acemannan
{{Chembox
| ImageFile = Acemannan.JPG
| ImageSize = 250px
| ImageCaption = A representative 6-sugar fragment of acemannan
| IUPACName = (2S,3S,4R,5S,6S)-6-[(2R,3R,4R,5S,6R)-6-[(2R,3S,4R,5S,6R)-5-acetamido-6-[(2R,3R,4R,5S,6R)-4-acetyloxy-6-[(2R,3R,4R,5S,6R)-4-acetyloxy-6-[(2R,3R,4R,5S,6S)-4-acetyloxy-5-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-acetyloxy-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-acetyloxy-3-[(2R,3S,4R,5R,6R)-4-acetyloxy-5-[(2R,3S,4R,5R,6R)-4-acetyloxy-3-hydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxyoxane-2-carboxylate
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 110042-95-0
| ChemSpiderID = 65033
| EINECS = 600-942-8
| UNII = UZ29E6L2X8
| PubChem = 72041
| StdInChI=1S/C66H101NO49/c1-18(75)67-33-34(83)42(26(11-68)102-59(33)110-44-29(14-71)106-63(38(87)51(44)97-21(4)78)113-46-30(15-72)107-64(39(88)53(46)99-23(6)80)111-45-28(13-70)103-60(94-10)35(84)50(45)96-20(3)77)109-61-37(86)52(98-22(5)79)48(32(17-74)105-61)114-66-41(90)55(101-25(8)82)56(57(116-66)58(91)92)115-65-40(89)54(100-24(7)81)47(31(16-73)108-65)112-62-36(85)49(95-19(2)76)43(93-9)27(12-69)104-62/h26-57,59-66,68-74,83-90H,11-17H2,1-10H3,(H,67,75)(H,91,92)/p-1/t26-,27-,28-,29-,30-,31-,32-,33+,34-,35+,36+,37+,38+,39+,40+,41+,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56+,57+,59-,60+,61-,62-,63-,64-,65-,66+/m1/s1
| StdInChIKey = XOYXESIZZFUVRD-UVSAJTFZSA-M
| SMILES = CC(=O)N[C@H]1[C@H]([C@@H]([C@H](O[C@@H]1O[C@@H]2[C@H](O[C@@H]([C@H]([C@H]2OC(=O)C)O)O[C@@H]3[C@H](O[C@@H]([C@H]([C@H]3OC(=O)C)O)O[C@@H]4[C@H](O[C@@H]([C@H]([C@H]4OC(=O)C)O)OC)CO)CO)CO)CO)O[C@@H]5[C@H]([C@H]([C@@H]([C@H](O5)CO)O[C@@H]6[C@H]([C@H]([C@@H]([C@H](O6)C(=O)[O-])O[C@@H]7[C@H]([C@H]([C@@H]([C@H](O7)CO)O[C@@H]8[C@H]([C@H]([C@@H]([C@H](O8)CO)OC)OC(=O)C)O)OC(=O)C)O)OC(=O)C)O)OC(=O)C)O)O
}}
| Section2 = {{Chembox Properties
| C=66|H=100|N=1|O=49
| Appearance =
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| Section3 = {{Chembox Hazards
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}}
Acemannan is a D-isomer mucopolysaccharide in aloe vera leaves. This compound has potential immunostimulant,{{cite book|url=https://books.google.com/books?id=CMJKgfhCKzIC&q=Acemannan+Immunostimulant+mucopolysaccharide&pg=PA152|title=Pharmacodynamic Basis of Herbal Medicine|edition= Second |accessdate=23 May 2015|isbn=978-1-4200-0645-2|last1=Ebadi|first1=Manuchair|date=2006-09-06|publisher=CRC Press }} antiviral, antineoplastic, and gastrointestinal properties.{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=596005&loc=es_rss|title=SID 596005 – PubChem|author=Pubchem|work=nih.gov|accessdate=23 May 2015}}
Chemical structure and properties
Acemannan's monomer is mannoacetate linked by β-1,4-glycosidic bonds.{{cite web|url=http://chemdb.niaid.nih.gov/struct_search/class/class_many.asp?class%3DGLYCOSYLATION+INHIBITORS |title=Archived copy |accessdate=2009-04-02 |url-status=dead |archiveurl=https://web.archive.org/web/20090927064827/http://chemdb.niaid.nih.gov/struct_search/class/class_many.asp?class=GLYCOSYLATION%20INHIBITORS |archivedate=2009-09-27 }}{{cite web|url=https://www.drugs.com/vet/acemannan-immunostimulant.html|title=Acemannan Immunostimulant|work=drugs.com|accessdate=23 May 2015}} This polymer is hydrophilic.
Immunostimulant properties
Acemannan has been demonstrated to induce macrophages to secrete interferon (IFN), tumor necrosis factor-α (TNF-α) and interleukins (IL-1); therefore, it might help to prevent or abrogate viral infection. These three cytokines are known to cause inflammation, and interferon is released in response to viral infections. In vitro studies have shown acemannan to inhibit HIV replication; however, in vivo studies have been inconclusive.
Acemannan is currently being used for treatment and clinical management of fibrosarcoma in dogs and cats. Administration of acemannan has been shown to increase tumor necrosis and prolonged host survival; the animals have demonstrated lymphoid infiltration and encapsulation.{{cite journal|pmid=1768373|pages=207–13|year=1991|last1=Harris|first1=C|title=Efficacy of acemannan in treatment of canine and feline spontaneous neoplasms|journal=Molecular Biotherapy|volume=3|issue=4|last2=Pierce|first2=K|last3=King|first3=G|last4=Yates|first4=K. M.|last5=Hall|first5=J|last6=Tizard|first6=I}}
The compound has been found to have an {{LD50}} of >80 mg/kg and LC50 >5,000 mg/kg IV.{{cite web|url=http://msds.farnam.com/m000855.htm |title=MSDS: Acemannan Immunostimulant |accessdate=2009-04-02 |url-status=dead |archiveurl=https://web.archive.org/web/20080703194253/http://msds.farnam.com/m000855.htm |archivedate=2008-07-03 }}