8-O-4'-Neolignans from flower buds of Magnolia fargesii and their biological activities

Abstract

Três novos derivados de 8-O-4'-neolignanas, fargesifenols A-C, juntamente com seis neolignanas conhecidas, foram isoladas de botões de flores de Magnolia fargesii. As estruturas foram elucidadas por métodos espectroscópicos, incluindo técnicas de RMN 1D e 2D. Os compostos foram também testados quanto à sua atividade anti-HIV-1 e quanto às citotoxicidades.Three new 8-O-4'-neolignans, fargesiphenols A-C, together with six known neolignans, were isolated from the flower buds of Magnolia fargesii. The structures were elucidated by spectroscopic methods, including extensive 1D and 2D-NMR techniques. Compounds were also tested for their anti-HIV-1 activities and cytotoxicities.

Lignans Isolated From Flower Buds of Magnolia fargesii Attenuate Airway Inflammation Induced by Cigarette Smoke in vitro and in vivo

“…The Magnolia genus of herbs has been traditionally used to treat inflammatory diseases such as headache, sinusitis, and allergic rhinitis ( Gao et al, 2012 ). In particular, the dried flower buds of M. fargesii , or Xinyi, exhibit efficacy in treating airway inflammatory diseases including asthma, bronchitis, and emphysema ( Park et al, 2012 ; Oh et al, 2016 ).…”

Insights into the inhibitory activities of neolignans and diarylnonanoid derivatives from nutmeg ( Myristica fragrans Houtt.) seeds on soluble epoxide hydrolase using in vitro and in silico approaches

“…However, the absolute configuration of this compound has not yet been elucidated. The optical rotation of 16 ([α] −24.4 in CHCl 3 and −27.6 in MeOH) was opposite to those of fargesiphenol A ([α] +38.5 in MeOH), fargesiphenol B ([α] +41.2 in MeOH), and fargesiphenol C ([α] +42.5 in MeOH), suggesting 7 R ,8 R -configuration 37 . The absolute configuration of 16 was verified through the presence of a negative Cotton effect observed in the 237–240 nm region instead of the positive effect in fargesiphenols A–C ( Figure S2.11 ) 37 .…”

“…The optical rotation of 16 ([α] −24.4 in CHCl 3 and −27.6 in MeOH) was opposite to those of fargesiphenol A ([α] +38.5 in MeOH), fargesiphenol B ([α] +41.2 in MeOH), and fargesiphenol C ([α] +42.5 in MeOH), suggesting 7 R ,8 R -configuration 37 . The absolute configuration of 16 was verified through the presence of a negative Cotton effect observed in the 237–240 nm region instead of the positive effect in fargesiphenols A–C ( Figure S2.11 ) 37 . Thus, the structure of 16 was clearly established as (7 R ,8 R )-1–(4′-hydroxy-3′-methoxyphenyl)-1-methoxy-2–(2″-methoxy-4″-(1‴-( E )-propenyl)-phenoxy) propane.…”

Antiviral Fluorenone Derivatives from Arundina gramnifolia

“…The S configuration at C-2' was assigned by a comparison of NMR and optical rotation data with those of stachylines A 10 , of which absolute configuration was established by the Mosher method. Since certain of the phenolic compounds exhibit potential cytotoxicity [15][16][17] . Compound 1 was tested for their cytotoxicity against five human tumor cell lines (NB4, A549, SHSY5Y, PC3 and MCF7) using the MTT method as reported previously 18 .…”