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Published February 29, 2016 | Version v1
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Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium)

Creators

  • 1. USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States
  • 2. USDA, Agricultural Research Service, Southern Regional Research Center, New Orleans, LA 70124, United States
  • 3. Cotton Incorporated, 6399 Weston Parkway, Cary, NC 27513, United States

Description

Stipanovic, Robert, Puckhaber, Lorraine, Jr., James Frelichowski, Esquivel, Jesus, Westbrook, John, O'Neil, Mike, Bell, Alois, Dowd, Michael, Hake, Kater, Duke, Sara (2016): Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium). Phytochemistry 122: 165-171, DOI: 10.1016/j.phytochem.2015.12.009, URL: http://dx.doi.org/10.1016/j.phytochem.2015.12.009

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Additional details

Identifiers

URL
https://www.checklistbank.org/dataset/285319
LSID
urn:lsid:plazi.org:pub:8D7DBF0AFF8DFFA2FFD69C76FFC7FFAB
URL
http://publication.plazi.org/id/8D7DBF0AFF8DFFA2FFD69C76FFC7FFAB

Has part
Taxonomic treatment: 10.5281/zenodo.10514919 (DOI)
Taxonomic treatment: http://treatment.plazi.org/id/7144C772FF8FFFA0FFA49B2DFC5BFCE0 (URL)
Taxonomic treatment: 10.5281/zenodo.10514921 (DOI)
Taxonomic treatment: http://treatment.plazi.org/id/7144C772FF8FFFA1FCE99F19FD73F875 (URL)
Figure: 10.5281/zenodo.10514962 (DOI)
Dataset: 10.5281/zenodo.15144015 (DOI)
Dataset: 10.5281/zenodo.15144017 (DOI)
Dataset: 10.5281/zenodo.15144019 (DOI)
Dataset: 10.5281/zenodo.15144021 (DOI)
Figure: 10.5281/zenodo.10485479 (DOI)
Figure: 10.5281/zenodo.10485481 (DOI)
Figure: 10.5281/zenodo.10485483 (DOI)
Is source of
Dataset: https://www.gbif.org/dataset/5b997348-5f35-4147-812e-77402b84742b (URL)

References

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  • Dao, V.-T., Dowd, M.K., Martin, M.-T., Gaspard, C., Mayer, M., Michelot, R.J., 2004. Cytotoxicity of enantiomers of gossypol Schiff's bases and optical stability of gossypolone. Eur. J. Med. Chem. 39, 619-624.
  • Gilbert, N.E., O'Reilly, J.E., Chang, C.J.G., Lin, Y.C., Brueggemeier, R.W., 1995. Antiproliferative activity of gossypol and gossypolone on human breast cancer cells. Life Sci. 57, 61-67.
  • Gonzalez-Garza, M.T., Said-Fernandez, S., 1988. Entamoeba histolytica: potent in vitro antiamoebic effect of gossypol. Exp. Parasitol. 66, 253-255.
  • Hass, R.A., Shirley, D.A., 1965. The oxidation of gossypol. II. Formation of gossypolone with ferric chloride. J. Org. Chem. 30, 411-413.
  • Jaroszewski, J.W., Strom-Hansen, T., Hansen, S.H., Thastrupo, O., Kofod, H., 1992. On the botanical distribution of chiral forms of gossypol. Planta Med. 58, 454-458.
  • Karban, R., 1993. Costs and benefits of induced resistance and plant density for a native shrub, Gossypium thurberi. Ecology 74, 9-19.
  • Kim, I.C., Waller, D.P., Marcelle, G.B., 1984. Comparative in vitro spermicidal effects of (±)-gossypol, (+)-gossypol, (-)-gossypol, and gossypolone. Contraception 30, 253-259.
  • Loberg, R.D., McGregor, N., Ying, C., Sargent, E., Pienta, K.J., 2007. In vivo evaluation of AT-101 (R-(-)-gossypol acetic acid) in androgen-independent growth of VCaP prostate cancer cells in combination with surgical castration. Neoplasia 9, 1030-1037.
  • Lukefahr, M.J., Martin, D.F., 1966. Cotton-plant pigments as a source of resistance to the bollworm and tobacco budworm. J. Econ. Entomol. 59, 176-179.
  • Mellon, J.E., Zelaya, C.A., Dowd, M.K., 2011. Inhibitory effects of gossypol-related compounds on growth of Aspergillus flavus. Lett. Appl. Microbiol. 52, 406-412.
  • Oliver, C.L., Miranda, M.B., Shangary, S., Land, S., Wang, S., Johnson, D.E., 2005. (-)- Gossypol acts directly on the mitochondria to overcome Bcl-2- and Bcl-XLmediated apoptosis resistance. Mol. Cancer Ther. 4, 23-31.
  • Phillips, V.A., Hedin, P.A., 1990. Spectral techniques for structural analysis of cotton terpenoid aldehydes gossypol and gossypolone. J. Agric. Food Chem. 38, 525- 528.
  • Percival, A.E., Wendel, J.E., McStewart, J.M., 1999. Taxonomy and germplasm resources. In: Smith, C., Cothren, J.T. (Eds.), Cotton: Origin, History, Technology, and Production. John Wiley and Sons Inc, New York, pp. 33-63.
  • Ready, N., Karaseva, H.A., Orlov, S.V., Luft, A.V., Popovych, O., Holmlund, J.T., Wood, B.A., Leopold, L., 2011. Double blind, placebo-controlled, randomized phase 2 study of the proapoptotic agent AT-101 plus docetaxel, in second-line nonsmall cell lung cancer. J. Thorac. Oncol. 6, 781-785.
  • Shelly, M.D., Hartley, L., Groundwater, P.W., Fish, R.G., 2000. Structure-activity studies on gossypol in tumor cell lines. Anticancer Drugs 11, 209-216.
  • Stipanovic, R.D., Altman, D.W., Begin, D.L., Greenblatt, G.A., Benedict, J.H., 1988. Terpenoid aldehydes in upland cotton: analysis by aniline and HPLC methods. J. Agric. Food Chem. 88, 509-515.
  • Stipanovic, R.D., Bell, A.A., Lukefahr, M.J., 1977. Natural insecticides from cotton (Gossypium). In: Hedin, P.A. (Ed.), Host Plant Resistance to Pests, Symposium Series #62. American Chemical Society, Washington, DC, pp. 197-214.
  • Stipanovic, R., Esquivel, J., Westbrook, J., Puckhaber, L., O'Neil, M., Bell, A., Duke, S., Dowd, M., Lopez Jr., J.D., Hake, K., 2014. The effect of gossypolone on the growth and development of Helicoverpa zea (Boddie). Southwest Entomol. 39, 1-7.
  • Stipanovic, R.D., Puckhaber, L.S., Bell, A.A., Percival, A.E., Jacobs, J., 2005. Occurrence of (+)- and (-)-gossypol in seed of wild species of cotton and in Gossypium hirsutum var. marie-galante (Watt) Hutchinson. J. Agric. Food Chem. 53, 6266- 6271.
  • Stipanovic, R.D., Williams, H.J., Smith, L., 1986. Cotton terpenoid inhibition of Heliothis virescens development. In: Green, M.A., Hedin, P.A. (Eds.), Natural Resistance of Plants to Pests, Symposium Series #296. American Chemical Society, Washington, DC, pp. 79-94.
  • Yildirim-Aksoy, P., Lim, C., Dowd, M.K., Wan, P.J., Klesius, P.H., Shoemaker, C., 2004. In vitro inhibitory effect of gossypol from gossypol-acetic acid, and (+)- and (-)- isomers of gossypol on the growth of Edwardsiella ictaluri. J. Appl. Microbiol. 97, 87-92.