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

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Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA
2
University of Hawaii Cancer Center, Honolulu, HI 96813, USA
3
Department of Medicinal Chemistry, University of Utah, College of Pharmacy, Salt Lake City, UT 84112, USA
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(7), 423; https://doi.org/10.3390/md17070423
Received: 28 June 2019 / Revised: 16 July 2019 / Accepted: 16 July 2019 / Published: 19 July 2019
Several known sesquiterpenoid quinones and quinols (19), 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 19 exhibited moderate to potent inhibition of growth of human glioma (U251) cells. Compounds 12 and 47 were also active against human pancreatic carcinoma (Panc-1) cells. View Full-Text
Keywords: sesquiterpenoid quinones; 11-membered heterocycle; Dactylospongia elegans; DFT computations; BACE1; human glioma; human pancreatic carcinoma sesquiterpenoid quinones; 11-membered heterocycle; Dactylospongia elegans; DFT computations; BACE1; human glioma; human pancreatic carcinoma
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Neupane, R.P.; Parrish, S.M.; Bhandari Neupane, J.; Yoshida, W.Y.; Yip, M.L.R.; Turkson, J.; Harper, M.K.; Head, J.D.; Williams, P.G. Cytotoxic Sesquiterpenoid Quinones and Quinols, and an 11-Membered Heterocycle, Kauamide, from the Hawaiian Marine Sponge Dactylospongia elegans. Mar. Drugs 2019, 17, 423.

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Mar. Drugs, EISSN 1660-3397, Published by MDPI AG
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