Cytotoxic Sesquiterpenoid Quinones and Quinols, and an 11-Membered Heterocycle, Kauamide, from the Hawaiian Marine Sponge <i>Dactylospongia elegans</i>

Ram  P. Neupane; Stephen  M. Parrish; Jayanti Bhandari Neupane; Wesley  Y. Yoshida; M.  L. Richard Yip; James Turkson; Mary  Kay Harper; John  D. Head; Philip  G. Williams

doi:10.3390/md17070423

Marine Drugs (Jul 2019)

Cytotoxic Sesquiterpenoid Quinones and Quinols, and an 11-Membered Heterocycle, Kauamide, from the Hawaiian Marine Sponge <i>Dactylospongia elegans</i>

Ram P. Neupane,
Stephen M. Parrish,
Jayanti Bhandari Neupane,
Wesley Y. Yoshida,
M. L. Richard Yip,
James Turkson,
Mary Kay Harper,
John D. Head,
Philip G. Williams

Affiliations

Ram P. Neupane: Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA
Stephen M. Parrish: Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA
Jayanti Bhandari Neupane: Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA
Wesley Y. Yoshida: Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA
M. L. Richard Yip: University of Hawaii Cancer Center, Honolulu, HI 96813, USA
James Turkson: University of Hawaii Cancer Center, Honolulu, HI 96813, USA
Mary Kay Harper: Department of Medicinal Chemistry, University of Utah, College of Pharmacy, Salt Lake City, UT 84112, USA
John D. Head: Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA
Philip G. Williams: Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA

DOI: https://doi.org/10.3390/md17070423
Journal volume & issue: Vol. 17, no. 7
p. 423

Abstract

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Several known sesquiterpenoid quinones and quinols (1−9), and kauamide (10), a new polyketide-peptide containing an 11-membered heterocycle, were isolated from the extracts of the Hawaiian marine sponge Dactylospongia elegans. The planar structure of 10 was determined from spectroscopic analyses, and its relative and absolute configurations were established from density functional theory (DFT) calculations of the GIAO NMR shielding tensors, and advanced Marfey’s analysis of the N-MeLeu residue, respectively. Compounds 1 and 3 showed moderate inhibition of β-secretase 1 (BACE1), whereas 1−9 exhibited moderate to potent inhibition of growth of human glioma (U251) cells. Compounds 1−2 and 4−7 were also active against human pancreatic carcinoma (Panc-1) cells.

Published in Marine Drugs

ISSN: 1660-3397 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Biology (General)
Website: http://www.mdpi.com/journal/marinedrugs

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