Citation: Jinyan Zhang, Fen Liu, Qian Jin, Xueyi Li, Qiong Zhan, Mu Chen, Sisi Wang, Zhenlong Wu, Wencai Ye, Lei Wang. Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking[J]. Chinese Chemical Letters, ;2024, 35(6): 108881. doi: 10.1016/j.cclet.2023.108881 shu

Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking

Jinyan Zhang ^{a, b, 1} ,
Fen Liu ^{a, b, 1} ,
Qian Jin ^c ,
Xueyi Li ^{a, b} ,
Qiong Zhan ^{a, b} ,
Mu Chen ^{a, b} ,
Sisi Wang ^{a, b} ,
Zhenlong Wu ^{a, b, *,} ,
Wencai Ye ^{a, b, *,} ,
Lei Wang ^{a, b, *,}

a.
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Jinan University, Guangzhou 510632, China
b.
Center for Bioactive Natural Molecules and Innovative Drugs, and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China
c.
College of Pharmacy, Jinan University, Guangzhou 510632, China

zhenlongwu@jnu.edu.cn

chywc@aliyun.com

cpuwanglei@126.com

Received Date: 24 May 2023
Revised Date: 29 July 2023
Accepted Date: 2 August 2023
Available Online: 3 August 2023

Figures(5)

The first phloroglucinol-triterpenoid hybrids, myrtphlotritins A–E (1–5), were rapidly recognized and isolated from two species of Myrtaceae by employing the building blocks-based molecular network (BBMN) strategy. Compounds 1–5 featured new carbon skeletons in which phloroglucinol derivatives were coupled with lupane- and dammarane-type triterpenoids through different linkage patterns. Their structures and absolute configurations were elucidated by comprehensive analysis of spectroscopic data and quantum chemical calculations. Biosynthetic pathways for compounds 1–5 were proposed on the basis of the coexisting precursors. Guided by the biogenetic pathways, the biomimetic synthesis of compound 1 was also achieved. Additionally, compounds 2, 3, and 5 exhibited potent antiviral activities against herpes simplex virus type-1 (HSV-1) infection, and compounds 2 and 5 displayed significant anti-inflammatory activities on RAW264.7 cells.
- Phloroglucinol-triterpenoid adduct,
- Myrtaceae,
- Building blocks-based molecular network,
- Biomimetic synthesis,
- Antiviral activity,
- Anti-inflammatory activity
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