Ursene hydroxy

Triterpenic Acids. The following pentacyclic mono- and dihydroxy triterpenic acids are present in virgin olive oil (35, 43, 44) 3p-hydroxy-17-carboxy-5-12-olea-nene (oleanolic acid) 3 3,2a-dihydroxy-17-carboxy-5-12-oleanene (maslinic acid) 3p-hydroxy-17-carboxy-8-12-ursene (ursolic acid) 2a,3p-dihydroxy-17-carboxy-5-12-ursene (2a-hydroxyursolic acid) and deoxyursolic acid (structure not fully elucidated). 

Compound (30) showed a ketone, a carboxylic carbon, one double bond and one oxygenated methine in its 13C NMR spectrum. Its spectroscopic l3C NMR data were very similar of that of ursolic acid [51]. The position of the functional groups were determined by means of a HMBC experiment and the stereochemistry of H-22 was determined based on its coupling constant, indicating an equatorial configuration. Therefore, (30) was elucidated to be 22p-hydroxy-3-oxo-12-ursen-30-oic acid, Fig. (21). 

More than 150 ursanes of plant origin are documented (+)-3p-Hydroxyursan-28-oic acid, for example, represents a saturated triterpene found in the leaves of oleander Nerium oleander (Apocynaceae). (-l-)-3p-Hydroxy-12-ursen-28-oic acid is the most prominent derivative this was first isolated from the leaves and berries of bearberry Arctostaphylos uva-ursi, and therefore is commonly known as ursolic acid. It is also found in Rhododendron species, in cranberries Vaccinum macrocar-pon (Ericaceae), and in the protective wax coating of apples, pears, prunes, and other fruits. Ursolic acid is reported to have antileukemic and cytotoxic activities it is also used as an emulsifier in pharmaceuticals and foods, and is similar to (-1-)-3p,19a-dihydroxy-12-ursen-28-oic acid (known as pomolic acid) extracted from the wax coats of apples. 

Hydroxy-2-undecylchromone, see H-20248 3-Hydroxy-12-ursene-23,28-dioic acid,... 

Hydroxy-12-ursen-28-oic acid, H-10242 3)5-Hydroxy-ll-ursen-28,13-olide, in D-10258 20-Hydroxy-12-ursen-3-one, H-10243 21a-Hydroxyursolic acid, in D-10259 21)5-Hydroxyursolic acid, in D-10259 16a-Hydroxyverazine, see E-10206... 

Hydroxy-6-friedelen-3-one, H-20141 11-Hydroxy-l-friedelen-3-one, H-30135 21a-Hydroxy-4(23)-friedelen-3-one, in F-10021 23-Hydroxy-18-oleanen-3-one, H-20203 20-Hydroxy-12-ursen-3-one, H-10243 Isokarounidiol, 1-10034 Kokoonal, in D-10167 1 l,13(18)-01eanadiene-3,22-diol, 0-10020... 

Constit. of Centipeda minima. Needles. Mp 139°. 2(X-Hydroxy l(X,2(x,3P, 9(x,23-Pentahydroxy- 2-ursen-2 -oic acid... 

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