Skip to Content
Merck
All Photos(1)

Documents

SML0642

Sigma-Aldrich

Chaetoglobosin A

from Chaetomium globosum, ≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C32H36N2O5
CAS Number:
Molecular Weight:
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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

David C Straus
Frontiers in bioscience (Elite edition), 3, 562-580 (2011-01-05)
The following is a review of some of the work that we have done since 2007 regarding the importance of molds in the phenomenon of sick building syndrome (SBS). In these studies we first examined mold contamination in air handling
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
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
Guo-Bo Xu et al.
Rapid communications in mass spectrometry : RCM, 26(18), 2115-2122 (2012-08-14)
Chaetoglobosins are a family of macrocyclic polyketide alkaloids. They possess many similar isomers and exhibit a wide range of biological activities. Thus, there is a need for reliable, fast, and low-cost analysis of this class of compounds. A series of
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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service