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Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ

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Chinese Chemical Letters 2024年第10期35卷 331-334页

作者： Zhengyi Shi Jie Yin Yang Xiao Zhangrong Hou Fei Song Jianping Wang Qingyi Tong Changxing Qi Yonghui Zhang Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation School of Pharmacy Tongji Medical College Huazhong University of Science and Technology

Monosescinol A(1), the first example of sesquiterpene–polycyclic polyprenylated acylphloroglucinol(PPAP) adduct, which represented a new subclass of PPAP-type natural products, along with two new congeners with normal spiro 6/6/5 tricyclic architecture, were isolated from Hypericum longistylum. Monosescinol A possessed an unprecedented 6/5/5/6/6 pentacyclic carbon skeleton that might be assembled from the 6/6/5 carbon skeleton, via the splitting decomposition of C-3/C-14, and the attack from the C-3 in the PPAP core to C-28 in sesquiterpene section. In addition, we have firstly confirmed that 24R configuration was existed in sec–Bu containing PPAPs by single crystal diffraction data analysis of monosescinol B(2), that might provide an enlightenment in the configurational determination of sec–Bu containing PPAPs. Significantly, further pharmacological research has found that compound 1 exhibited remarkable pharmacological effects against acute myeloid leukemia(AML) cell lines, with direct inhibition of mitochondrial complex V and an increase in mitochondrial membrane potential, and led to an induction of oxidative stress, endogenous inflammation, and apoptosis of AML cells.

关键词： Cytotoxic activity Keto-enol tautomerism plausible biosynthetic pathway PPAP adduct Single-crystal X-ray diffraction

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Flavidanolides A and B from Isodon flavidus

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中国化学快报:英文版 2023年第9期34卷 160-164页

作者： Jiang-Hai Ye Guo-Yong Luo Chen-Liang Zhao Zheng-Ming Liang Jin-Huai Wei Ya-Hua Liu Kang He Lu-Tai Pan Jing-Jie Zhang Juan Zou Hong-Jie Zhang School of Pharmacy Guizhou University of Traditional Chinese MedicineGuiyang 550025China School of Chinese Medicine Hong Kong Baptist UniversityHong Kong SAR 999077China

A phytochemical investigation on Isodon flavidus led to the isolation of flavidanolide A(1),a rearranged diterpenoid featuring a six/seven/five-membered tricyclic skeleton,together with flavidanolide B(2),an uncommon heterodimeric diterpenoid consisting of a norabietane and a seco-isopimarane monomeric *** structures were elucidated by extensive spectroscopic data and single-crystal X-ray diffraction *** plausible biosynthetic routes were also *** the bioassay,flavidanolide B was found to exhibit good inhibitory effect against lipopolysaccharide(LPS)-induced nitric oxide(NO)production in RAW264.7 cells comparable to positive control pyrrolidinedithiocarbamate ammonium(PDTC),which provided evidence for the medicinal value of *** as a folk medicine for treating inflammatory diseases.

关键词： Isodon flavidus Rearranged six/seven/five-membered skeleton Heterodimeric diterpenoid plausible biosynthetic pathway Antiinflammatory effects

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