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Sulfur-Containing Compounds from Plants

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Natural Secondary Metabolites

Abstract

Sulfur (S) is an essential nutrient assimilated through the diet and incorporated into organic structures such as amino acids, coenzymes, and other bioactive compounds. Plants’ ability to regulate stress resistance via secondary metabolism has extended the interest in S-containing compounds, driven by their additional properties as bioactive molecules. Among plant families that produce S-compounds, the Brassicaceae, which includes broccoli, cabbage, and cauliflower, and the Liliaceae family, which includes garlic and onion, stand out. In recent years, the research has been focused on S-containing amino acids (mainly methionine and cysteine) and glucosinolates (GSLs) and their hydrolysis products like isothiocyanates but also in other S-containing compounds such as phytoalexins or cysteine sulfoxides. GSLs are becoming more popular because of their specific biological properties, including antioxidant, anti-inflammatory, or antimicrobial, among others. Accordingly, a diet rich in vegetables containing S-containing compounds has been associated with a lower risk of developing cancer, neurological diseases like Alzheimer’s, inflammatory bowel disease, cardiovascular diseases, several skin disorders, and obesity. Hence, S-metabolites can therefore be used as therapeutic and preventative components in functional foods and nutraceuticals, as well as cosmeceutical products. This chapter aims to revise the most important features related to sulfur metabolism and S-containing compounds from plant sources, with emphasis on their involvement in secondary metabolism, natural sources, structural classification, biological functions, and applications in human nutrition and health.

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Abbreviations

ATP:

Adenosine triphosphate

APS:

Adenosine 5′-phosphosulfate

PAPS:

Phospoadenosine 5′-phosphosulfate

PAP:

Adenosine 5′-phosphate

Cys:

Cysteine

Met:

Methionine

GSH:

Reduced glutathione

GSSG:

Oxidized glutathione

SAM:

S-adenosylmethionine

SIR:

Sulfite reductase

Cysta:

Cystathionine

Hcy:

Homocysteine

OAS:

O-acetylserine

Glu:

l-glutamate

Gly:

Glycine

AMPS:

Antimicrobial peptides

CRT:

Chloroquine-resistance transporter

γ-EC:

γ-Glutamylcysteine

TAAC:

Paps/chloroplast thylakoid atp/adp carrier

SULTR:

Sulfur transporters

SOT:

Sulfotransferase

Ser:

Serine

SMM:

S-methylmethionine

NA:

Nicotianamine

MBIT:

Methoxybenzyl isothiocyanate

SQDG:

Sulfoquinovosyl diacylglycerol

AITC:

allyl isothiocyanate,

SFN:

Sulforaphane

PEITC:

phenethyl isothiocyanate

MIC-1:

4-[(α-l-Rhamnosyloxy) benzyl] isothiocyanate extracted from Moringa oleifera

7-MSI:

7-methylsulfinylheptyl isothiocyanate

GSL:

Glucosinolates

TSN:

Thiosulfinate

ITC:

Isothiocyanate

6-MITC:

6-(methylsulfinyl)hexyl isothiocyanate

DNCB:

2,4-dinitrochlorobenzene

DSS:

Dextran sulfate sodium

AD:

Alzheimer’s disease

T2D:

Type-2-diabetes

IL:

Interleukin

NF-κB:

Nuclear factor-κB

TNF-α:

Tumor necrosis factor-α

Nrf2:

Nuclear factor erythroid 2

TC:

Total cholesterol

TG:

Triglycerides

TrkB:

Tropomyosin receptor kinase B

LDL-C:

Low-density lipoprotein cholesterol

HDL-C:

High-density lipoprotein cholesterol

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Acknowledgments

The research leading to these results was supported by MICINN supporting the Ramón y Cajal grant for M.A. Prieto (RYC-2017-22891), the María Zambrano grant for R. Perez-Gregorio (CO34991493-20220101ALE481), the FPU grant for A. Soria-Lopez (FPU2020/06140) and the Juan de la Cierva Incorporación for Hui Cao (IJC2020-046055-I); by Xunta de Galicia for supporting the program EXCELENCIA-ED431F 2020/12, the post-doctoral grant of M. Fraga-Corral (ED481B-2019/096), and the pre-doctoral grant of M. Carpena (ED481A 2021/313). The research leading to these results was supported by the European Union through the “NextGenerationEU” program supporting the “Margarita Salas” grant awarded to P. Garcia-Perez. Authors are grateful to Ibero-American Program on Science and Technology (CYTED—AQUA-CIBUS, P317RT0003), to the Bio Based Industries Joint Undertaking (JU) under grant agreement No 888003 UP4HEALTH Project (H2020-BBI-JTI-2019) that supports the work of M. Barral-Martínez. The JU receives support from the European Union’s Horizon 2020 research and innovation program and the Bio Based Industries Consortium. The project SYSTEMIC Knowledge hub on Nutrition and Food Security has received funding from national research funding parties in Belgium (FWO), France (INRA), Germany (BLE), Italy (MIPAAF), Latvia (IZM), Norway (RCN), Portugal (FCT), and Spain (AEI) in a joint action of JPI HDHL, JPI-OCEANS, and FACCE-JPI launched in 2019 under the ERA-NET ERA-HDHL (n° 696295). The authors acknowledge the financial support provided by the FCT-Portuguese Foundation for Science and Technology (PD/BD/150264/2019) under the Doctoral Program “Agricultural Production Chains – from fork to farm” (PD/00122/2012) and from the European Social Funds and the Regional Operational Program Norte 2020. This study was also supported by CITAB research unit (UIDB/04033/2020).

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Author notes

  1. Vera Castro and M. Carpena contributed equally with all other contributors.

Authors and Affiliations

  1. Department of Biology, Centre of Molecular and Environmental Biology, CBMA, University of Minho, Braga, Portugal

    Vera Castro

  2. Department of Biology, Centre for the Research and Technology of Agro-Environmental and Biological Sciences, CITAB, University of Trás-os-Montes e Alto Douro, Vila Real, Portugal

    Vera Castro

  3. Department of Analytical Chemistry and Food Science, Faculty of Science, Universidade de Vigo, Nutrition and Bromatology Group, Ourense, Spain

    M. Carpena, M. Fraga-Corral, A. Lopez-Soria, P. Garcia-Perez, M. Barral-Martinez, R. Perez-Gregorio, Hui Cao, J. Simal-Gandara & M. A. Prieto

  4. Centro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Bragança, Portugal

    M. Fraga-Corral & M. A. Prieto

  5. Department for Sustainable Food Process, Università Cattolica del Sacro Cuore, Piacenza, Italy

    P. Garcia-Perez

  6. LAQV-REQUIMTE Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Porto, Portugal

    R. Perez-Gregorio

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  1. Centro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Bragança, Portugal

    Márcio Carocho

  2. Centro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Bragança, Portugal

    Sandrina A. Heleno

  3. Centro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Bragança, Portugal

    Lillian Barros

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Castro, V. et al. (2023). Sulfur-Containing Compounds from Plants. In: Carocho, M., Heleno, S.A., Barros, L. (eds) Natural Secondary Metabolites. Springer, Cham. https://doi.org/10.1007/978-3-031-18587-8_11

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