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Gossypol

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-G2004

  • Specification : 98%

  • CAS number : 303-45-7

  • Formula : C30H30O8

  • Molecular Weight : 518.55

  • PUBCHEM ID : 3503

  • Volume : 20mg

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Catalogue Number

BF-G2004

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

518.55

Appearance

Brownish yellow powder

Botanical Source

herbs of Gossypium spp

Structure Type

Tannins

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O

Synonyms

1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl[2,2'-binaphthalene]-8,8'-dicarboxaldehyde/1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarbaldehyde/2,2'-BI[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE]/2,2'-Bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene]/1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-di(propan-2-yl)-2,2'-binaphthalene-8,8'-dicarbaldehyde/Gossypol/gossypol from cotton seeds/(rac)-2,2'-bis(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)/2,2'-bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene]/(-)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde/2,2'-BIS[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPTHALENE]/1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-(2,2'-binaphthalene)-8,8'-dicarboxaldehyde/1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalen-8,8'-dicarbaldehyd/Thespesin/[2,2'-Binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-/1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene-8,8'-dicarbaldehyde/roduct Name/(+/-)-gossypol/1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde

IUPAC Name

7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde

Density

1.4±0.1 g/cm3

Solubility

Flash Point

395.9±28.0 °C

Boiling Point

707.9±55.0 °C at 760 mmHg

Melting Point

181-183ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2912490000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:303-45-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31844979

Abstract

PURPOSE:
Glioblastoma multiforme (GBM) is a poorly curable disease due to its profound chemoresistance. Despite recent advances in surgery, radiotherapy and chemotherapy, the efficient treatment of GBMs is still a clinical challenge. Beside others, AT101, the R-(-) enantiomer of gossypol, and demethoxycurcumin (DMC), a curcumin-related demethoxy compound derived from Curcuma longa, were considered as possible alternative drugs for GBM therapy.

METHODS:
Using different human primary GBM cell cultures in a long-term stimulation in vitro model, the cytotoxic and anti-proliferative effects of single and combined treatment with 5 µM AT101 and 5 µM or 10 µM DMC were investigated. Furthermore, western blots on pAkt and pp44/42 as well as JC-1 staining and real-time RT-PCR were performed to understand the influence of the treatment at the molecular and gene level.

RESULTS:
Due to enhanced anti-proliferative effects, we showed that combined therapy with both drugs was superior to a single treatment with AT101 or DMC. Here, by determination of the combination index, a synergism of the combined drugs was detectable. Phosphorylation and thereby activation of the kinases p44/42 and Akt, which are involved in proliferation and survival processes, were inhibited, the mitochondrial membrane potential of the GBM cells was altered, and genes involved in dormancy-associated processes were regulated by the combined treatment strategy.

CONCLUSION:
Combined treatment with different drugs might be an option to efficiently overcome chemoresistance of GBM cells in a long-term treatment strategy.

KEYWORDS

AT101; Cytotoxicity; Demethoxycurcumin; Glioblastoma; Proliferation

Title

Combined treatment of AT101 and demethoxycurcumin yields an enhanced anti-proliferative effect in human primary glioblastoma cells.

Author

Mehner M1, Kubelt C1, Adamski V1, Schmitt C2, Synowitz M1, Held-Feindt J3.

Publish date

2020 Jan

PMID

31319793

Abstract

BACKGROUND:
Besides fibers, cotton plants also produce a large amount of seeds with a high oil and protein content. The use of these seeds is restricted by their high contents of the terpenoid gossypol, which is harmful to humans and livestock. Using a genetic engineering approach, “Ultra-low gossypol cottonseed” (ULGCS) plants were produced by knocking down an enzyme that catalyzes the formation of a precursor of gossypol. This was accomplished via RNAi-mediated silencing of the target gene using a seed-specific α-globulin promotor. Since gossypol is also a crucial defense mechanism against leaf-feeding herbivores, ULGCS plants might possess lower herbivore resistance than non-engineered plants. Therefore, we tested the constitutive and inducible direct insect resistance of two ULGCS cotton lines against the African cotton leafworm, Spodoptera littoralis.

RESULT:
The herbivore was equally affected by both ULGCS lines and the control (Coker 312) line when feeding on fully expanded true leaves from undamaged plants and plants induced by jasmonic acid. When plants were induced by caterpillar-damage, however, S. littoralis larvae performed better on the ULGCS plants. Terpenoid analyses revealed that the ULGCS lines were equally inducible as the control plants. Levels of terpenoids were always lower in one of the two lines. In the case of cotyledons, caterpillars performed better on ULGCS cotton than on conventional cotton. This was likely caused by reduced levels of gossypol in ULGCS cotyledons.

CONCLUSION:
Despite those effects, the insect resistance of ULGSC cotton can be considered as largely intact and the plants may, therefore, be an interesting alternative to conventional cotton varieties.

KEYWORDS

Genetically modified crops; Glandless cotton; Gossypium hirsutum; Gossypol; Spodoptera littoralis; TAM66274; ULGCS

Title

Constitutive and induced insect resistance in RNAi-mediated ultra-low gossypol cottonseed cotton.

Author

Hagenbucher S1, Eisenring M1, Meissle M1, Rathore KS2, Romeis J3.

Publish date

2019 Jul 18

PMID

31311388

Abstract

To be commercialized and grown in the US, genetically engineered (GE) crops typically go through an extensive food, feed, and environmental safety assessment process which, in certain instances, requires complex consultations with three different US regulatory agencies. Many small market, niche, and specialty crops have been genetically engineered using the modern tools of recombinant DNA but few have been commercialized due to real or perceived regulatory constraints. This workshop discussed the practical aspects of developing dossiers on GE specialty, niche, or small-market crops/products for submission to US regulatory agencies. This workshop focused on actual case studies, and provided an opportunity for public or private sector scientists and crop developers to spend time with regulatory officials to learn the specifics of compiling a dossier for regulatory approval. The objective of the workshop was to explain and demystify data requirements and regulatory dossier compilation by small companies, academics, and other developers.

KEYWORDS

EPA; FDA; USDA APHIS BRS; regulatory dossiers; small crop developers; transgenic crops

Title

Report on the SCRA Nuts and Bolts Workshop II: case studies of citrus greening, Ultra-low Gossypol Cotton, and blight tolerant, low-acrylamide potato.

Author

Hood EE1, Eversole KA2, Leach L2, Hogan M2, McHughen A3, Cordts J4, Rathore K5, Rood T6, Collinge S6, Irey M7

Publish date

2019


Description :

Gossypol, a natural product isolated from cottonseeds and roots, binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively.