Ipobscurines C and D: macrolactam-type indole alkaloids from the seeds of Ipomoea obscura

Jenett‐Siems, Kristina; Weigl, Robert; Kaloga, M.; Schulz, Jutta; Eich, Eckart

doi:10.1016/s0031-9422(02)00756-2

Cited by 28 publications

(16 citation statements)

References 20 publications

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“…From that results, the most active subfractions were purified by chromatographic methods affording indolinone and N-substituted tryptamine alkaloid type compounds (1)(2)(3)(4)(5) which chemical structures are shown in Figure 1. In addition, were isolated flavonoids derived from kaempferol and quercetin (6-9), as well was benzoic acid derivatives (10)(11)(12). The structures of the isolated compounds were elucidated by analysis of their NMR spectroscopic data (including NMR 2D) and HR-ESIMS, and by comparison with those reported.…”

Section: Resultsmentioning

confidence: 99%

“…The alkaloids (1-5), flavonoids (6-9) and benzoic acid derivatives (10)(11)(12) were evaluated for their antioxidant activity by the free scavenging DPPH method. The results for compounds 1-5, expressed by IC 50 , are shown in Table 2 ) showed that the hydroxy group at the C-5 of the tryptamine moiety is fundamental for the antioxidant activity of these indole alkaloids.…”

Section: Resultsmentioning

confidence: 99%

“…Soc. 2204 3-methoxybenzoic acid (11) and 4-hydroxy-3,5-dimethoxybenzoic acid (12) 17 from the stem bark of Croton echioides. The in vitro cytotoxicity against the HCT-116 human cancer cell line was determined for the isolated alkaloids 1-5 and the free radical (2,2-diphenyl-1-picrylhydrazyl, DPPH) scavenging activities were also determined for the compounds 1-12.…”

Section: N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine (4)mentioning

confidence: 99%

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Bioactive Indole Alkaloids fromCroton echioides

Novello

Marques

Pires

et al. 2016

Journal of the Brazilian Chemical Society

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Bioguided fractionation of a hydroethanolic extract from the stem bark of Croton echioides Baill. led to isolation of the new indole alkaloid N-trans-feruloyl-3,5-dihydroxyindolin-2-one as a stereoisomeric mixture and the known alkaloids N-trans-p-coumaroyl-tryptamine, N-trans-pcoumaroyl-5-hydroxytryptamine, N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine, N-transferuloyl-5-hydroxytryptamine (moschamine), from the ethyl acetate fraction. The flavonoids 3-o-methyl kaempferol, 3-o-methyl quercetin, 3,7-di-o-methyl quercetin and 3,3'-di-o-methyl quercetin, together with the benzoic acid derivatives 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid and 4-hydroxy-3,5-dimethoxybenzoic acid were also isolated. Alkaloids and the flavonoids showed strong antioxidant properties in vitro radical scavenging assay (2,2-diphenyl-1-picrylhydrazyl, DPPH), with IC 50 values ranging from 9.2 to 17.5 µmol L

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine (4)mentioning

confidence: 99%

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Bioactive Indole Alkaloids fromCroton echioides

Novello

Marques

Pires

et al. 2016

Journal of the Brazilian Chemical Society

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“…Methanolic seed extract of I. obscura afforded indole alkaloids, such as ipobscurines B-D (Jenett-Siems et al, 2003). Active calystegins B1 (16), B2 (17), C1(18) and B3 (19), besides calistegin B4, and were also isolated of this species (Asano et al, 2001;Schimming et al, 1998).…”

Section: Ipomoea Nil (L) Rothmentioning

confidence: 97%

Review of the genus Ipomoea: traditional uses, chemistry and biological activities

Meira¹,

Silva²,

David³

et al. 2012

Rev. bras. farmacogn.

156

120

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Approximately 600-700 species of Ipomoea, Convolvulaceae, are found throughout tropical and subtropical regions of the world. Several of those species have been used as ornamental plants, food, medicines or in religious ritual. The present work reviews the traditional uses, chemistry and biological activities of Ipomoea species and illustrates the potential of the genus as a source of therapeutic agents. These species are used in different parts of the world for the treatment of several diseases, such as, diabetes, hypertension, dysentery, constipation, fatigue, arthritis, rheumatism, hydrocephaly, meningitis, kidney ailments and infl ammations. Some of these species showed antimicrobial, analgesic, spasmolitic, spasmogenic, hypoglycemic, hypotensive, anticoagulant, anti-infl ammatory, psychotomimetic and anticancer activities. Alkaloids, phenolics compounds and glycolipids are the most common biologically active constituents from these plant extracts.

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“…285) (Li et al, 1998), the Convolvulaceae family possesses macrolactam-type indole alkaloids (ipobscurines) (e.g. 248) (Jenett-Siems et al, 2003) and the Euphorbiaceae family contains cyanogenic and non-cyanogenic pyridone derivatives (e.g. 257) (Hungeling et al, 2009).…”

Section: Q10mentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

126

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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Ipobscurines C and D: macrolactam-type indole alkaloids from the seeds of Ipomoea obscura

Cited by 28 publications

References 20 publications

Bioactive Indole Alkaloids fromCroton echioides

Bioactive Indole Alkaloids fromCroton echioides

Review of the genus Ipomoea: traditional uses, chemistry and biological activities

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

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