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Mar. Drugs 2019, 17(1), 60; https://doi.org/10.3390/md17010060

Molecular Networking Reveals Two Distinct Chemotypes in Pyrroloiminoquinone-Producing Tsitsikamma favus Sponges

1
Department of Biochemistry and Microbiology, Rhodes University, PO Box 94, Grahamstown 6140, South Africa
2
Division of Pharmaceutical Sciences, University of Wisconsin-Madison, Madison, WI 53705, USA
3
South African Environmental Observation Network, Elwandle Node, Nelson Mandela University Ocean Sciences Campus, Summerstrand, Port Elizabeth 6001, South Africa
4
Department of Chemistry, Rhodes University PO Box 94, Grahamstown 6140, South Africa
5
Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, OR 97331, USA
*
Authors to whom correspondence should be addressed.
Received: 17 December 2018 / Revised: 9 January 2019 / Accepted: 11 January 2019 / Published: 16 January 2019
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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Abstract

The temperate marine sponge, Tsitsikamma favus, produces pyrroloiminoquinone alkaloids with potential as anticancer drug leads. We profiled the secondary metabolite reservoir of T. favus sponges using HR-ESI-LC-MS/MS-based molecular networking analysis followed by preparative purification efforts to map the diversity of new and known pyrroloiminoquinones and related compounds in extracts of seven specimens. Molecular taxonomic identification confirmed all sponges as T. favus and five specimens (chemotype I) were found to produce mainly discorhabdins and tsitsikammamines. Remarkably, however, two specimens (chemotype II) exhibited distinct morphological and chemical characteristics: the absence of discorhabdins, only trace levels of tsitsikammamines and, instead, an abundance of unbranched and halogenated makaluvamines. Targeted chromatographic isolation provided the new makaluvamine Q, the known makaluvamines A and I, tsitsikammamine B, 14-bromo-7,8-dehydro-3-dihydro-discorhabdin C, and the related pyrrolo-ortho-quinones makaluvamine O and makaluvone. Purified compounds displayed different activity profiles in assays for topoisomerase I inhibition, DNA intercalation and antimetabolic activity against human cell lines. This is the first report of makaluvamines from a Tsitsikamma sponge species, and the first description of distinct chemotypes within a species of the Latrunculiidae family. This study sheds new light on the putative pyrroloiminoquinone biosynthetic pathway of latrunculid sponges. View Full-Text
Keywords: Latrunculiidae; makaluvamine Q; damirone; pyrrolo-ortho-quinone; discorhabdin; tsitsikammamine; HR-ESI-LC-MS/MS; pyrroloquinoline; GNPS Latrunculiidae; makaluvamine Q; damirone; pyrrolo-ortho-quinone; discorhabdin; tsitsikammamine; HR-ESI-LC-MS/MS; pyrroloquinoline; GNPS
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Kalinski, J.-C.J.; Waterworth, S.C.; Siwe Noundou, X.; Jiwaji, M.; Parker-Nance, S.; Krause, R.W.M.; McPhail, K.L.; Dorrington, R.A. Molecular Networking Reveals Two Distinct Chemotypes in Pyrroloiminoquinone-Producing Tsitsikamma favus Sponges. Mar. Drugs 2019, 17, 60.

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