D-Apiose - Aqueous solution

D-Apiose is a triterpenoid saponin that is isolated from the bark of the Quillaja saponaria tree. It has been shown to inhibit tumor growth and induce cell death in animal models. D-Apiose is also known to be an inhibitor of sugar transport, hydroxylation, and ribitol dehydrogenase, which are all important cellular processes. This compound induces cell lysis by binding to cellular organelles such as the mitochondria and endoplasmic reticulum. Cell lysis leads to the release of intracellular contents into the extracellular environment, which can have potent antitumor activity. The hydroxyl group on D-Apiose allows it to react with ribitol dehydrogenase, which catalyzes a reaction involving the conversion of ribitol into 2-deoxyribose 5-phosphate. 

D-Apiose is very soluble (in water) and a very weakly acidic compound (based on its pKa). Outside of the human body, D-apiose can be found in parsley. This makes D-apiose a potential biomarker for the consumption of this food product.

Title: Apiose

CAS Registry Number: 639-97-4

CAS Name: D-Apiose

Additional Names: tetrahydroxyisovaleraldehyde; 3-C-(hydroxymethyl)-D-glyceroaldotetrose

Molecular Formula: C5H10O5

Molecular Weight: 150.13

Percent Composition: C 40.00%, H 6.71%, O 53.29%

Literature References: First found in parsley in which it occurs as the flavinoid glycoside apiin, q.v. Isoln from apiin: Vongerichten, Ann. 318, 126 (1901); 321, 74 (1902); Hemming, Ollis, Chem. Ind. (London) 1953, 85. From the rubber plant, Hevea brasiliensis, Euphorbiaceae: Patrick, Nature 178, 216 (1956). Discussion of structure and isoln from the Australian marine plant Posidonia australis Kon., Potamogetonaceae: Bell, Methods in Carbohydrate Chemistry vol. I (Academic Press, New York, 1962) pp 260-263. Synthesis: Gorin, Perlin, Can. J. Chem. 36, 480 (1958); Khalique, J. Chem. Soc. 1962, 2515; Ezekiel et al., Tetrahedron Lett. 1969, 1635. Synthesis of L-form: Weygand, Schmiechen, Ber. 92, 535 (1959); of DL-form: Kinoshita, Miwa, Carbohydr. Res. 28, 175 (1973); Y. Araki et al., ibid. 58, C4 (1977); of D- and L-forms: P. Ho, Can. J. Chem. 57, 381 (1979). Chemistry, configuration and synthesis studies: Williams, Jones, ibid. 42, 69 (1964); Hulyalker et al., ibid. 43, 2085 (1965). Review: Watson, Orenstein, Adv. Carbohydr. Chem. Biochem. 31, 135-184 (1975).

Properties: Syrup. [a]D15 +5.6°; [a]D19 +9.1°. Soluble in water.

Optical Rotation: [a]D15 +5.6°; [a]D19 +9.1°

Derivative Type: D-Apiose di-O-isopropylidene

Molecular Formula: C11H18O5

Molecular Weight: 230.26

Percent Composition: C 57.38%, H 7.88%, O 34.74%

Properties: Plates from water containing a trace of NH3, mp 81-83°. [a]D20 +55.5° (c = 1.1 in ethanol).

Melting point: mp 81-83°

Optical Rotation: [a]D20 +55.5° (c = 1.1 in ethanol)