Abstract
S-1-propenyl-l-cysteine (S1PC) is a stereoisomer of S-allyl-l-cysteine (SAC), an important sulfur-containing amino acid that plays a role for the beneficial pharmacological effects of aged garlic extract (AGE). The existence of S1PC in garlic preparations has been known since the 1960’s. However, there was no report regarding the biological and/or pharmacological activity of S1PC until 2016. Recently, we performed a series of studies to examine the chemical, biological, pharmacological and pharmacokinetic properties of S1PC, and obtained some interesting results. S1PC existed only in trace amounts in raw garlic, but its concentration increased almost up to the level similar of SAC through aging process of AGE. S1PC showed immunomodulatory effects in vitro and in vivo, and reduced blood pressure in a hypertensive animal model. A pharmacokinetic study revealed that S1PC was readily absorbed after oral administration in rats and dogs with bioavailability of 88–100%. Additionally, S1PC had little inhibitory influence on human cytochrome P450 activities, even at a concentration of 1 mM. Based on these findings, S1PC was suggested to be another important, pharmacologically active and safe component of AGE similar to SAC. In this review, we highlight some results from recent studies on S1PC and discuss the potential medicinal value of S1PC.
Highlights
Several plants belonging to the genus Allium have been historically used by humans
Organic Synthesis of trans-S-1-propenyl-L-cysteine (R)-3-[(E)-Prop-1-enylsulfinyl]-2-aminopropanoic acid, an odorless sulfur-containing amino acid referred to as trans-S1PCSO or isoalliin, has been isolated from onion (Allium cepa L.) and confirmed to be a precursor of the lachrymatory compound, a biologically active compound that is beneficial for human health [5,16,17,30,31]
The proton signals of C1, C2 and C3 in the propenyl group of the incubation mixtures changed gradually, until the intensities of cis- and trans-signals were almost equal. These results indicated that isomerization of S1PC between the cis-form and trans-form is reversible, and the amount of cis-S1PC observed in aged garlic extract (AGE) might be partly derived from trans-S1PC through the isomerization reaction during the aging process (Figure 3D)
Summary
Several plants belonging to the genus Allium have been historically used by humans. Among these plants, garlic (Allium sativum L.) has been widely recognized to possess medicinal properties against several diseases or symptoms during the time when other medicinal supplies were limited [1]. 2. Organic Synthesis of trans-S-1-propenyl-L-cysteine (R)-3-[(E)-Prop-1-enylsulfinyl]-2-aminopropanoic acid, an odorless sulfur-containing amino acid referred to as trans-S1PCSO or isoalliin, has been isolated from onion (Allium cepa L.) and confirmed to be a precursor of the lachrymatory compound, a biologically active compound that is beneficial for human health [5,16,17,30,31]. Organic Synthesis of trans-S-1-propenyl-L-cysteine (R)-3-[(E)-Prop-1-enylsulfinyl]-2-aminopropanoic acid, an odorless sulfur-containing amino acid referred to as trans-S1PCSO or isoalliin, has been isolated from onion (Allium cepa L.) and confirmed to be a precursor of the lachrymatory compound, a biologically active compound that is beneficial for human health [5,16,17,30,31] The content of this compound in onion is less than 0.2% [16], and its purification is difficult because many compounds with similar chemical characteristics exist in onion.
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