Acemannan

Chemical compound From Wikipedia, the free encyclopedia

Acemannan is a D-isomer mucopolysaccharide in aloe vera leaves. This compound has potential immunostimulant,[1] antiviral, antineoplastic, and gastrointestinal properties.[2]

Quick facts Names, Identifiers ...
Acemannan
A representative 6-sugar fragment of acemannan
Names
IUPAC name
(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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.122.396 Edit this at Wikidata
EC Number
  • 600-942-8
UNII
  • InChI=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
    Key: XOYXESIZZFUVRD-UVSAJTFZSA-M
  • 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
Properties
C66H100NO49
Molar mass 1691.484 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical structure and properties

Acemannan's monomer is mannoacetate linked by β-1,4-glycosidic bonds.[3][4] 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.[5]

The compound has been found to have an LD50 of >80 mg/kg and LC50 >5,000 mg/kg IV.[6]

References

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