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G8761

Sigma-Aldrich

(±)-Gossypol from cotton seeds

≥95% (HPLC), powder, PAF antagonist/inhibitor

Sinónimos:

(±)-2,2′-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)

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About This Item

Fórmula empírica (notación de Hill):
C30H30O8
Número de CAS:
303-45-7
Peso molecular:
518.55
MDL number:
MFCD00017352
UNSPSC Code:
12352200
PubChem Substance ID:
24895349
NACRES:
NA.77

product name

(±)-Gossypol from cotton seeds, ≥95% (HPLC)

Quality Level

200

assay

≥95% (HPLC)

storage temp.

2-8°C

SMILES string

O=C([H])C1=C(C(O)=C(C2=C(C)C=C(C(C(C)C)=C(O)C(O)=C3C([H])=O)C3=C2O)C(C)=C4)C4=C(C(C)C)C(O)=C1O

InChI

1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3

Inchi Key

QBKSWRVVCFFDOT-UHFFFAOYSA-N

Gene Information

human ... AKR1B1(231) , BAD(572) , BCL2(596) , LDHA(3939) , LDHB(3945) , MCL1(4170)

General description

Gossypol is considered as an antifertility agent. It is present in cottonseed as a yellowish pigment. This reactive sesquiterpene aldehyde is present in the family Malvaceae and has a molecular mass of 518.54.

Application

(±)-Gossypol from cotton seeds has been used:
  • as a standard to quantify the gossypol content in the extracts of leaves and flower buds
  • to study its antifertility effects on spermatogenesis in NMRI mice
  • to analyse its impact on human spermatozoa
  • to incorporate into the artificial diet for larval rearing

Biochem/physiol Actions

Gossypol is a male antifertility agent and PAF antagonist/inhibitor. Gossypol is a poisonous pigment found in cottonseed and its name is derived from the botanical name of the cotton plant, Gossypium.. Gossypium is extracted from selected hybrid species between two Gossypium species, Gossypium hirsutum and Gossypium barbadens. As a PAF antagonist/inhibitor, Gossypium markedly inhibited the contractile responses of guinea pig lung parenchyma strips stimulated with leukotriene B4, seukotriene D4, and PAF-acether.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Peter Kovacic
Current medicinal chemistry, 10(24), 2711-2718 (2003-10-08)
Gossypol, a constituent of cottonseeds, displays various drug properties, including antifertility and anticancer. Toxicity is shown against the reproductive system, heart, liver, and membranes. The compound exhibits pro- and anti-oxidant behavior. Electron transfer (ET) functionalities, present in gossypol and its
Expression of the ?glanded-plant and glandless-seed? trait of Australian diploid cottons in different genetic backgrounds
Benbouza H, et al.
Euphytica, 165(2), 211-221 (2009)
The effects of gossypol on spermatogenesis in NMRI mice
Amini, A and Kamkar F
Iranian journal of science and technology. Transaction A, Science, 29(1), 123-133 (2005)
Transcriptional responses underlying the hormetic and detrimental effects of the plant secondary metabolite gossypol on the generalist herbivore Helicoverpa armigera
de la Paz Celorio-Mancera M, et al.
BMC Genomics, 12(1), 575-575 (2011)
Nariman Ansari et al.
Methods in cell biology, 113, 295-309 (2013-01-16)
Cell-based assays are essential in both basic research and drug discovery. Three-dimensional cellular spheroids are more realistic models of tumors and healthy tissues compared to standard two-dimensional cultures. Employing spheroids improves the reliability and the physiological significance of cell-based assays.
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