Hydroxycinnamic acid amides from Iochroma cyaneum
References (21)
- et al.
Phytochemistry
(1988) - et al.
Phytochemistry
(1978) - et al.
Tetrahedron Letters
(1980) - et al.
Phytochemistry
(1972) - et al.
J. Chromatogr.
(1979) - et al.
Phytochemistry
(1986) - et al.
C. R. Acad. Sci. (Ser. D)
(1976) - et al.
Physiol. Veg.
(1977) - et al.
C. R. Acad. Sci. (Ser. D)
(1976) - et al.
J. Antibiot.
(1978)
Cited by (18)
Nature spermidine and spermine alkaloids: Occurrence and pharmacological effects
2022, Arabian Journal of ChemistryCitation Excerpt :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).
Amides From Plants: Structures and Biological Importance
2018, Studies in Natural Products ChemistryCitation Excerpt :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].
Spermidine alkaloid from Banara parviflora
2016, Revista Brasileira de FarmacognosiaCitation Excerpt :The 1H and 13C NMR data of the compound N1,N8-dibenzoylspermidine, provided in the literature, were compared to the substance 1 data, here characterized, and the similarity of the signals allowed us to confirm the structure elucidation. Other derivatives of spermidine have also been reported from other plants, such as N1,N10-di-dihydrocaffeoylspermidine from extracts of Iochroma cyaneum, Solanaceae, and a feruloylspermidine of Corylus avellana L., Betulaceae (Meurer et al., 1986; Sattar et al., 1990) as well a siderephore (iron transport compound), parabactin A and its derivatives, from Micrococcus denitrificans and also excreted by the soil bacterium Paracoccus denitrificans, featuring iron chelator properties, this substance acts like a transport system to assimilate iron in the microorganism with a high affinity to the ferric l-parabactin receptor in membranes (Bergeron et al., 1980, 1988). Additionally, a siderophore also very similar to the substance 1, agrobactin was identified as a constituent of Agrobacterium tumefaciens (Ong et al., 1979).
Evolutionary correlations in flavonoid production across flowers and leaves in the Iochrominae (Solanaceae)
2016, PhytochemistryCitation Excerpt :Although the majority of the compounds identified in the methanolic extracts were flavonoids, chlorogenic acid (11) and four major phenolamide compounds were found in petals and leaves of all species: a bis(dihydrocaffeoyl)-spermidine (12), a tris(dihydrocaffeoyl)-spermidine (13), and two N-caffeoyl putrescine isomers (14, 15) (Supplementary Fig. 1). Phenolamides have been previously found in I. cyaneum, as well as other Solanaceae (Sattar et al., 1990). These phenolamides were found in higher concentrations in petals than in leaves.
Putrescine, spermidine, spermine, and related polyamine alkaloids
2002, Alkaloids: Chemistry and Biology