Gossypin
[CAS# 652-78-8]

Identification

• Classification: Biochemical >> Inhibitor >> Stem cells & wnt signaling paths (Stem cells & wnt)
• Name: Gossypin
• Synonyms: Gossypetin 8-glucoside; 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• Molecular Formula: C₂₁H₂₀O₁₃
• Molecular Weight: 480.38
• CAS Registry Number: 652-78-8
• EC Number: 613-767-7
• SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O

Properties

• Solubility: Slightly soluble (1.7 g/L) (25 ºC), Calc.^*
• Density: 1.883±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 230 ºC (dec.)^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Neelakantam, K.; Proceedings - Indian Academy of Sciences, Section A 1936, V4A, P54-8.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Gossypin is a naturally occurring flavonoid compound classified as a flavonol glycoside. It is chemically characterized as 3,5,7,3′,4′,5′-hexahydroxyflavone 8-O-glucoside, with the molecular formula C₂₁H₂₀O₁₃. Gossypin is primarily found in plants belonging to the *Hibiscus* and *Gossypium* genera, particularly in the flowers of *Hibiscus vitifolius*. As a member of the flavonoid family, gossypin has attracted scientific interest for its biological properties and potential therapeutic applications.

The compound was first isolated in the mid-20th century during investigations of plant constituents with potential medicinal value. Phytochemical studies of *Hibiscus vitifolius* and related species revealed gossypin as one of the key flavonoids present in the petals and other aerial parts. Its structure was determined through a combination of chemical degradation, spectroscopic analysis, and chromatography, confirming the presence of multiple hydroxyl groups and a glucose moiety.

Gossypin has been extensively studied in experimental settings for a range of biological activities. One of its most documented properties is its antioxidant capacity. The compound exhibits strong free radical scavenging ability due to its polyhydroxylated structure, which allows it to donate electrons or hydrogen atoms to reactive oxygen species. This property has been examined in vitro and in vivo for its protective effects against oxidative stress in cellular systems.

In addition to its antioxidant activity, gossypin has shown anti-inflammatory effects in laboratory studies. It modulates the production of pro-inflammatory cytokines and enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), thereby attenuating inflammatory responses. These properties have been observed in animal models of inflammation, where gossypin administration resulted in reduced edema and tissue damage.

Gossypin has also been explored for its potential anticancer properties. Research has demonstrated that it can inhibit the proliferation of various cancer cell lines, including those from colon, breast, and liver cancers. The mechanisms proposed for these effects include the induction of apoptosis, inhibition of cell cycle progression, and modulation of signaling pathways involved in cell growth and survival. These findings are limited to preclinical studies, and gossypin has not been developed as an approved anticancer agent.

Other areas of research involving gossypin include its possible antidiabetic effects, hepatoprotective activity, and neuroprotective potential. In experimental models of diabetes, gossypin has been reported to lower blood glucose levels and improve insulin sensitivity. It has also been shown to protect liver tissue from chemically induced damage and reduce markers of liver toxicity. Neuroprotective studies suggest that gossypin may help mitigate neuronal damage under oxidative stress conditions, although these findings remain preliminary.

Despite these varied effects, gossypin has not been developed into a pharmaceutical drug. Its poor water solubility and low oral bioavailability pose challenges for formulation and systemic delivery. Ongoing research includes the synthesis of gossypin derivatives and development of nanoparticle-based delivery systems to enhance its pharmacological utility.

Gossypin is also studied in the context of traditional medicine. Plants containing gossypin have been used in folk remedies for their purported health benefits, including wound healing and fever reduction. However, these uses are not standardized, and clinical evidence supporting them is lacking.

In summary, gossypin is a flavonol glycoside isolated from species in the *Hibiscus* and *Gossypium* genera. It has been studied for its antioxidant, anti-inflammatory, anticancer, and other biological properties in experimental models. While its therapeutic potential remains under investigation, gossypin continues to serve as a useful compound in pharmacological and phytochemical research.

References

2024. Exploring polyphenolic profiles by using a multivariate approach in Citrullus colocynthis (L.) Schrad. Discover Applied Sciences, 6(10).
DOI: 10.1007/s42452-024-06205-5

2024. A comprehensive tool in recycling plant-waste of Gossypium barbadense L agricultural and industrial waste extracts containing gossypin and gossypol: hepatoprotective, anti-inflammatory and antioxidant effects. Plant Methods, 20(1).
DOI: 10.1186/s13007-024-01181-8

2021. Evaluation of the protective effects of gossypin for ischemia/reperfusion injury in ovary tissue. The Journal of Obstetrics and Gynaecology Research, 47(12).
DOI: 10.1111/jog.15127