10140-70-2

Basic information

• Product Name: curvularin
• Synonyms: curvularin;S-Curvularin, NSC 166071;2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-,(4S)-
• CAS NO: 10140-70-2
• Molecular Formula: C16H20O5
• Molecular Weight: 292.329
• Product Categories: Antibiotic
• Mol File: 10140-70-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 206-206.5°
• Boiling Point: 557°Cat760mmHg
• Flash Point: 207.9°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 5.18E-13mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble1mg/mL
• PKA: 7.58±0.40(Predicted)
• CAS DataBase Reference: curvularin(CAS DataBase Reference)
• NIST Chemistry Reference: curvularin(10140-70-2)
• EPA Substance Registry System: curvularin(10140-70-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 10140-70-2(Hazardous Substances Data)

Usage

Description

Curvularin is a 12-membered macrocyclic lactone incorporating a resorcinyl moiety, produced by a number of fungal species, including Curvularia, Penicillium, and Alternaria. It exhibits a distinctly different biological profile compared to structurally similar resorcylic acid lactones such as the zearalenones, radicicol, and LL Z1640-2. Curvularin inhibits cell division by disrupting mitotic spindle formation and is known to be phytotoxic. More recent investigations have shown that curvularin is a highly selective transcription-based inhibitor of iNOS-dependent NO production, acting on the Janus tyrosine kinase-STAT pathway. This action offers an approach to the development of drugs inhibiting iNOS overproduction associated with NO pathophysiology.

Uses

Used in Antifungal Applications:
Curvularin is used as an antifungal agent for its potent activity against various fungal species. Its ability to inhibit cell division by disrupting mitotic spindle formation makes it a valuable compound in the fight against fungal infections.
Used in Mycotoxin Applications:
Curvularin is used as a mycotoxin for its role in the study and understanding of the effects of mycotoxins on organisms. This knowledge can be applied to develop strategies for prevention and mitigation of mycotoxin-related issues in agriculture and food safety.
Used in Inhibiting iNOS Overproduction:
Curvularin is used as a selective transcription-based inhibitor for iNOS-dependent NO production, acting on the Janus tyrosine kinase-STAT pathway. This application is crucial in the development of drugs that can help manage conditions associated with iNOS overproduction and NO pathophysiology.
Used in Pharmaceutical Development:
Curvularin is used as a potential pharmaceutical candidate for its ability to inhibit cell division and NO production. Its unique biological profile and action on the Janus tyrosine kinase-STAT pathway make it a promising compound for the development of new drugs targeting various diseases and conditions.

InChI:InChI=1/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m1/s1

Upstream product

• 21178-57-4 10,11-dehydrocurvularin 
• 65732-22-1 (S)-di-O-benzylcurvularin 
• 181655-23-2 (7S)-7-{2-[3,5-bis(benzyloxy)phenyl]acetoxy}octanoic acid 
• 1068474-47-4 C₃₀H₃₀O₅ 
• 120982-13-0 tert-butyl (7S)-7-hydroxyoctanoate 
• 625-31-0 (S)-4-penten-2-ol 
• 93382-53-7 (+)-(5S)-hydroxy-(2E)-hexenal 
• 88980-13-6 (S)-hept-6-en-2-ol 
• 100905-80-4 (S,E)-11,13-dimethoxy-4-methyl-4,5,6,7-tetrahydro-1H-benzo[d][1]oxacyclododecine-2,10-dione 
• 393109-13-2 (S)-tert-butyl(hept-6-en-2-yloxy)dimethylsilane 

Downstream Products

• 95416-14-1 10-dihydrocurvularin 

Relevant articles and documents

A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7

Five curvularin macrolides (1-5) were isolated from the cultured broth of marine actinomycete Pseudonocardia sp. HS7 that was obtained from the cloacal aperture of sea cucumber Holothuria moebii. The structures of these isolates were characterized as (11S,15R)-11-hydroxycurvularin (1), (11R,15R)-11-hydroxycurvularin (2), curvularin-7-O-α-D-glucopyranoside (3), trans-dehydrocurvularin (4) and curvularin (5) based on their NMR and HRESIMS data as well as chemical degradation. Compound 3 is a new macrolide with a rare α-D-glucopyranose substituent. Compounds 1-4, 5a and 5c (the acyl products of 5), suppressed the proliferation of all six tested cancer cell lines and 4 is the most active compound with IC50 values ranging from 0.59 to 3.39 M. The 11-hydroxycurvularins 1 and 2 also showed antibacterial activity inhibiting the growth of Escherichia coli.

Stereoselective total synthesis of (-)-curvularin

A concise total synthesis of (-)-Curvularin have been synthesized from commercially available (S)-(?)-propylene epoxide and (3,5-Dimethoxyphenyl)acetic acid. The key steps involved in the synthesis are Vilsmeier-Haack formylation, Grignard reaction, alkyl

Umpolung Pd-Catalyzed α-arylation reactions in natural product synthesis: Syntheses of (+)-xestodecalactone A, (-)-curvularin, (+)-12-oxocurvularin and (-)-citreofuran

The syntheses (total and formal) of four phenylacetic acid lactone (PAL) natural products have been accomplished by utilizing a unified strategy of an umpolung Pd-catalyzed α-arylation of complex α-bromo esters and boronic acids under mild reaction conditions. As part of the synthetic approaches to these natural products, it was observed that the mild coupling reaction conditions readily tolerated terminal alkenes, other labile ester functionalities, an α,β-unsaturated ester moiety, and a protected allylic alcohol, while chemoselectively engaging the α-bromo ester. The completion of (+)-xestodecalactone A and (-)-curvularin coupled with the formal syntheses of (+)-12-oxocurvularin and (-)-citreofuran highlight the umpolung Pd-catalyzed α-arylation strategy as a key convergent tactic in complex natural product synthesis.