Reaction chemistry of gossypol and its derivatives

Abstract

Gossypol, a complex polyphenolic compound, is a naturally occurring highly colored yellow pigment found in the small intercellular pigment glands in the leaves, stems, roots, and seed of cotton plants. In cottonseed, gossypol contributes to its toxicity and therefore it is regarded as an unwanted processing component. It was not until its antitumor and male infertility activities were discovered that gossypol was considered as a valueadded natural product from cottonseed with useful physiological and chemical properties. These serendipitous discoveries created much excitement, and an enormous amount of research on gossypol has ensued. Since then, much research has focused on the preparation of suitable gossypol derivatives for medicinal applications. This review summarizes current knowledge about gossypol, its stereochemistry, tautomerism, and the many varied reactions the gossypol molecule can undergo.

Identification of natural products and their derivatives as promising inhibitors of protein glycation with non-toxic nature against mouse fibroblast 3T3 cells

“…A large number of gossypol derivatives, such as Schiff's bases, esters, and ethers have been prepared. Several gossypol derivatives and analogs, such as compounds 3-6, possess activities such as antimalarial, anti-cancer, HIV (human immunodeficiency virus), and antiparasitic properties [31][32][33][34][35][36][37]. High throughput screening studies on a gossypol derivative 5 were performed in vivo and in vitro.…”

Pengaruh Waktu Perebusan Terhadap Kandungan Proksimat, Mineral Dan Kadar Gosipol Tepung Biji Kapas

“…Kadar gosipol bebas biasanya berkisar antara 0,39-1,70%, sedangkan kadar keseluruhan dapat mencapai 6,64%. Selisih antara keduanya adalah gosipol terikat 10 . Hasil penelitian Alexander et.al 11 menyatakan bahwa kandungan gosipol bebas pada berbagai varietas tanaman kapas pada berbagai lokasi berkisar antara 4,7-7,0 mg/kg.…”

“…Terjadinya peningkatan kadar gosipol pada perebusan 4 dan 5 jam disebabkan tingginya kandungan air yang sudah diserap oleh biji ketika proses perebusan, sehingga mengakibatkan kadar air yang tinggi dan kadar gosipol seolah-olah meningkat karena nilai yang didapat berdasarkan pada berat kering (dry base). Berdasarkan penelitian Kenar 10 bahwa proses pemanasan dapat menurunkan konsentrasi gosipol bebas, namun tidak pada gosipol total. Disamping itu, proses pemanasan dapat mengaktifkan beberapa enzim yang dapat menyebabkan terjadinya pemecahan ikatan gosipol dan bahkan bisa mengakibatkan terjadinya proses imbibisi yang tidak dapat balik (irreversible), selain itu pemanasan lebih lanjut tidak efektif dalam menurunkan kandungan gosipol.…”

Gossypol Promotes the Degeneration of Chicken Ovarian Follicles in Vitro

“…Gossypol (2,2-bi(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)) is a phenolic compound produced by the pigment glands in cotton stems, leaves, seeds and flower buds (Rogers et al, 2002;Kenar, 2006;Alexander et al, 2008;Soto-Blanco, 2008). This compound is known to affect male reproduction, inhibiting spermatogenesis and reducing spermatozoid motility and viability (Randel et al, 1992;Fornes et al, 1993;Brocas et al, 1997;Yuan & Shi, 2000;El-Sharaky et al, 2010).…”