title: Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium).
abstract: The report that the cotton leaf perforator, Bucculatrix thurberiella, is one of the few insect herbivores to attack Gossypium thurberi prompted an investigation of the terpenoids present in the leaves of this wild species of cotton. Members of Gossypium produce subepidermal pigment glands in their leaves that contain the dimeric sesquiterpenoid gossypol as well as other biosynthetically related terpenoids. In addition to gossypol, a previously unknown dimeric sesquiterpenoid, gossypolhemiquinone (GHQ), was identified in trace amounts in G. thurberi, a member of the D genome. Other members of the D genome of Gossypium were subsequently found to contain this compound, but GHQ was not detected in commercial cotton cultivars. When fed to Helicoverpa zea in an artificial diet, GHQ delayed days-to-pupation, reduced pupal weights, and survival to adulthood to a lesser or equal extent than gossypol in comparison to the control diet. However, GHQ had a synergistic effect on survival and days-to-pupation when combined with gossypol at the highest dosage tested (0.18%; 15.5:84.5 GHQ:gossypol). Because gossypol exhibits anti-cancer activity, GHQ was also evaluated for its anti-cancer activity against the National Cancer Institute's 60-Human Tumor Cell Line Screen. Significant inhibitory activity against most of these cell lines was not observed, but the results may offer some promise against leukemia cancer cell lines.
authors.affiliation: USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States. Electronic address: bob.stipanovic@ars.usda.gov.
authors.forename: Robert
authors.initials: R
authors.lastname: Stipanovic
authors.affiliation: USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States.
authors.forename: Lorraine
authors.initials: L
authors.lastname: Puckhaber
authors.affiliation: USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States.
authors.forename: James
authors.initials: J
authors.lastname: Frelichowski
authors.affiliation: USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States.
authors.forename: Jesus
authors.initials: J
authors.lastname: Esquivel
authors.affiliation: USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States.
authors.forename: John
authors.initials: J
authors.lastname: Westbrook
authors.affiliation: USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States.
authors.forename: Mike
authors.initials: M
authors.lastname: O'Neil
authors.affiliation: USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States.
authors.forename: Alois
authors.initials: A
authors.lastname: Bell
authors.affiliation: USDA, Agricultural Research Service, Southern Regional Research Center, New Orleans, LA 70124, United States.
authors.forename: Michael
authors.initials: M
authors.lastname: Dowd
authors.affiliation: Cotton Incorporated, 6399 Weston Parkway, Cary, NC 27513, United States.
authors.forename: Kater
authors.initials: K
authors.lastname: Hake
authors.affiliation: USDA, Agricultural Research Service, Southern Plains Agricultural Research Center, College Station, TX 77845, United States.
authors.forename: Sara
authors.initials: S
authors.lastname: Duke
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D003368:Gossypium / Q000737:chemistry* / Q000235:genetics; D006072:Gossypol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D018515:Plant Leaves / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; C000610927:gossypolhemiquinone; D006072:Gossypol
keywords: Di-sesquiterpenoid; Gossypium thurberi; Gossypol; Gossypolhemiquinone; Helicoverpa zea; Insect herbivory resistance; Malvaceae