大蒜中S-1-丙烯基-L-半胱氨酸的合成及生物学特性研究进展

doi:10.6023/cjoc202505028

摘要/Abstract

S-1-丙烯基-L-半胱氨酸(S-1-propenyl-L-cysteine, S1PC)是一种天然存在于葱属植物中的含硫氨基酸, 最早于20世纪60年代在大蒜制剂中被发现, 也是老化大蒜提取物(Aged garlic extract, AGE)中的重要组分, 在其发挥药理作用过程中扮演重要角色. 自2016年起, 已发现S1PC具有多种生物活性, 包括抗高血压、抗炎和调节免疫特性. 相较于完整大蒜, S1PC不仅气味更淡、毒性更低, 还能规避消化不良、口臭等不良反应, 对于期望获取大蒜健康益处的人群而言, 是一种更具吸引力的选择. S1PC已被发现在高血压动物模型中有降低血压的作用, 并且在体内、体外均有免疫调节作用. 此外, S1PC具有抗炎作用, 该特性有助于预防或管理与慢性炎症相关的疾病, 如牙龈炎和动脉粥样硬化. 基于上述发现, S1PC被认为与其同分异构体S-烯丙基-L-半胱氨酸(S-allyl-L-cysteine, SAC)一样, 是AGE中另一种重要的、具有药理活性且安全的成分. 综述了S1PC的理化性质等方面最新研究进展, 并提出了其未来潜在的应用发展方向.

关键词: S-1-丙烯基-L-半胱氨酸(S1PC), 葱属植物, 理化性质, 合成方法, 生物活性, 药代动力学

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

引用此文

田灵燕, 王守锋, 曾伟. 大蒜中S-1-丙烯基-L-半胱氨酸的合成及生物学特性研究进展[J]. 有机化学, 2026, 46(1): 74-86.

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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图/表 16

图1. 大蒜中含硫化合物的化学结构式

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

图2. S-1-丙烯基-L-半胱氨酸的化学结构

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

图式1. Carson和Boggs合成S1PC的路线

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

图式2. Nishimura合成S1PC的路线

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

图式3. Parry合成S1PC的路线

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

图式4. Herndon合成S1PC的路线

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

图式5. Namyslo和Stanitzek合成S1PC的路线

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

图式6. Lee合成S1PC的路线

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

图式7. 洋葱中含硫化合物的生物合成路径

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

图式8. 大蒜中含硫化合物的生物合成路径

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	↑↑	↓

表1. SHR口服S1PC后血浆中代谢产物水平的变化

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

图3. S1PC诱导Xbp1表达的推测机制

Figure 3. Putative mechanism of S1PC-induced Xbp1 expression

图4. S1PC诱导自噬激活

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

表2. 大鼠和犬在口服给药后的药代动力学参数

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

图式9. S1PC在(A)大鼠和(B)犬中的代谢途径

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

表3. 大鼠和犬在口服和静脉注射S1PC后S1PC、NAc-S1PC、NAc-S1PC的尿液和胆汁排泄参数

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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