah Yean Lum et al. Mar Drugs. .

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: Capillaster multiradiatus; Crinoid; HIV-1; capillasterin A; feather star; naphthopyrones; pyrano[2,3-f]chromene.

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Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study, in the collection, analyses, or interpretation of data, in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
Chemical structures of capillasterin A (1) and naphthopyrones (2–8) isolated from the Australian crinoid C. multiradiatus.
Figure 2
Figure 2
COSY and key HMBC/ROESY correlations for capillasterin A (1).
Figure 3
Figure 3
Proposed biosynthetic pathway for capillasterin A (1).
See this image and copyright information in PMC

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