Cycasin - Revision history

Bfesser: /* Presence in sago */Corrected insure to ensure.

2024-05-19T02:44:35Z

Presence in sago: Corrected insure to ensure.

← Previous revision		Revision as of 02:44, 19 May 2024
Line 50:		Line 50:

	===Presence in sago===		===Presence in sago===
	In order to produce [[sago]], cycasin and other cycad toxins must be removed from the flesh of the plants. The flesh, seeds, and roots of the cycad are first dried and ground into a fine powder, before being submerged in boiling water. The water is then allowed to drain, leaching out the toxic material while leaving the starch behind. The extracted starch is then alternately dried and pounded until a fine powder is obtained. This repeated pounding and leaching process ~~insures~~ that there is as little cycasin as possible left behind.<ref>{{cite journal\|last1=Whiting\|first1=Marjorie Grant\|title=Toxicity of cycads\|journal=Economic Botany\|date=October 1963\|volume=17\|issue=4\|pages=270–302\|doi=10.1007/BF02860136\|s2cid=31799259}}</ref>		In order to produce [[sago]], cycasin and other cycad toxins must be removed from the flesh of the plants. The flesh, seeds, and roots of the cycad are first dried and ground into a fine powder, before being submerged in boiling water. The water is then allowed to drain, leaching out the toxic material while leaving the starch behind. The extracted starch is then alternately dried and pounded until a fine powder is obtained. This repeated pounding and leaching process ensures that there is as little cycasin as possible left behind.<ref>{{cite journal\|last1=Whiting\|first1=Marjorie Grant\|title=Toxicity of cycads\|journal=Economic Botany\|date=October 1963\|volume=17\|issue=4\|pages=270–302\|doi=10.1007/BF02860136\|s2cid=31799259}}</ref>

	==Structure==		==Structure==

Citation bot: Added bibcode. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | #UCB_webform 577/3364

2024-04-05T13:56:23Z

Added bibcode. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | #UCB_webform 577/3364

← Previous revision		Revision as of 13:56, 5 April 2024
Line 55:		Line 55:
	Cycasin is a [[glucose]]-derived [[glycoside]] with a [[methylazoxymethanol]] substitution at the beta position.		Cycasin is a [[glucose]]-derived [[glycoside]] with a [[methylazoxymethanol]] substitution at the beta position.

	Stereochemistry at the azoxy group is (''Z'') (or ''trans'' (''E'') when oxygen removed formally to form azo- group).<ref>{{cite journal \|last1=Kawaminami \|first1=M. \|last2=Kawano \|first2=I. \|last3=Kobayashi \|first3=A. \|last4=Tadera \|first4=K. \|last5=Yaki \|first5=F. \|last6=Kawano \|first6=S. \|title=The fundamental structure of cycasin, (methyl-ONN-azoxy)methyl β-D-glucopyranoside \|journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry \|date=15 November 1981 \|volume=37 \|issue=11 \|pages=2026–2029 \|doi=10.1107/S0567740881007887}}</ref>		Stereochemistry at the azoxy group is (''Z'') (or ''trans'' (''E'') when oxygen removed formally to form azo- group).<ref>{{cite journal \|last1=Kawaminami \|first1=M. \|last2=Kawano \|first2=I. \|last3=Kobayashi \|first3=A. \|last4=Tadera \|first4=K. \|last5=Yaki \|first5=F. \|last6=Kawano \|first6=S. \|title=The fundamental structure of cycasin, (methyl-ONN-azoxy)methyl β-D-glucopyranoside \|journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry \|date=15 November 1981 \|volume=37 \|issue=11 \|pages=2026–2029 \|doi=10.1107/S0567740881007887\|bibcode=1981AcCrB..37.2026K }}</ref>

	==Toxicity==		==Toxicity==

Kku: link [nN]eurotoxin

2023-11-04T19:00:52Z

link [nN]eurotoxin

← Previous revision		Revision as of 19:00, 4 November 2023
Line 71:		Line 71:
	The [[Lytico-bodig disease]], also known as lateral sclerosis-parkinsonism-dementia, is a [[neurodegenerative]] disease of unknown origin that occurs exclusively in the [[Chamorro people\|Chamorro]] people of the island of [[Guam]] that has characteristics of both [[amyotrophic lateral sclerosis]] (ALS) and [[parkinsonism]]. It is characterized by muscle atrophy, maxillofacial paralysis, inability to speak or swallow, and dementia. The disease is fatal in all cases, with the diaphragm and respiratory accessory muscles becoming paralyzed in the later stages of the disease.<ref name=Bradley>{{cite journal\|last1=Bradley\|first1=Walter G.\|last2=Mash\|first2=Deborah C.\|title=Beyond Guam: The cyanobacteria/BMAA hypothesis of the cause of ALS and other neurodegenerative diseases\|journal=Amyotrophic Lateral Sclerosis\|date=25 November 2009\|volume=10\|issue=sup2\|pages=7–20\|doi=10.3109/17482960903286009\|pmid=19929726\|s2cid=41622254}}</ref>		The [[Lytico-bodig disease]], also known as lateral sclerosis-parkinsonism-dementia, is a [[neurodegenerative]] disease of unknown origin that occurs exclusively in the [[Chamorro people\|Chamorro]] people of the island of [[Guam]] that has characteristics of both [[amyotrophic lateral sclerosis]] (ALS) and [[parkinsonism]]. It is characterized by muscle atrophy, maxillofacial paralysis, inability to speak or swallow, and dementia. The disease is fatal in all cases, with the diaphragm and respiratory accessory muscles becoming paralyzed in the later stages of the disease.<ref name=Bradley>{{cite journal\|last1=Bradley\|first1=Walter G.\|last2=Mash\|first2=Deborah C.\|title=Beyond Guam: The cyanobacteria/BMAA hypothesis of the cause of ALS and other neurodegenerative diseases\|journal=Amyotrophic Lateral Sclerosis\|date=25 November 2009\|volume=10\|issue=sup2\|pages=7–20\|doi=10.3109/17482960903286009\|pmid=19929726\|s2cid=41622254}}</ref>

	Observation of the diets of the native Chamorro people led to the creation of the so-called "Cycad hypothesis." Starches prepared from the seeds of a native cycad species, ''[[Cycas micronesica]]'', are used to create the [[sago]]-like flour ''fadang'', which forms a major part of the diet of the Chamorro people. As the seeds contain the highest amount of the toxin found in the plant, it was proposed that a dietary explanation relating to the consumption of poorly processed fadang was poisoning the natives. After failing to reproduce the symptoms of the disease in animal models, the hypothesis was rejected.<ref name=Bradley /> Though the initial cycad hypothesis was rejected, a revised form of the hypothesis was proposed by [[Paul Alan Cox]] and [[Oliver Sacks]] after observing other elements of the Chamorro diet, specifically [[flying foxes]]. The bats accumulate [[BMAA]] in their fat by consuming cycad seeds, resulting a in a high concentration of the neurotoxin.<ref name = "Cox1">{{cite journal \|vauthors=Cox PA, Banack SA, Murch SJ \|year = 2003 \|title = Biomagnification of cyanobacterial neurotoxins and neurodegenerative disease among the Chamorro people of Guam \|journal = PNAS \|volume = 100 \|issue = 23 \|pages = 13380–13383 \|doi=10.1073/pnas.2235808100\| bibcode = 2003PNAS..10013380C\|pmc = 263822 \|pmid=14612559\|doi-access = free }}</ref>		Observation of the diets of the native Chamorro people led to the creation of the so-called "Cycad hypothesis." Starches prepared from the seeds of a native cycad species, ''[[Cycas micronesica]]'', are used to create the [[sago]]-like flour ''fadang'', which forms a major part of the diet of the Chamorro people. As the seeds contain the highest amount of the toxin found in the plant, it was proposed that a dietary explanation relating to the consumption of poorly processed fadang was poisoning the natives. After failing to reproduce the symptoms of the disease in animal models, the hypothesis was rejected.<ref name=Bradley /> Though the initial cycad hypothesis was rejected, a revised form of the hypothesis was proposed by [[Paul Alan Cox]] and [[Oliver Sacks]] after observing other elements of the Chamorro diet, specifically [[flying foxes]]. The bats accumulate [[BMAA]] in their fat by consuming cycad seeds, resulting a in a high concentration of the [[neurotoxin]].<ref name = "Cox1">{{cite journal \|vauthors=Cox PA, Banack SA, Murch SJ \|year = 2003 \|title = Biomagnification of cyanobacterial neurotoxins and neurodegenerative disease among the Chamorro people of Guam \|journal = PNAS \|volume = 100 \|issue = 23 \|pages = 13380–13383 \|doi=10.1073/pnas.2235808100\| bibcode = 2003PNAS..10013380C\|pmc = 263822 \|pmid=14612559\|doi-access = free }}</ref>
	[[File:Cycas micronesica photo courtesy A. Gawel (15391498081).jpg\|thumb\|''[[Cycas micronesica]]'', one of the cycad species consumed by the Chamorro]]		[[File:Cycas micronesica photo courtesy A. Gawel (15391498081).jpg\|thumb\|''[[Cycas micronesica]]'', one of the cycad species consumed by the Chamorro]]

Citation bot: Add: bibcode. | Use this bot. Report bugs. | Suggested by Spinixster | Category:Glucosides | #UCB_Category 43/60

2023-07-03T07:39:05Z

Add: bibcode. | Use this bot. Report bugs. | Suggested by Spinixster | Category:Glucosides | #UCB_Category 43/60

← Previous revision		Revision as of 07:39, 3 July 2023
Line 42:		Line 42:

	==Sources==		==Sources==
	Cycasin is found in all known [[cycad]] genera and is distributed throughout the body of the plant, but with the highest concentration in the seeds. It is one of several toxins found in cycad plants, along with the neurotoxic amino acid [[BMAA]]. The origin and biological role of these toxins is unknown, as there does not appear to be a statistically significant correlation between the concentration of toxic material and the types of herbivory observed in animals consuming the plants.<ref>{{cite journal\|last1=Moretti\|first1=A.\|last2=Sabato\|first2=S.\|last3=Gigliano\|first3=G.Siniscalco\|title=Taxonomic significance of methylazoxymethanol glycosides in the cycads\|journal=Phytochemistry\|date=January 1983\|volume=22\|issue=1\|pages=115–117\|doi=10.1016/S0031-9422(00)80069-2}}</ref><ref>{{cite journal\|last1=Castillo-Guevara\|first1=Citlalli\|last2=Rico-Gray\|first2=Victor\|title=The Role of Macrozamin and Cycasin in Cycads (Cycadales) as Antiherbivore Defenses\|journal=Journal of the Torrey Botanical Society\|date=July 2003\|volume=130\|issue=3\|pages=206\|doi=10.2307/3557555\|jstor=3557555}}</ref>		Cycasin is found in all known [[cycad]] genera and is distributed throughout the body of the plant, but with the highest concentration in the seeds. It is one of several toxins found in cycad plants, along with the neurotoxic amino acid [[BMAA]]. The origin and biological role of these toxins is unknown, as there does not appear to be a statistically significant correlation between the concentration of toxic material and the types of herbivory observed in animals consuming the plants.<ref>{{cite journal\|last1=Moretti\|first1=A.\|last2=Sabato\|first2=S.\|last3=Gigliano\|first3=G.Siniscalco\|title=Taxonomic significance of methylazoxymethanol glycosides in the cycads\|journal=Phytochemistry\|date=January 1983\|volume=22\|issue=1\|pages=115–117\|doi=10.1016/S0031-9422(00)80069-2\|bibcode=1983PChem..22..115M }}</ref><ref>{{cite journal\|last1=Castillo-Guevara\|first1=Citlalli\|last2=Rico-Gray\|first2=Victor\|title=The Role of Macrozamin and Cycasin in Cycads (Cycadales) as Antiherbivore Defenses\|journal=Journal of the Torrey Botanical Society\|date=July 2003\|volume=130\|issue=3\|pages=206\|doi=10.2307/3557555\|jstor=3557555}}</ref>

	The enzyme [[methyl-ONN-azoxymethanol beta-D-glucosyltransferase]] uses the two substrates [[UDP-glucose]] and [[methyl-ONN-azoxymethanol]] to produce [[Uridine diphosphate\|UDP]] and cycasin.<ref>{{cite journal \|vauthors=Tadera K, Yagi F, Arima M, Kobayashi A \| year = 1985 \| title = Formation of cycasin from methylazoxymethanol by UDP-glucosyltransferase from leaves of Japanese cycad \| journal = Agric. Biol. Chem. \| volume = 49 \| pages = 2827–2828 \| doi = 10.1271/bbb1961.49.2827 \| issue = 9 \| doi-access = free }}</ref>		The enzyme [[methyl-ONN-azoxymethanol beta-D-glucosyltransferase]] uses the two substrates [[UDP-glucose]] and [[methyl-ONN-azoxymethanol]] to produce [[Uridine diphosphate\|UDP]] and cycasin.<ref>{{cite journal \|vauthors=Tadera K, Yagi F, Arima M, Kobayashi A \| year = 1985 \| title = Formation of cycasin from methylazoxymethanol by UDP-glucosyltransferase from leaves of Japanese cycad \| journal = Agric. Biol. Chem. \| volume = 49 \| pages = 2827–2828 \| doi = 10.1271/bbb1961.49.2827 \| issue = 9 \| doi-access = free }}</ref>

	===Ecological significance===		===Ecological significance===
	The butterfly ''[[Eumaeus atala]]'', whose larvae feed on ''Z. pumila'', contain the poison as a consequence of their diet.<ref>{{cite journal\|last1=Rothschild\|first1=Miriam\|last2=Nash\|first2=Robert J.\|last3=Bell\|first3=E.Arthur\|title=Cycasin in the endangered butterfly Eumaeus atala florida\|journal=Phytochemistry\|date=July 1986\|volume=25\|issue=8\|pages=1853–1854\|doi=10.1016/S0031-9422(00)81161-9}}</ref>		The butterfly ''[[Eumaeus atala]]'', whose larvae feed on ''Z. pumila'', contain the poison as a consequence of their diet.<ref>{{cite journal\|last1=Rothschild\|first1=Miriam\|last2=Nash\|first2=Robert J.\|last3=Bell\|first3=E.Arthur\|title=Cycasin in the endangered butterfly Eumaeus atala florida\|journal=Phytochemistry\|date=July 1986\|volume=25\|issue=8\|pages=1853–1854\|doi=10.1016/S0031-9422(00)81161-9\|bibcode=1986PChem..25.1853R }}</ref>

	===Presence in sago===		===Presence in sago===

LegionMammal978: fix mistake, add semisystematic name

2023-04-30T15:28:07Z

fix mistake, add semisystematic name

← Previous revision		Revision as of 15:28, 30 April 2023
Line 3:		Line 3:
	\| ImageSize = 200px		\| ImageSize = 200px
	\| ImageAlt = Chemical structure of cycasin		\| ImageAlt = Chemical structure of cycasin
			\| IUPACName = (''Z'')-1-[(β-<small>D</small>-Glucopyranosyloxy)methyl]-2-methyldiazene 2-oxide
	\| ~~PIN~~ = (''Z'')-1-Methyl-2-({[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)diazene 2-oxide		\| SystematicName = (''Z'')-1-Methyl-2-({[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)diazene 1-oxide
	\| SystematicName = [(''Z'')-Methyl-''ONN''-azoxy]methyl β-<small>D</small>-glucopyranoside<ref>[http://www.chemspider.com/Chemical-Structure.4573631.html b-D-Glucosyloxyazoxymethane], [[ChemSpider]]</ref>
	\| OtherNames = β-<small>D</small>-Glucosyloxyazoxymethane; Methylazoxymethanol β-<small>D</small>-glucoside; Cycas revoluta glucoside		\| OtherNames = β-<small>D</small>-Glucosyloxyazoxymethane; Methylazoxymethanol β-<small>D</small>-glucoside; Cycas revoluta glucoside; [(''Z'')-Methyl-''ONN''-azoxy]methyl β-<small>D</small>-glucopyranoside<ref>[http://www.chemspider.com/Chemical-Structure.4573631.html b-D-Glucosyloxyazoxymethane], [[ChemSpider]]</ref>
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo = 14901-08-7		\| CASNo = 14901-08-7

JCW-CleanerBot: /* Structure */task, replaced: Acta Crystallographica Section B → Acta Crystallographica Section B:

2022-07-25T10:20:01Z

Structure: task, replaced: Acta Crystallographica Section B → Acta Crystallographica Section B:

← Previous revision		Revision as of 10:20, 25 July 2022
Line 55:		Line 55:
	Cycasin is a [[glucose]]-derived [[glycoside]] with a [[methylazoxymethanol]] substitution at the beta position.		Cycasin is a [[glucose]]-derived [[glycoside]] with a [[methylazoxymethanol]] substitution at the beta position.

	Stereochemistry at the azoxy group is (''Z'') (or ''trans'' (''E'') when oxygen removed formally to form azo- group).<ref>{{cite journal \|last1=Kawaminami \|first1=M. \|last2=Kawano \|first2=I. \|last3=Kobayashi \|first3=A. \|last4=Tadera \|first4=K. \|last5=Yaki \|first5=F. \|last6=Kawano \|first6=S. \|title=The fundamental structure of cycasin, (methyl-ONN-azoxy)methyl β-D-glucopyranoside \|journal=Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry \|date=15 November 1981 \|volume=37 \|issue=11 \|pages=2026–2029 \|doi=10.1107/S0567740881007887}}</ref>		Stereochemistry at the azoxy group is (''Z'') (or ''trans'' (''E'') when oxygen removed formally to form azo- group).<ref>{{cite journal \|last1=Kawaminami \|first1=M. \|last2=Kawano \|first2=I. \|last3=Kobayashi \|first3=A. \|last4=Tadera \|first4=K. \|last5=Yaki \|first5=F. \|last6=Kawano \|first6=S. \|title=The fundamental structure of cycasin, (methyl-ONN-azoxy)methyl β-D-glucopyranoside \|journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry \|date=15 November 1981 \|volume=37 \|issue=11 \|pages=2026–2029 \|doi=10.1107/S0567740881007887}}</ref>

	==Toxicity==		==Toxicity==

Neils51: replaced: gound → ground

2022-06-13T10:36:56Z

replaced: gound → ground

← Previous revision		Revision as of 10:36, 13 June 2022
Line 37:		Line 37:
	}}		}}
	}}		}}
	'''Cycasin''' is a [[carcinogenic]] and [[neurotoxic]] [[glucoside]] found in [[cycad]]s such as ''[[Cycas revoluta]]'' and ''[[Zamia pumila]]''. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and [[hepatotoxicity]]. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into [[formaldehyde]] and [[diazomethane]]. <ref name=Laq>{{cite journal\|last1=Laqueur\|first1=G. L.\|last2=Spatz\|first2=M.\|title=Toxicology of Cycasin\|journal=Cancer Research\|date=November 1968\|volume=28\|issue=11\|pages=2262–2267\|pmid=4881504}}</ref>		'''Cycasin''' is a [[carcinogenic]] and [[neurotoxic]] [[glucoside]] found in [[cycad]]s such as ''[[Cycas revoluta]]'' and ''[[Zamia pumila]]''. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and [[hepatotoxicity]]. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into [[formaldehyde]] and [[diazomethane]].<ref name=Laq>{{cite journal\|last1=Laqueur\|first1=G. L.\|last2=Spatz\|first2=M.\|title=Toxicology of Cycasin\|journal=Cancer Research\|date=November 1968\|volume=28\|issue=11\|pages=2262–2267\|pmid=4881504}}</ref>

	It induces [[hepatotoxicity]] and [[Zamia staggers]], a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.<ref name=Zam />		It induces [[hepatotoxicity]] and [[Zamia staggers]], a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.<ref name=Zam />
Line 50:		Line 50:

	===Presence in sago===		===Presence in sago===
	In order to produce [[sago]], cycasin and other cycad toxins must be removed from the flesh of the plants. The flesh, seeds, and roots of the cycad are first dried and ~~gound~~ into a fine powder, before being submerged in boiling water. The water is then allowed to drain, leaching out the toxic material while leaving the starch behind. The extracted starch is then alternately dried and pounded until a fine powder is obtained. This repeated pounding and leaching process insures that there is as little cycasin as possible left behind.<ref>{{cite journal\|last1=Whiting\|first1=Marjorie Grant\|title=Toxicity of cycads\|journal=Economic Botany\|date=October 1963\|volume=17\|issue=4\|pages=270–302\|doi=10.1007/BF02860136\|s2cid=31799259}}</ref>		In order to produce [[sago]], cycasin and other cycad toxins must be removed from the flesh of the plants. The flesh, seeds, and roots of the cycad are first dried and ground into a fine powder, before being submerged in boiling water. The water is then allowed to drain, leaching out the toxic material while leaving the starch behind. The extracted starch is then alternately dried and pounded until a fine powder is obtained. This repeated pounding and leaching process insures that there is as little cycasin as possible left behind.<ref>{{cite journal\|last1=Whiting\|first1=Marjorie Grant\|title=Toxicity of cycads\|journal=Economic Botany\|date=October 1963\|volume=17\|issue=4\|pages=270–302\|doi=10.1007/BF02860136\|s2cid=31799259}}</ref>

	==Structure==		==Structure==

Citation bot: Alter: title. Add: doi-access, s2cid, jstor, pmid, issue, title. Changed bare reference to CS1/2. | Use this bot. Report bugs. | Suggested by Headbomb | Linked from Wikipedia:WikiProject_Academic_Journals/Journals_cited_by_Wikipedia/Sandbox | #UCB_webform_linked 874/1015

2021-08-26T08:42:03Z

Alter: title. Add: doi-access, s2cid, jstor, pmid, issue, title. Changed bare reference to CS1/2. | Use this bot. Report bugs. | Suggested by Headbomb | Linked from Wikipedia:WikiProject_Academic_Journals/Journals_cited_by_Wikipedia/Sandbox | #UCB_webform_linked 874/1015

← Previous revision		Revision as of 08:42, 26 August 2021
Line 29:		Line 29:
	\| MeltingPt =		\| MeltingPt =
	\| BoilingPt =		\| BoilingPt =
	\| Solubility = 56.6 g/L<ref>https://foodb.ca/compounds/FDB018287</ref>		\| Solubility = 56.6 g/L<ref>{{Cite web\|url=https://foodb.ca/compounds/FDB018287\|title=Showing Compound Cycasin (FDB018287) - FooDB}}</ref>
	}}		}}
	\|Section3={{Chembox Hazards		\|Section3={{Chembox Hazards
Line 37:		Line 37:
	}}		}}
	}}		}}
	'''Cycasin''' is a [[carcinogenic]] and [[neurotoxic]] [[glucoside]] found in [[cycad]]s such as ''[[Cycas revoluta]]'' and ''[[Zamia pumila]]''. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and [[hepatotoxicity]]. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into [[formaldehyde]] and [[diazomethane]]. <ref name=Laq>{{cite journal\|last1=Laqueur\|first1=G. L.\|last2=Spatz\|first2=M.\|title=Toxicology of Cycasin\|journal=Cancer Research\|date=November 1968\|volume=28\|pages=2262–2267}}</ref>		'''Cycasin''' is a [[carcinogenic]] and [[neurotoxic]] [[glucoside]] found in [[cycad]]s such as ''[[Cycas revoluta]]'' and ''[[Zamia pumila]]''. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and [[hepatotoxicity]]. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into [[formaldehyde]] and [[diazomethane]]. <ref name=Laq>{{cite journal\|last1=Laqueur\|first1=G. L.\|last2=Spatz\|first2=M.\|title=Toxicology of Cycasin\|journal=Cancer Research\|date=November 1968\|volume=28\|issue=11\|pages=2262–2267\|pmid=4881504}}</ref>

	It induces [[hepatotoxicity]] and [[Zamia staggers]], a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.<ref name=Zam />		It induces [[hepatotoxicity]] and [[Zamia staggers]], a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.<ref name=Zam />

	==Sources==		==Sources==
	Cycasin is found in all known [[cycad]] genera and is distributed throughout the body of the plant, but with the highest concentration in the seeds. It is one of several toxins found in cycad plants, along with the neurotoxic amino acid [[BMAA]]. The origin and biological role of these toxins is unknown, as there does not appear to be a statistically significant correlation between the concentration of toxic material and the types of herbivory observed in animals consuming the plants.<ref>{{cite journal\|last1=Moretti\|first1=A.\|last2=Sabato\|first2=S.\|last3=Gigliano\|first3=G.Siniscalco\|title=Taxonomic significance of methylazoxymethanol glycosides in the cycads\|journal=Phytochemistry\|date=January 1983\|volume=22\|issue=1\|pages=115–117\|doi=10.1016/S0031-9422(00)80069-2}}</ref><ref>{{cite journal\|last1=Castillo-Guevara\|first1=Citlalli\|last2=Rico-Gray\|first2=Victor\|title=The Role of Macrozamin and Cycasin in Cycads (Cycadales) as Antiherbivore Defenses\|journal=Journal of the Torrey Botanical Society\|date=July 2003\|volume=130\|issue=3\|pages=206\|doi=10.2307/3557555}}</ref>		Cycasin is found in all known [[cycad]] genera and is distributed throughout the body of the plant, but with the highest concentration in the seeds. It is one of several toxins found in cycad plants, along with the neurotoxic amino acid [[BMAA]]. The origin and biological role of these toxins is unknown, as there does not appear to be a statistically significant correlation between the concentration of toxic material and the types of herbivory observed in animals consuming the plants.<ref>{{cite journal\|last1=Moretti\|first1=A.\|last2=Sabato\|first2=S.\|last3=Gigliano\|first3=G.Siniscalco\|title=Taxonomic significance of methylazoxymethanol glycosides in the cycads\|journal=Phytochemistry\|date=January 1983\|volume=22\|issue=1\|pages=115–117\|doi=10.1016/S0031-9422(00)80069-2}}</ref><ref>{{cite journal\|last1=Castillo-Guevara\|first1=Citlalli\|last2=Rico-Gray\|first2=Victor\|title=The Role of Macrozamin and Cycasin in Cycads (Cycadales) as Antiherbivore Defenses\|journal=Journal of the Torrey Botanical Society\|date=July 2003\|volume=130\|issue=3\|pages=206\|doi=10.2307/3557555\|jstor=3557555}}</ref>

	The enzyme [[methyl-ONN-azoxymethanol beta-D-glucosyltransferase]] uses the two substrates [[UDP-glucose]] and [[methyl-ONN-azoxymethanol]] to produce [[Uridine diphosphate\|UDP]] and cycasin.<ref>{{cite journal \|vauthors=Tadera K, Yagi F, Arima M, Kobayashi A \| year = 1985 \| title = Formation of cycasin from methylazoxymethanol by UDP-glucosyltransferase from leaves of Japanese cycad \| journal = Agric. Biol. Chem. \| volume = 49 \| pages = 2827–2828 \| doi = 10.1271/bbb1961.49.2827 \| issue = 9 \| doi-access = free }}</ref>		The enzyme [[methyl-ONN-azoxymethanol beta-D-glucosyltransferase]] uses the two substrates [[UDP-glucose]] and [[methyl-ONN-azoxymethanol]] to produce [[Uridine diphosphate\|UDP]] and cycasin.<ref>{{cite journal \|vauthors=Tadera K, Yagi F, Arima M, Kobayashi A \| year = 1985 \| title = Formation of cycasin from methylazoxymethanol by UDP-glucosyltransferase from leaves of Japanese cycad \| journal = Agric. Biol. Chem. \| volume = 49 \| pages = 2827–2828 \| doi = 10.1271/bbb1961.49.2827 \| issue = 9 \| doi-access = free }}</ref>
Line 50:		Line 50:

	===Presence in sago===		===Presence in sago===
	In order to produce [[sago]], cycasin and other cycad toxins must be removed from the flesh of the plants. The flesh, seeds, and roots of the cycad are first dried and gound into a fine powder, before being submerged in boiling water. The water is then allowed to drain, leaching out the toxic material while leaving the starch behind. The extracted starch is then alternately dried and pounded until a fine powder is obtained. This repeated pounding and leaching process insures that there is as little cycasin as possible left behind.<ref>{{cite journal\|last1=Whiting\|first1=Marjorie Grant\|title=Toxicity of cycads\|journal=Economic Botany\|date=October 1963\|volume=17\|issue=4\|pages=270–302\|doi=10.1007/BF02860136}}</ref>		In order to produce [[sago]], cycasin and other cycad toxins must be removed from the flesh of the plants. The flesh, seeds, and roots of the cycad are first dried and gound into a fine powder, before being submerged in boiling water. The water is then allowed to drain, leaching out the toxic material while leaving the starch behind. The extracted starch is then alternately dried and pounded until a fine powder is obtained. This repeated pounding and leaching process insures that there is as little cycasin as possible left behind.<ref>{{cite journal\|last1=Whiting\|first1=Marjorie Grant\|title=Toxicity of cycads\|journal=Economic Botany\|date=October 1963\|volume=17\|issue=4\|pages=270–302\|doi=10.1007/BF02860136\|s2cid=31799259}}</ref>

	==Structure==		==Structure==
Line 58:		Line 58:

	==Toxicity==		==Toxicity==
	Cycasin has an oral [[LD50]] of 500 mg/kg.<ref>{{cite book\|last1=Sax\|first1=N Irving\|last2=Feiner\|first2=Benjamin\|title=Dangerous properties of industrial materials\|date=1984\|publisher=Van Nostrand Reinhold\|location=New York\|isbn=0442283040\|page=828\|edition=6th}}</ref> Exposure to cycasin by injection does not cause any permanent ill effects.<ref>{{cite journal\|last1=Whiting\|first1=Marjorie Grant\|title=Toxicity of Cycads\|journal=Economic Botany\|date=1 January 1963\|volume=17\|issue=4\|pages=270–302\|jstor=4252455\|doi=10.1007/bf02860136}}</ref> As a consequence, consumption is not immediately lethal, but will cause a host of liver and neurological problems, as well as causing cancer with long-term exposure. The mechanism of cycasin's toxicity relies on [[β-glucosidase]] enzymes found in the gut. Treatment with β-glucosidase causes cycasin to release [[methylazoxymethanol]] (MAM), which spontaneously decomposes to form [[formaldehyde]] and [[Diazonium compound\|methyl-diazonium]]. The amount of formaldehyde released is too small to induce toxicity, but methyl-diazonium is a potent [[Methylation\|methylating]] agent. The presence of this molecule methylates DNA, causing long-term damage and potentially giving rise to cancers.<ref name=Laq />		Cycasin has an oral [[LD50]] of 500 mg/kg.<ref>{{cite book\|last1=Sax\|first1=N Irving\|last2=Feiner\|first2=Benjamin\|title=Dangerous properties of industrial materials\|date=1984\|publisher=Van Nostrand Reinhold\|location=New York\|isbn=0442283040\|page=828\|edition=6th}}</ref> Exposure to cycasin by injection does not cause any permanent ill effects.<ref>{{cite journal\|last1=Whiting\|first1=Marjorie Grant\|title=Toxicity of Cycads\|journal=Economic Botany\|date=1 January 1963\|volume=17\|issue=4\|pages=270–302\|jstor=4252455\|doi=10.1007/bf02860136\|s2cid=31799259}}</ref> As a consequence, consumption is not immediately lethal, but will cause a host of liver and neurological problems, as well as causing cancer with long-term exposure. The mechanism of cycasin's toxicity relies on [[β-glucosidase]] enzymes found in the gut. Treatment with β-glucosidase causes cycasin to release [[methylazoxymethanol]] (MAM), which spontaneously decomposes to form [[formaldehyde]] and [[Diazonium compound\|methyl-diazonium]]. The amount of formaldehyde released is too small to induce toxicity, but methyl-diazonium is a potent [[Methylation\|methylating]] agent. The presence of this molecule methylates DNA, causing long-term damage and potentially giving rise to cancers.<ref name=Laq />
	[[File:Methylazoxymethanol.svg\|thumb\|[[Methylazoxymethanol]] (MAM)]]		[[File:Methylazoxymethanol.svg\|thumb\|[[Methylazoxymethanol]] (MAM)]]

Line 66:		Line 66:

	===Zamia staggers===		===Zamia staggers===
	Livestock that consume raw leaves, nuts, and flour of cycads develop a neurologic syndrome known as [[zamia staggers]], named for the cycad genus ''[[Zamia]]'' native to Central and South America. It is clinically characterized by weight loss followed by lateral swaying of the hind quarters, with weakness, [[ataxia]], and proprioceptive defects in the rear limbs, and results in [[demyelination]] and [[axonal]] degeneration in the brain, spinal cord, and [[dorsal root ganglia]].<ref name=Zam>{{cite journal\|last1=Reams\|first1=Rachel Y.\|last2=Janovitz\|first2=Evan B.\|last3=Robinson\|first3=Farrel R.\|last4=Sullivan\|first4=John M.\|last5=Casanova\|first5=Carlos Rivera\|last6=Más\|first6=Edwin\|title=Cycad Toxicosis in a Group of Dairy Heifers in Puerto Rico\|journal=Journal of Veterinary Diagnostic Investigation\|date=July 1993\|volume=5\|issue=3\|pages=488–494\|doi=10.1177/104063879300500337\|doi-access=free}}</ref>		Livestock that consume raw leaves, nuts, and flour of cycads develop a neurologic syndrome known as [[zamia staggers]], named for the cycad genus ''[[Zamia]]'' native to Central and South America. It is clinically characterized by weight loss followed by lateral swaying of the hind quarters, with weakness, [[ataxia]], and proprioceptive defects in the rear limbs, and results in [[demyelination]] and [[axonal]] degeneration in the brain, spinal cord, and [[dorsal root ganglia]].<ref name=Zam>{{cite journal\|last1=Reams\|first1=Rachel Y.\|last2=Janovitz\|first2=Evan B.\|last3=Robinson\|first3=Farrel R.\|last4=Sullivan\|first4=John M.\|last5=Casanova\|first5=Carlos Rivera\|last6=Más\|first6=Edwin\|title=Cycad Toxicosis in a Group of Dairy Heifers in Puerto Rico\|journal=Journal of Veterinary Diagnostic Investigation\|date=July 1993\|volume=5\|issue=3\|pages=488–494\|doi=10.1177/104063879300500337\|pmid=8373871\|doi-access=free}}</ref>

	===Suspected association with Lytico-bodig disease===		===Suspected association with Lytico-bodig disease===
	The [[Lytico-bodig disease]], also known as lateral sclerosis-parkinsonism-dementia, is a [[neurodegenerative]] disease of unknown origin that occurs exclusively in the [[Chamorro people\|Chamorro]] people of the island of [[Guam]] that has characteristics of both [[amyotrophic lateral sclerosis]] (ALS) and [[parkinsonism]]. It is characterized by muscle atrophy, maxillofacial paralysis, inability to speak or swallow, and dementia. The disease is fatal in all cases, with the diaphragm and respiratory accessory muscles becoming paralyzed in the later stages of the disease.<ref name=Bradley>{{cite journal\|last1=Bradley\|first1=Walter G.\|last2=Mash\|first2=Deborah C.\|title=Beyond Guam: The cyanobacteria/BMAA hypothesis of the cause of ALS and other neurodegenerative diseases\|journal=Amyotrophic Lateral Sclerosis\|date=25 November 2009\|volume=10\|issue=sup2\|pages=7–20\|doi=10.3109/17482960903286009\|pmid=19929726}}</ref>		The [[Lytico-bodig disease]], also known as lateral sclerosis-parkinsonism-dementia, is a [[neurodegenerative]] disease of unknown origin that occurs exclusively in the [[Chamorro people\|Chamorro]] people of the island of [[Guam]] that has characteristics of both [[amyotrophic lateral sclerosis]] (ALS) and [[parkinsonism]]. It is characterized by muscle atrophy, maxillofacial paralysis, inability to speak or swallow, and dementia. The disease is fatal in all cases, with the diaphragm and respiratory accessory muscles becoming paralyzed in the later stages of the disease.<ref name=Bradley>{{cite journal\|last1=Bradley\|first1=Walter G.\|last2=Mash\|first2=Deborah C.\|title=Beyond Guam: The cyanobacteria/BMAA hypothesis of the cause of ALS and other neurodegenerative diseases\|journal=Amyotrophic Lateral Sclerosis\|date=25 November 2009\|volume=10\|issue=sup2\|pages=7–20\|doi=10.3109/17482960903286009\|pmid=19929726\|s2cid=41622254}}</ref>

	Observation of the diets of the native Chamorro people led to the creation of the so-called "Cycad hypothesis." Starches prepared from the seeds of a native cycad species, ''[[Cycas micronesica]]'', are used to create the [[sago]]-like flour ''fadang'', which forms a major part of the diet of the Chamorro people. As the seeds contain the highest amount of the toxin found in the plant, it was proposed that a dietary explanation relating to the consumption of poorly processed fadang was poisoning the natives. After failing to reproduce the symptoms of the disease in animal models, the hypothesis was rejected.<ref name=Bradley /> Though the initial cycad hypothesis was rejected, a revised form of the hypothesis was proposed by [[Paul Alan Cox]] and [[Oliver Sacks]] after observing other elements of the Chamorro diet, specifically [[flying foxes]]. The bats accumulate [[BMAA]] in their fat by consuming cycad seeds, resulting a in a high concentration of the neurotoxin.<ref name = "Cox1">{{cite journal \|vauthors=Cox PA, Banack SA, Murch SJ \|year = 2003 \|title = Biomagnification of cyanobacterial neurotoxins and neurodegenerative disease among the Chamorro people of Guam \|journal = PNAS \|volume = 100 \|issue = 23 \|pages = 13380–13383 \|doi=10.1073/pnas.2235808100\| bibcode = 2003PNAS..10013380C\|pmc = 263822 \|pmid=14612559}}</ref>		Observation of the diets of the native Chamorro people led to the creation of the so-called "Cycad hypothesis." Starches prepared from the seeds of a native cycad species, ''[[Cycas micronesica]]'', are used to create the [[sago]]-like flour ''fadang'', which forms a major part of the diet of the Chamorro people. As the seeds contain the highest amount of the toxin found in the plant, it was proposed that a dietary explanation relating to the consumption of poorly processed fadang was poisoning the natives. After failing to reproduce the symptoms of the disease in animal models, the hypothesis was rejected.<ref name=Bradley /> Though the initial cycad hypothesis was rejected, a revised form of the hypothesis was proposed by [[Paul Alan Cox]] and [[Oliver Sacks]] after observing other elements of the Chamorro diet, specifically [[flying foxes]]. The bats accumulate [[BMAA]] in their fat by consuming cycad seeds, resulting a in a high concentration of the neurotoxin.<ref name = "Cox1">{{cite journal \|vauthors=Cox PA, Banack SA, Murch SJ \|year = 2003 \|title = Biomagnification of cyanobacterial neurotoxins and neurodegenerative disease among the Chamorro people of Guam \|journal = PNAS \|volume = 100 \|issue = 23 \|pages = 13380–13383 \|doi=10.1073/pnas.2235808100\| bibcode = 2003PNAS..10013380C\|pmc = 263822 \|pmid=14612559\|doi-access = free }}</ref>
	[[File:Cycas micronesica photo courtesy A. Gawel (15391498081).jpg\|thumb\|''[[Cycas micronesica]]'', one of the cycad species consumed by the Chamorro]]		[[File:Cycas micronesica photo courtesy A. Gawel (15391498081).jpg\|thumb\|''[[Cycas micronesica]]'', one of the cycad species consumed by the Chamorro]]

2600:4040:10FF:8800:4127:87E4:9EAD:9BF1 at 04:41, 18 May 2021

2021-05-18T04:41:28Z

← Previous revision		Revision as of 04:41, 18 May 2021
Line 37:		Line 37:
	}}		}}
	}}		}}
	'''Cycasin''' is a [[carcinogenic]] and [[neurotoxic]] [[glucoside]] found in [[cycad]]s such as ''[[Cycas revoluta]]'' and ''[[Zamia pumila]]''. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and [[~~hepatoxicity~~]]. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into [[formaldehyde]] and [[diazomethane]]. <ref name=Laq>{{cite journal\|last1=Laqueur\|first1=G. L.\|last2=Spatz\|first2=M.\|title=Toxicology of Cycasin\|journal=Cancer Research\|date=November 1968\|volume=28\|pages=2262–2267}}</ref>		'''Cycasin''' is a [[carcinogenic]] and [[neurotoxic]] [[glucoside]] found in [[cycad]]s such as ''[[Cycas revoluta]]'' and ''[[Zamia pumila]]''. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and [[hepatotoxicity]]. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into [[formaldehyde]] and [[diazomethane]]. <ref name=Laq>{{cite journal\|last1=Laqueur\|first1=G. L.\|last2=Spatz\|first2=M.\|title=Toxicology of Cycasin\|journal=Cancer Research\|date=November 1968\|volume=28\|pages=2262–2267}}</ref>

	It induces [[hepatotoxicity]] and [[Zamia staggers]], a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.<ref name=Zam />		It induces [[hepatotoxicity]] and [[Zamia staggers]], a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.<ref name=Zam />

108.178.91.202: added link for diazomethane

2021-03-06T22:15:44Z

added link for diazomethane

← Previous revision		Revision as of 22:15, 6 March 2021
Line 37:		Line 37:
	}}		}}
	}}		}}
	'''Cycasin''' is a [[carcinogenic]] and [[neurotoxic]] [[glucoside]] found in [[cycad]]s such as ''[[Cycas revoluta]]'' and ''[[Zamia pumila]]''. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and [[hepatoxicity]]. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into [[formaldehyde]] and diazomethane. <ref name=Laq>{{cite journal\|last1=Laqueur\|first1=G. L.\|last2=Spatz\|first2=M.\|title=Toxicology of Cycasin\|journal=Cancer Research\|date=November 1968\|volume=28\|pages=2262–2267}}</ref>		'''Cycasin''' is a [[carcinogenic]] and [[neurotoxic]] [[glucoside]] found in [[cycad]]s such as ''[[Cycas revoluta]]'' and ''[[Zamia pumila]]''. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and [[hepatoxicity]]. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into [[formaldehyde]] and [[diazomethane]]. <ref name=Laq>{{cite journal\|last1=Laqueur\|first1=G. L.\|last2=Spatz\|first2=M.\|title=Toxicology of Cycasin\|journal=Cancer Research\|date=November 1968\|volume=28\|pages=2262–2267}}</ref>

	It induces [[hepatotoxicity]] and [[Zamia staggers]], a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.<ref name=Zam />		It induces [[hepatotoxicity]] and [[Zamia staggers]], a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.<ref name=Zam />

← Previous revision		Revision as of 19:00, 4 November 2023
Line 71:		Line 71:
	The [[Lytico-bodig disease]], also known as lateral sclerosis-parkinsonism-dementia, is a [[neurodegenerative]] disease of unknown origin that occurs exclusively in the [[Chamorro people\|Chamorro]] people of the island of [[Guam]] that has characteristics of both [[amyotrophic lateral sclerosis]] (ALS) and [[parkinsonism]]. It is characterized by muscle atrophy, maxillofacial paralysis, inability to speak or swallow, and dementia. The disease is fatal in all cases, with the diaphragm and respiratory accessory muscles becoming paralyzed in the later stages of the disease.<ref name=Bradley>{{cite journal\|last1=Bradley\|first1=Walter G.\|last2=Mash\|first2=Deborah C.\|title=Beyond Guam: The cyanobacteria/BMAA hypothesis of the cause of ALS and other neurodegenerative diseases\|journal=Amyotrophic Lateral Sclerosis\|date=25 November 2009\|volume=10\|issue=sup2\|pages=7–20\|doi=10.3109/17482960903286009\|pmid=19929726\|s2cid=41622254}}</ref>		The [[Lytico-bodig disease]], also known as lateral sclerosis-parkinsonism-dementia, is a [[neurodegenerative]] disease of unknown origin that occurs exclusively in the [[Chamorro people\|Chamorro]] people of the island of [[Guam]] that has characteristics of both [[amyotrophic lateral sclerosis]] (ALS) and [[parkinsonism]]. It is characterized by muscle atrophy, maxillofacial paralysis, inability to speak or swallow, and dementia. The disease is fatal in all cases, with the diaphragm and respiratory accessory muscles becoming paralyzed in the later stages of the disease.<ref name=Bradley>{{cite journal\|last1=Bradley\|first1=Walter G.\|last2=Mash\|first2=Deborah C.\|title=Beyond Guam: The cyanobacteria/BMAA hypothesis of the cause of ALS and other neurodegenerative diseases\|journal=Amyotrophic Lateral Sclerosis\|date=25 November 2009\|volume=10\|issue=sup2\|pages=7–20\|doi=10.3109/17482960903286009\|pmid=19929726\|s2cid=41622254}}</ref>

	Observation of the diets of the native Chamorro people led to the creation of the so-called "Cycad hypothesis." Starches prepared from the seeds of a native cycad species, ''[[Cycas micronesica]]'', are used to create the [[sago]]-like flour ''fadang'', which forms a major part of the diet of the Chamorro people. As the seeds contain the highest amount of the toxin found in the plant, it was proposed that a dietary explanation relating to the consumption of poorly processed fadang was poisoning the natives. After failing to reproduce the symptoms of the disease in animal models, the hypothesis was rejected.<ref name=Bradley /> Though the initial cycad hypothesis was rejected, a revised form of the hypothesis was proposed by [[Paul Alan Cox]] and [[Oliver Sacks]] after observing other elements of the Chamorro diet, specifically [[flying foxes]]. The bats accumulate [[BMAA]] in their fat by consuming cycad seeds, resulting a in a high concentration of the neurotoxin.<ref name = "Cox1">{{cite journal \|vauthors=Cox PA, Banack SA, Murch SJ \|year = 2003 \|title = Biomagnification of cyanobacterial neurotoxins and neurodegenerative disease among the Chamorro people of Guam \|journal = PNAS \|volume = 100 \|issue = 23 \|pages = 13380–13383 \|doi=10.1073/pnas.2235808100\| bibcode = 2003PNAS..10013380C\|pmc = 263822 \|pmid=14612559\|doi-access = free }}</ref>		Observation of the diets of the native Chamorro people led to the creation of the so-called "Cycad hypothesis." Starches prepared from the seeds of a native cycad species, ''[[Cycas micronesica]]'', are used to create the [[sago]]-like flour ''fadang'', which forms a major part of the diet of the Chamorro people. As the seeds contain the highest amount of the toxin found in the plant, it was proposed that a dietary explanation relating to the consumption of poorly processed fadang was poisoning the natives. After failing to reproduce the symptoms of the disease in animal models, the hypothesis was rejected.<ref name=Bradley /> Though the initial cycad hypothesis was rejected, a revised form of the hypothesis was proposed by [[Paul Alan Cox]] and [[Oliver Sacks]] after observing other elements of the Chamorro diet, specifically [[flying foxes]]. The bats accumulate [[BMAA]] in their fat by consuming cycad seeds, resulting a in a high concentration of the [[neurotoxin]].<ref name = "Cox1">{{cite journal \|vauthors=Cox PA, Banack SA, Murch SJ \|year = 2003 \|title = Biomagnification of cyanobacterial neurotoxins and neurodegenerative disease among the Chamorro people of Guam \|journal = PNAS \|volume = 100 \|issue = 23 \|pages = 13380–13383 \|doi=10.1073/pnas.2235808100\| bibcode = 2003PNAS..10013380C\|pmc = 263822 \|pmid=14612559\|doi-access = free }}</ref>
	[[File:Cycas micronesica photo courtesy A. Gawel (15391498081).jpg\|thumb\|''[[Cycas micronesica]]'', one of the cycad species consumed by the Chamorro]]		[[File:Cycas micronesica photo courtesy A. Gawel (15391498081).jpg\|thumb\|''[[Cycas micronesica]]'', one of the cycad species consumed by the Chamorro]]