A New Norsesquiterpenoid from the Roots of Ligularia Fischeri

Abstract

A new norsesquiterpenoid, (4aS,5S)-5,6,7,8-tetrahydro-3-hydroxy-4a,5-dimethylnaphthalen-2(4aH)-one, along with three known compounds were isolated from the roots of Ligularia fischeri. Their structures were identified by IR, EI-MS, HR-ESI-MS, 1D NMR and 2D NMR.

Discovery of Antifungal Norsesquiterpenoids from a Soil-Derived Streptomyces microflavus: Targeting Biofilm Formation and Synergistic Combination with Amphotericin B against Yeast-like Fungi

“…1 H– 1 H COSY correlations between 1-OH/H-1/H-2/H-3/H-4/H 3 -10 and between H-5/H-6/H-7/H-8 further confirmed the planar structure of 16 (Figure A). 16 is a trinoreremophilane-type sesquiterpenoid, and several related trinoreremophilanes were reported from the plant. − To our knowledge, this is the first time to report a trinoreremophilane isoated from bacteria origin. The key correlations of protons in NOE spectra of 16 determined in DMSO- d 6 were indistinct.…”

Robinson Annulation Applied to the Total Synthesis of Natural Products

“…[211] Another natural derivative, (4aS,5S,8R)-5,6,7,8tetrahydro-3,8-dihydroxy-4a,5-dimethylnaphthalen-2(4aH)-one was effectively extracted from the roots of Ligularia sagittal by this research group in 2008. [212] In 2010, the Shen et al extracted a new natural product, (4aS,5S)-5,6,7,8-tetrahydro-3-hydroxy-4a,5-dimethylnaphthalen-2(4aH)-one, [213] while examining effective ingredients from the roots of Ligularia fischeri. In addition, six novel eremophilanes, involving nigriterpene D, were extracted from termite-nest-derived medicinal fungus Xylaria nigripes by Lee et al [214] Liu et al in 2018 reported the first total syntheses of five natural eremophilane-type sesquiterpenoids in 4-12 steps from the usual intermediate 227.…”

“…In 2010, the Shen et al . extracted a new natural product, (4aS,5S)‐5,6,7,8‐tetrahydro‐3‐hydroxy‐4a,5‐dimethylnaphthalen‐2(4a H )‐one, [213] while examining effective ingredients from the roots of Ligularia fischeri. In addition, six novel eremophilanes, involving nigriterpene D, were extracted from termite‐nest ‐derived medicinal fungus Xylaria nigripes by Lee et al [214] …”

Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites

“…The structure of a new nor-sesquiterpenoid was isolated from the roots of the perennial herb Ligularia fischeri collected in Nanchuan county of Chongqing city in China. The new compound was determined to be (4aS,5S)-5,6,7,8-tetrahydro-3-hydroxy-4a,5dimethylnaphthalen-2(4aH)-one (48), a tri-nor-eremophilane sesquiterpene elucidated with the aid of key 1 H, 1 H-COSY and HMBC correlations [193].…”

“…This genus has antipyretic properties, loosens phlegm, relieves cough, invigorates blood circulation and sooths pain. Previous phytochemical studies on the genus Ligularia revealed that it is a rich source of eremophilane derivatives [ 193 , 194 ]. According to Chinese pharmacopoeia, Ligularia has been used to treat hemoptysis, rheumatism, pulmonary tuberculosis, urinary tract blockages, asthma, hepatitis and bronchitis for hundreds of years.…”