Aphananoid A is an Anti-Inflammatory Limonoid with a New 5/6/5 Fused Ring Featuring a C₂₄ Carbon Skeleton from Aphanamixis polystachya

Abstract

Aphananoid A, a limonoid which features a rare C 24 appendage and new 5/6/5 fused-ring framework, was obtained from Aphanamixis polystachya. The planar structure as well as the absolute configuration was identified based on extensive spectroscopic analysis and electronic circular dichroism calculations. The biogenetic pathway of aphananoid A was also speculated, which arises from the triterpene by the 3,4-seco-7,8-seco-6,8 cyclo-7,30-decarbon key pattern. In addition, bioassays indicated that aphananoid A inhibited NO production in the RAW264.7 cell line (46.80 ± 1.93%).

Antiinflammatory activity of natural triterpenes—An overview from 2006 to 2021

“…The antiinflammatory potential of hederacoside-C against osteoarthritis was also evaluated (H. C. Aphanamixis polystachya as a novel 5/6/5 fused ring featuring a C 24 carbon skeleton (B. J. Yang, Fan, et al, 2020), was reported to reduce the levels of TNF-α, IL-6, IL-1β, TLR4, and NF-κB.…”

“…Limonoid azadirachtin A ( 272 ), isolated from Azadirachta indica , markedly reduced the levels of TNF‐α, IL‐6, IL‐1β, TLR4, and NF‐κB (He et al, 2020) (Figures 29 and 30). Aphananoid A ( 273 ), isolated from Aphanamixis polystachya as a novel 5/6/5 fused ring featuring a C 24 carbon skeleton (B. J. Yang, Fan, et al, 2020), was reported to reduce the levels of TNF‐α, IL‐6, IL‐1β, TLR4, and NF‐κB.…”

Chemistry and Biology of Novel Meliaceae Limonoids

“…Limonoids (462)(463)(464)(465)(466)(467)(468) are derivatives of compound (461) but differ in substitution at C1 and C23. The furan ring at C17 in 28-deoxonimbolide is replaced by α,β-unsaturated-21-hydroxy γ-lactone ring in limonoid (469). Nimbolide B (470) differs from compound (469) in additional keto carbonyl at C28.…”

Chemistry and Biology of Novel Meliaceae Limonoids

“…Limonoids (462-468) are derivatives of compound (461) but differ in substitution at C1 and C23. The furan ring at C17 in 28-deoxonimbolide is replaced by α,β-unsaturated-21-hydroxy γ-lactone ring in limonoid (469). Nimbolide B (470) differs from compound (469) in additional keto carbonyl at C28.…”

“…The furan ring at C17 in 28-deoxonimbolide is replaced by α,β-unsaturated-21-hydroxy γ-lactone ring in limonoid (469). Nimbolide B (470) differs from compound (469) in additional keto carbonyl at C28. Compounds (471,472,473) are structural analogs of compounds (469, 460, 467) respectively differing in substitution at C17.…”