Structures and absolute configurations of penicillactones A-C from an endophytic microorganism, Penicillium dangeardii Pitt.

Structures and absolute configurations of penicillactones A-C from an endophytic microorganism, Penicillium dangeardii Pitt.

Organic letters (2013-10-08)

Yunbao Liu, Guangzhi Ding, Yong Li, Jing Qu, Shuanggang Ma, Haining Lv, Yang Liu, Wenjie Wang, Jungui Dai, Yi Tang, Shishan Yu

PMID24093807

ZUSAMMENFASSUNG

Penicillactones A-C (1-3) are structurally related natural products with a spirocyclic anhydride structure and were isolated from the endophytic fungus Penicillium dangeardii Pitt. Penicillactones B and C showed inhibition of the release of β-glucuronidase from polymorphonuclear leukocytes with ED50 values of 2.58 and 1.57 μM. A 2D INADEQUATE experiment of 1 was performed at natural abundance to confirm the arrangement of its carbon skeleton. The configurations of 1-3 were established through extensive NMR spectroscopic analysis, selective structural modifications, and CD analysis.

MATERIALIEN

Produktnummer

Marke

Produktbeschreibung

G7017

Sigma-Aldrich

β-Glucuronidase aus Helix pomatia, Type HP-2, aqueous solution, ≥100,000 units/mL

G7396

Sigma-Aldrich

ββ-Glucuronidase aus E. coli, Type IX-A, lyophilized powder, 1,000,000-5,000,000 units/g protein (30 min assay)

G0876

Sigma-Aldrich

β-Glucuronidase aus Helix pomatia, Type H-2, aqueous solution, ≥85,000 units/mL

G0751

Sigma-Aldrich

β-Glucuronidase aus Helix pomatia, Type H-1, partially purified powder, ≥300,000 units/g solid

G1512

Sigma-Aldrich

β-Glucuronidase aus Helix pomatia, Type H-5, lyophilized powder, ≥400,000 units/g solid

G8132

Sigma-Aldrich

β-Glucuronidase aus Napfschnecke (Patella vulgata), Type L-II, lyophilized powder, 1,000,000-3,000,000 units/g solid

G7770

Sigma-Aldrich

β-Glucuronidase aus Helix pomatia, Type HP-2S, aqueous solution, ≥90,000 units/mL

G7646

Sigma-Aldrich

ββ-Glucuronidase aus E. coli, Type VII-A, lyophilized powder, 5,000,000-20,000,000 units/g protein, pH 6.8 (30 min assay)

G0251

Sigma-Aldrich

β-Glucuronidase aus Rinderleber, Type B-1, ≥1,000,000 units/g solid

G8885

Sigma-Aldrich

β-Glucuronidase aus Helix pomatia, Type H-3, aqueous solution, ≥90,000 units/mL

G0799

Sigma-Aldrich

ββ-Glucuronidase aus E. coli, >20,000,000 units/g protein, recombinant, expressed in E. coli, aqueous glycerol solution

G8420

Sigma-Aldrich

ββ-Glucuronidase aus E. coli, ≥20,000 units/mg protein, recombinant, expressed in E. coli overproducing strain, lyophilized powder

G8295

Sigma-Aldrich

ββ-Glucuronidase aus E. coli, ≥10,000,000 units/g protein (30 min assay), recombinant, expressed in E. coli overproducing strain, lyophilized powder

G8162

Sigma-Aldrich

ββ-Glucuronidase aus E. coli, aqueous glycerol solution, ≥5,000,000 units/g protein, pH 6.8 (biuret)

G2174

Sigma-Aldrich

β-Glucuronidase aus Napfschnecke (Patella vulgata), aqueous solution, ≥85,000 units/mL

G0376

Sigma-Aldrich

β-Glucuronidase aus Rinderleber, Type B-3, ≥2,000,000 units/g solid

G0762

Sigma-Aldrich

β-Glucuronidase aus Helix pomatia, Type H-3AF, aqueous solution, ≥60,000 units/mL

G4259

Sigma-Aldrich

β-Glucuronidase from Helix aspersa (garden snail), Type HA-4