Isolation andBioinspired Synthesis of Lauenones Aand B, Skeleton-Rearranged Diterpenoids with Antiadipogenic Activityfrom <i>Croton laui</i>

Two skeleton-rearranged labdane diterpenoids, lauenones A (<b>1</b>) and B (<b>2</b>) were isolated from <i>Croton laui</i>. Their bioinspired synthesis was accomplished in 9 and 10 steps, respectively, without using any protecting groups. Key steps include a semipinacol rearrangement and a substrate-controlled one-pot reaction cascade involving photooxidation and aldol condensation. Notably, both lauenones A and B exhibit antiadipogenesis in 3T3-L1 adipocytes by downregulating the differentiation factors and liposynthesis enzymes at mRNA transcription and protein expression levels.

Publication Details

Journal
Figshare
Published
2025-02-27
DOI
https://doi.org/10.1021/acs.orglett.5c00445.s001
Primary Topic
Bioactive Natural Diterpenoids Research
Type
article
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article

Isolation andBioinspired Synthesis of Lauenones Aand B, Skeleton-Rearranged Diterpenoids with Antiadipogenic Activityfrom Croton laui

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Bioactive Natural Diterpenoids Research
article

Isolation andBioinspired Synthesis of Lauenones Aand B, Skeleton-Rearranged Diterpenoids with Antiadipogenic Activityfrom Croton laui

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Abstract

Two skeleton-rearranged labdane diterpenoids, lauenones A (<b>1</b>) and B (<b>2</b>) were isolated from <i>Croton laui</i>. Their bioinspired synthesis was accomplished in 9 and 10 steps, respectively, without using any protecting groups. Key steps include a semipinacol rearrangement and a substrate-controlled one-pot reaction cascade involving photooxidation and aldol condensation. Notably, both lauenones A and B exhibit antiadipogenesis in 3T3-L1 adipocytes by downregulating the differentiation factors and liposynthesis enzymes at mRNA transcription and protein expression levels.

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Openalex Percentile: Top 61%
Bioactive Natural Diterpenoids Research
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Isolation andBioinspired Synthesis of Lauenones Aand B, Skeleton-Rearranged Diterpenoids with Antiadipogenic Activityfrom <i>Croton laui</i> · Figshare (2025) | TGRS Research Map | TGRS