Maculosin

Names

[ Name ]:
Maculosin

[Synonym ]:
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
TYP
CYCLO-(L-TYROSINE-L-PROLINE) INHIBITOR
cyclo-L-Tyr-L-Pro
cyclo(D-Pro-D-Tyr)
(3s,8as)-3-(4-hydroxybenzyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
cycl(L-pro-L-tyr)
1w1y
cyclo(L-prolinyl-L-tyrosine)
(3S,8AR)-3-(4-HYDROXYBENZYL)HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE
Cyclo(L-pro-L-tyr)
Maculosin
Cyclo-(Pro-Tyr)

Biological Activity

[Description]:

Maculosin is a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Maculosin is a quorum-sensing molecule involved in cell-cell communication by Pseudomonas aeruginosa. Maculosin also acts as a signaling molecule regulating virulence gene expression in Lactobacillus reuteri. Maculosin shows antioxidant, anti-cancer and non-toxicity properties. Maculosin shows cytotoxic activity against the human liver cancer cell lines, with an IC50 of 48.90 µg/mL[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[References]

[1]. Lee W, et al. Vibrio vulnificus quorum-sensing molecule cyclo(Phe-Pro) inhibits RIG-I-mediated antiviral innate immunity. Nat Commun. 2018 Apr 23;9(1):1606.

[2]. Stierle AC, et al. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Proc Natl Acad Sci U S A. 1988 Nov;85(21):8008-11.

[3]. Paudel B, et al. Maculosin, a non-toxic antioxidant compound isolated from Streptomyces sp. KTM18. Pharm Biol. 2021 Dec;59(1):933-936.

Chemical & Physical Properties

[ Density]:
1.36g/cm3

[ Boiling Point ]:
581.4ºC at 760mmHg

[ Melting Point ]:
156-159 °C

[ Molecular Formula ]:
C₁₄H₁₆N₂O₃

[ Molecular Weight ]:
260.29

[ Flash Point ]:
305.4ºC

[ Exact Mass ]:
260.11600

[ PSA ]:
69.64000

[ LogP ]:
0.69080

[ Index of Refraction ]:
1.644

[ Storage condition ]:
-15°C

Safety Information

[ Hazard Codes ]:
T+

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%