Citation: Xue-Jiao Wang, Jun-Li Xin, Hong Xiang, Ze-Yu Zhao, Yu-Hang He, Haibo Wang, Guangyao Mei, Yi-Cheng Mao, Juan Xiong, Jin-Feng Hu. Holotrichones A and B, potent anti-leukemic lindenane-type sesquiterpene trimers with unprecedented complex carbon skeletons from a rare Chloranthus species[J]. Chinese Chemical Letters, ;2024, 35(12): 109682. doi: 10.1016/j.cclet.2024.109682 shu

Holotrichones A and B, potent anti-leukemic lindenane-type sesquiterpene trimers with unprecedented complex carbon skeletons from a rare Chloranthus species

Xue-Jiao Wang ^{a, b} ,
Jun-Li Xin ^b ,
Hong Xiang ^b ,
Ze-Yu Zhao ^{a, b} ,
Yu-Hang He ^b ,
Haibo Wang ^c ,
Guangyao Mei ^c ,
Yi-Cheng Mao ^{b, *,} ,
Juan Xiong ^{b, *,} ,
Jin-Feng Hu ^{a, b, *,}

a.
Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Evolutionary Ecology and Conservation, Taizhou University, Taizhou 318000, China
b.
School of Pharmacy, Fudan University, Shanghai 201203, China
c.
Zhejiang Hongyuan Pharmaceutical Co., Ltd., Linhai 317016, China

Received Date: 13 January 2024
Revised Date: 19 February 2024
Accepted Date: 20 February 2024
Available Online: 1 March 2024

Figures(6)

Two lindenane-type sesquiterpene (LDS) trimers with unprecedented carbon skeletons, holotrichones A (1) and B (2), were obtained from the whole plant of Chloranthus holostegius var. trichoneurus by a ultra performance liquid chromatography-photodiode array detector-mass spectrometry (UPLC-PDA-MS)-guided isolation strategy. Compound 1 represents the first LDS trimer incorporating a unique 3/5/6/6-fused framework, in which a lindenane-type monomer and the 2-methylbutyryl substituent of an LDS dimer is bridged by a six-membered ring system. Compound 2 is the first hetero-trimer fused by an LDS dimer with a p-benzoquinone-meroterpenoid, featuring an unusual 3/5/6/6/3/5/6/6/6 nonacyclic system fused by the sesquiterpenoid unit and a 2-geranyl-6-methyl-2,5-cyclohexadien-1,4-dione moiety. In compound 2, the dimeric LDS moiety is equipped with a rare oxaspiro[4.5]decane system. Their structures, including absolute configurations, were established by spectroscopic methods, GIAO NMR calculations and DP4+ probability analyses, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. The plausible biogenetic pathway speculation indicated that hetero- and homo-Diels-Alder additions may dominate the formation of these highly fused polycyclic frameworks. Both compounds 1 and 2 induced the human acute myeloid leukemia MV-4–11 cell death via apoptosis induction, which deserves further investigation on this new chemical class of LDS oligomers for their anti-leukemic potential.
- Chloranthus holostegius var. trichoneurus,
- Holotrichones,
- Lindenane-type sesquiterpene trimers,
- Acute myeloid leukemia,
- Cell apoptosis
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