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Merck
CN

SML0642

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

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About This Item

Empirical Formula (Hill Notation):
C32H36N2O5
CAS Number:
50335-03-0
Molecular Weight:
528.64
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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SMILES string

[nH]1c2c(c(c1)C[C@@H]3NC(=O)[C@]54[C@H]3[C@@H]([C@]6(O[C@H]6C5\C=C\C[C@@H](\C=C(\[C@H](C(=O)\C=C\C4=O)O)/C)C)C)C)cccc2

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

biological source

Chaetomium globosum

assay

≥98% (HPLC)

solubility

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

storage temp.

−20°C

Quality Level

200

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.
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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
098M4099V
14130502
053M4057V
32130501

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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
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)
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
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.
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
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