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

Huda A Wahab; Ngoc B Pham; Tengku S Tengku Muhammad; John N A Hooper; Ronald J Quinn

doi:10.3390/md15010006

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

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

Authors

Huda A Wahab^{1

2}, Ngoc B Pham³, Tengku S Tengku Muhammad^{4

5}, John N A Hooper^{6

7}, Ronald J Quinn⁸

Affiliations

¹ Eskitis Institute for Drug Discovery, Griffith University, Brisbane 4111, Australia. nuruhuda.abdulwahab@griffithuni.edu.au.
² School of Fundamental Science, Universiti Malaysia Terengganu, Kuala Terengganu 21030, Malaysia. nuruhuda.abdulwahab@griffithuni.edu.au.
³ Eskitis Institute for Drug Discovery, Griffith University, Brisbane 4111, Australia. nhuda@umt.edu.my.
⁴ School of Fundamental Science, Universiti Malaysia Terengganu, Kuala Terengganu 21030, Malaysia. sifzizul@umt.edu.my.
⁵ Institute of Marine Biotechnology, Universiti Malaysia Terengganu, Kuala Terengganu 21030, Malaysia. sifzizul@umt.edu.my.
⁶ Eskitis Institute for Drug Discovery, Griffith University, Brisbane 4111, Australia. n.pham@griffith.edu.au.
⁷ Queensland Museum, Brisbane 4101, Australia. n.pham@griffith.edu.au.
⁸ Eskitis Institute for Drug Discovery, Griffith University, Brisbane 4111, Australia. r.quinn@griffith.edu.au.

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.

MeSH terms

Animals
Atherosclerosis / drug therapy*
Australia
Cardiovascular Agents / chemistry
Cardiovascular Agents / pharmacology
Cell Line, Tumor
Hep G2 Cells
Humans
Porifera / chemistry*
Sesquiterpenes / chemistry*
Sesquiterpenes / pharmacology*
Xanthones / chemistry*
Xanthones / pharmacology*

Substances

Cardiovascular Agents
Sesquiterpenes
Xanthones
puupehenone