Molecular Networking Revealed Unique UV-Absorbing Phospholipids: Favilipids from the Marine Sponge <i>Clathria faviformis</i>

Analysis of extracts of the marine sponge <i>Clathria faviformis</i> by high-resolution LC-MS<sup>2</sup> and molecular networking resulted in the discovery of a new family of potentially UV-protecting phospholipids, the favilipids. One of them, favilipid A (<b>1</b&...

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Main Authors: Silvia Scarpato, Roberta Teta, Paola De Cicco, Francesca Borrelli, Joseph R. Pawlik, Valeria Costantino, Alfonso Mangoni
Format: Article
Language:English
Published: MDPI AG 2023-01-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/21/2/58
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author Silvia Scarpato
Roberta Teta
Paola De Cicco
Francesca Borrelli
Joseph R. Pawlik
Valeria Costantino
Alfonso Mangoni
author_facet Silvia Scarpato
Roberta Teta
Paola De Cicco
Francesca Borrelli
Joseph R. Pawlik
Valeria Costantino
Alfonso Mangoni
author_sort Silvia Scarpato
collection DOAJ
description Analysis of extracts of the marine sponge <i>Clathria faviformis</i> by high-resolution LC-MS<sup>2</sup> and molecular networking resulted in the discovery of a new family of potentially UV-protecting phospholipids, the favilipids. One of them, favilipid A (<b>1</b>), was isolated and its structure determined by mass and tandem mass spectrometry, NMR, electronic circular dichroism (ECD), and computational studies. Favilipid A, which has no close analogues among natural products, possesses an unprecedented structure characterized by a 4-aminodihydropiridinium core, resulting in UV-absorbing properties that are very unusual for a phospholipid. Consequently, favilipid A could inspire the development of a new class of molecules to be used as sunscreen ingredients. In addition, favilipid A inhibited by 58–48% three kinases (JAK3, IKKβ, and SYK) involved in the regulation of the immune system, suggesting a potential use for treatment of autoimmune diseases, hematologic cancers, and other inflammatory states.
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spelling doaj.art-9e55be62eee9407a8e917cc4823d4ff62023-11-16T21:47:15ZengMDPI AGMarine Drugs1660-33972023-01-012125810.3390/md21020058Molecular Networking Revealed Unique UV-Absorbing Phospholipids: Favilipids from the Marine Sponge <i>Clathria faviformis</i>Silvia Scarpato0Roberta Teta1Paola De Cicco2Francesca Borrelli3Joseph R. Pawlik4Valeria Costantino5Alfonso Mangoni6Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via Domenico Montesano 49, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via Domenico Montesano 49, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via Domenico Montesano 49, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via Domenico Montesano 49, 80131 Napoli, ItalyDepartment of Biology and Marine Biology and Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K Moss Lane, Wilmington, NC 28409, USADipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via Domenico Montesano 49, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via Domenico Montesano 49, 80131 Napoli, ItalyAnalysis of extracts of the marine sponge <i>Clathria faviformis</i> by high-resolution LC-MS<sup>2</sup> and molecular networking resulted in the discovery of a new family of potentially UV-protecting phospholipids, the favilipids. One of them, favilipid A (<b>1</b>), was isolated and its structure determined by mass and tandem mass spectrometry, NMR, electronic circular dichroism (ECD), and computational studies. Favilipid A, which has no close analogues among natural products, possesses an unprecedented structure characterized by a 4-aminodihydropiridinium core, resulting in UV-absorbing properties that are very unusual for a phospholipid. Consequently, favilipid A could inspire the development of a new class of molecules to be used as sunscreen ingredients. In addition, favilipid A inhibited by 58–48% three kinases (JAK3, IKKβ, and SYK) involved in the regulation of the immune system, suggesting a potential use for treatment of autoimmune diseases, hematologic cancers, and other inflammatory states.https://www.mdpi.com/1660-3397/21/2/58natural productsmarine spongessunscreensecondary metabolitesLC-MSmolecular networking
spellingShingle Silvia Scarpato
Roberta Teta
Paola De Cicco
Francesca Borrelli
Joseph R. Pawlik
Valeria Costantino
Alfonso Mangoni
Molecular Networking Revealed Unique UV-Absorbing Phospholipids: Favilipids from the Marine Sponge <i>Clathria faviformis</i>
Marine Drugs
natural products
marine sponges
sunscreen
secondary metabolites
LC-MS
molecular networking
title Molecular Networking Revealed Unique UV-Absorbing Phospholipids: Favilipids from the Marine Sponge <i>Clathria faviformis</i>
title_full Molecular Networking Revealed Unique UV-Absorbing Phospholipids: Favilipids from the Marine Sponge <i>Clathria faviformis</i>
title_fullStr Molecular Networking Revealed Unique UV-Absorbing Phospholipids: Favilipids from the Marine Sponge <i>Clathria faviformis</i>
title_full_unstemmed Molecular Networking Revealed Unique UV-Absorbing Phospholipids: Favilipids from the Marine Sponge <i>Clathria faviformis</i>
title_short Molecular Networking Revealed Unique UV-Absorbing Phospholipids: Favilipids from the Marine Sponge <i>Clathria faviformis</i>
title_sort molecular networking revealed unique uv absorbing phospholipids favilipids from the marine sponge i clathria faviformis i
topic natural products
marine sponges
sunscreen
secondary metabolites
LC-MS
molecular networking
url https://www.mdpi.com/1660-3397/21/2/58
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