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. 2016 Dec 27;15(1):6.
doi: 10.3390/md15010006.

Merosesquiterpene Congeners from the Australian Sponge Hyrtios digitatus as Potential Drug Leads for Atherosclerosis Disease

Huda A Wahab  1   2 , Ngoc B Pham  3 , Tengku S Tengku Muhammad  4   5 , John N A Hooper  6   7 , Ronald J Quinn  8
Affiliations

Merosesquiterpene Congeners from the Australian Sponge Hyrtios digitatus as Potential Drug Leads for Atherosclerosis Disease

Huda A Wahab et al. Mar Drugs. .

Abstract

A study of the chemical constituents from the Australian Sponge Hyrtios digitatus has provided a perspective on the connection between the chemistry and biology of the puupehenones, a unique and unusual class of merosesquiterpenes. In this study, a new tetracyclic merosesquiterpene, 19-methoxy-9,15-ene-puupehenol (1) was isolated from the marine sponge Hyrtios digitatus along with the known 20-methoxy-9,15-ene-puupehenol (2). Their structures were elucidated on the basis of spectroscopic data (¹H and 13C NMR) in combination with experimental electronic circular dichroism (ECD) data. Compounds 1 and 2 are active at 1.78 μM and 3.05 μM, respectively, on Scavenger Receptor-Class B Type 1 HepG2 (SR-B1 HepG2) stable cell lines, targeting atherosclerosis disease.

Keywords: HepG2; Hyrtios digitatus; SR-B1; atherosclerosis; merosesquiterpene.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of compound 1, 2, and Trichostatin.
Figure 2
Figure 2
Key of heteronuclear multiple bond correlations (gHMBC) of 1.
Figure 3
Figure 3
Selected nuclear overhauser effect spectroscopy (NOESY) correlations of 1.
Figure 4
Figure 4
Experimental of an electronic circular dichroism (ECD) and ultraviolet (UV) spectra of 1 and 2.
Figure 5
Figure 5
Comparison of the calculated ECD of four possible diastereomers of 1.
Figure 6
Figure 6
Comparison of the predominant conformer (5S,8S,10S)-1 and (5R,8R,10R)-1.
Figure 7
Figure 7
Dose-response curve of (a) Compound 1 and TSA; (b) Compound 2 and TSA.
See this image and copyright information in PMC

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