2-hydroxyursolic-acid and beta-amyrin

The neotropical lianas Souroubea gilgii and Souroubea sympetala (Marcgraviaceae) were chosen for study as part of a phytochemical discovery strategy focusing on rare plant families in Central America. In participatory research, Q'eqchi' healers in Belize reported the use of these plants to reverse psychological symptoms inflicted by witchcraft. Extracts of two Souroubea species showed significant anti-anxiety activity in the elevated plus maze, a standardized test paradigm. Bioassay guided isolation led to the active principle, the pentacyclic triterpene, betulinic acid, which had activity in the elevated plus maze at 0.5mg/kg. Other phytochemicals isolated included α- and β-amyrin, 2-hydroxyursolic acid, taraxenyl trans-4-hydroxy-cinnamate, naringenin, methyl ursolate, eriodytiol, methyl 2-α-hydroxyursolate, methyl 2-α-hydroxymaslinate, methyl betulinate, and condrilla sterol.

Topics: Animals; Anti-Anxiety Agents; Betulinic Acid; Costa Rica; Diazepam; Dose-Response Relationship, Drug; Ethnopharmacology; Fruit; Magnoliopsida; Male; Medicine, Traditional; Oleanolic Acid; Pentacyclic Triterpenes; Phytochemicals; Phytotherapy; Plant Extracts; Plant Leaves; Plant Stems; Plants, Medicinal; Rats; Rats, Sprague-Dawley; Triterpenes

To determine the chemical constituents of Gentiana rhodantha.. To isolate the constituents, column chromatography over silica gel, MCI, Sephadex LH-20 and C18 reverse-phased silica gel were used. Spectroscopic methods were used to elucidate the structures of the isolated compounds.. Sixteen compounds were isolated and elucidated as ten phonemic compounds, namely 1,3,7,8-tetrahydroxylxanthone (1), rhodanthenone D (2), 1,3,6,7-tetrahydroxylxanthone (3), 1,3,7-trihydroxy-4,8-dimethoxyxanthone (4), quercetin (5), isoorientin (6), mangiferin (7), norswertianolin (8), gallic acid ethyl ester (9) and salicylic acid (10), and six triterpenes including alpha-amyrin (11), erythrodiol 3-O-palmitate (12), ursolic aldehyde (13), uvaol 3-O-acetyl (14), ursolic acid (15) and 2alpha-hydroxyursolic acid (16).. Compounds 4-6, 8, 10-12, 15 and 16 were isolated from this plant for the first time. Compounds 1 and 3 were obtained firstly from the genus Gentiana and compounds 9, 13-14 were firstly from the family Gentianaceae.

Topics: Chromatography, Gel; Chromatography, Reverse-Phase; Dextrans; Gentianaceae; Mass Spectrometry; Oleanolic Acid; Plant Extracts; Plants, Medicinal; Quercetin; Salicylic Acid; Silica Gel; Triterpenes; Ursolic Acid; Xanthones

Triterpenoid compounds found in free and ester forms in extracts of entire fruits and leaves and in fruit and leaf cuticular waxes of bilberry (Vaccinium myrtillus L.) collected in Finland and Poland were identified and quantitated by gas chromatography-mass spectrometry coupled to a flame ionization detector (GC-MS/FID). The main bilberry triterpenoid profile consisted of α- and β-amyrin, α- and β-amyrenone, campesterol, cholesterol, citrostadienol (in berries), cycloartanol, erythrodiol, lupeol, 24-methylenecycloartanol, sitosterol, sitostanol, stigmasterol, stigmasta-3,5-dien-7-one, uvaol, oleanolic and ursolic aldehydes, and oleanolic, ursolic, 2α-hydroxyoleanolic, and 2α-hydroxyursolic acids. Friedelin and D:A-friedooleanan-3β-ol were found only in Finnish plants, whereas D:C-friedours-7-en-3β-ol and taraxasterol were found only in Polish plants. To our knowledge, this is the first thorough description of triterpenoid compounds in this species. The presented results revealed that the triterpenoid profile of bilberry varied considerably between different organs of the plant, regardless of the plant origin, as well as between plant samples obtained from the two geographical locations.

Topics: Anthocyanins; Cholesterol; Finland; Fruit; Gas Chromatography-Mass Spectrometry; Molecular Structure; Oleanolic Acid; Phytosterols; Plant Extracts; Plant Leaves; Poland; Sitosterols; Triterpenes; Vaccinium myrtillus