Oleandrose Explained

Oleandrose is a type of carbohydrate with the chemical formula C₇H₁₄O₄. With a six-carbon chain, it is classified as a hexose. With two hydroxyl groups replaced with hydrogen atoms, it is a dideoxy sugar. The hydroxyl group at C3 is methylated.

Occurrence

Oleandrdose is found in the leaves of Nerium oleander and may contribute to the toxicity of the plant.^{[1] [2]} Oleandrose is also a component of several naturally-occurring chemical compounds including the avermectins (emamectin, abamectins, ivermectin, and others), the macrolide antibiotic oleandomycin, and the cardiac glycoside oleandrin.

Laboratory syntheses of L-oleandrose^[3] and DL-oleandrose^[4] have been reported.

See also

• Sarmentose, a diastereomeric dideoxy sugar

Notes and References

1. 10.1016/j.phytochem.2012.01.001 . Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity . 2012 . Siddiqui . Bina Shaheen . Khatoon . Nasima . Begum . Sabira . Farooq . Ahsana Dar . Qamar . Kehkashan . Bhatti . Huma Aslam . Ali . Syed Kashif . Phytochemistry . 77 . 238–244 . 22281382 . 2012PChem..77..238S .
2. 10.1038/s41598-022-26087-0 . Qualitative and quantitative phytochemical screening of Nerium oleander L. Extracts associated with toxicity profile . 2022 . Bakir Çilesizoğlu . Neşe . Yalçin . Emine . Çavuşoğlu . Kültiğin . Sipahi Kuloğlu . Selin . Scientific Reports . 12 . 1 . 21421 . 36504046 . 9742154 . 2022NatSR..1221421B .
3. 10.1080/00397919208021642 . Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose¹Preparation of Glycals . 1992 . Bredenkamp . Martin W. . Holzapfel . Cedric W. . Toerien . Francois . Synthetic Communications . 22 . 17 . 2459–2477 .
4. 10.1016/0040-4020(82)80194-4 . A highly diastereoselective synthesis of dl-oleandrose . 1982 . Berti . G. . Catelani . G. . Colonna . F. . Monti . L. . Tetrahedron . 38 . 20 . 3067–3072 .