Indole alkaloids as systematic markers of the Apocynaceae

Bolsani, Vanderlan Da S.; Silva, Maria Fátima Das G.F. Da; Rocha, Arnaldo I. Da; Gottlieb, Otto R.

doi:10.1016/0305-1978(84)90029-2

Cited by 13 publications

(5 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…It is especially rich in complex mixtures of monoterpenic indole alkaloids and several Brazilian native species have been chemically investigated being good candidates to furnish cholinesterase inhibitory compounds (Batina et al 2000, Batista et al 1996, Bolzani et al 1984, Cardoso and Vilegas 1999, Cardoso et al 1997, 1998, Kato et al 2002, Lemos et al 1996, Marques et al 1996, Medeiros et al 1999, Monnerat et al 2005, Pereira et al 2004, Rattmann et al 2005, Zocoler et al 2005.…”

Section: Introductionmentioning

confidence: 99%

Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

Vieira

Medeiros

Monnerat

et al. 2008

An. Acad. Bras. Ciênc.

View full text Add to dashboard Cite

The pharmacotherapy for Alzheimer's disease (AD) includes the use of acetylcholinesterase inhibitors (AChEI). Recent investigations for novel AD therapeutic agents from plants suggested that Tabernaemontana genus is a promising source of novel anticholinesterasic indole alkaloids. In this work two fast screening techniques were combined in order to easily identify novel cholinesterase inhibitors (ChEI). Gas chromatography-mass spectrometry (GC-MS) of the less polar alkaloidic fractions obtained from the acid-base extraction of the stalk of T. laeta revealed thirteen monoindole alkaloids, four of them confirmed by co-injection with previously isolated alkaloids. The others were tentatively identified by mass fragmentation analysis. By gas chromatography with flame ionization detection (GC-FID) and using isatin as internal standard, affinisine and voachalotine were determined as major compounds. These fractions and fourteen previously isolated alkaloids, obtained from root bark of T. laeta and T. hystrix were investigated for acetyl (AChE) and butyrylcholinesterase (BuChE) inhibitory activities by the modified Ellman's method in thin layer chromatography (TLC-ChEI). Results showed selective inhibition of the alkaloids heyneanine and N b -methylvoachalotine for BuChE, and 19-epi-isovoacristine for AChE, whereas olivacine, affinisine, ibogamine, affinine, conodurine and hystrixnine inhibited both enzymes. In addition to confirming that monoterpenoid indole alkaloids can be novel therapeutic agents for AD, this is the first report of the ChEI activity of olivacine, a pyridocarbazole alkaloid.

show abstract

Section: Introductionmentioning

confidence: 99%

Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

Vieira

Medeiros

Monnerat

et al. 2008

An. Acad. Bras. Ciênc.

View full text Add to dashboard Cite

show abstract

“…General comments: Rich in indole alkaloids, glycosides and glycoalkaloids, cardioactive, anticancer, broad antimicrobial activity, ornamental (Bolzani & al. 1984;Akyalçin & al.…”

Section: Statusmentioning

confidence: 99%

Flora of Greece Volume 1. Apocynaceae: Amsonia (ed. 1)

Goula

2023

View full text Add to dashboard Cite

Description: Annual or perennial erect herbs, with latex. Leaves alternate, blades without colleters at base. Inflorescence a terminal corymbose or paniculate cyme. Sepals acuminate, without colleters at base within. Corolla blue or bluish, hypocrateriform, with spreading lobes, overlapping to left in bud; tube cylindric, slender, widened above middle; throat hairy. Corona absent. Stamens included, inserted on upper part of corolla tube; filaments short; anthers ovate or oblong, obtuse at base, without sterile basal appendages, free from style head; gynostegium absent. Distinct nectaries absent. Ovary composed of 2 free carpels, with numerous ovules, arranged in 2 series on each placenta; style filiform; style head with a thick ring of hairs at apex and collar at base. Fruit a pair of erect, cylindric-fusiform follicles. Seeds oblong-cylindric, obliquely truncate, glabrous, without coma.

show abstract

“…We have demonstrated such chemical gradients for the members of numerous classes of compounds within various major plant groups. Available evidence refers to carotenoids in algae (Gottlieb, 1989;Teixeira & al., 1990); flavonoids and lignins in land plants (Gottlieb, 1989); steroids in angiosperms (Borin & Gottlieb, 1992); benzylisoquinoline alkaloids in the magnolialean block (Gottlieb, 1989); labdanes in the HDR complex (Gottlieb, 1989); quassinoids and limonoids in Rutales (Silva & al., 1984;Silva & Gottlieb, 1987;Simao & al., 1991); iridoids in Corniflorae, Gentianiflorae, and Lamiiflorae (Kaplan & Gottlieb, 1982); sesquiterpene lactones and polyacetylenes in Araliiflorae and Asteriflorae (Ferreira & Gottlieb, 1982;Emerenciano & al., 1985Emerenciano & al., , 1986Emerenciano & al., , 1987; indole alkaloids in Apocynaceae (Bolzani & al., 1984); quinolizidine alkaloids in Fabaceae (Salatino & Gottlieb, 1983); and terpenoids in Icacinaceae (Kaplan & al., 1991).…”

Section: Chemosystematic Backgroundmentioning

confidence: 99%

A suggested role of galloyl esters in the evolution of dicotyledons

Gottlieb

Kaplan

Kubitzki

1993

TAXON

View full text Add to dashboard Cite

Summary Gottlieb, O. R., Kaplan, M. A. C. & Kubitzki, K.: A suggested role of galloyl esters in the evolution of dicotyledons. – Taxon 42: 539–552. 1993. – ISSN 0040‐0262. Galloyl esters (gallo‐ and ellagitannins), which occur throughout the more primitive members of the Hamamelididae, Dilleniidae and Rosidae (the “HDR complex”), are important chemosystematic markers. Their significance is not limited to their strong protein‐binding activity, as was formerly believed, or to their toxic properties, which have more recently been recognized. They also have powerful electron scavenging properties, thus inhibiting oxidation, a reaction that is fundamental in the synthesis of secondary metabolites. The HDR complex indeed is poor in shikimate‐derived compounds; polyketide, mevalonate, and Krebs cycle‐derived substances, which originate primarily by reactions such as condensation, esterification, and reduction, prevail but lack systematic continuity. The absence of coherent chemosystematic markers reflects the systematic isolation of the orders and superorders in the HDR complex, where phylogenetic relationships are less obvious than in the other dicotyledonous subclasses. Phytoalexins are mostly found in members of the HDR complex that are poor in galloyl esters. In view of their molecular properties (small, planar, highly conjugated molecules) it is suggested that they equally act as antioxidants. The superorders belonging to the subclasses Magnoliidae, Caryophyllidae, and Asteridae, which lack galloyl esters, are endowed with antioxidants of weak efficacy (proanthocyanidins and/or caffeic acid esters) and have a rich array of secondary metabolites, which permits the recognition of major evolutionary lines.

show abstract

Indole alkaloids as systematic markers of the Apocynaceae

Cited by 13 publications

References 16 publications

Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

Flora of Greece Volume 1. Apocynaceae: Amsonia (ed. 1)

A suggested role of galloyl esters in the evolution of dicotyledons

Contact Info

Product

Resources

About