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

Zhang, Jinyan; Liu, Fen; Qian, Jin; Li, Xueyi; Zhan, Qiong; Mu, Chunlai; Wang, Sisi; Wu, Zhen‐Long; Ye, Wen-Cai; Wang, Lei

doi:10.1016/j.cclet.2023.108881

Cited by 1 publication

(1 citation statement)

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“…[12] Recently, the building blocks-based molecular network (BBMN) strategy presented by our group further facilitated the efficient discovery of novel alkaloids and phloroglucinol derivatives, which was fulfilled by the integration of the building blocks recognition of target natural products and molecular network dereplication. [13,14] In an ongoing program for exploring novel alkaloids from the genus Alstonia, we had isolated a series of MIAs with diverse structures and broad bioactivities. [15,16] To facilitate the discovery of novel bisindole alkaloids, we carried out an in-depth phytochemical investigation on the stem barks and leaves of Alstonia macrophylla with the guide of the BBMN strategy.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Unusual Ajmaline‐Macroline Type Bisindole Alkaloids from Alstonia macrophylla by Building Blocks‐Based Molecular Networking

Li,

Fan,

Sun

et al. 2023

Chemistry A European J

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Three unusual ajmaline‐macroline type bisindole alkaloids, alsmaphylines A–C, together with their postulated biogenetic precursors, were isolated from the stem barks and leaves of Alstonia macrophylla via the building blocks‐based molecular network (BBMN) strategy. Alsmaphyline A represents a rare ajmaline‐macroline type bisindole alkaloid with an S‐shape polycyclic ring system. Alsmaphylines B and C are two novel ajmaline‐macroline type bisindole alkaloids with N‐1−C‐21′ linkages, and the former possesses an unconventional stacked conformation due to the presence of intramolecular noncovalent interactions. The chemical structures including absolute configurations of alsmaphylines A–C were established by comprehensive spectroscopic analyses, electronic circular dichroism (ECD) calculations, and single‐crystal X‐ray crystallography. In addition, a plausible biosynthetic pathway of these bisindole alkaloids as well as their ability to promote the protein synthesis on HT22 cells were discussed.

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