Simple synthesis of allobetulin, 28-oxyallobetulin and related biomarkers from betulin and betulinic acid catalysed by solid acids

Li, Tong‐Shuang; Wang, Jianxin; Zheng, Xuejing

doi:10.1039/a806735j

Cited by 62 publications

(53 citation statements)

References 24 publications

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“…A number of interesting rearranged betulinic acid analogs have also been prepared using clay catalysts. 49 Furthermore, microorganisms have been utilized as biocatalysts for the preparation of betulinic acid derivatives. 42,45,46 Results of the microbial transformation studies of betulinic acid are discussed in 'Metabolism.…”

Section: B Derivatizationmentioning

confidence: 99%

Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection

Cichewicz

Kouzi

2003

Medicinal Research Reviews

463

220

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3beta-Hydroxy-lup-20(29)-en-28-oic acid (betulinic acid) is a pentacyclic lupane-type triterpene that is widely distributed throughout the plant kingdom. A variety of biological activities have been ascribed to betulinic acid including anti-inflammatory and in vitro antimalarial effects. However, betulinic acid is most highly regarded for its anti-HIV-1 activity and specific cytotoxicity against a variety of tumor cell lines. Interest in developing even more potent anti-HIV agents based on betulinic acid has led to the discovery of a host of highly active derivatives exhibiting greater potencies and better therapeutic indices than some current clinical anti-HIV agents. While its mechanism of action has not been fully determined, it has been shown that some betulinic acid analogs disrupt viral fusion to the cell in a post-binding step through interaction with the viral glycoprotein gp41 whereas others disrupt assembly and budding of the HIV-1 virus. With regard to its anticancer properties, betulinic acid was previously reported to exhibit selective cytotoxicity against several melanoma-derived cell lines. However, more recent work has demonstrated that betulinic acid is cytotoxic against other non-melanoma (neuroectodermal and malignant brain tumor) human tumor varieties. Betulinic acid appears to function by means of inducing apoptosis in cells irrespective of their p53 status. Because of its selective cytotoxicity against tumor cells and favorable therapeutic index, even at doses up to 500 mg/kg body weight, betulinic acid is a very promising new chemotherapeutic agent for the treatment of HIV infection and cancer.

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Section: B Derivatizationmentioning

confidence: 99%

Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection

Cichewicz

Kouzi

2003

Medicinal Research Reviews

463

220

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“…252-253°C [lit. 255-256°C (Li et al, 1998) (CHCl 3 -EtOAc-MeOH-acetic acid, 10 : 10 : 1 : 0.01), betulin was disubstituted. After cooling, the obtained brownish mass was dissolved in acetone (30 mL) and poured into water (90 mL), heated at 95°C for 2 h, dissolved with water (100 mL), cooled, and then extracted with EtOAc (3 × 50 mL).…”

Section: Isolation and Purifi Cation Of Betulin [Lup-20(29)-en-3b 28mentioning

confidence: 99%

“…Betulin was isolated from birch bark of Betula verrucosa Roth according to Eckerman and Ekman (1985) and Li et al (1998). The triterpene was purifi ed by crystallization from methanol-toluene mixture (4 : 1) and fi nally from acetone.…”

Section: Isolation and Purifi Cation Of Betulin [Lup-20(29)-en-3b 28mentioning

confidence: 99%

Synthesis of betulin derivatives and the determination of their relative lipophilicities using reversed‐phase thin‐layer chromatography

Achrem-Achremowicz

Kępczyńska

Zylewski

et al. 2009

Biomedical Chromatography

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A series of superlipophilic or highly lipophilic semisynthetic betulin derivatives was prepared and their relative lipophilicity was measured by reversed-phase thin-layer chromatography (RP-TLC) at different pH values using 1,4-dioxane-acetate buffer mixtures as mobile phases. Cholesterol, 17beta-estradiol and pure betulin were used as the reference compounds. Linear relationships were found between R(M) values and 1,4-dioxane concentrations in the mobile phases. LogP values were also calculated with computer programs ACD/LogP (ChemSketch 11.0, Advanced Chemistry Development Inc.) and ClogP (Daylight Chemical Information Systems Inc.). The empirical and theoretical data were compared, and the R(M0) values correlated well with logP. Two of the synthesized betulin derivatives are reported for the first time.

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“…Le bétulinol 2, malgré le fait qu'il soit relativement stable, se réarrange lorsqu'il est soumis à certaines conditions acides [Li et al, 1998]. Comme le montre la figure 16, le bétulinol 2 se réarrange en allobétulinol 10 en milieu acide.…”

Section: Réarrangements Du Bétulinolunclassified

Formation de glycoside à partir de l'acide bétulinique /

Gagnon¹

2004

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Simple synthesis of allobetulin, 28-oxyallobetulin and related biomarkers from betulin and betulinic acid catalysed by solid acids

Cited by 62 publications

References 24 publications

Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection

Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection

Synthesis of betulin derivatives and the determination of their relative lipophilicities using reversed‐phase thin‐layer chromatography

Formation de glycoside à partir de l'acide bétulinique /

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