Progress in the Synthesis and Biological Studies of S-1-Propenyl-L-cysteine from Garlic

doi:10.6023/cjoc202505028

Abstract

S-1-Propenyl-L-cysteine (S1PC), a sulfur-containing amino acid naturally present in Allium sativum and first iden- tified in garlic preparations in the 1960s, plays an important role in aged garlic extract (AGE) and a key pharmacological role. Since 2016, it has been found to possess a variety of biological activities, including anti-hypertensive, anti-inflammatory and immunomo- dulatory properties. S1PC has less odour and is less toxic than whole garlic, making it a more attractive option for those looking to reap the health benefits of garlic without the adverse side effects of indigestion and bad breath. S1PC has been found to have blood pressure lowering effects in animal models of hypertension and has immunomodulatory effects both in vivo and in vitro. In addition, S1PC has anti-inflammatory effects, which may help prevent or manage diseases associated with chronic inflammation, such as gingivitis and atherosclerosis. Based on the above findings, S1PC is considered to be another important, pharmacologically active and safe component of AGE, along with its isomer S-allyl-L-cysteine (SAC). In this review, the latest research progress on the physicochemical properties and other aspects of S1PC is summarized, and the possible directions of its application development in the future are also proposed.

Key words: S-1-propenyl-L-cysteine (S1PC), genus allium, physical and chemical properties, synthesis method, biological activity, pharmacokinetics

Cite this article

Lingyan Tian, Shoufeng Wang, Wei Zeng. Progress in the Synthesis and Biological Studies of S-1-Propenyl-L-cysteine from Garlic[J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 74-86.

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Fig. & Tab. 16

Figure 1. Chemical structures of sulfur-containing compounds in garlic

Figure 2. Chemical structure of S-1-propenyl-L-cysteine

Scheme 1. Carson and Boggs' route to the synthesis of S1PC

Scheme 2. Nishimura's route to the synthesis of S1PC

Scheme 3. Parry's route to the synthesis of S1PC

Scheme 4. Herndon's route to the synthesis of S1PC

Scheme 5. Namyslo and Stanitzek's route to the synthesis of S1PC

Scheme 6. Lee's route to the synthesis of S1PC

Scheme 7. Biosynthetic pathways of sulphur-containing compounds in onions

Scheme 8. Biosynthetic pathways of sulfur-containing compounds in garlic The dashed arrow represents the reaction inferred from the biosynthesis pathway of alliin reported by Yoshimoto et al.

Metabolite	Control vs WKY^a	S1PC vs Control^a
Betaine	↑↑^b	↓
Tryptophan	↓↓	↑↑
LysoPC (16∶0)	↓↓	↑↑
LysoPC (18∶3)	↓↓	↑↑
LysoPC (20∶4)	↓↓	↑
3-(Acetyloxy)-2-hydroxypropyl icosanoate	↑	↓↓
Caproic acid	↑↑	↓

Table 1. Changes in plasma levels of metabolites after oral administration of S1PC in SHR

Figure 3. Putative mechanism of S1PC-induced Xbp1 expression

Figure 4. S1PC induces the activation of autophagy

Animal	Compound	T_1/2/h	c_max^c/(mg•L^－1)	BA/%
Rat	S1PC^a	0.56±0.072	4.2±0.92	88.0
Dog	S1PC^b	5.6±0.58	2.0±0.22	100

Table 2. Pharmacokinetic parameters after oral administration in rats and dogs

Scheme 9. Metabolic pathways of S1PC in (A) rats and (B) dogs

Animal	Excreta		Excretion^a/% of dose
Animal	Excreta		S1PC	NAc-S1PC	NAc-S1PCS	Total
Rat^b	Urine	i.v.	2.2±0.42	73±2.8	13±1.1	88±2.2
	Urine	Oral	3.1±1.5	69±1.4	15±1.2	87±1.2
	Bile	i.v.	0.35±0.15	0.26±0.18	0.01±0.01	0.62±0.34
	Bile	Oral	0.10±0.04	0.22±0.06	0.02±0.004	0.34±0.09
Dog^c	Urine	i.v.	0.21±0.06	0.86±0.44	2.3±1.2	3.4±1.7
Dog^c	Urine	Oral	0.22±0.14	0.62±0.34	3.3±2.4	4.2±2.7

Table 3. Urine and biliary excretion parameters of S1PC, NAc-S1PC and NAc-S1PC in rats and dogs after oral and intravenous S1PC administration

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