Next Article in Journal
Newly Developed Prodrugs and Prodrugs in Development; an Insight of the Recent Years
Next Article in Special Issue
Pectenovarin, A New Ovarian Carotenoprotein from Japanese Scallop Mizuhopecten yessoensis
Previous Article in Journal
Reduced-Dimensionality Quantum Dynamics Study of the 3Fe(CO)4 + H21FeH2(CO)4 Spin-inversion Reaction
Previous Article in Special Issue
Biologically Active Echinulin-Related Indolediketopiperazines from the Marine Sediment-Derived Fungus Aspergillus niveoglaucus
Open AccessArticle

Isolation, Structure Determination, and Synthesis of Cyclic Tetraglutamic Acids from Box Jellyfish Species Alatina alata and Chironex yamaguchii

1
Department of Natural Sciences, Hawaii Pacific University, Kaneohe, HI 96744, USA
2
Daniel K. Inouye College of Pharmacy, University of Hawaii at Hilo, Hilo, HI 96720, USA
3
Department of Marine Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan
4
Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan
5
German Center for Neurodegenerative Diseases (DZNE), Sigmund-Freud-Str. 27, 53127 Bonn, Germany
6
Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 98622, USA
7
Békésy Laboratory of Neurobiology, Pacific Biosciences Research Center, School of Ocean and Earth Science and Technology, and Department of Tropical Medicine, John A. Burns School of Medicine, University of Hawaii at Manoa, Honolulu, HI 96822, USA
*
Authors to whom correspondence should be addressed.
Academic Editor: Ryuichi Sakai
Molecules 2020, 25(4), 883; https://doi.org/10.3390/molecules25040883
Received: 21 January 2020 / Revised: 8 February 2020 / Accepted: 10 February 2020 / Published: 17 February 2020
Cubozoan nematocyst venoms contain known cytolytic and hemolytic proteins, but small molecule components have not been previously reported from cubozoan venom. We screened nematocyst extracts of Alatina alata and Chironex yamaguchii by LC-MS for the presence of small molecule metabolites. Three isomeric compounds, cnidarins 4A (1), 4B (2), and 4C (3), were isolated from venom extracts and characterized by NMR and MS, which revealed their planar structure as cyclic γ-linked tetraglutamic acids. The full configurational assignments were established by syntheses of all six possible stereoisomers, comparison of spectral data and optical rotations, and stereochemical analysis of derivatized degradation products. Compounds 13 were subsequently detected by LC-MS in tissues of eight other cnidarian species. The most abundant of these compounds, cnidarin 4A (1), showed no mammalian cell toxicity or hemolytic activity, which may suggest a role for these cyclic tetraglutamates in nematocyst discharge. View Full-Text
Keywords: cubozoa; cnidarian; cnidarin; cyclicpeptide; polyglutamic acid; venom cubozoa; cnidarian; cnidarin; cyclicpeptide; polyglutamic acid; venom
Show Figures

Graphical abstract

MDPI and ACS Style

Reinicke, J.; Kitatani, R.; Masoud, S.S.; Galbraith, K.K.; Yoshida, W.; Igarashi, A.; Nagasawa, K.; Berger, G.; Yanagihara, A.; Nagai, H.; Horgen, F.D. Isolation, Structure Determination, and Synthesis of Cyclic Tetraglutamic Acids from Box Jellyfish Species Alatina alata and Chironex yamaguchii. Molecules 2020, 25, 883.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop