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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H32O16
Molecular Weight 504.4371
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELEZITOSE

SMILES

OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]1O

InChI

InChIKey=QWIZNVHXZXRPDR-WSCXOGSTSA-N
InChI=1S/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-15-10(25)7(3-21)33-18(15,4-22)34-17-14(29)12(27)9(24)6(2-20)31-17/h5-17,19-29H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15+,16-,17-,18+/m1/s1

HIDE SMILES / InChI

Description

Melezitose is a nonreducing trisaccharide sugar that is produced by many plant sap-eating insects, including aphids such as Cinara pilicornis. Melezitose is beneficial to the insects, as it reduces the stress of osmosis by reducing their own water potential. The melezitose is part of the honeydew which acts as an attractant for ants and also as a food for bees. Melezitose fatty acid monoesters are potential surfactants, that may solubilize hydrophobic drugs for parenteral formulations.

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Plastic insect cage (height: 12.5 cm; diam: 10.0 cm) was provided with four calibrated glass micropipettes (5.0 μl, Blaubrand Intramark, Wertheim, Germany) filled with 4.0 μl of the test sugar solution (Melezitose) and inert mineral oil overlay (1.0 μl) to minimize evaporation. These capillaries were inserted through the lid (at the corners of a square of 4.5 × 4.5 cm, in the middle of the lid) via truncated 200 μl yellow pipette tips. To meet the water requirements of the parasitoids, a filter paper imbibed with 500 μl of sterile demineralized water was placed at the bottom of the cage at the start of the experiment, and supplemented with another 500 μl of water each day for the longevity experiments. To allow entry of air, the lid of the cage was pierced and covered with a fine mesh (2.5 × 2.5 cm; mesh size 0.27 × 0.88 mm). For each experiment, after being subjected to a dark period of 8 h, five replicates of 15 adult parasitoids were released in each cage. Each experiment also included an identical CAFE chamber without parasitoids to determine evaporative losses, which were subtracted from experimental readings. All experiments were conducted under controlled conditions of 22 °C, 70 % RH and a 16:8 h L:D cycle, starting with the light period.