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{{Short description|Chemical compound}}
{{Drugbox
{{Infobox drug
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 477318559
| verifiedrevid = 477318559
| IUPAC_name = '''Aloin&nbsp;A:'''&nbsp;(10S)-10-Glucopyranosyl-1,8-dihydroxy-<br/> 3-(hydroxymethyl)-9(10H)-anthracenone
| IUPAC_name = '''Aloin&nbsp;A:'''&nbsp;(10''S'')-10-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10''H'')-anthracenone
| image = Aloin structure.png
| image = Aloin structure.png
| image2 = Aloin.jpg
| image2 = Aloin.jpg
Line 42: Line 43:
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W41H6S09F4
| UNII = W41H6S09F4
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10305


<!--Chemical data-->
<!--Chemical data-->
| chemical_formula =
| chemical_formula =
| C=21 | H=22 | O=9
| C=21 | H=22 | O=9
| molecular_weight = 418.39
| smiles = c1cc2c(c(c1)O)C(=O)c3c(cc(cc3O)CO)[C@H]2[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
| smiles = c1cc2c(c(c1)O)C(=O)c3c(cc(cc3O)CO)[C@H]2[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
Line 57: Line 59:
}}
}}


'''Aloin''', also known as '''barbaloin''',<ref>Reynolds, Aloes - The genus ''Aloe'', 2004</ref> is a bitter, yellow-brown colored compound noted in the exudate of at least 68 ''[[Aloe]]'' species at levels from 0.1 to 6.6% of leaf dry weight (making between 3% and 35% of the total exudate) (Groom & Reynolds, 1987), and in another 17 species at indeterminate levels [Reynolds, 1995b]. It is used as a stimulant-[[laxative]], treating [[constipation]] by inducing [[bowel]] movements.<ref>The Merck Index, 12th Edition. 314</ref> The compound is present in what is commonly referred to as the aloe [[latex]] that exudes from cells adjacent to the vascular bundles, found under the rind of the leaf and in between it and the gel. When dried, it has been used as a [[bittering agent]] in commerce (alcoholic beverages) [21 CFR 172.510. Scientific names given include ''Aloe perryi'', ''A. barbadensis'' (= ''A. vera''), ''A. ferox'', and hybrids of ''A. ferox'' with ''A. africana'' and ''A. spicata''.]. Aloe is listed in federal regulations as a natural substance that may be "safely used in food" when used "in the minimum quantity required to produce their intended physical or technical effect and in accordance with all the principles of good manufacturing practice." This food application is generally limited to use in quite small quantities as a flavoring in alcoholic beverages and may usually be identified only as a "natural flavor."
'''Aloin''', also known as '''barbaloin''',<ref>{{cite book | vauthors = Reynolds T | chapter = Analytical Methodology: the Exudate | chapter-url = https://books.google.com/books?id=rn0QjO7FYEYC&pg=128 | veditors = Reynolds T | title = Aloes: the genus Aloe | publisher = CRC Press | date = January 2004 | isbn = 978-0-203-47634-5 | page = 128 }}</ref> is a bitter, yellow-brown colored compound noted in the exudate of at least 68 ''[[Aloe]]'' species at levels from 0.1 to 6.6% of leaf dry weight (making between 3% and 35% of the total exudate),<ref name="Groom_1987">{{cite journal | vauthors = Groom QJ, Reynolds T | title = Barbaloin in aloe species | journal = Planta Medica | volume = 53 | issue = 4 | pages = 345–348 | date = August 1987 | pmid = 17269040 | doi = 10.1055/s-2006-962735 | s2cid = 36296239 }}</ref> and in another 17 species at indeterminate levels [Reynolds, 1995b]. It is used as a stimulant-[[laxative]], treating [[constipation]] by inducing [[bowel]] movements.<ref>{{cite book | title = The Merck Index | edition = 12th | page = 314 }}</ref> The compound is present in what is commonly referred to as the aloe [[latex]] that exudes from cells adjacent to the vascular bundles, found under the rind of the leaf and in between it and the gel. When dried, it has been used as a [[bittering agent]] in commerce (alcoholic beverages) [21 CFR 172.510. Scientific names given include ''Aloe perryi'', ''A. barbadensis'' (= ''A. vera''), ''A. ferox'', and hybrids of ''A. ferox'' with ''A. africana'' and ''A. spicata''.]. Aloe is listed in federal regulations as a natural substance that may be "safely used in food" when used "in the minimum quantity required to produce their intended physical or technical effect and in accordance with all the principles of good manufacturing practice." This food application is generally limited to use in quite small quantities as a flavoring in alcoholic beverages and may usually be identified only as a "natural flavor."


In May 2002, the [[Food and Drug Administration (United States)|U.S. Food and Drug Administration]] (FDA) issued a ruling that aloe laxatives are no longer [[generally recognized as safe]] (GRAS) and effective, meaning that aloin-containing products are no longer available in [[over-the-counter drug]] products in the United States, because they may be [[carcinogen]]ic and more data is needed to establish otherwise.<ref name="fda.gov">[http://www.fda.gov/ohrms/dockets/98fr/050902a.htm FDA docket] Sec. 310.545 (a)(12)(iv)(c)</ref> Aloe vera leaf latex is a concentrate of an herb or other botanical, and so meets the statutory description of an ingredient that may be used in dietary supplements.
In May 2002, the [[Food and Drug Administration (United States)|U.S. Food and Drug Administration]] (FDA) issued a ruling that aloe laxatives are no longer [[generally recognized as safe]] (GRAS) and effective, meaning that aloin-containing products are no longer available in [[over-the-counter drug]] products in the United States, because they may be [[carcinogen]]ic and more data is needed to establish otherwise.<ref name="fda.gov">{{cite web | url = https://www.fda.gov/ohrms/dockets/98fr/050902a.htm | title = FDA docket Sec. 310.545 (a)(12)(iv)(c) | publisher = U.S. Food and Drug Administration }}</ref> Aloe vera leaf latex is a concentrate of an herb or other botanical, and so meets the statutory description of an ingredient that may be used in dietary supplements.


== Structure and preparation ==
== Structure and preparation ==
Aloin extracted from natural sources is a mixture of two [[diastereomer]]s, termed aloin A (also called barbaloin) and aloin B (or isobarbaloin), which have similar chemical properties. Aloin is an anthraquinone [[glycosyl]], meaning that its anthraquinone skeleton has been modified by the addition of a sugar molecule. [[Anthraquinones]] are a common family of naturally occurring yellow, orange, and red pigments of which many have cathartic properties, attributes shared by aloin. Aloin is related to [[aloe emodin]], which lacks a sugar group but shares aloin's biological properties.<ref>{{cite journal |last=Grün |first=M |author2=G. Franz |date=October 1981 |title=In vitro biosynthesis of the C-glycosidic bond in aloin |journal=Planta |volume=152 |issue=6 |pages=562–564 |doi=10.1007/BF00380828 |pmid=24301161}}</ref>
Aloin extracted from natural sources is a mixture of two [[diastereomer]]s, termed aloin A (also called barbaloin) and aloin B (or isobarbaloin), which have similar chemical properties. Aloin is an anthraquinone [[glycosyl]], meaning that its anthraquinone skeleton has been modified by the addition of a sugar molecule. [[Anthraquinones]] are a common family of naturally occurring yellow, orange, and red pigments of which many have cathartic properties, attributes shared by aloin. Aloin is related to [[aloe emodin]], which lacks a sugar group but shares aloin's biological properties.<ref>{{cite journal | vauthors = Grün M, Franz G | title = In vitro biosynthesis of the C-glycosidic bond in aloin | journal = Planta | volume = 152 | issue = 6 | pages = 562–564 | date = October 1981 | pmid = 24301161 | doi = 10.1007/BF00380828 | bibcode = 1981Plant.152..562G | s2cid = 6759708 }}</ref>


Aloin is usually prepared by extraction from aloe latex (the term "Cape aloe" also refers to the dried latex of the leaves of several species of the ''Aloe'' genus, especially ''A. ferox'' [Blumenthal, 1998]), the bitter yellow exudate that seeps out from just underneath the skin of aloe leaves. The latex is then dried and powdered to make the final product, often made into tablets or a beverage, though aloin does not have good stability in aqueous solutions. Products derived from the gel of the aloe plant do not contain appreciable amounts of aloin, and have not been proven effective for any disease or condition when taken orally.<ref name=AloeVeraNotes>{{cite web| url=http://www.quackwatch.com/01QuackeryRelatedTopics/DSH/aloe.html | title=Some notes on Aloe Vera | author=Lulinski, B. |author2=Cathy Kapica | accessdate=2007-11-12}}</ref>
Aloin is usually prepared by extraction from aloe latex (the term "Cape aloe" also refers to the dried latex of the leaves of several species of the genus ''Aloe'', especially ''A. ferox'' [Blumenthal, 1998]), the bitter yellow exudate that seeps out from just underneath the skin of aloe leaves. The latex is then dried and powdered to make the final product, often made into tablets or a beverage, though aloin does not have good stability in aqueous solutions. Products derived from the gel of the aloe plant do not contain appreciable amounts of aloin, and have not been proven effective for any disease or condition when taken orally.<ref name=AloeVeraNotes>{{cite web| url=http://www.quackwatch.com/01QuackeryRelatedTopics/DSH/aloe.html | title=Some notes on Aloe Vera | vauthors = Lulinski B, Kapica C | date=23 June 1998 | access-date=2007-11-12}}</ref>


==Effects==
==Effects==
Once ingested, aloin increases [[peristalsis|peristaltic contractions]] in the colon, which induces bowel movements.<ref name="Tenney1997">{{cite book|last=Tenney|first=Deanne|title=Aloe Vera|url=https://books.google.com/books?id=d58OliJ3HbgC&pg=PA12|accessdate=29 April 2012|date=February 1997|publisher=Woodland Publishing|isbn=978-1-885670-60-1|page=12}}</ref> Aloin also prevents the colon from re-absorbing water from the gastrointestinal tract, which leads to softer stools.<ref name=AloeVeraNotes /> This effect is caused by aloin's opening of chloride channels of the colonic membrane. In higher doses, these effects may lead to electrolyte imbalance, diarrhea, and abdominal pain, which are common side-effects of the drug.<ref name=AloeVeraNotes /> Because aloin can potentially cause uterine contractions, pregnant women should avoid ingesting aloe products containing aloin in more than trace amounts.<ref>{{cite journal |last=Teske |first=Sabine |date=July 2006 |title=Adding Product Crunch |journal=Asia Food Journal |pages=26–27 |accessdate= 2007-11-12| url=http://www.burdockgroup.com/downloads/Publications/JUL06_Asia%20Food%20Journal_Adding%20Product%20Crunch_ST.pdf|format=PDF}} {{Dead link|date=October 2010|bot=H3llBot}}</ref>
Once ingested, aloin increases [[peristalsis|peristaltic contractions]] in the colon, which induces bowel movements. Aloin also prevents the colon from re-absorbing water from the gastrointestinal tract, which leads to softer stools.<ref name=AloeVeraNotes /> This effect is caused by aloin's opening of chloride channels of the colonic membrane. In higher doses, these effects may lead to electrolyte imbalance, diarrhea, and abdominal pain, which are common side-effects of the drug.<ref name=AloeVeraNotes /> Because aloin can potentially cause uterine contractions, pregnant women should avoid ingesting aloe products containing aloin in more than trace amounts.<ref>{{cite journal | vauthors = Teske S |date=July 2006 |title=Adding Product Crunch |journal=Asia Food Journal |pages=26–27 |access-date= 2007-11-12| url=http://www.burdockgroup.com/downloads/Publications/JUL06_Asia%20Food%20Journal_Adding%20Product%20Crunch_ST.pdf}} {{Dead link|date=October 2010|bot=H3llBot}}</ref>


In a study on consumption of aloe in rats and [[tilapia]] (with no separation of gel from aloin), significant negative health effects were found, including normocytic normochromic [[anaemia]] (low red blood cell count, but normal cells), [[hypoproteinaemia]], and high [[Alanine transaminase|AST]] levels.<ref>Taiwo, V. O., et al.. "Consumption of Aqueous Extract of Raw Aloe Vera Leaves: Histopathological and Biochemical Studies in Rat and Tilapia". ''[[African Journal of Biomedical Research]]''. February 2005: 169-178.</ref> As many studies involving aloe gel (without aloin) have not observed these negative effects, it is possible that the negative effects could in large part be due to aloin.
In a study on consumption of aloe in rats and [[tilapia]] (with no separation of gel from aloin), significant negative health effects were found, including normocytic normochromic [[anaemia]] (low red blood cell count, but normal cells), [[hypoproteinaemia]], and high [[Alanine transaminase|AST]] levels.<ref>{{cite journal | vauthors = Taiwo VO, Olukunle OA, Ozor IC, Oyejobi AT | title = Consumption of aqueous extract of raw Aloe vera leaves: histopathological and biochemical studies in rat and tilapia. | journal = African Journal of Biomedical Research | date = February 2005 | volume = 8 | issue = 3 | pages = 169–78 | doi = 10.4314/ajbr.v8i3.35746 | doi-access = free }}</ref> As many studies involving aloe gel (without aloin) have not observed these negative effects, it is possible that the negative effects could in large part be due to aloin.


== Legal status ==
== Legal status ==
Plant-derived remedies containing aloin and other anthraquinones have been used as traditional medicines since antiquity,<ref>{{cite journal |last=Wamer |first=WG |author2= Vath, P|author3= Falvey, DE |date=January 2003 |title=In vitro studies on the photobiological properties of aloe emodin and aloin A |journal=Free Radic Biol Med. |volume=34 |issue=2 |pages=233–42 |pmid=12521605 |doi=10.1016/S0891-5849(02)01242-X}}</ref> but harsh side effects make aloin generally unsuitable for household or daily use. In 2002, the US FDA mandated that manufacturers reformulate or stop manufacturing over-the-counter products containing aloe because the agency did not receive necessary safety data.<ref name="fda.gov"/><ref>{{cite web |url=http://nccam.nih.gov/health/aloevera/ |title=Herbs at a glance: Aloe Vera (''text is public domain'') |accessdate=2008-06-25 |author=NCCAM |date=December 2006| archiveurl= https://web.archive.org/web/20080515132323/http://nccam.nih.gov/health/aloevera/| archivedate= 15 May 2008 <!--DASHBot-->| deadurl= no}}</ref> The substance is still allowed in dietary supplements [21 U.S.C. 321 (ff)(1)] and is allowed for use in foods (primarily alcoholic beverages).
Plant-derived remedies containing aloin and other anthraquinones have been used as traditional medicines since antiquity,<ref>{{cite journal | vauthors = Wamer WG, Vath P, Falvey DE | title = In vitro studies on the photobiological properties of aloe emodin and aloin A | journal = Free Radical Biology & Medicine | volume = 34 | issue = 2 | pages = 233–242 | date = January 2003 | pmid = 12521605 | doi = 10.1016/S0891-5849(02)01242-X }}</ref> but harsh side effects make aloin generally unsuitable for household or daily use. In 2002, the US FDA mandated that manufacturers reformulate or stop manufacturing over-the-counter products containing aloe because the agency did not receive necessary safety data.<ref name="fda.gov"/><ref>{{cite web |url=http://nccam.nih.gov/health/aloevera/ |title=Herbs at a glance: Aloe Vera |access-date=2008-06-25 | work = National Center for Complementary and Integrative Health (NCCIH) | publisher = U.S. National Institutes of Health |date=December 2006| archive-url= https://web.archive.org/web/20080515132323/http://nccam.nih.gov/health/aloevera/| archive-date= 15 May 2008 | url-status= live}}</ref> The substance is still allowed in dietary supplements [21 U.S.C. 321 (ff)(1)] and is allowed for use in foods (primarily alcoholic beverages).


== References ==
== References ==
Line 78: Line 80:


== External links ==
== External links ==
*[http://gis.wvdep.org/tri/cheminfo/msds161.txt Aloin [[MSDS]]]{{dead link|date=July 2017 |bot=InternetArchiveBot |fix-attempted=yes }}
*[http://gis.wvdep.org/tri/cheminfo/msds161.txt Aloin MSDS]{{dead link|date=July 2017 |bot=InternetArchiveBot |fix-attempted=yes }}

{{Authority control}}


[[Category:Anthraquinone glucosides]]
[[Category:Anthraquinone glucosides]]
[[Category:Bitter compounds]]
[[Category:Bitter compounds]]
[[Category:Plant toxins]]

Latest revision as of 09:31, 23 March 2024

Aloin
Clinical data
Routes of
administration		Oral
ATC code
  • none
Identifiers
  • Aloin A: (10S)-10-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.014.371 Edit this at Wikidata
Chemical and physical data
FormulaC21H22O9
Molar mass418.398 g·mol−1
3D model (JSmol)
Melting point148 °C (298 °F) (70–80 °C for monohydrate)
  • c1cc2c(c(c1)O)C(=O)c3c(cc(cc3O)CO)[C@H]2[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
  • InChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2/t13-,14+,17-,19+,20-,21+/m1/s1 ☒N
  • Key:AFHJQYHRLPMKHU-OSYMLPPYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Aloin, also known as barbaloin,[1] is a bitter, yellow-brown colored compound noted in the exudate of at least 68 Aloe species at levels from 0.1 to 6.6% of leaf dry weight (making between 3% and 35% of the total exudate),[2] and in another 17 species at indeterminate levels [Reynolds, 1995b]. It is used as a stimulant-laxative, treating constipation by inducing bowel movements.[3] The compound is present in what is commonly referred to as the aloe latex that exudes from cells adjacent to the vascular bundles, found under the rind of the leaf and in between it and the gel. When dried, it has been used as a bittering agent in commerce (alcoholic beverages) [21 CFR 172.510. Scientific names given include Aloe perryi, A. barbadensis (= A. vera), A. ferox, and hybrids of A. ferox with A. africana and A. spicata.]. Aloe is listed in federal regulations as a natural substance that may be "safely used in food" when used "in the minimum quantity required to produce their intended physical or technical effect and in accordance with all the principles of good manufacturing practice." This food application is generally limited to use in quite small quantities as a flavoring in alcoholic beverages and may usually be identified only as a "natural flavor."

In May 2002, the U.S. Food and Drug Administration (FDA) issued a ruling that aloe laxatives are no longer generally recognized as safe (GRAS) and effective, meaning that aloin-containing products are no longer available in over-the-counter drug products in the United States, because they may be carcinogenic and more data is needed to establish otherwise.[4] Aloe vera leaf latex is a concentrate of an herb or other botanical, and so meets the statutory description of an ingredient that may be used in dietary supplements.

Structure and preparation

[edit]

Aloin extracted from natural sources is a mixture of two diastereomers, termed aloin A (also called barbaloin) and aloin B (or isobarbaloin), which have similar chemical properties. Aloin is an anthraquinone glycosyl, meaning that its anthraquinone skeleton has been modified by the addition of a sugar molecule. Anthraquinones are a common family of naturally occurring yellow, orange, and red pigments of which many have cathartic properties, attributes shared by aloin. Aloin is related to aloe emodin, which lacks a sugar group but shares aloin's biological properties.[5]

Aloin is usually prepared by extraction from aloe latex (the term "Cape aloe" also refers to the dried latex of the leaves of several species of the genus Aloe, especially A. ferox [Blumenthal, 1998]), the bitter yellow exudate that seeps out from just underneath the skin of aloe leaves. The latex is then dried and powdered to make the final product, often made into tablets or a beverage, though aloin does not have good stability in aqueous solutions. Products derived from the gel of the aloe plant do not contain appreciable amounts of aloin, and have not been proven effective for any disease or condition when taken orally.[6]

Effects

[edit]

Once ingested, aloin increases peristaltic contractions in the colon, which induces bowel movements. Aloin also prevents the colon from re-absorbing water from the gastrointestinal tract, which leads to softer stools.[6] This effect is caused by aloin's opening of chloride channels of the colonic membrane. In higher doses, these effects may lead to electrolyte imbalance, diarrhea, and abdominal pain, which are common side-effects of the drug.[6] Because aloin can potentially cause uterine contractions, pregnant women should avoid ingesting aloe products containing aloin in more than trace amounts.[7]

In a study on consumption of aloe in rats and tilapia (with no separation of gel from aloin), significant negative health effects were found, including normocytic normochromic anaemia (low red blood cell count, but normal cells), hypoproteinaemia, and high AST levels.[8] As many studies involving aloe gel (without aloin) have not observed these negative effects, it is possible that the negative effects could in large part be due to aloin.

[edit]

Plant-derived remedies containing aloin and other anthraquinones have been used as traditional medicines since antiquity,[9] but harsh side effects make aloin generally unsuitable for household or daily use. In 2002, the US FDA mandated that manufacturers reformulate or stop manufacturing over-the-counter products containing aloe because the agency did not receive necessary safety data.[4][10] The substance is still allowed in dietary supplements [21 U.S.C. 321 (ff)(1)] and is allowed for use in foods (primarily alcoholic beverages).

References

[edit]
  1. ^ Reynolds T (January 2004). "Analytical Methodology: the Exudate". In Reynolds T (ed.). Aloes: the genus Aloe. CRC Press. p. 128. ISBN 978-0-203-47634-5.
  2. ^ Groom QJ, Reynolds T (August 1987). "Barbaloin in aloe species". Planta Medica. 53 (4): 345–348. doi:10.1055/s-2006-962735. PMID 17269040. S2CID 36296239.
  3. ^ The Merck Index (12th ed.). p. 314.
  4. ^ a b "FDA docket Sec. 310.545 (a)(12)(iv)(c)". U.S. Food and Drug Administration.
  5. ^ Grün M, Franz G (October 1981). "In vitro biosynthesis of the C-glycosidic bond in aloin". Planta. 152 (6): 562–564. Bibcode:1981Plant.152..562G. doi:10.1007/BF00380828. PMID 24301161. S2CID 6759708.
  6. ^ a b c Lulinski B, Kapica C (23 June 1998). "Some notes on Aloe Vera". Retrieved 2007-11-12.
  7. ^ Teske S (July 2006). "Adding Product Crunch" (PDF). Asia Food Journal: 26–27. Retrieved 2007-11-12. [dead link‍]
  8. ^ Taiwo VO, Olukunle OA, Ozor IC, Oyejobi AT (February 2005). "Consumption of aqueous extract of raw Aloe vera leaves: histopathological and biochemical studies in rat and tilapia". African Journal of Biomedical Research. 8 (3): 169–78. doi:10.4314/ajbr.v8i3.35746.
  9. ^ Wamer WG, Vath P, Falvey DE (January 2003). "In vitro studies on the photobiological properties of aloe emodin and aloin A". Free Radical Biology & Medicine. 34 (2): 233–242. doi:10.1016/S0891-5849(02)01242-X. PMID 12521605.
  10. ^ "Herbs at a glance: Aloe Vera". National Center for Complementary and Integrative Health (NCCIH). U.S. National Institutes of Health. December 2006. Archived from the original on 15 May 2008. Retrieved 2008-06-25.
[edit]
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