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Planta Med 2021; 87(01/02): 113-123
DOI: 10.1055/a-1315-0666
Natural Product Chemistry and Analytical Studies
Original Papers

Molecular Networking Discloses the Chemical Diversity of Flavonoids and Selaginellins in Selaginella convoluta

Fernanda Priscila Santos Reginaldo
1   Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal/RN, Brazil
,
Paula Carolina Pires Bueno
2   Faculty of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Ribeirão Preto/SP, Brazil
3   Max-Planck Institute of Molecular Plant Physiology, Potsdam-Golm, Germany
,
Isabelly CristinaMatos Costa de
1   Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal/RN, Brazil
,
AlanAraújo Roque de
4   Institute for Sustainable Development and Environment, Dunas Park Herbarium, Natal/RN, Brazil
,
Arthur Germano Fett-Neto
5   Laboratory of Plant Physiology, Center for Biotechnology and Department of Botany, Federal University of Rio Grande do Sul (UFRGS), Porto Alegre/RS, Brazil
,
Alberto José Cavalheiro
6   Institute of Chemistry, São Paulo State University (UNESP), Araraquara/SP, Brazil
,
Raquel Brandt Giordani 
1   Department of Pharmacy, Federal University of Rio Grande do Norte (UFRN), Natal/RN, Brazil
› Author AffiliationsSupported by: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior Finance Code 001
Supported by: Conselho Nacional de Desenvolvimento Científico e Tecnológico CNPq [445149/2014-0]
Supported by: Conselho Nacional de Desenvolvimento Científico e Tecnológico CNPq/INCTBioNat [465637/2014-0]
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo #2017/19702-6
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo #2019/08477-7
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo FAPESP - INCTBioNat 2014/50926-0
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Abstract

Selaginella convoluta is a desiccation tolerant plant native to the Brazilian semiarid region (Caatinga), endowed with an effective drought resistance mechanism. As part of our research efforts to understand the chemical diversity of S. convoluta, dehydrated (harvested in their natural habitat in the dry season) and hydrated (plant acclimated in a laboratory after rehydration) specimens were analyzed by HR-LC-ESI-MS/MS followed by a structural annotation on the Global Natural Products Social Molecular Networking Web platform. The molecular networking approach allowed for putative annotation of 39 metabolites, mainly selaginellins and flavonoids. Based on MS/MS data, three unprecedented selaginellins were annotated: 29-hydroxy selaginellin O, 29-hydroxy selaginellin A, and 4-{[2-(4-hydrophenyl)-6-[2-(4-hydroxyphenyl)ethynyl]phenyl](4-oxocyclohexa-2,5-dien-1-ylidene)methyl}benzaldehyde. Th results pointed out that valuable scientific knowledge can be obtained from studies conducted with plants in their natural habitat by allowing a more realistic profile of chemical diversity. The present study adds new information on specialized metabolites of S. convoluta, mainly flavonoids and selaginellins, and highlights the species as an untapped source of chemobiodiversity from Caatinga.

Key words

Selaginella convoluta - Selaginellaceae - selaginellins - flavonoids - Caatinga

Supporting Information

    Base peak chromatogram in positive and negative electrospray ionization modes of the methanol extract of shoots and S. convoluta at different hydration states (Fig. 1S), representation of all MN (Fig. 2S), representation of MN after blank removal showing O-glycosyl metabolite clusters (Fig. 3S), the general structure of selaginellins (Fig. 4S), proposal of fragmentation of original selaginellins (Fig. S5), proposal of fragmentation of the annotated selaginellins (Fig. 6S), the MS/MS spectral of the O-glycosyl metabolite cluster (Fig. 7S), and the MS/MS spectral of phenolic derivatives (Fig. 8S) are available as Supporting Information.

  • Supporting Information


Publication History

Received: 30 April 2020

Accepted after revision: 11 November 2020

Article published online:
09 December 2020

© 2020. Thieme. All rights reserved.

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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