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Mar. Drugs 2018, 16(9), 297; https://doi.org/10.3390/md16090297

Sesterterpenoid and Steroid Metabolites from a Deep-Water Alaska Sponge Inhibit Wnt/β-Catenin Signaling in Colon Cancer Cells

1
Department of Chemistry, Yale University, New Haven, CT 06520, USA
2
Chemical Biology Institute, Yale University, West Haven, CT 06516, USA
3
Department of Pharmacognosy, College of Pharmacy, Chungnam National University, Daejeon 34134, Korea
4
Phúthọ College of Pharmacy, Viettri City, Phúthọ Province 293500, Vietnam
5
Department of Bio and Fermentation Convergence Technology, BK21 PLUS program, Kookmin University, Seoul 136-702, Korea
6
Department of Drug Discovery and Biomedical Sciences, Medical University of South Carolina, Charleston, SC 29425, USA
7
Auke Bay Laboratories, Alaska Fisheries Science Center, NOAA National Marine Fisheries Service, Juneau, AK 99801, USA
8
Coast and Oceans National Centre, National Institute of Water and Atmospheric Research, Auckland Central 1149, New Zealand
These authors contributed equal to this work.
*
Authors to whom correspondence should be addressed.
Received: 18 July 2018 / Revised: 1 August 2018 / Accepted: 23 August 2018 / Published: 27 August 2018
(This article belongs to the Special Issue Bioactive Compounds from Marine Sponges)
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Abstract

The Wnt/β-catenin signaling pathway is known to play critical roles in a wide range of cellular processes: cell proliferation, differentiation, migration and embryonic development. Importantly, dysregulation of this pathway is tightly associated with pathogenesis in most human cancers. Therefore, the Wnt/β-catenin pathway has emerged as a promising target in anticancer drug screening programs. In the present study, we have isolated three previously unreported metabolites from an undescribed sponge, a species of Monanchora (Order Poecilosclerida, Family Crambidae), closely related to the northeastern Pacific species Monanchora pulchra, collected from deep waters off the Aleutian Islands of Alaska. Through an assortment of NMR, MS, ECD, computational chemical shifts calculation, and DP4, chemical structures of these metabolites have been characterized as spirocyclic ring-containing sesterterpenoid (1) and cholestane-type steroidal analogues (2 and 3). These compounds exhibited the inhibition of β-catenin response transcription (CRT) through the promotion of β-catenin degradation, which was in part implicated in the antiproliferative activity against two CRT-positive colon cancer cell lines. View Full-Text
Keywords: natural products; marine sponge; sesterterpenoid; steroid; colorectal cancer; Wnt; β-catenin; Alaska natural products; marine sponge; sesterterpenoid; steroid; colorectal cancer; Wnt; β-catenin; Alaska
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Park, H.B.; Tuan, N.Q.; Oh, J.; Son, Y.; Hamann, M.T.; Stone, R.; Kelly, M.; Oh, S.; Na, M. Sesterterpenoid and Steroid Metabolites from a Deep-Water Alaska Sponge Inhibit Wnt/β-Catenin Signaling in Colon Cancer Cells. Mar. Drugs 2018, 16, 297.

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