Sulfur compounds: From plants to humans and their role in chronic disease prevention

Figures & data

Figure 1. Overview of sulfur metabolism in plants; adapted from (Jez 2019; Maruyama-Nakashita 2017).

Table 1. Common dietary sulfur-containing metabolites and their main derivatives within cruciferous and allium vegetables.

Major secondary metabolite/s	Post-hydrolysis derivative	Common food sources	References
Glucosinolates:
Glucoraphanin ^AL	Sulforaphane (ITC)	Broccoli sprouts, broccoli, cabbage, cauliflower, rocket, kale	(Farag and Motaal 2010; Bell et al. 2018; Vermeulen et al. 2006; J. Chang, Wang, et al. 2019; Liang et al. 2018)
Glucoerucin ^AL	Erucin (ITC)	Rocket, cabbage, radish, cauliflower, turnip, swede (rutabaga)	(J. Chang, Wang, et al. 2019; Vermeulen et al. 2006; Bell et al. 2018; Mithen 2007; Hwang et al. 2019; Liang et al. 2018)
Sinigrin ^AL	Allyl isothiocyanate (ITC) Allyl thiocyanate (TC)	Mustard seeds, wasabi, cabbage, cauliflower, broccoli, Brussels sprouts	(Vermeulen et al. 2006; Bell et al. 2018; Mithen 2007; Mazumder, Dwivedi, and du Plessis 2016; Liang et al. 2018)
Glucobrassicin ^IND	Indole-3-carbinol (I3C) (IND) 3,3-diindolymethane (DIM)	Broccoli, Chinese cabbage, green cabbage, red cabbage	(J. Chang, Wang, et al. 2019; Vermeulen et al. 2006; Bell et al. 2018; Hwang et al. 2019)
Glucoiberin ^AL	Iberin (ITC)	Chinese kale, broccoli, Brussels sprouts, cabbage, cauliflower	(J. Chang, Wang, et al. 2019; Vermeulen et al. 2006; Mithen 2007; Liang et al. 2018)
Glucobrassicanapin ^AL	4-pentanyl isothiocyanate (ITC)	Broccoli, Chinese cabbage, turnip, bok choi, pak choi, choy sum	(Vermeulen et al. 2006; Paul et al. 2019; Mithen 2007; Liang et al. 2018; Bell et al. 2018; Nugrahedi et al. 2017)
Gluconapin ^AL	3-butenyl isothiocyanate (ITC)	Chinese cabbage, Brussels sprouts, broccoli, kale, bok choi, brown mustard, kale, turnip	(J. Chang, Wang, et al. 2019; Vermeulen et al. 2006; Bell et al. 2018; Paul et al. 2019; Mithen 2007; Liang et al. 2018)
Gluconasturtiin ^ARO	Phenethyl isothiocyanate (ITC)	Radish, watercress, broccoli, cabbage, cauliflower, Brussels sprouts, turnip	(Paul et al. 2019; Mithen 2007; Liang et al. 2018)
Glucotropaeolin ^ARO	Benzyl isothiocyanate (ITC)	Broccoli, cabbage, watercress, nasturtium	(Bell et al. 2018; Dinh et al. 2021)
S-alk(en)yl cysteine Sulfoxides:
Alliin	Allicin (diallyl thiosulfinate) (TS)	Garlic	(Bernaert et al. 2012; P. Rose et al. 2005)
Methiin	Methanic acid, MMTSI, MMTSO (TS)	Garlic, onion, leek, kale, Brussels sprouts, cauliflower broccoli	(Bernaert et al. 2012; P. Rose et al. 2005; Coode-Bate et al. 2019)
Isoalliin	Propenyl-thiosulfinates (TS) Thiopropanal-S-oxide (LF)	Onion, leek, shallots	(Bernaert et al. 2012; P. Rose et al. 2005), Thomas 94

(ITC) isothiocyanate; (TC) thiocyanate; (IND) indole phytoalexin; TS thiosulfinate; MMTSI S-methyl methanethiosulfinate; MMTSO S-methyl methanethiosulfonate; LF lachrymatory factor; ^AL aliphatic glucosinolate; ^ARO aromatic glucosinolate; ^IND indole glucosinolate, classifications as per (Nguyen et al. 2020).

Table 2. Antioxidant and anti-inflammatory activity of the main sulfur-containing derivatives (sourced from the hydrolysis of glucosinolates and S-alk(en)yl cysteine sulfoxides) found in cruciferous and allium vegetables.

Secondary metabolite	Post-hydrolysis derivative given	Study/Model	Effect	Reference
GLUCOSINOLATES
Glucoraphanin	Sulforaphane	BALB-/c mice with LPS-induced lung inflammation	↑ Nrf2 ↓ NF-ĸβ	(Qi et al. 2016)
	Sulforaphane	Mouse cell model Alzheimer’s Disease, (in vitro)	↑ Nrf2 ↓ inflammatory cytokines ↓ ROS	(Zhao, Zhang, and Chang 2018)
	Sulforaphane	Mice with T2DM-induced nephropathy	↑ Nrf2	(Z. Li et al. 2020)
	Sulforaphane	Mice with T2DM-induced cardiomyopathy	↑ Nrf2 ↑ AMPK activation	(Y. Sun et al. 2020)
	Sulforaphane	Dystrophin deficient C57BL/10ScSn-Dmdmdx/NJU mice	↓ NF-ĸB in muscle cells, ↑ Nrf2 ↓ TNF-α, IL-1β, IL-6	(C.-C. Sun et al. 2015)
	Sulforaphane	Bronchial epithelial cells exposed to SARS-CoV-2 (in vitro)	↓ IL-6 and IL-8	(Gasparello et al. 2021)
	Sulforaphane	T2DM patients	↑ glucose control ↓ gluconeogenesis	(Axelsson et al. 2017)
	Sulforaphane	C57BL/6J T2DM mice fed high-fat diet	↑ Nrf2 ↓ aortic wall thickness, fibrosis, inflammation, oxidative stress	(Y. Wang et al. 2014)
	Sulforaphane	LPS-induced RAW 264.7 murine macrophages (in vitro)	↑ Nrf2 ↓ inflammatory cytokines, ↓ iNOS and NO expression	(Ruhee, Ma, and Suzuki 2019)
	Sulforaphane	Male C57BL/6J mice induced with neuropathic pain	↓ inflammatory cytokines,	(C. Wang and Wang 2017)
Glucoerucin	Erucin	LPS-stimulated RAW 264.7 mice macrophages and skin	↓ NF-ĸβ ↓TNF-α, IL-6, IL-1β, NO and COX-2	(Cho, Lee, and Park 2013)
	Erucin	Streptozotocin-diabetes-induced mice with diabetic neuropathic pain	↓ nociceptive pain and pain-related behavior	(Lucarini et al. 2019)
	Erucin	Erucin-treated human platelets (in vitro) and a bolus dose given to C57BL/6 mice induced with thrombosis	↓ NF-ĸβ, ↓ thromboxanes, TGF-1β, CCL5, IL-1β (in vitro) ↓ thrombosis formation (in vivo—mice)	(Fuentes et al. 2014)
	Erucin	LPS-induced RAW 264.7 macrophages (in vitro)	↓ TLR4, TNF-α, COX-2, IL-8 and IL-1β, ↑ IL-10 ↓ inflammatory mediators	(Gugliandolo et al. 2018)
Sinigrin	Allyl ITC	LPS-induced inflammation in macrophages (in vitro)	↓ NF-ĸβ, ↓ NO, COX-2, PGE2, TNF-α, ↓ IL-6, IL-Iβ, IL-18	(H. W. Lee et al. 2017)
	Allyl ITC	TNF-α-induced inflammation, in vascular smooth muscle cells (in vitro)	↓ NF-ĸβ, ↓ VCAM-1	(H. W. Lee and Lee 2015)
	Allyl ITC	ApoE-deficient mice, fed high cholesterol	↓ atherosclerosis ↓ NF-ĸβ, ↓ VCAM-1, ICAM-1, ↓ oxLDL, CHL, HDL, LDL, TG, ↓ IL-6, ↓ TNF-α	(Jang et al. 2017; Jang and Pyo 2015)
Glucobrassican	I3C (and DIM)	Doxorubicin-induced toxicity in Swiss Albino mice	↑ Nrf2 ↓ NF-ĸβ	(Hajra et al. 2018)
	I3C	Sprague-Dawley cirrhotic rats	↓ NF-ĸβ	(T. Chang, Ho, et al. 2019)
	I3C	LPS-induced RAW 264.7 cells; LPS-induced lung injury mice	↓ NO, IL-6, IL-1β	(J. Jiang et al. 2013)
Glucoiberin	Iberin	A2780 and OVCAR-3 (ovarian cancer) cells (in vitro) and BALB/c nude mice	↓ cell growth, ↑ cell cycle arrest & apoptosis, mediated ROS production	(Gong et al. 2021)
	Iberin (plus iberverin & cheirolin)	NIH3T3 fibroblast cells (in vitro)	↑ Nrf2 ↑ HO-1 and $\gamma$GCS	(Ernst et al. 2013)
	Iberin (plus alyssin)	Hepatocellular carcinoma cell HepG2 (in vitro)	↑ apoptosis	(Pocasap, Weerapreeyakul, and Thumanu 2019)
	Iberin	Human neuroblastoma cells (in vitro)	↓ cell growth, ↑ cytotoxicity, ↑ apoptosis (via ↑ caspase and PARP activation)	(Jadhav et al. 2007)
Gluconasturtiin	Phenethyl-ITC (PEITC)	High-fat induced hypercholesterolemic C57BL/6 mice, fed PEITC for 13-wks	↓ NF-ĸβ, ↓ TC, LDL, TG, ↓ HOMA-IR and BW ↓LOX-1, COX-2, p-mTOR, PPAR$\gamma$ and ↑-AMPK	(Gwon et al. 2020; Gwon and Yun 2021)
	PEITC	Human THP-1 derived macrophages exposed to oxidized-LDL and LPS to mimic foam cell formation (in vitro)	↓ NF-ĸβ, ↓ foam cell formation and lipid accumulation	(Im, Gwon, and Yun 2021)
Glucotropaeolin	PEITC and BITC	High-fat-induced hypercholesterolemic C57BL/6 mice, fed PEITC/BITC for 18-wks	↓ TC, TG and BW ↓ lipogenic/adipogenic transcription (e.g., via PPAR$\gamma$, LXRα) expression	(Chuang et al. 2019)
Gluconapin	3-butenyl ITC	SLC mice fed corn oil to induce hypercholesterolemia	↓ postprandial hypertriglyceridemia	(Washida et al. 2010)
ALLIUMS
Alliin	–	LPS-stimulated inflammation in 3T3-L1 adipocytes (in vitro)	↓ pro-inflammatory gene expression, IL-6, MCP-1, Egr-1	(Quintero-Fabián et al. 2013)
	–	Dextran sulfate sodium-induced colitic mice	↓ NF-ĸβ, MAPK, NO ↓ iNOS, TNF-α, IL-6	(Shi et al. 2017)
	–	LPS-stimulated RAW264.7 macrophages treated w/wo alliin (in vitro)	↓ iNOS, IL-1β, IL-6, TNF-α, and NO	(Shi et al. 2017)
	–	8-wk old C57BL/6 mice randomized to control or high-fat diet w/wo alliin	↓ hyperglycemia, ↓ adipocyte hypertrophy, adipocytokines, ↓ IL-6	(Sánchez-Sánchez et al. 2020)
	–	MDA-TBA-induced oxidative damage (in vitro) and NBT-induced generation of superoxide	↑ hydroxyl and superoxide scavenging activity	(Chung 2006)
	Allicin	High-glucose/hypoxia-induced endothelial cell injury in murine aortic-endothelial cells (in vitro)	↓ NF-ĸβ ↓ ROS production	(S.L. Wang et al. 2015)
	allicin	LPS-induced oxidative stress in human vein endothelial cells (in vitro)	↑ Nrf2, ↓ lipid peroxidation, ↓ LPS-induced apoptosis	(M. Zhang et al. 2017)
	DATS	LPS-induced inflammation in BV-2 microglial cells (in vitro)	↓ NF-ĸβ, ↓ NO, PGE2, iNOS, COX-2	(H.H. Lee et al. 2018)
	DAS	LPS and d-galactosamine-induced acute liver injury in mice	↓ MDA ↓ TNF-α, IL-1β and MCP-1 ↑ GSH, SOD and CAT (liver)	(M. Li et al. 2018)
	DAS	Malathion (insecticide)-induced oxidative stress in cerebral, hepatic, renal tissue of rats	↓ expression of inflammatory cytokines (NF-kB, IL-1B, TNF-α) ↓ ROS via suppression of CYP-2E1 hepatic enzyme	(Abdel-Daim et al. 2020)
	DADS	Liver microsomes from male Wistar rats (in vitro)	↑ hydroxyl scavenging activity ↓ lipid peroxidation	(Chung 2006)
Methiin (SMCSO)	–	Alloxan-induced diabetic Sprague-Dawley rats	↓ lipid peroxidation	(Kumari and Augusti 2002)
	–	Streptozotocin-induced diabetic rats	↓ NF-ĸβ	(Castro et al. 2021)
	–	Streptozotocin-induced diabetic rats	↓ hyperglycemia, TG and VLDL ↑ IL-10, ↑ SOD and CAT	(Lemos et al. 2021)
Isoalliin (deoxy)	–	SHRats and male Wistar Kyoto rats (control) given S-propenylcysteine compared to SAC, (Metabolomic studies)	↓ hypertension	(Matsutomo et al. 2017, 2019)
	–	SHRats and Wistar Kyoto rats (control) given S-propenylcysteine	↓ hypertension	(Ushijima et al. 2018)
	–	Human vascular endothelial cells stimulated with TNF-α, w/wo S-propenylcysteine (in vitro)	↓ TNF-α-induced vascular endothelial hyperpermeability	(Kunimura et al. 2021)

LPS lipopolysaccharide; Nrf2 nuclear factor-erythroid factor 2-related factor; NF-ĸβ nuclear factor kappa-light-chain-enhancer of activated B cells; ROS reactive oxygen species; T2DM type-2 diabetes mellitus; AMPK adenosine monophosphate-activated protein kinase; TNF-α tumor necrosis factors alpha; IL interleukin; iNOS inducible nitric oxide synthase; NO nitric oxide; COX-2 cycoloxygenase-2; TGF-1β transforming growth factor beta 1; CCL5 C-C motif chemokine ligand 5; TLR4 toll-like receptor-4; PGE2 prostaglandin E₂; VCAM-1 vascular adhesion molecule-1; ICAM Intercellular adhesion molecule-1; oxLDL oxidized low-density lipoprotein, CHL cholesterol; HDL high-density lipoprotein; LDL low-density lipoprotein; TG triglycerides; HO-1 heme oxygenase; $\gamma$GCS $\gamma$-glutamylcysteine synthetase; PARP poly(ADP-ribose) polymerase; HOMO-IR Homeostatic model assessment of insulin resistance; BW body weight; LOX-1 lectin-like oxidized low-density lipoprotein receptor-1; p-mTOR phosphorylated-mammalian target of rapamycin; PPAR$\gamma$ peroxisome proliferator-activated receptor gamma; LXRα liver X receptor; MCP-1 monocyte chemoattractant protein-1; Egr-1 early growth response 1; MAPK mitogen-activated protein kinase; MDA malondialdehyde; GSH glutathione; SOD superoxide dismutase; CAT catalase; I3C indole 3-carbinol; DIM 3,3-diindolymethane; MDA-TBA malondialdehyde/thiobarbituric acid; VLDL very-low-density lipoprotein; SAC S-allylcysteine.

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