Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking
Jinyan Zhang, Fen Liu, Qian Jin, Xueyi Li, Qiong Zhan, Mu Chen, Sisi Wang, Zhen‐Long Wu, Wen‐Cai Ye, Lei Wang
Abstract
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.