Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series

1997 ◽  
Vol 62 (11) ◽  
pp. 1776-1798 ◽  
Author(s):  
Eva Klinotová ◽  
Václav Křeček ◽  
Jiří Klinot ◽  
Magdalena Endová ◽  
Jana Eisenreichová ◽  
...  
Keyword(s):  
Betulinic Acid ◽  
Dimethyl Ester ◽  
Dioic Acid ◽  
Triterpene Alcohols ◽  
Silver Silicate ◽  
Subsequent Deacetylation

A series of 3- and 28-glucosides and glucosyl esters of betulinic acid (1a), 28-hydroxy-3,4-secolupa-4(23),20(29)-dien-3-oic acid (22a), dimethyl ester of 28-hydroxy-2,3-secolup-20(29)-en-2,3-dioic acid (43a), their 20(29)-dihydro derivatives (1b, 22b, 43b) and several other triterpenes of the lupane (12a, 12b) and 3,4-secolupane series (18a, 18b, 32a) has been prepared by reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide in acetonitrile in the presence of mercury(II) cyanide and subsequent deacetylation of the obtained tetra-O-acetyl-β-D-glucopyranosyl derivatives. In several cases attempted glucosylation in the presence of silver silicate afforded predominantly the corresponding 1,2-orthoacetates of α-D-glucopyranose.

scholarly journals New Galloyl Derivative from Winged Sumac (Rhus copallinum) Fruit

2012 ◽  
Vol 7 (1) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Hang Ma ◽  
Tao Yuan ◽  
Antonio González-Sarrías ◽  
Liya Li ◽  
Maxwell E. Edmonds ◽  
...  
Keyword(s):  
Malic Acid ◽  
Betulinic Acid ◽  
Dimethyl Ester ◽  
Human Colon ◽  
Methyl Gallate ◽  
Mass Spectral Data ◽  
Antiproliferative Effects ◽  
Mass Spectral ◽  
Rhus Copallinum ◽  
Hct 116

Twelve compounds were isolated from Winged Sumac ( Rhus copallinum) fruit and their structures were elucidated on the basis of NMR and mass spectral data. The isolates included a new galloyl derivative, (R)-galloyl malic acid dimethyl ester (1), and eleven known compounds, gallic acid (2), methyl gallate (3), glucogallin (4), methyl m-digallate (5), methyl p-digallate (6), quercetin (7), myricetin (8), rhamnazin (9), kaempferol (10), betulinic acid (11), and oleanolic acid (12). All of the compounds were evaluated for antiproliferative effects against human colon tumorigenic (HCT-116, Caco-2) and non-tumorigenic (CCD18-Co) cell lines.

scholarly journals Cassane diterpenoids from Lonchocarpus laxiflorus

2008 ◽  
Vol 3 (1) ◽  
pp. 1934578X0800300
Author(s):  
John O. Igoli ◽  
Samuel O. Onyiriuka ◽  
Matthias C. Letzel ◽  
Martin N. Nwaji ◽  
Alexander I. Gray
Keyword(s):  
Betulinic Acid ◽  
Stem Bark ◽  
Spectroscopic Methods ◽  
Dioic Acid ◽  
Phytochemical Investigation

Phytochemical investigation of the stem bark of Lonchocarpus laxiflorus yielded three new cassane diterpenoids, lonchocassane A [cassa-13 (14), 15-dien-18, 20-dioic acid], lonchocassane B [cassa-13 (14), 15-dien-20-oxo-18-oic acid] and lonchocassane C [cassa-13 (14), 15-dien-20-carboxyl-18-methylcarboxylate]. The known compounds betulinic acid, betulinic acid acetate, betulin, lupeol, lupenone, trilinoleate, hexacosanyl and triacontanyl caffeates, 4-hydroxy-4-methylpentan-2-one, β-sitosterol, β-sitosterol acetate and stigmasterol were also isolated. The structures and identities of the compounds were established by spectroscopic methods.

3β-Hydroxylup-20(29)-ene-27,28-dioic acid dimethyl ester, a novel natural product from Plumbago zeylanica inhibits the proliferation and migration of MDA-MB-231 cells

2010 ◽  
Vol 188 (3) ◽  
pp. 412-420 ◽  
Author(s):  
Shanmugaraj Sathya ◽  
Selvaraj Sudhagar ◽  
Murugan Vidhya Priya ◽  
Rajaganapathy Bharathi Raja ◽  
Velusamy Shanmuganathan Muthusamy ◽  
...  
Keyword(s):  
Natural Product ◽  
Dimethyl Ester ◽  
Plumbago Zeylanica ◽  
Dioic Acid ◽  
Acid Dimethyl Ester ◽  
And Migration ◽  
Proliferation And Migration

The chemistry of Eremophila spp. XIX. New cembrane diterpenes from E. granitica and E. abietina

1983 ◽  
Vol 36 (6) ◽  
pp. 1187 ◽  
Author(s):  
EL Ghisalberti ◽  
PR Jefferies ◽  
TA Mori ◽  
VA Patrick ◽  
AH White
Keyword(s):  
Single Crystal ◽  
Diffraction Analysis ◽  
Dimethyl Ester ◽  
Structural Elucidation ◽  
Structural Studies ◽  
X Ray Diffraction ◽  
Dioic Acid ◽  
X Ray

The isolation and structural elucidation of five new cembrane diterpenes from two Eremophila species is reported. (1R,3S,4S,7E,11Z)-3,15-Epoxy-19-oxocembra-7,11-dien-18-oic acid (3) and (1R,3S,4S,7Z,11Z)-3,15-epoxycembra-7,11-dien-18-oic acid (7) were isolated from E. granitica, and dimethyl(1R,3S,4S,7E,11Z)-3,15-epoxycembra-7,11-diene-18,19-dioate (16), (1R,3S,4S,8R,11Z)-3,15-epoxycembr-11-ene-18,19-dioic acid (14) and its dimethyl ester were isolated from E. abietina. Structural studies on the diol derived from (14) were carried out by single-crystal X-ray diffraction analysis.

In vivo toxicological evaluations for betulinic acid and ramified cyclodextrins applied on experimental melanoma models

Planta Medica ◽  
2009 ◽  
Vol 75 (09) ◽  
Author(s):  
CA Dehelean ◽  
C Peev ◽  
C Soica ◽  
S Cinta-Pinzaru ◽  
Z Aigner
Keyword(s):  
Betulinic Acid

Identification and isolation of betulin, betulinic acid and lupeol from birch bark

Planta Medica ◽  
2009 ◽  
Vol 75 (09) ◽  
Author(s):  
E Kovac-Besovic ◽  
K Duric ◽  
Z Kaloðera ◽  
E Sofic
Keyword(s):  
Betulinic Acid ◽  
Birch Bark

NOXA as Target for the Combination Therapy of Betulinic Acid and Conventional Cytotoxic Drugs

2010 ◽  
Vol 223 (01) ◽  
Author(s):  
I Jeremias ◽  
H Ehrhardt ◽  
I Höfig ◽  
N Terziyska ◽  
P Obexer
Keyword(s):  
Combination Therapy ◽  
Betulinic Acid ◽  
Cytotoxic Drugs

Lupane Type Triterpene Isolated from the Leaves of Thecacoris Annobonea (Euphorbiaceae)

2013 ◽  
Vol 12 (10) ◽  
pp. 695-701
Author(s):  
Herve Martial Poumale Poumale ◽  
Alphonsine Nkapwa Guedem ◽  
Louis Pergaud Sandjo ◽  
Bonaventure Tchaleu Ngadjui ◽  
Yoshihito Shiono
Keyword(s):  
Antimicrobial Activity ◽  
Root Growth ◽  
Betulinic Acid ◽  
Aristolochic Acid ◽  
2D Nmr ◽  
Aristolochic Acid I

A new lupane type triterpene (1), together with betulinic acid (2), friedelin (3), aristolochic acid I (4), alpinumisoflavone (5) and 4’-O-methylepinumisoflavone (6) have been isolated from the leaves of Thecacoris annobonea. The structure of the new compound was elucidated on the basis of 1 and 2D NMR experiments. The isolated compounds were evaluated for their phytotoxicity and antimicrobial activity. 1 exhibited significant antimicrobial activity at 30 μg/ml and compounds 1, 2, 3, 4, 5 and 6 inhibited root growth lettuce at 100 μg/ml. 

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