New Synthesis of Allobetulin 3-O-Acylates

Левданский, А.В.; Kondrasenko, Alexandеr A.; Levdanskii, V. A.; Кузнецов, Б. Н.

doi:10.1007/s10600-018-2483-z

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“…Regarding the configuration of H-18, the hydrogen atom at C-18 of allobetulin is in α-configuration rather than β-configurationin oleanane-type triterpenoids [20]. Allobetulin (5) is converted from the rearrangement reaction of botulin [21][22][23]. Therefore, allobetulin (5) not only belongs to the oleanane terpenoidsbut also as a "re-arranged"betulin derivative [24].…”

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confidence: 99%

Synthesis and Biological Evaluation of Novel Allobetulon/Allobetulin–Nucleoside Conjugates as AntitumorAgents

et al. 2022

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Allobetulin is structurally similar tobetulinic acid, inducing the apoptosis of cancer cells with low toxicity. However, both of them exhibited weak antiproliferation against several tumor cell lines. Therefore, the new series of allobetulon/allobetulin–nucleoside conjugates 9a–10i were designed and synthesized for potency improvement. Compounds 9b, 9e, 10a, and 10d showed promising antiproliferative activity toward six tested cell lines, compared to zidovudine, cisplatin, and oxaliplatin based on their antitumor activity results. Among them, compound 10d exhibited much more potent antiproliferative activity against SMMC-7721, HepG2, MNK-45, SW620, and A549 human cancer cell lines than cisplatin and oxaliplatin. In the preliminary study for the mechanism of action, compound 10d induced cell apoptosis and autophagy in SMMC cells, resulting in antiproliferation and G0/G1 cell cycle arrest by regulating protein expression levels of Bax, Bcl-2, and LC3. Consequently, the nucleoside-conjugated allobetulin (10d) evidenced that nucleoside substitution was a viable strategy to improve allobetulin/allobetulon’s antitumor activity based on our present study.

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