Amide Alkaloids from Scopolia tangutica

Abstract

Four new hydroxycinnamic acid amides, scotanamines A?D (1?4), and seven known alkaloids, including N 1,N 10-di-dihydrocaffeoylspermidine (5), scopolamine (6), anisodamine (7), hyoscyamine (8), anisodine (9), caffeoylputrescine (10), and N 1-caffeoyl-N 3-dihydrocaffeoylspermidine (11), were obtained from the roots of Scopolia tangutica. The present study represents the first recognition of hydroxycinnamic acid amides containing putrescine or spermidine in S. tangutica. Compound 1, in particular, contains a moiety resulting from the condensation of nortropinone and putrescine. Compound 2 exhibited moderate agonist activity at the ?-opioid receptor (EC50?=?7.3??M). Compound 2 was tested in vivo and induced analgesia in mice. The analgesic effect was recorded using the tail-flick assay and was reversed by naloxone.

Hydroxycinnamic acid amides from Scopolia tangutica inhibit the activity of M1 muscarinic acetylcholine receptor in vitro

“…Eleven alkaloids have been isolated from S. tangutica [11, 12]. They include seven HCA amides (1-7): scotanamine A-D (1-4), N 1 , N 10 -di-dihydrocaffeoylspermidine (5), cafeoylputrescine (6), N 1 -caffeoyl-N 3 -dihydrocaffeoylspermidine (7), one cinnamic acid amide: carboxyscotangamine A (8) and three well-known anticholinergic compounds (9-10): scopolamine (9), atropine (10) and anisodine (11).…”

“…An aliquot of 0.1 mL of crude extract sample was applied to the conditioned SCX-based solid phase extraction column. The isolation and identification of pure compounds from S. tangutica are extensively described by our most recent report [12]. Briefly, S. tangutica were extracted by 95% ethanol.…”

“…mAChR antagonists block the transmission of parasympathetic nerve impulses by acetylcholine and consequently lessen the spasms of smooth muscle [9, 10]. Recently we have isolated five new hydroxycinnamic acid (HCA) amides along with two known HCA amides, one cinnamic acid amide from S. Tangutica [11, 12]. The conjugates of HCAs with polyamines have been found in a wide variety of plants and are concentrated in the reproductive organs of many higher plants[13-15].…”

Discovery of new muscarinic acetylcholine receptor antagonists from Scopolia tangutica

“…The elucidation and specific assignments of these compounds were in supporting information. Other known compounds are isolated as scopolamine3940 ( 1 ), anisodamine4142 ( 2 ), hyoscyamine4344 ( 3 ), anisodine31 ( 4 ), N-Caffeoylputrescine364546 ( 14 ), N1,N10-di-dihydrocaffeoylspermidine2147 ( 17 ), Scotanamine D21 (19), and N1-caffeoyl-N3-dihydrocaffeoyl spermidine48 ( 20 )…”

“…First, traditional approaches such as solvent extraction followed by thin-layer chromatography1415 or one-dimensional (1D) high performance liquid chromatography-mass spectrometry (HPLC-MS)161718 often result in isolation and identification of small sets of compounds because of the chemical diversity of many medicinal plants. Second, our recent non-aqueous solid phase extraction (SPE)19 and 2D-HPLC methods20 have resulted in the identification of four hydroxycinnamic acid amides from S. tangutica for the first time21. This study also suggested the presence of a large number of minor alkaloids.…”