Citation: Zhengyi Shi, Jie Yin, Yang Xiao, Zhangrong Hou, Fei Song, Jianping Wang, Qingyi Tong, Changxing Qi, Yonghui Zhang. Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ[J]. Chinese Chemical Letters, ;2024, 35(10): 109458. doi: 10.1016/j.cclet.2023.109458 shu

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

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China

qytong@hust.edu.cn

qichangxing@hust.edu.cn

zhangyh@mails.tjmu.edu.cn

Received Date: 31 October 2023
Revised Date: 22 December 2023
Accepted Date: 22 December 2023
Available Online: 29 December 2023

Figures(4)

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.
- PPAP adduct,
- Single-crystal X-ray diffraction,
- Keto-enol tautomerism,
- Plausible biosynthetic pathway,
- Cytotoxic activity
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