Occurrence of (+)- and (−)-Gossypol in Wild Species of Cotton and in Gossypium hirsutum Var. marie-galante (Watt) Hutchinson

Stipanovic, Robert D.; Puckhaber, Lorraine S.; Bell, Alois A.; Percival, and Albert E.; Jacobs, John

doi:10.1021/jf050702d

Cited by 60 publications

(56 citation statements)

References 16 publications

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“…One such example is the study of gossypol (+) and (-) enantiomers, found in the cotton plant. These enantiomers have been shown to differ in toxicity to herbivores and pathogens (22,23).…”

Section: Discussionmentioning

confidence: 99%

Amyris and Siam-wood Essential Oils: Insect Activity of Sesquiterpenes

Paluch¹,

Zhu

Coats³

2009

ACS Symposium Series

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Recent investigations on the sesquiterpene-rich Amyris (Amyris balsamifera L.) and Siam-wood (Fokienia hodginsii L.) essential oils revealed significant arthropod repellency and toxicity responses. Amyris essential oil and one of its major components, elemol, were evaluated in laboratory bioassays and identified as effective mosquito repellents, specifically characterized by high levels of contact and minimal spatial repellency. Mosquito responses to catnip (Nepeta cataria L.) essential oil are characterized with high spatial activity, but lack significant contact repellency. Sampling within the staticair bioassay chamber with solid-phase microextraction provided measurements of the relative concentration and distribution of volatiles. These results supported the differences observed in repellency between essential oil treatments. Essential oil mixtures containing both spatial (catnip) and contact (Amyris) repellents were made and showed high levels of residual control via both modes of action. Siam-wood essential oil scored high in both spatial and contact efficacy against mosquitoes. Observations during this study included signs of toxicity. Two of the primary components of Siam-wood essential oil were tested for 24-hour house fly (Musca domestica L.) topical mortality. Transnerolidol and fokienol were found to possess similar insecticidal activity (topical LD50 values ranged from 0.17-0.21 µmol/fly). Amyris essential oil was selected for additional testing with brown dog ticks (Rhipicephalus sanguineusLatreille) in a 'barrier' repellency assay. Individuals were observed repeatedly avoiding and moving away from surfaces treated with Amyris essential oil. RightsWorks produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted. Recent investigations on the sesquiterpene-rich Amyris (Amyris balsamifera L.) and Siam-wood (Fokienia hodginsii L.) essential oils revealed significant arthropod repellency and toxicity responses. Amyris essential oil and one of its major components, elemol, were evaluated in laboratory bioassays and identified as effective mosquito repellents, specifically characterized by high levels of contact and minimal spatial repellency. Mosquito responses to catnip (Nepeta cataria L.) essential oil are characterized with high spatial activity, but lack significant contact repellency. Sampling within the staticair bioassay chamber with solid-phase microextraction provided measurements of the relative concentration and distribution of volatiles.These results supported the differences observed in repellency between essential oil treatments. Essential oil mixtures containing both spatial (catnip) and contact (Amyris) repellents were made and showed high levels of residual control via both modes of action. Siam-wood essential oil scored high in both spatial and contact efficacy against mosquitoes. Observations during this study included signs of toxicity. Two of the primary components of Siam...

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“…One such example is the study of gossypol (+) and (-) enantiomers, found in the cotton plant. These enantiomers have been shown to differ in toxicity to herbivores and pathogens (22,23).…”

Section: Discussionmentioning

confidence: 99%

Amyris and Siam-wood Essential Oils: Insect Activity of Sesquiterpenes

Paluch¹,

Zhu

Coats³

2009

ACS Symposium Series

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“…Among G. hirsutum entriesin the 2012 National Cotton Variety Test, percent total gossypol ranged from 0.55% to 1.89% (www.ars.usda.gov/SP2UserFiles/Place/64021500/2012NCVT.pdf). Gossypol exists as enantiomers (isomers) referred to as (+)-and (−)-gossypol [5] [6] with the (−) enantiomer reported to be more toxic than the (+)-enantiomer. For example, the (−)-enantiomer exhibited a greater ability to inhibit the growth of cancer cell lines [7] [8].…”

Section: Introductionmentioning

confidence: 99%

Evaluating Protective Terpenoid Aldehyde Compounds in Cotton (Gossypium hirsutum L.) Roots

Scheffler¹

2016

AJPS

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Cotton (Gossypium hirsutum L.) has epidermal glands containing terpenoid aldehyde (TA) compounds that protect the plant from pests and diseases. One TA, gossypol, has two forms (+) and (−) that are present in varying amounts. This study evaluated the variation in roots for TA compounds and how environment affected the levels of these compounds. Similar to seed, gossypol was the predominant TA in roots. No heliocides were detected with only trace amounts of other TAs, such as hemigossypolone or hemigossypol, detected in a few lines. Among the glanded lines, there were significant differences in gossypol content. Percent plus gossypol was consistently 4% -10% higher in roots than seed. One line, "Mac7", had 12 -14 ug/mg gossypol in roots and 18 ug/mg in seed as well as >90% (+) gossypol in both roots and seed. Unlike other tissues in glandless cotton, the roots of glandless lines consistently produced detectable amounts of gossypol with 77% to 82% in the (+) form. Multi-year field tests showed that although gossypol levels in the roots were more affected by insect pressure or other environmental conditions than seed, there was selectable variation in upland cotton for root gossypol content. Unlike other parts of a glandless plant, the roots retained a functioning biochemical pathway for gossypol production.

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“…(+)-gossypol is the dominant form, which could make up to 97% in G. hirsutum var. mariegalante (Stipanovic et al, 2005). Moreover, the content and ratio also vary in tissues.…”

Section: Sesquiterpenoids In Cottonmentioning

confidence: 99%

“…in G. hirsutum var. mariegalante, the (+)-gossypol accounts for about 98% (Stipanovic et al, 2005). In plants, a family of dirigent proteins plays a key role in determining the stereo specificity.…”

Section: Peroxidase Laccase and Dirigent Proteinmentioning

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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Occurrence of (+)- and (−)-Gossypol in Wild Species of Cotton and in Gossypium hirsutum Var. marie-galante (Watt) Hutchinson

Cited by 60 publications

References 16 publications

Amyris and Siam-wood Essential Oils: Insect Activity of Sesquiterpenes

Amyris and Siam-wood Essential Oils: Insect Activity of Sesquiterpenes

Evaluating Protective Terpenoid Aldehyde Compounds in Cotton (<i>Gossypium hirsutum</i> L.) Roots

Gossypol: phytoalexin of cotton

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Occurrence of (+)- and (−)-Gossypol in Wild Species of Cotton and in Gossypium hirsutum Var. marie-galante (Watt) Hutchinson

Cited by 60 publications

References 16 publications

Amyris and Siam-wood Essential Oils: Insect Activity of Sesquiterpenes

Amyris and Siam-wood Essential Oils: Insect Activity of Sesquiterpenes

Evaluating Protective Terpenoid Aldehyde Compounds in Cotton (&lt;i&gt;Gossypium hirsutum&lt;/i&gt; L.) Roots

Gossypol: phytoalexin of cotton

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Evaluating Protective Terpenoid Aldehyde Compounds in Cotton (<i>Gossypium hirsutum</i> L.) Roots