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Discovery of four modified classes of triterpenoids delineated a metabolic cascade: compound characterization and biomimetic synthesis.

ABSTRACT: Chemical studies on Dichapetalum gelonioides have afforded 18 highly modified complex triterpenoids belonging to four compound classes as defined by the newly adapted functional motifs associated with the A ring of the molecules. Their structures were determined by solid data acquired by diverse methods. The biosynthetic pathway for the four compound classes was rationalized via cascade modifications involving diverse chemical events. The subsequent biomimetic syntheses afforded all the desired products, including compounds 16 and 19 that were not obtained in our purification, which validated the proposed biosynthetic pathway. Besides, some compounds exhibited strong cytotoxic activities, especially 2 and 4 showed nanomolar potency against the NAMALWA tumor cell line, and a gross structure-activity relationship (SAR) of these compounds against the tested tumor cell lines was delineated.

SUBMITTER: Zhou B

PROVIDER: S-EPMC8293979 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Discovery of four modified classes of triterpenoids delineated a metabolic cascade: compound characterization and biomimetic synthesis.

Zhou Bin B Gao Xin-Hua XH Zhang Min-Min MM Zheng Cheng-Yu CY Liu Hong-Chun HC Yue Jian-Min JM

Chemical science 20210618 28

Chemical studies on <i>Dichapetalum gelonioides</i> have afforded 18 highly modified complex triterpenoids belonging to four compound classes as defined by the newly adapted functional motifs associated with the A ring of the molecules. Their structures were determined by solid data acquired by diverse methods. The biosynthetic pathway for the four compound classes was rationalized <i>via</i> cascade modifications involving diverse chemical events. The subsequent biomimetic syntheses afforded al ...[more]

PMID: 34349957

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Project description:Tumor heterogeneity, immune-suppressive microenvironment and the precise killing of tumor cells by drugs are important factors affecting tumor treatment. In this study, we developed environment-responsive drug delivery system (FM@IQ/PST&ZIF-8/DOX) based on ZIF-8 for tumor photothermal/immunotherapy/chemotherapy synergistic therapy. The prepared FM@IQ/PST&ZIF-8/DOX nanoplatfrom not only has highly drug loading capacity for chemotherapeutic drug-doxorubicin, but also erythrocyte membrance modified on their surface can endow their immunity-escaping property and prolong their blood circulation time. More important, the neurotransmitter serotonin was encapsulated on the surface of ZIF-8/DOX by oxidative polymerization, which can effectively avoid the premature leakage of DOX in the blood circulation. And the formed polyserotonin shell has superior photothermal conversion performance, as well as the adsorption property of polyserotonin shell was utilized to load imiqumod. When FM@IQ/PST&ZIF-8/DOX entered the tumor tissue, the surface modified folate molecules can specifically bind to the folate receptors on the surface of tumor cells to improve FM@IQ/PST&ZIF-8/DOX uptake by tumor cells. In vitro and in vivo results showed that FM@IQ/PST&ZIF-8/DOX nanoplatform could generate a large amount of heat under near-infrared light irradiation, and then induce the apoptosis of tumor cells, release tumor associated antigens, and effectively solve the problem of tumor heterogeneity. In addition, the loaded imiquimod could effectively improve the immunosuppressive microenvironment, enhance the body's anti-tumor immune response, to inhibit tumor metastasis and recurrence. Therefore, the novel FM@IQ/PST&ZIF-8/DOX nanoplatform designed in this research can not only achieve controllable and precise drug release, but also it is expected to become a promising new strategy for tumor treatment and provide corresponding inspiration for the later research and development of environment-responsive drugs.

Dataset Information

Discovery of four modified classes of triterpenoids delineated a metabolic cascade: compound characterization and biomimetic synthesis.

Publications

Discovery of four modified classes of triterpenoids delineated a metabolic cascade: compound characterization and biomimetic synthesis.

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