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Merck

SML0642

Sigma-Aldrich

Chaetoglobosin A

from Chaetomium globosum, ≥98% (HPLC)

Sinónimos:

4,7,14,14a,15,15a,16a,16b-Octahydro-7-hydroxy-14-(1H-indol-3-ylmethyl)-4,6,15,15a-tetramethyl-, 3H-Cyclotridec[d]oxireno[f]isoindole-8,11,12(13H)-trione

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About This Item

Fórmula empírica (notación de Hill):
C32H36N2O5
Número de CAS:
Peso molecular:
528.64
UNSPSC Code:
12352200
NACRES:
NA.77

biological source

Chaetomium globosum

Quality Level

assay

≥98% (HPLC)

solubility

DMSO: soluble 10 mg/mL
methanol: soluble 10 mg/mL

storage temp.

−20°C

InChI

1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-14,16-17,19,22,24,27-29,33,37H,8,15H2,1-4H3,(H,34,38)/b10-7+,13-12+,18-14+/t17-,19-,22?,24-,27-,28+,29-,31+,32+/m0/s1

InChI key

OUMWCYMRLMEZJH-VIRVUJSBSA-N

Application

Chaetoglobosin A has been used as a standard for the detection and quantification of chaetoglobosin A from Chaetomium globosum by HPLC.

Biochem/physiol Actions

Chaetomium globosum is a fungus commonly found in water-damaged walls and causes Sick Building Syndrome (SBS). Chaetoglobosin A is a mycotoxic cytochalasin. Over 40 chaetoglobosins were characterized, many of which show acute toxicity to mammals, as well as cytotoxicity to human cancer cell lines such as KB, K562, MCF-7, and HepG2.

Cytochalasins were also found to inhibit glucose transport in human erythrocytes by binding to the glucose carrier on the erythrocyte membrane. Chaetoglobosin A was found to inhibit nematode proliferation and egg hatching. It also causes mortality of second stage juveniles of Meloidogyne incognita.

Other Notes

Store the product sealed at −20 °C. Under these conditions the product is stable for at least 2 years.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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David R McMullin et al.
Mycotoxin research, 29(1), 47-54 (2013-01-22)
Chaetomium globosum is one of the most common species of fungi found growing on damp building materials in North America and Europe. At doses that could be experienced in a building with some mould damage, exposure to metabolites from other
Omar E Christian et al.
Journal of natural products, 68(11), 1592-1597 (2005-11-29)
The isolation and structure elucidation of three new secondary metabolites, chaetoglobosin-510 (1), -540 (2), and -542 (3), are described. These compounds were produced by cultures of the marine-derived fungus Phomopsis asparagi, challenged with the known F-actin inhibitor jasplakinolide. Chaetoglobosin-542 (3)
Jian-Chun Qin et al.
Bioorganic & medicinal chemistry letters, 19(6), 1572-1574 (2009-02-28)
A novel cytotoxic chlorinated azaphilone derivative named chaetomugilin D (1), together with three known metabolites, chaetomugilin A (2), chaetoglobosins A (3) and C (4), has been isolated by a bioassay-guided fractionation from the EtOAc extract of the cultures of Chaetomium
Yang Hu et al.
Science China. Life sciences, 55(12), 1100-1108 (2012-12-13)
Chaetomium globosum is one of the most common fungi in nature. It is best known for producing chaetoglobosins; however, the molecular basis of chaetoglobosin biosynthesis is poorly understood in this fungus. In this study, we utilized RNA interference (RNAi) to
Hui Ming Ge et al.
Chemical communications (Cambridge, England), 47(8), 2321-2323 (2010-12-15)
Precursor-fed cultivation of endophytic Chaetomium globosum 1C51 afforded nine novel "unnatural" halogenated chaetoglobosins including those with more preferable immunosuppressive activity.

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