Chukfuransins A–D, Four New Phragmalin Limonoids with β-Furan Ring Involved in Skeleton Reconstruction from <i>Chukrasia tabularis</i>

Hu, Kun; Liu, Jie‐Qing; Li, Xiaonian; Chen, Jianchao; Zhang, Weiming; Li, Yan; Li, Liang-qun; Guo, Lin-lin; Ma, Weiguang; Qiu, Ming‐Hua

doi:10.1021/ol401650m

Cited by 17 publications

(4 citation statements)

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“…Slightly-degraded limonoids. Abundant and varied slight fragmentations have been observed in diverse structural type limonoids:16nor type limonoid backbone (Zhang et al 2007a(Zhang et al , 2008, 16,19-dinor degraded limonoid backbone (Liu et al 2012) and some examples have been described where the furan ring is involved in the deconstruction of the common limonoid types (Zhang et al 2008;Hu et al 2013;Liu et al 2014).…”

Section: Melazolidesmentioning

confidence: 99%

Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

et al. 2023

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Phytochemical studies on the roots, twigs and leaves of Meliaceae and Rutaceae family plants have revealed the presence of non-complex terpenes derived from limonoid fragmentation. The occurrence and chemical structure of these degraded limonoids isolated from 1930 to March 2022 are reported in this review. Particular attention is given to the degradation levels in these compounds and their absolute configuration to discover presumable deconstruction pathways from more complex limonoids. Plausible intermediates have been postulated for most of them that would explain their origin from limonoids. The total or semi-synthesis of the most isolated degraded limonoids or analogues remains undescribed. This review focuses on the bioactivity of these fragmented limonoids and their synthesized analogues. Based on pharmacological and agrochemical studies, degraded limonoids appear to be excellent structural leads to consider for the total or semi-synthesis of more potent derivatives with the aim of discovering new hits and clarifying their modes of action.

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Section: Melazolidesmentioning

confidence: 99%

Degraded limonoids: biologically active limonoid fragments re-enhancing interest in Meliaceae and Rutaceae sources

et al. 2023

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“…In another case, the furan ring undergoes isomerization to form an α,β-unsaturated ketone, and cyclization occurs between C-15 and C-20 through a Michael addition mechanism ( 33 , 34 ). 54 …”

Section: Latest Limonoids Discovered From the Meliaceae Familymentioning

confidence: 99%

Research progress of meliaceous limonoids from 2011 to 2021

Luo

Sun

et al. 2022

Nat. Prod. Rep.

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“…These novel phragmalin derivatives are mainly distributed in the genera Chukrasia and Entandrophragma of the Meliaceae (Ansell and Taylor, 1988;Hu et al, 2013;Luo et al, 2009a;Zhang et al, 2007). In previous research, a series of phragmalins with a propionyl or isobutyryl units at C-15 were isolated (Luo et al, 2012;Luo et al, 2009a;Luo et al, 2009b); however, phragmalins with an acetyl unit at C-15 were only isolated as 16-norphragmalin derivatives (Luo et al, 2010).…”

Section: Introductionmentioning

confidence: 98%