Elsevier

Phytochemistry

Volume 29, Issue 12, 1990, Pages 3931-3933
Phytochemistry

Hydroxycinnamic acid amides from Iochroma cyaneum

https://doi.org/10.1016/0031-9422(90)85363-KGet rights and content

Abstract

Three hydroxycinnamic acid amides were isolated from the herb of Iochroma cyaneum and identified by means of spectral data and hydrolysis as caffeoylputrescine (paucine), feruloylputrescine (subaphylline) and the new N1,N10-di-dihydrocaffeoylspermidine.

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    N1- and N8-coumaroyl and feruloyl spermidines were detected in Solanum dulcamara (Panagabko et al., 2000). Di-substituted open chain spermidines such as N1, N5-di-dihydrocaffeoylspermidine or N5, N10-di-dihydrocaffeoylspermidine (Gancel et al., 2008; Rodrigues et al., 2013), N1, N10-di-dihydrocaffeoylspermidine (Sattar et al., 1990; Gancel et al., 2008; Narvaez-Cuenca et al., 2013; Long et al., 2014), N1, N10-di-benzoylspermidine (Alemayehu et al., 1988), N1-methoxycaffeoyl, N10-dihydrocaffeoylspermidine (scotanamine B) (Long et al., 2014), N1, N10-di-dihydroferuloylspermidine (scotanamine C) (Long et al., 2014), N1-(E)-caffeoyl, N10-dihydrocaffeoylspermidine (scotanamine D) (Long et al., 2014; Yahia et al., 2020; Chen et al., 2021), N1-(E)-caffeoyl, N10-dihydrocaffeoylspermidine (Long et al., 2014; Zhao et al., 2014), and N1, N10-ditigiloylspermidine (Schimming et al., 2005) have been found. Scotanamine B exhibited analgesic effects, with moderate agonist activity at the µ-opioid receptor (EC50 = 7.3 µM) and induced analgesia in mice (Long et al., 2014).

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    Such compounds were already known to be potential antifungal agents [87], but it was the first report about the antitumor potential of this class. Sattar et al. reported a new spermidine amide, named as N1,N10-di-dihydrocaffeoylspermine (218) along with two known spermidine amides feruloylputrescine (219) and caffeoylputrescine (220) from the herb of Iochroma cyaneum [88]. Three novel hydroxycinnamic acid amides containing spermidine and putrescine moieties and known compound N1,N10-di-dihydrocaffeoylspermidine (224) were isolated from the root of Scopolia tangutica [89].

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