- Betulin 3,28-Bis-O-trifluoroacetate: Synthesis and molecular structure
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The reaction of betulin with excess trifluoroacetic anhydride gave the corresponding 3,28-bis-O-trifluoroacetate whose molecular structure as a slightly bent "stairway" was determined by X-ray analysis.
- Trishin,Chernyavskii,Shafeeva,Nelyubina
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- Three new lupane-type triterpenes from Ceriops tagal
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Three new lupane-type triterpenes, 3α-O-trans-feruloylbetulinic acid (1), 3α-O-trans-coumaroylbetulinic acid (2) and 3β-O-cis- feruloylbetulin (3), together with 10 known triterpenes (4-13), were isolated from the aerial parts of the mangrove plant Ceriop
- Wang, Xia-Chang,Ouyang, Xiao-Wei,Hu, Li-Hong
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- Anti-tumor betulinic acid derivative and preparation method thereof
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The invention discloses an anti-tumor betulinic acid derivative and a preparation method thereof. The preparation method comprises the following steps: by taking betulinic acid as a raw material, carrying out carboxyl reduction, generating sulfonate by hydroxyl and sulfonyl chloride, eluting and purifying by a silica gel column and the like to obtain the betulinic acid derivative with a novel structure. Pathological experiments show that the compound has a remarkable in-vitro proliferation inhibition effect on human ovarian cancer cells (A2780), human lung cancer cells (A-549) and human cervical cancer cells (Hela), and can be used as a pilot compound for development of antitumor drugs. The method for preparing the betulinic acid derivative provided by the invention has the characteristics of simple preparation process, low cost and suitability for industrial mass production.
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Paragraph 0021-0022
(2021/07/28)
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- Cytotoxic and NF-κB and mitochondrial transmembrane potential inhibitory pentacyclic triterpenoids from Syzygium corticosum and their semi-synthetic derivatives
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Syzygium is a large genus of flowering plants, with several species, including the clove tree, used as important resources in the food and pharmaceutical industries. In our continuing search for anticancer agents from higher plants, a chloroform extract of the leaves and twigs of Syzygium corticosum collected in Vietnam was found to be active toward the HT-29 human colon cancer cell line. Separation of this extract guided by HT-29 cells and nuclear factor-kappa B (NF-κB) inhibition yielded 19 known natural products, including seven triterpenoids, three ellagic acid derivatives, two methylated flavonoids, a cyclohexanone, four megastigmanes, a small lactone, and an aromatic aldehyde. The full stereochemistry of (+)-fouquierol (2) was defined for the first time. Biological investigations showed that (+)-ursolic acid (1) is the major cytotoxic component of S. corticosum, which exhibited also potent activities in the NF-κB and mitochondrial transmembrane potential (MTP) inhibition assays conducted, with IC50 values of 31 nM and 3.5 μM, respectively. Several analogues of (+)-ursolic acid (1) were synthesized, and a preliminary structure-activity relationship (SAR) study indicated that the C-3 hydroxy and C-28 carboxylic acid groups and 19,20-dimethyl substitution are all essential in the mediation of the bioactivities observed for this triterpenoid.
- Ren, Yulin,Anaya-Eugenio, Gerardo D.,Czarnecki, Austin A.,Ninh, Tran Ngoc,Yuan, Chunhua,Chai, Hee-Byung,Soejarto, Djaja D.,Burdette, Joanna E.,de Blanco, Esperanza J. Carcache,Kinghorn, A. Douglas
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supporting information
p. 4452 - 4460
(2018/07/31)
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- Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis
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Chaenomeles sinensis has been consumed traditionally for the treatment of throat diseases, diarrhea, inflammatory diseases, and dry beriberi. Repeated chromatography of the CHCl3-soluble fraction from the 80% MeOH extract of C. sinensis twigs led to the isolation of three new triterpenoids, sinenic acid A (1), 3β-O-cis-feruloyl-2α,19α-dihydroxyurs-12-en-28-oic acid (2), and 3β-O-cis-caffeoylbetulin (3), together with 20 analogues. The chemical structures of 1-3 were determined using diverse NMR techniques and HRMS data analysis, chemical methods, and computational approaches supported by advanced statistics (CP3). All the purified compounds were evaluated not only for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) but for their potential neuroprotective effects through induction of nerve growth factor in C6 glioma cells. Their anti-inflammatory effects were also assessed by measuring nitric oxide levels in lipopolysaccharide-insulted murine microglia BV2 cells.
- Kim, Chung Sub,Subedi, Lalita,Oh, Joonseok,Kim, Sun Yeou,Choi, Sang Un,Lee, Kang Ro
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p. 1134 - 1140
(2017/05/05)
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- Synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al with antileukemic activity
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An easy and efficient route to partial synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al (1), starting from betulinic acid (2), has been developed (eight steps, 44% overall yield). Structures of all the compounds were determined by spectral studies (IR, 1H, 13C NMR, MS, NOESY, COSY, etc.). Compound 1 and the precursors (2, 3, 5, and 7) showed antiproliferative activities against human K562 leukemia, murine WEHI3 leukemia, and murine MEL erythroid progenitor.
- Ghosh, Pranab,Mandal, Amitava,Ghosh, Joydip,Pal, Chiranjib,Nanda, Ashis Kumar
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experimental part
p. 141 - 153
(2012/05/05)
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- Structure and bioassay of triterpenoids and steroids isolated from sinocalamus affinis
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Five triterpenoids with a new 25-norfern carbon skeleton (1-5), a lupane triterpenoid (6), and four 20-hydroxyprogesterone acyl esters (7-10), together with 23 known compounds, were isolated from the stem (with skin removed) of Sinocalamus af f inis. The absolute configuration of compound 1 was confirmed by single-crystal X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Compounds 1-5 exhibited inhibitory activity against protein tyrosine phosphatase 1B.
- Xiong, Liang,Zhu, Mei,Zhu, Chenggeng,Lin, Sheng,Yang, Yongchun,Shi, Jiangong
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p. 1160 - 1166
(2012/11/13)
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- METHOD AND APPARATUS FOR SIMULTANEOUSLY MANUFACTURING ULTRA PURE BETULIN AND HIGHLY PURE BETULINIC ACID FROM BIRCH BARK
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The present invention provides a method of simultaneously producing ultrapure betulin and highly-pure betulinic acid a from bark of a birch tree, which is configured such that a crude extract including 70 ～ 83% of betulin, 4 ～ 8% of betulinic acid and polar pigment components are prepared from the bark (mainly outer bark) of a birch tree naturally growing in the northern hemisphere of 34° north latitude, such as Korea, China, Europe and the like, using a polar organic solvent, and highly-pure betulin included in this crude extract is crystallized using a mixed polar organic solvent to obtain a crystallized product, and then ultrapure betulin, having purity of 99.5% or more and highly-pure betulinic acid having purity of 95% or more are simultaneously produced from the crystallized product including highly-pure betulin as a major component.
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- Synthetic transformations of higher terpenoids: XXIV.* synthesis of cyanoethyl derivatives of lupane triterpenoids and their transformation into 1,2,4-oxadiazoles
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Cyanoethylation of lupane triterpenoids was performed. Amide oximes of 3β-O-(2-cyanoethyl)- betulinic acid methyl ester and 3β-O-acetyl-28-O- (2-cyanoethyl)betulin and the corresponding O-[2-(1,2,4-oxadiazol- 3-yl)ethyl] lupane derivatives were obtained. Pleiades Publishing, Ltd., 2011.
- Antimonova,Uzenkova,Petrenko,Shakirov,Shul'ts,Tolstikov
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experimental part
p. 589 - 601
(2011/07/29)
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- Synthesis and biological evaluation of antitumor-active γ-butyrolactone substituted betulin derivatives
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The plant triterpenes betulin and betulinic acid (BA) are triterpenes featuring interesting pharmacological properties. Starting from substituted betulinic aldehydes, we used them as lead structures for the synthesis of several γ-butyrolactones and butenolides. Their antitumor activity was examined for 15 cancer cell lines using a SRB-assay and their apoptotic action was documented by trypan-blue test and DNA laddering. Several compounds revealed a higher activity than betulinic acid.
- Csuk, René,Barthel, Alexander,Schwarz, Stefan,Kommera, Harish,Paschke, Reinhard
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experimental part
p. 2549 - 2558
(2010/06/16)
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- METHOD OF PREPARATION AND ISOLATION OF BETULIN DIACETATE FROM BIRCH BARK FROM PAPER MILLS AND ITS OPTIONAL PROCESSING TO BETULIN
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The invention relates to a method of preparation and isolation of betulin diacetate from birch bark from paper mills and its optional processing to betulin, wherein the birch bark is ground, mixed with two- to twenty-fold excess volume of water and is stirred so that all birch bark is dipped, then the fraction of the birch bark which floats on the surface is collected, said collected fraction is dried at the temperature in the range of from 50 to 85 °C and the betulin contained in the dried birch bark is then subjected to an acetylation reaction, after the acetylation the birch bark is dried at the temperature of from 50 to 100 °C and the formed betulin diacetate is then isolated from the birch bark by supercritical extraction of the birch bark with carbon dioxide at the pressure of 28-35 MPa and the temperature of from 50 to 100 °C and subsequently, the supercritical extract is recrystallized for direct use or for further processing. The further processing can be basic hydrolysis of the re-crystallized betulin diacetate to betulin.
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Page/Page column 10-11
(2008/12/07)
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- Regioselective glycosylation of unprotected mannosides: A convenient access to high-mannose type saponins
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3-O-Acetyl- and 28-O-acetyl-betulin were mannosylated with tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate. Debenzoylation of the monosaccharide obtained followed by treatment with 2 equiv of tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate selectively gave O-3,O-6-linked trimannosides.
- Pakulski
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p. 361 - 367
(2007/10/03)
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- Methods of treating fungal infections using lupeol
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The invention is directed to methods of treating fungal and yeast infections using lupeol or solvates, hydrates, or clathrates thereof. The method also encompasses methods of treating fungal and yeast infections by administering to a mammal in need of such treatment a therapeutically effective amount of lupeol. Among the methods used include topical formulations for the improvement of skin appearance.
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- Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145
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A new stemodinoside, stemodin-α-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2α,7β,13(S)-trihydroxystemodane (17) and 2α,3β,13(S),16α-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6α,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2β,13(S)-dihydroxystemodane (10) by the fungus yielded 2β,7β,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7β,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion.
- Martin, Glenroy D.A.,Reynolds, William F.,Reese, Paul B.
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p. 701 - 710
(2007/10/03)
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- Triterpenoid derivatives
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The present invention relates to the use of a compound of formula (I), or a pharmaceutically acceptable salt, crystal form, complex, hydrate, or hydrolysable ester thereof, in the preparation of a medicament for treating a patient suffering from leukaemia, cancer or other proliferative disorder. A further embodiment relates to the use a compound of formula (I) in an assay for detecting the phosphorylation state of cellular substrates. The present invention also relates to novel compounds of formula (I), and the chemical synthesis thereof.
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- Methods of treating antifungal infections using lupeol
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The invention is directed to methods of treating fungal and yeast infections using lupeol or solvates, hydrates, or clathrates thereof. The method also encompasses methods of treating fungal and yeast infections by administering to a mammal in need of such treatment a therapeutically effective amount of lupeol. Among the methods used include topical formulations for the improvement of skin appearance.
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- New triterpenoids from Gentiana lutea.
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Three new triterpenoids, 2,3-seco-3-oxours-12-en-2-oic acid, 2,3-seco-3-oxoolean-12-en-2-oic acid, and betulin 3-O-palmitate, have been isolated from the rhizomes and roots of Gentiana lutea, together with five known ones. The structures of the new compou
- Toriumi, Yoshitaka,Kakuda, Rie,Kikuchi, Masafumi,Yaoita, Yasunori,Kikuchi, Masao
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- Process for obtaining betulin
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The invention relates to an improved process for obtaining pure crystalline betulin which is substantially free from betulinic acid, from an extract of birch bark.
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- Synthesis of betulonic acid derivatives containing amino-acid fragments
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New derivatives of betulonic acid containing on C-28 fragments of amino acids or their methyl esters were prepared as potential biologically active agents.
- Petrenko,Elantseva,Petukhova,Shakirov,Shul'ts,Tolstikov
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p. 331 - 339
(2007/10/03)
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- Triterpenes having human antifungal and antiyeast activity
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Methods of treating a fungal or yeast infection and of killing or inhibiting fungi or yeast are disclosed. The methods use derivatives of triterpenes that are abundant in birch bark and other plants. The triterpenes include betulin, allobetulin, and lupeol.
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- Biologically active aqueous fraction of an extract obtained from a mangrove plant Salvadora persica L
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The invention discloses a process of extracting, fractionating and purifying bioactive molecules from an associated mangrove plant, methods of screening for pharmacological activities of crude extract, it fractions and purified compounds and the use of the aqueous fraction of the crude extract as a tocolytic agent.
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- Triterpenes having antibacterial activity
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Methods of treating a bacterial infection and of killing or inhibiting bacteria are disclosed. The methods use derivatives of triterpenes that are abundant in birch bark and other plants. The triterpenes include betulin, allobetulin, and lupeol.
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- Acylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof
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Betulin and dihydrobetulin acyl derivatives according to the present invention have been found to have potent anti-HIV activity. The compounds of the present invention have the following formulae: or pharmaceutically acceptable salts thereof, wherein R1 is a C2-C20 substituted or unsubstituted carboxyacyl, R2 is a C2-C20 substituted or unsubstituted carboxyacyl; and R3 is hydrogen, halogen, amino, optionally substituted mono- or di-alkylamino, or —OR4, where R4 is hydrogen, C1-4 alkanoyl, benzoyl, or C2-C20 substituted or unsubstituted carboxyacyl; wherein the dashed line represents an optional double bond between C20 and C29.
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- Montmorillonite clays catalysis IX: A mild and efficient method for removal of tetrahydropyranyl ethers
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A variety of tetrahydropyranyl ethers of alcohols and phenols are easily removed in the presence of catalytic of amount of montmorillonite clays in methanol at 40-50 °C in excellent yield.
- Li, Tong-Shuang,Zhang, Zhan-Hui,Jin, Tong-Shou
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p. 181 - 188
(2007/10/03)
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- Anti-AIDS agents. 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents
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Succinyl and 3'-substituted glutaryl betulin derivatives showed stronger anti-HIV activity and higher therapeutic index (TI) values than their dihydrobetulin counterparts, with ratios of 1.2:1 to 15:1 (cf. 7 and 15, 9 and 17, 10 and 18, 11 and 19, and 12 and 20). For various 3'-substituted glutaryl compounds, the order of anti-HIV effects, from strong to weak inhibition, was 3',3'-dimethyl, 3'-methyl, 3'-ethyl-3'-methyl, followed by 3',3'-tetramethylene glutaryl derivatives (10 > 9 > 11 > 12, 18 > 17 > 19 > 20). The most potent compound, 10, has two 3',3'-dimethylglutaryl groups and displays significant anti-HIV potency with an EC50 value of 0.000 66 μM and a TI of 21 515. Results for compounds (22 and 23) without a C-3 acyl group confirmed the importance of the C-3 acyl group to the anti-HIV effect. With 3',3'-tetramethylene glutaryl derivatives, triacyl 29 showed stronger inhibition than diacyl 12; in contrast, 3',3'-dimethylglutaryl compounds displayed opposite results. 3-Keto compounds (35 and 36) and 2,3-dihydro compounds (39 and 40) had EC50 values in the range of 4.3-10.0 μM, suggesting that A ring modification led to decreased potency. The reduced activity of amide (33 and 34), ester (41), and oxime (42) analogues suggested that the orientation and linkage of the C-3 acyl side chain play crucial roles in the potent anti-HIV activity. Finally, replacing the C-28 acyl group with a bulky non-carboxylic group produced a less potent compound (44). In the study of mechanism of action, our results indicated that fusion is not the primary target for the anti-HIV activity of 10. It appears to inhibit HIV replication at a late stage of the viral life cycle, i.e., after viral protein synthesis.
- Sun, I.-Chen,Wang, Hui-Kang,Kashiwada, Yoshiki,Shen, Jing-Kang,Cosentino, L. Mark,Chen, Chin-Ho,Yang, Li-Ming,Lee, Kuo-Hsiung
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p. 4648 - 4657
(2007/10/03)
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- Simple synthesis of allobetulin, 28-oxyallobetulin and related biomarkers from betulin and betulinic acid catalysed by solid acids
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Allobetulin (3a) and allobetulin acetate (3b) were efficiently prepared in excellent yield from betulin (2a) and betulin 3-acetate (2b) catalysed by a number of solid acids in refluxing dichloromethane. Sulfuric acid on silica, montmorillonite clays (both K10 and KSF), kaolinite, bleaching clay and toluene-p-sulfonic acid on silica are efficient catalysts for these conversions. Similarly, 28-oxyallobetulin (3c) and 28-oxyallobetulin acetate (3d) were obtained in good and excellent yield from betulinic acid (2c) and betulinic acid acetate (2d) respectively catalysed by montmorillonite K10. Two allobetulin related biomarkers, 19β,28-epoxy-A-neo-18α-olean-3(5)-ene (4a) and A-neo-18α-olean-3(5)-en-28→19β-olide (4b) were synthesised either from 3a and 3c or directly from 2a and 2c in refluxing benzene or cyclohexane catalysed by montmorillonite K10. Two other biomarkers, 19β,28-epoxy-18α-olean-2-ene (10a) and 18α-olean-2-en-28→19β-olide (10b) were also synthesised based on the above transformations. The direct formation of allobetulane related biomarkers from natural betulin 2a and betulinic acid 2c catalysed by clay mineral (montmorillonite) is of great geochemical interest.
- Li, Tong-Shuang,Wang, Jian-Xin,Zheng, Xue-Jing
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p. 3957 - 3965
(2007/10/03)
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- A reagent for selective deprotection of alkyl acetates
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The use of magnesium methoxide for selective deprotection of alkyl esters is described. By adjusting the equivalents of the magnesium methoxide reagent, it is possible to selectively cleave primary acetate in the presence of secondary and tertiary acetate and to cleave secondary acetate in the presence of tertiary acetate. A high selectivity can also be obtained for the same primary acetates if the β-positions of the acetates render a different steric bulkiness. This mild reagent has been successfully applied to the selective deprotection of many natural-occurring molecules including hydroxycitronnellol diacetate, trans-sobrerol diacetate, betulin diacetate, and baccatin III.
- Xu, Yao-Chang,Bizuneh, Amsalu,Walker, Clint
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p. 9086 - 9089
(2007/10/03)
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- POTENTIAL ALLELOPATHIC LUPANE TRITERPENES FROM BIOACTIVE FRACTIONS OF MELILOTUS MESSANENSIS
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The aerial parts of Melilotus messanenis (sweet clover) afforded, from the medium polar bioactive fractions, in addition to the known lupane triterpenes lupeol, betulin, betulin aldehyde and betulinic acid, the new norlupane messagenin (30-norlupane-3β,28-diol-20-one) which have been tested as allelochemicals.Structures and their stereochemistries were elucidated by spectral methods and chemical transformations.Messagenin has been synthesized from betulinic acid.The effect of a series of aqueous solutions at 10-4-10-9 M of eight natural and synthetic lupane derivatives were tested for their effects on the germination and growth of the dicotyledon species Lactuca sativa and Lepidium sativum and the monocotyledon species Hordeum vulgare and Triticum aestivum.All eight lupane triterpenes possess potential allelopathic activity in particular over dicotyledon species and they are likely to be significantly involved in the alleopathic action of Melilotus messanensis. - Key words: Melilotus messanensis; Leguminoseae; Fabaceae; sweet clover; lupane triterpenes; messagenin; 30-nor-lupane-3β,28-diol-20-one; allelopathy; Lactuca sativa; lepidium sativa; Hordeum vulgare; Triticum aestivum.
- Macias, Francisco A.,Simonet, Ana M.,Esteban, M. Dolores
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p. 1369 - 1380
(2007/10/02)
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- A SULPHATED TRITERPENOID SAPONIN FROM SCHEFFLERA OCTOPHYLLA
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Dried leaves of Schefflera octophylla afforded a new sulphated triterpene glycoside.From spectroscopic data and chemical transformations the structure of the new constituent was determined as 3-epi-betulinic acid 3-O-sulphate 28-O-4)-O-β-D-glucopyranosyl(1->6)>-β-D-glucopyranoside.Key Word Index - Schefflera octophylla; Araliaceae; lupane glycoside 3-O-sulphate.
- Sung, T. V.,Adam, G.
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p. 2717 - 2720
(2007/10/02)
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- ORGANIC PHOTOCHEMISTRY- PART II, PHOTOCHEMICAL SYNTHESIS OF THE NATURALLY OCCURING TRITERPENE LACTONE, 3β-HYDROXY LUPAN-28,13β-OLIDE
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The photochemical synthesis of the title lactone was achieved by irradiation in the presence of Pb(IV) acetate alone or Pb(IV) acetate + calcium carbonate + iodine or mercuric oxide + iodine.Chiroptical measurements (CD) of this and other related lactones provided convincing evidence in support of the lactone ring structure.
- Nag, Swapan K.,Bose, Samarendra N.
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p. 2855 - 2856
(2007/10/02)
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- α-L-RHAMNOPYRANOSYL-3β-HYDROXY-LUP-20(29)-EN-28-OIC ACID FROM THE STEM OF DILLENIA PENTAGYNA
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Key Word Index: Dillenia pentagyna; Dilleniaceae; α-L-rhamnopyranosyl-3β-hydroxy-lup-20(29)-en-28-oic acid; a new saponin.
- Tiwari, Kamala P.,Srivastava, Savitri D.,Srivastava, Santosh K.
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p. 980 - 981
(2007/10/02)
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- Triterpene constituents of Tabernaemontana laurifolia and Haplophyton cimicidum
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The triterpene bauerenyl acetate was isolated directly by crystallization from the non-polar neutral extract of the bark of Tabernaemontana laurifolia D.C. A similar extract of Haplophyton cimicidum (whole plant) yielded, after chromatography, the triterpenes erythrodiol monostearate, bauerenol and betulin, as well as the steroid β-sitosterol.
- Cava,Shubber,Rao, Kota V.
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p. 1301 - 1303
(2007/10/12)
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