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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

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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

biological source

Chaetomium globosum

Quality Level

200

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_germany

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’.

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Tatyana S Sidorova et al.
Pharmaceutical research, 25(6), 1297-1308 (2007-11-28)
The purpose of the present study was to identify the biochemical mechanism(s) of the preventative and reversal effects of Chaetoglobosin K (ChK), a bioactive natural product, on inhibition of gap junction-mediated communication and connexin phosphorylation by the tumor promoting organochlorine
Min Xue et al.
Chirality, 24(8), 668-674 (2012-05-18)
One new cytochalasan alkaloid, chaetoglobosin V(b) (1), together with two structurally related known compounds, chaetoglobosin V (2) and chaetoglobosin G (3), was isolated from the ethyl acetate extract of a culture of the endophytic fungus Chaetomium globosum, associated with the
Yanhong Wang et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(3-4), 364-368 (2011-11-25)
An endophytic fungus, strain L18, isolated from the medicinal plant Curcuma wenyujin Y.H. Chen et C. Ling was identified as Chaetomium globosum Kunze based on morphological characteristics and sequence data for the internal transcribed spacer (ITS-5.8S-ITS2) of the nuclear ribosomal
Gang Ding et al.
Journal of natural products, 69(2), 302-304 (2006-02-28)
A new cytotoxic cytochalasan-based alkaloid named chaetoglobosin U (1), along with four known analogues, chaetoglobosins C (2), F (3), and E (5) and penochalasin A (4), has been characterized from the EtOAc extract of a solid culture of Chaetomium globosum
A PKS gene, pks-1, is involved in chaetoglobosin biosynthesis,
pigmentation and sporulation in Chaetomium globosum
HU Yang
Life Sciences (2012)
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