Bioactive Asarone-Derived Phenylpropanoids from the Rhizome of Acorus tatarinowii Schott

Abstract

Eight new (1a/1b, 2a, 3a, 4a/4b, and 5a/5b) and seven known (2b, 3b, and 6-10) asarone-derived phenylpropanoids, a known asarone-derived lignan (12), and four known lignan analogues (11 and 13-15) were isolated from the rhizome of Acorus tatarinowii Schott. The structures were elucidated via comprehensive spectroscopic analyses, modified Mosher's method, and quantum chemical calculations. Compounds 1-8 were present as enantiomers, and 1-5 were successfully resolved via chiral-phase HPLC. Compounds 1a/1b were the first cases of asarone-derived phenylpropanoids with an isopropyl C-3 side-chain tethered to a benzene core from nature. Hypoglycemic, antioxidant, and AChE inhibitory activities of 1-15 were assessed by the α-glucosidase inhibitory, ORAC, DPPH radical scavenging, and AChE inhibitory assays, respectively. All compounds except 3a showed α-glucosidase inhibitory activity. Compound 3b has the highest α-glucosidase inhibitory effect with an IC of 80.6 μM (positive drug acarbose IC of 442.4 μM). In the antioxidant assays, compounds 13-15 exhibited ORAC and DPPH radical scavenging activities. The results of the AChE inhibitory assay indicated that all compounds exhibited weak AChE inhibitory activities.

Tatarinan T, an α‐asarone‐derived lignin, attenuates osteoclastogenesis induced by RANKL via the inhibition of NFATc1/c‐Fos expression

“…It has been reported that the rhizome extract of Acorus tatarinowii Schott possesses various biological activities including hypoglycemic, antioxidant, anticonvulsive, antimicrobial, and anti‐epileptic properties, and activity against Alzheimer's disease (Gao et al, ). In previous studies, we found that the α‐asarone‐derived lignins extracted from Acorus tatarinowii Schott rhizome, TO and TN, can effectively inhibit RANKL‐induced osteoclastogenesis.…”

“…Employed as a traditional Chinese medicine, the rhizome of Acorus tatarinowii Schott has low toxicity and is used to treat dementia, central nervous system‐associated disorders, rheumatosis, and other inflammatory diseases (Xu et al, ; Gao et al, ; Tian et al, ). Previous studies have investigated several extracts from Acorus tatarinowii Schott and found that the lignin‐like components, TO (Xu et al, ) and TN (Zhang et al, ), can both inhibit osteoclastogenesis; however, Tatarinan U (TU) and Tatarinan V (TV) lack this suppressive activity.…”

New Drimane Sesquiterpenes and Polyketides from Marine-Derived Fungus Penicillium sp. TW58-16 and Their Anti-Inflammatory and α-Glucosidase Inhibitory Effects

“…The α -glucosidase inhibitory assay was conducted as per a previous report [ 34 ]. Acarbose was used as the positive control.…”

Nonsurgical treatment of chronic subdural hematoma with Chinese herbal medicine

“…[ 28 ] Modern pharmacologic studies have shown that extract of A tatarinowii Schott has a variety of biologic activities, such as antioxidant, anti-Alzheimer disease, antimicrobial, anticonvulsive, and antiepileptic effects. [ 29 ] Nevertheless, there is little evidence about of the potential mechanism of Chinese herbs for CSDH. The high proportions of L heterophyllus Sweet, S persicae , and A tatarinowii Schott which included in a single prescription suggested that they may play a crucial role in promoting CSDH absorption.…”