Maculosin is a host-specific toxin of Xanthomonas melanogaster. Maculosin is a quorum sensing molecule involved in cell-cell communication in Pseudomonas aeruginosa. Maculosin is also a signaling molecule that regulates the expression of virulence genes in Lactobacillus reuteri. Maculosin has antioxidant, anti-cancer and non-toxic properties. Maculosin is cytotoxic to human liver cancer/tumor cell lines, with IC50 of 48.90 μg/mL.

Physicochemical Properties

Molecular Formula	C14H16N2O3
Molecular Weight	260.28844
Exact Mass	260.116
CAS #	4549-02-4
PubChem CID	119404
Appearance	White to off-white solid powder
Density	1.36g/cm3
Boiling Point	581.4ºC at 760mmHg
Melting Point	156-159 °C
Flash Point	305.4ºC
Index of Refraction	1.644
LogP	0.69
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Heavy Atom Count	19
Complexity	377
Defined Atom Stereocenter Count	2
SMILES	C1C[C@H]2C(=O)N[C@H](C(=O)N2C1)CC3=CC=C(C=C3)O
InChi Key	LSGOTAXPWMCUCK-RYUDHWBXSA-N
InChi Code	InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1
Chemical Name	(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1]. Vibrio vulnificus quorum-sensing molecule cyclo(Phe-Pro) inhibits RIG-I-mediated antiviral innate immunity. Nat Commun. 2018 Apr 23;9(1):1606. [2]. 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]. Maculosin, a non-toxic antioxidant compound isolated from Streptomyces sp. KTM18. Pharm Biol. 2021 Dec;59(1):933-936.

Additional Infomation

Maculosin is a homodetic cyclic peptide that is a dipeptide composed of L-proline and L-tyrosine joined by peptide linkages. It has a role as a metabolite. It is a dipeptide, a homodetic cyclic peptide, a pyrrolopyrazine and a member of phenols. It is functionally related to a L-proline and a L-tyrosine. Maculosin has been reported in Aspergillus versicolor, Leptoxyphium, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~384.19 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.8419 mL	19.2093 mL	38.4187 mL
	5 mM	0.7684 mL	3.8419 mL	7.6837 mL
	10 mM	0.3842 mL	1.9209 mL	3.8419 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.