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Phytochemical and Analytical Characterization of Novel Sulfated Coumarins in the Marine Green Macroalga Dasycladus vermicularis (Scopoli) Krasser

1
Institute of Pharmacy, Pharmacognosy, CMBI, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria
2
Institute of Biological Sciences, Applied Ecology & Phycology, University of Rostock, Albert-Einstein-Str. 3, 18059 Rostock, Germany
3
Department of Phytochemistry, Iovel Kutateladze Institute of Pharmacochemistry, Tbilisi State Medical University, 0159 Tbilisi, Georgia
*
Author to whom correspondence should be addressed.
Academic Editor: Pinarosa Avato
Molecules 2018, 23(11), 2735; https://doi.org/10.3390/molecules23112735
Received: 11 September 2018 / Revised: 17 October 2018 / Accepted: 17 October 2018 / Published: 23 October 2018
(This article belongs to the Special Issue Natural Products and Drug Discovery)
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Abstract

The siphonous green algae form a morphologically diverse group of marine macroalgae which include two sister orders (Bryopsidales and Dasycladales) which share a unique feature among other green algae as they are able to form large, differentiated thalli comprising of a single, giant tubular cell. Upon cell damage a cascade of protective mechanisms have evolved including the extrusion of sulfated metabolites which are involved in the formation of a rapid wound plug. In this study, we investigated the composition of sulfated metabolites in Dasycladus vermicularis (Dasycladales) which resulted in the isolation of two phenolic acids and four coumarins including two novel structures elucidated by nuclear magnetic resonance spectroscopy (NMR) as 5,8′-di-(6(6′),7(7′)-tetrahydroxy-3-sulfoxy-3′-sulfoxycoumarin), a novel coumarin called dasycladin A and 7-hydroxycoumarin-3,6-disulfate, which was named dasycladin B. In addition, an analytical assay for the chromatographic quantification of those compounds was developed and performed on a reversed phase C-18 column. Method validation confirmed that the new assay shows good linearity (R2 ≥ 0.9986), precision (intra-day R.S.D ≤ 3.71%, inter-day R.S.D ≤ 7.49%), and accuracy (recovery rates ranged from 104.06 to 97.45%). The analysis of several samples of Dasycladus vermicularis from different collection sites, water depths and seasons revealed differences in the coumarin contents, ranging between 0.26 to 1.61%. View Full-Text
Keywords: siphonous green algae; sulfated coumarins; Dasycladus vermicularis; isolation and quantification siphonous green algae; sulfated coumarins; Dasycladus vermicularis; isolation and quantification
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Hartmann, A.; Ganzera, M.; Karsten, U.; Skhirtladze, A.; Stuppner, H. Phytochemical and Analytical Characterization of Novel Sulfated Coumarins in the Marine Green Macroalga Dasycladus vermicularis (Scopoli) Krasser. Molecules 2018, 23, 2735.

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