Synthesis and cytotoxicity of gossypol related compounds

Dao, Vi-Thuy; Gaspard, Christiane; Mayer, Michel; Gh, Werner; Nguyen, Suong; Michelot, Robert

doi:10.1016/s0223-5234(00)00165-3

Cited by 93 publications

(36 citation statements)

References 30 publications

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“…They are also used as intermediates in organic synthesis as well as polymers stabilizers 7 . Schiff bases are known to exhibit a broad range of biological activities including antifungal, antibacterial, antimalaria, antiproliferative, antiinflammatory, antiviral and antipyretic properties [8][9][10][11] . The imine group present in such compounds has been shown to be critical to their biological activities 12,13 .…”

Section: Research Articlementioning

confidence: 99%

“…The singlet peak at 8.28 ppm is for H 11 4 and H 5 protons in axial position. For a given carbon atom, proton in equatorial position is more deblinded than in axial position one 14 .…”

Section: Nmr Studymentioning

confidence: 99%

“…Table 1. Selected bond lengths and angles (Å, °) C 5 -C 6 1.510 (5) C 6 -C 5 -C 4 111.7 (4) C 5 -C 4 1.511 (6) C 5 -C 4 -C 3 109,55(4) C 4 -C 3 1.523 (5) C 4 -C 3 -C 2 112.6 (4) C 2 -C 3 1.522 (4) 7 1.259 (4) N 2 =C 7 -C 8 119.7 (3) C 7 -C 8 1.474 (4) C 8 -C 13 -C 12 119.6 (3) C 8 -C 9 1.404 (4) C 13 -C 12 -C 11 122.7 (4) C 9 -C 10 1.372 (5) C 12 -C 11 -C 10 118.4 (4) C 10 -C 11 1.370 (5) C 11 -C 10 -C 9 120.0 (4) C 11 -C 12 1.383 (5) C 9 -C 8 -C 13 117.8 (4) C 12 -C 13 1 16 1.401 (4) C 7 -N 2 -C 1 -C 2 126,0(4) C 17 -C 18 1.386 (5) C 14 -N 3 -C 2 -C 1 123,4(3) C 18 -C 19 1.384 (5) Conformational analysis of the structure obtained clearly shows that the hexanic cycle adopts chair conformation more stable than the boat form [21][22][23] .…”

Section: X-ray Analysismentioning

confidence: 99%

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Preparation, Spectroscopy and X-Ray Structure Analysis of N, Nʹ-Bis(3-nitrophenylmethylene)- cyclohexane-1,2-diamine

2017

Chem Sci Trans

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The compound N,cyclohexane-1,2-diamine (α-diimine Shiff base) was synthesized and characterized by MS, IR, NMR 1 H and X-ray single crystal analysis. While the cyclohexane-1,2-diamine used for the synthesis of this composite is a racemic cis and trans mixture, we observed by x-ray diffraction for the product N,N'-bis(3-nitrophenylmethylene) cyclohexane-1,2-diamine only the (1R,2R)trans enantiopure. The crystalline network cohesion of this compound is assured by a combination of C-H ... O and C-H ... N hydrogen bonds. It crystallizes in the monoclinic non-standard I2/a space group.

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Section: Research Articlementioning

confidence: 99%

“…The singlet peak at 8.28 ppm is for H 11 4 and H 5 protons in axial position. For a given carbon atom, proton in equatorial position is more deblinded than in axial position one 14 .…”

Section: Nmr Studymentioning

confidence: 99%

Section: X-ray Analysismentioning

confidence: 99%

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Preparation, Spectroscopy and X-Ray Structure Analysis of N, Nʹ-Bis(3-nitrophenylmethylene)- cyclohexane-1,2-diamine

2017

Chem Sci Trans

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“…Gossypol is toxic to human and animals (Dao et al, 2000;Shelley et al, 1999). Recent reports also showed its anti-cancer, antiviral, spermicidal and antimicrobial activities (Dao et al, 2000;Kim et al, 1984;Yildirim-Aksoy et al, 2004), and of which the ()-gossypol seems to be more active than the (+)-gossypol (Blackstaffe et al, 1997;Shelley et al, 1999;Yildirim-Aksoy et al, 2004).…”

Section: Genetic Engineering Of Gossypol Traitsmentioning

confidence: 99%

“…Recent reports also showed its anti-cancer, antiviral, spermicidal and antimicrobial activities (Dao et al, 2000;Kim et al, 1984;Yildirim-Aksoy et al, 2004), and of which the ()-gossypol seems to be more active than the (+)-gossypol (Blackstaffe et al, 1997;Shelley et al, 1999;Yildirim-Aksoy et al, 2004). Thus the breeding goal towards gossypol traits is expected to increase or maintain the phytoalexins in most organs of cotton plants for high resistance to pests and pathogens, meanwhile to eliminate these compounds in seeds to reduce the usage cost for the high quality edible oil and protein.…”

Section: Genetic Engineering Of Gossypol Traitsmentioning

confidence: 99%

Gossypol: phytoalexin of cotton

Tian

Ruan

Huang

et al. 2016

Sci. China Life Sci.

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Sesquiterpenoids are a class of 15-carbon secondary metabolites that play diverse roles in plant adaptation to environment. Cotton plants accumulate a large amount of sesquiterpene aldehydes (including gossypol) as phytoalexins against pathogens and herbivores. They are stored in pigment glands of aerial organs and in epidermal layers of roots. Several enzymes of gossypol biosynthesis pathway have been characterized, including 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMGR) and farnesyl diphosphate synthase (FPS) that catalyze the formation of the precursor farnesyl diphosphate (FPP), (+)--cadinene synthase (CDN) which is the first enzyme committed to gossypol biosynthesis, and the downstream enzymes of CYP706B1 and methyltransferase. Expressions of these genes are tightly regulated during cotton plants development and induced by jasmonate and fungi elicitors. The transcription factor GaWRKY1 has been shown to be involved in gossypol pathway regulation. Recent development of new genomic platforms and methods and releases of diploid and tetraploid cotton genome sequences will greatly facilitate the elucidation of gossypol biosynthetic pathway and its regulation.cotton, secondary metabolism, gossypol, sesquiterpenoid Citation:

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