A macrocyclic lactone
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Hygrolidin

Item No. 28116

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2E-butenedioic acid, mono[(2R,4R,5S,6R)-6-ethyltetrahydro-2-hydroxy-2-[(1S,2R,3S)-2-hydroxy-3-[(2R,3S,4E,6E,9S,10S,11R,12E,14E)-10-hydroxy-3-methoxy-7,9,11,13,15-pentamethyl-16-oxooxacyclohexadeca-4,6,12,14-tetraen-2-yl]-1-methylbutyl]-5-methyl-2H-pyran-4-yl] ester
CAS Number
83329-73-1
Synonyms
  • Antibiotic 1166C
Molecular Formula
C38H58O11
Formula Weight
690.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Slightly Soluble: 0.1-1 mg/ml
SMILES
C/C1=C\C=C\[C@H](OC)[C@]([C@@H](C)[C@@H](O)[C@H](C)[C@]2(O)O[C@H](CC)[C@H](C)[C@H](OC(/C=C/C(O)=O)=O)C2)([H])OC(/C(C)=C\C(C)=C/[C@@H](C)[C@@H](O)[C@@H](C)C1)=O
InChi Code
InChI=1S/C38H58O11/c1-11-29-26(7)31(47-33(41)16-15-32(39)40)20-38(45,49-29)28(9)35(43)27(8)36-30(46-10)14-12-13-21(2)17-23(4)34(42)24(5)18-22(3)19-25(6)37(44)48-36/h12-16,18-19,23-24,26-31,34-36,42-43,45H,11,17,20H2,1-10H3,(H,39,40)/b14-12+,16-15+,21-13+,22-18-,25-19-/t23-,24+,26-,27-,28-,29+,30-,31+,34-,35+,36+,38+/m0/s1
InChi Key
UGIOXKVQFJIRMZ-VRHCWVDTSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $351

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    5 mg

    $1,404

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    Product Description

    Hygrolidin is a macrocyclic lactone originally isolated from S. hygroscopicus.1 It inhibits proliferation of a variety of cancer cell lines, including DLD-1 colon cancer, LNCaP prostate cancer, and K562 leukemia cells (IC50s = 2.9, 5.2, and 33 ng/ml, respectively).2 Hygrolidin induces the expression and levels of p21 in DLD-1 cells, but not WI-38 fibroblasts, and leads to cell accumulation in the G1 and S phases without inducing apoptosis. It has antiparasitic activity against T. cruzi, L. donovani, and T. b. brucei but also induces cytotoxicity in HepG2 cells (IC50s = 1.1, 72.5, 77, and 24.5 nM, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Seto, H., Akao, H., Furihata, K., et al. The structure of a new antibiotic, hygrolidin. Tetrahedron Lett. 23(26), 2667-2670 (1982).

    2. Kawada, M., Usami, I., Ohba, S., et al. Hygrolidin induces p21 expression and abrogates cell cycle progression at G1 and S phases. Biochem. Biophys. Res. Commun. 298(1), 178-183 (2002).

    3. Annang, F., Pérez-Moreno, G., García-Hernández, R., et al. High-throughput screening platform for natural product-based drug discovery against 3 neglected tropical diseases: Human African trypanosomiasis, leishmaniasis, and Chagas disease. J. Biomol. Screen. 20(1), 82-91 (2015).