S-1-Propenyl-L-cysteine

S-1-Propenyl-L-cysteine
Names
IUPAC name
(2R)-2-amino-3-(prop-1-en-1-ylsulfanyl)propanoic acid
Other names
  • S-1-Propenylcysteine
  • S-(1-Propenyl)-L-cysteine
  • S-Prop-1-en-1-ly-cysteine
  • S-(Prop-1-en-1-yl)-L-cysteine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/t5-/m0/s1
    Key: HYGGRRPFVXHQQW-HRJJCQLASA-N
  • C/C=C/SC[C@@H](C(O)=O)N
Properties
C6H11NO2S
Molar mass 161.22 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

S-1-Propenyl-L-cysteine (S1PC[a]) is a sulfur-containing amino acid characteristically included in processed garlic products, such as aged garlic extract.[1][2][3][4]

S1PC was initially identified in the 1960s as a garlic-derived compound[5][6] and used as a precursor for the synthesis of S1PC sulfoxide, the onion's lachrymatory factor precursor.[7][8] Regarding its pharmacological properties, its ability to enhance intestinal IgA production was first reported in 2016.[9]

Overview

S1PC is a sulfur-containing amino acid characterized by geometric isomerism (cis and trans forms) due to its propenyl group. While virtually absent in raw garlic, S1PC is generated during the aging process. This occurs through the enzymatic conversion of its precursor, γ-glutamyl-S1PC, by γ-glutamyltransferase (GGT).[1][6][10][11][12] This biosynthetic pathway is thought to contribute to the formation of other sulfur compounds characteristic of aged garlic.

Research

Anti-aging effects

In aged mouse models, S1PC has been reported to ameliorate age-related physical decline by enhancing skeletal muscle strength and improving frailty index. This effect is reportedly mediated by the ability of S1PC to elevate systemic levels of nicotinamide adenine dinucleotide (NAD+).[13] As a coenzyme essential for energy metabolism and sirtuin activation (longevity-associated factors), the age-dependent decline of NAD+ is considered a key driver of physiological aging.

The mechanism underlying S1PC-mediated physical function improvement involves the activation of Sirtuin 1 (SIRT1) in adipose tissue, which stimulates the secretion of extracellular nicotinamide phosphoribosyltransferase (eNAMPT), a key NAD+ biosynthetic enzyme. Once secreted into the bloodstream, eNAMPT elevates NAD+ levels in the hypothalamus, thereby enhancing sympathetic nerve activity and ultimately contributing to the amelioration of skeletal muscle function.[13]

Immunomodulatory effects

Oral administration of S1PC to mice increases IgA concentrations and the number of IgA-producing cells within Peyer's patches (gut-associated lymphoid tissue), suggesting an immunostimulatory effect on the intestinal mucosa. This effect is thought to be mediated by the enhanced differentiation of B cells into IgA-secreting plasma cells.[9]

Anti-inflammatory effects

Studies utilizing liver tissue from hypertensive rat models and murine splenic lymphocytes have demonstrated that S1PC exerts anti-inflammatory effects by suppressing the Toll-like receptor (TLR) signaling pathway. This suppression is achieved through the autophagic degradation of MyD88, a critical adapter protein in innate immunity.[14] Furthermore, in senescence-accelerated mice, S1PC promotes a shift in macrophage polarization toward the anti-inflammatory M2 phenotype.[15] Collectively, these mechanisms underscore S1PC’s potential to mitigate chronic inflammation, thereby addressing a fundamental driver of age-related pathologies, such as hypertension and atherosclerosis.

Vasoprotective effects

S1PC has been reported to improve hypertension and peripheral blood flow in animal models. These vascular benefits are primarily attributed to enhanced endothelial nitric oxide (NO) production and elevated plasma histidine concentrations, both of which promote vasodilation.[16][17][18][19]

At the cellular level, S1PC attenuates the increase in vascular endothelial permeability induced by inflammatory cytokines, thereby strengthening endothelial barrier function.[20] Furthermore, S1PC is suggested to exert antioxidant effects by upregulating the expression of heme oxygenase-1 (HO-1) in an NO-dependent manner.[21]

Endurance improvement

In normal mice treated with S1PC, an increase in swimming endurance was observed. This effect is thought to result from enhanced energy supply capacity, driven by the promotion of fatty acid metabolism and elevated ATP production.[22]

Pharmacokinetics

S1PC exhibits high bioavailability following oral administration. Furthermore, given its minimal impact on the cytochrome P450 (CYP) enzyme system, the risk of clinically significant drug interactions is expected to be low.[6][23][24][25]

See also

Notes

  1. ↑ 1. "S1PC" is a registered trademark of Wakunaga Holdings Co., Ltd. (Registration No. US7435338, etc.). https://branddb.wipo.int/en/brand/US502022079359410

References

  1. 1 2 Kodera, Yukihiro; Kurita, Masahiro; Nakamoto, Masato; Matsutomo, Toshiaki (2019-12-27). "Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions". Experimental and Therapeutic Medicine. 19 (2): 1574–1584. doi:10.3892/etm.2019.8393. ISSN 1792-0981. PMC 6966121. PMID 32010342.
  2. ↑ Woo, Hyuk-Je; Cha, Gun Su; Kang, Min Jung; Kyung, Kyu Hang (2022-01-23). "Assessment of standardization of domestic commercial black garlic extract for S-allyl-l-cysteine and S-1-propenyl-l-cysteine". Food Science and Biotechnology. 31 (2): 253–260. doi:10.1007/s10068-021-01028-1. ISSN 2092-6456. PMC 8818082. PMID 35186355.
  3. ↑ Matsutomo, Toshiaki; Kodera, Yukihiro (2016-01-13). "Development of an Analytic Method for Sulfur Compounds in Aged Garlic Extract with the Use of a Postcolumn High Performance Liquid Chromatography Method with Sulfur-Specific Detection". The Journal of Nutrition. 146 (2): 450S–455S. doi:10.3945/jn.114.208520. ISSN 1541-6100. PMID 26764330.
  4. ↑ Kodera, Yukihiro; Matsutomo, Toshiaki; Itoh, Kenji (2015). "The Evidence for the Production Mechanism of cis-S-1-Propenylcysteine in Aged Garlic Extract Based on a Model Reaction Approach Using Its Isomers and Deuterated Solvents". Planta Medica Letters. 2 (1): e69–e72. doi:10.1055/s-0035-1558260. ISSN 2199-157X. Archived from the original on 2025-04-18.
  5. ↑ Sugii, Michiyasu; Suzuki, Tomoji; Nagasawa, Shigeharu (1963). "Isolation of (-) S-Propenyl-L-cysteine from Garlic". Chemical & Pharmaceutical Bulletin. 11 (4): 548–549. doi:10.1248/cpb.11.548. PMID 13979120.
  6. 1 2 3 Kodera, Yukihioro; Ushijima, Mitsuyasu; Amano, Hirotaka; Suzuki, Jun-Ichiro; Matsutomo, Toshiaki (2017-03-31). "Chemical and Biological Properties of S-1-Propenyl-l-Cysteine in Aged Garlic Extract". Molecules. 22 (4): 570. doi:10.3390/molecules22040570. ISSN 1420-3049. PMC 6154623. PMID 28362335.
  7. ↑ Carson, J. F.; Boggs, Lois E. (1966-09-01). "The Synthesis and Base-Catalyzed Cyclization of (+)- and (-)-cis-S-(1-propenyl)-L-cysteine Sulfoxides". The Journal of Organic Chemistry. 31 (9): 2862–2864. doi:10.1021/jo01347a029. ISSN 0022-3263.
  8. ↑ Namyslo, Jan; Stanitzek, Claudia (2006-08-21). "A Palladium-Catalyzed Synthesis of Isoalliin, the Main Cysteine Sulfoxide in Onions (Allium cepa)". Synthesis. 2006 (20): 3367–3369. doi:10.1055/s-2006-950216. ISSN 0039-7881.
  9. 1 2 Suzuki, Jun-Ichiro; Yamaguchi, Takako; Matsutomo, Toshiaki; Amano, Hirotaka; Morihara, Naoaki; Kodera, Yukihiro (2016-03-02). "S-1-Propenylcysteine promotes the differentiation of B cells into IgA-producing cells by the induction of Erk1/2-dependent Xbp1 expression in Peyer's patches". Nutrition. 32 (7–8): 884–889. doi:10.1016/j.nut.2016.01.026. ISSN 1873-1244. PMID 27134204.
  10. ↑ Lawson, Larry D (1998-04-15). "Garlic: A Review of Its Medicinal Effects and Indicated Active Compounds". Phytomedicines of Europe. ACS Symposium Series. Vol. 691. American Chemical Society. pp. 176–209. doi:10.1021/bk-1998-0691.ch014. ISBN 9780841235595. Retrieved 2026-05-12.
  11. ↑ Saito, Hiroshi (2008-04-20). "Garlic Science". www.asakura.co.jp. Retrieved 2026-05-11.
  12. ↑ Colín-González, Ana L.; Santana, Ricardo A.; Silva-Islas, Carlos A.; Chánez-Cárdenas, Maria E.; Santamaría, Abel; Maldonado, Perla D. (2012-05-17). "The antioxidant mechanisms underlying the aged garlic extract- and S-allylcysteine-induced protection". Oxidative Medicine and Cellular Longevity. 2012 907162. doi:10.1155/2012/907162. ISSN 1942-0994. PMC 3363007. PMID 22685624.
  13. 1 2 Suzuki, Jun-Ichiro; Yoshioka, Kiyoshi; Kurita, Masahiro; Sugimoto, Takumi; Eguchi, Takahiro; Ito, Naoki; Kodama, Aoi; Kamei, Yasutomi; Ohtani, Masahiro; Matsutomo, Toshiaki; Imai, Shin-Ichiro (2026-05-07). "Garlic-derived metabolite activates LKB1, promotes adipose eNAMPT secretion, and improves age-related muscle function via hypothalamic signaling". Cell Metabolism. 38 (6): S1550–4131(26)00144–0. doi:10.1016/j.cmet.2026.04.006. ISSN 1932-7420. PMID 42102814.
  14. ↑ Suzuki, Jun-Ichiro; Kodera, Yukihiro; Miki, Satomi; Ushijima, Mitsuyasu; Takashima, Miyuki; Matsutomo, Toshiaki; Morihara, Naoaki (2018-09-20). "Anti-inflammatory action of cysteine derivative S-1-propenylcysteine by inducing MyD88 degradation". Scientific Reports. 8 (1): 14148. Bibcode:2018NatSR...814148S. doi:10.1038/s41598-018-32431-0. ISSN 2045-2322. PMC 6148218. PMID 30237533.
  15. ↑ Miki, Satomi; Suzuki, Jun-Ichiro; Takashima, Miyuki; Ishida, Mari; Kokubo, Hiroki; Yoshizumi, Masao (2021-11-17). "S-1-Propenylcysteine promotes IL-10-induced M2c macrophage polarization through prolonged activation of IL-10R/STAT3 signaling". Scientific Reports. 11 (1): 22469. Bibcode:2021NatSR..1122469M. doi:10.1038/s41598-021-01866-3. ISSN 2045-2322. PMC 8599840. PMID 34789834.
  16. ↑ Ushijima, Mitsuyasu; Kunimura, Kayo; Suzuki, Jun-Ichiro (2020-07-07). "S-1-Propenylcysteine, a sulfur compound in aged garlic extract, alleviates cold-induced reduction in peripheral blood flow in rat via activation of the AMPK/eNOS/NO pathway". Experimental and Therapeutic Medicine. 20 (3): 2815–2821. doi:10.3892/etm.2020.8969. ISSN 1792-0981. PMC 7401927. PMID 32765777.
  17. ↑ Matsutomo, Toshiaki; Ushijima, Mitsuyasu; Kunimura, Kayo; Ohtani, Masahiro (2019-05-10). "Metabolomic study reveals the acute hypotensive effect of S-1-propenylcysteine accompanied by alteration of the plasma histidine level in spontaneously hypertensive rats". Journal of Pharmaceutical and Biomedical Analysis. 168: 148–154. doi:10.1016/j.jpba.2019.01.043. ISSN 1873-264X. PMID 30807919.
  18. ↑ Ushijima, Mitsuyasu; Takashima, Miyuki; Kunimura, Kayo; Kodera, Yukihiro; Morihara, Naoaki; Tamura, Koichi (2018-01-30). "Effects of S-1-propenylcysteine, a sulfur compound in aged garlic extract, on blood pressure and peripheral circulation in spontaneously hypertensive rats". The Journal of Pharmacy and Pharmacology. 70 (4): 559–565. doi:10.1111/jphp.12865. ISSN 2042-7158. PMID 29380376.
  19. ↑ Matsutomo, Toshiaki; Ushijima, Mitsuyasu; Kodera, Yukihiro; Nakamoto, Masashi; Takashima, Miyuki; Morihara, Naoaki; Tamura, Koichi (2017-03-01). "Metabolomic study on the antihypertensive effect of S-1-propenylcysteine in spontaneously hypertensive rats using liquid chromatography coupled with quadrupole-Orbitrap mass spectrometry". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 1046: 147–155. doi:10.1016/j.jchromb.2017.01.029. ISSN 1873-376X. PMID 28183044.
  20. ↑ Kunimura, Kayo; Miki, Satomi; Takashima, Miyuki; Suzuki, Jun-Ichiro (2021-02-15). "S-1-propenylcysteine improves TNF-α-induced vascular endothelial barrier dysfunction by suppressing the GEF-H1/RhoA/Rac pathway". Cell Communication and Signaling. 19 (1): 17. doi:10.1186/s12964-020-00692-w. ISSN 1478-811X. PMC 7883441. PMID 33588881.
  21. ↑ Tsuneyoshi, Tadamitsu; Kunimura, Kayo; Morihara, Naoaki (2019-03-01). "S-1-Propenylcysteine augments BACH1 degradation and heme oxygenase 1 expression in a nitric oxide-dependent manner in endothelial cells". Nitric Oxide: Biology and Chemistry. 84: 22–29. doi:10.1016/j.niox.2019.01.003. ISSN 1089-8611. PMID 30630055.
  22. ↑ Kunimura, Kayo; Nakamoto, Masato; Ushijima, Mitsuyasu (2024-07-23). "S-1-Propenylcysteine Enhances Endurance Capacity of Mice by Stimulating Fatty Acid Metabolism via Muscle Isoform of Carnitine Acyltransferase-1". The Journal of Nutrition. 154 (9): 2707–2716. doi:10.1016/j.tjnut.2024.07.027. ISSN 1541-6100. PMID 39053609.
  23. ↑ Amano, Hirotaka; Kazamori, Daichi; Itoh, Kenji (2016). "Evaluation of the Effects of S-Allyl-L-cysteine, S-Methyl-L-cysteine, trans-S-1-Propenyl-L-cysteine, and Their N-Acetylated and S-Oxidized Metabolites on Human CYP Activities". Biological & Pharmaceutical Bulletin. 39 (10): 1701–1707. doi:10.1248/bpb.b16-00449. ISSN 1347-5215. PMID 27725449.
  24. ↑ Amano, Hirotaka; Kazamori, Daichi; Itoh, Kenji (2016-02-17). "Pharmacokinetics and N-acetylation metabolism of S-methyl-l-cysteine and trans-S-1-propenyl-l-cysteine in rats and dogs". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 46 (11): 1017–1025. doi:10.3109/00498254.2016.1144229. ISSN 1366-5928. PMID 26887651.
  25. ↑ Nakamoto, Masato; Kunimura, Kayo; Ohtani, Masahiro (2025-03-26). "Pharmacokinetics of sulfur?containing compounds in aged garlic extract: S?Allylcysteine, S?1?propenylcysteine, S?methylcysteine, S?allylmercaptocysteine and others (Review)". Experimental and Therapeutic Medicine. 29 (5): 102. doi:10.3892/etm.2025.12852. ISSN 1792-1015. PMC 11959343. PMID 40171136.
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