Recent progress in the chemistry of the monoterpenoid indole alkaloids

Saxton, J. E.

doi:10.1039/np9951200385

Cited by 44 publications

(19 citation statements)

References 374 publications

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“…Tubotaiwine is a member of the aspidospermatan alkaloids. The formation of the aspidospermatan alkaloids is biogenetically related to that of the strychnan alkaloids [32,33]. Fluorocarpamine and pleiocarpamine belong to ajmaline-sarpagine type alkaloids [32], generated in a number of steps from a dehydrogeissoschizine precursor via the early intermediate polyneuridine aldehyde [27].…”

Section: Effect Of Elicitation On Alkaloid Accumulationmentioning

confidence: 99%

“…The formation of the aspidospermatan alkaloids is biogenetically related to that of the strychnan alkaloids [32,33]. Fluorocarpamine and pleiocarpamine belong to ajmaline-sarpagine type alkaloids [32], generated in a number of steps from a dehydrogeissoschizine precursor via the early intermediate polyneuridine aldehyde [27]. Vallesiachotamine biosynthesis is initiated directly from deglycosylated strictosidine, a dialdehyde, which is not a common intermediate of TIA biosynthesis [34].…”

Section: Effect Of Elicitation On Alkaloid Accumulationmentioning

confidence: 99%

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Methyljasmonate Elicitation Increases Terpenoid Indole Alkaloid Accumulation in Rhazya stricta Hairy Root Cultures

Akhgari

Laakso

Maaheimo

et al. 2019

Plants

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Methyl jasmonate is capable of initiating or improving the biosynthesis of secondary metabolites in plants and therefore has opened up a concept for the biosynthesis of valuable constituents. In this study, the effect of different doses of methyl jasmonate (MeJA) elicitation on the accumulation of terpenoid indole alkaloids (TIAs) in the hairy root cultures of the medicinal plant, Rhazya stricta throughout a time course (one-seven days) was investigated. Gas chromatography-mass spectrometry (GC-MS) analyses were carried out for targeted ten major non-polar alkaloids. Furthermore, overall alterations in metabolite contents in elicited and control cultures were investigated applying proton nuclear magnetic resonance (1H NMR) spectroscopy. Methyl jasmonate caused dosage- and time course-dependent significant rise in the accumulation of TIAs as determined by GC-MS. The contents of seven alkaloids including eburenine, quebrachamine, fluorocarpamine, pleiocarpamine, tubotaiwine, tetrahydroalstonine, and ajmalicine increased compared to non-elicited cultures. However, MeJA-elicitation did not induce the accumulation of vincanine, yohimbine (isomer II), and vallesiachotamine. Furthermore, principal component analysis (PCA) of 1H NMR metabolic profiles revealed a discrimination between elicited hairy roots and control cultures with significant increase in total vindoline-type alkaloid content and elevated levels of organic and amino acids. In addition, elicited and control samples had different sugar and fatty acid profiles, suggesting that MeJA also influences the primary metabolism of R. stricta hairy roots. It is evident that methyl jasmonate is applicable for elevating alkaloid accumulation in “hairy root” organ cultures of R. strica.

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Section: Effect Of Elicitation On Alkaloid Accumulationmentioning

confidence: 99%

Section: Effect Of Elicitation On Alkaloid Accumulationmentioning

confidence: 99%

Methyljasmonate Elicitation Increases Terpenoid Indole Alkaloid Accumulation in Rhazya stricta Hairy Root Cultures

Akhgari

Laakso

Maaheimo

et al. 2019

Plants

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“…Monoterpenic indole alkaloids have been extensively investigated for exhibiting numerous biological activities (such as anti-tumor, anti-microbial, anti-hypertensive or as a central nervous system stimulant) (Andrade et al 2005, Saxton 1997). They can be found in plants of the Apocynaceae, Rubiaceae, and Loganiaceae families and a few have recently been reported as ChEI by different research groups (Hostettmann et al 2006).…”

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.

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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.

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“…Monoterpene indole alkaloids (MIAs) are undoubtedly an important class of natural products that have attracted much attention due to their structural diversity and remarkable biological activity. [1][2][3][4] The genus Melodinus (Apocynaceae) contains 53 species all over the world, 11 of which are mainly distributed in southern China and some of them have been used to treat conditions such as bellyache, dyspepsia, orchitis, and rheumatic heart disease and as a Chinese folk medicine. 5 It has been demonstrated that plants of the genus Melodinus are rich in MIAs.…”

Section: Introductionmentioning

confidence: 99%

Melodinines Y₁–Y₄, four monoterpene indole alkaloids from Melodinus henryi

Zhang

Feng

et al. 2021

RSC Adv.

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Recent progress in the chemistry of the monoterpenoid indole alkaloids

Cited by 44 publications

References 374 publications

Methyljasmonate Elicitation Increases Terpenoid Indole Alkaloid Accumulation in Rhazya stricta Hairy Root Cultures

Methyljasmonate Elicitation Increases Terpenoid Indole Alkaloid Accumulation in Rhazya stricta Hairy Root Cultures

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

Melodinines Y₁–Y₄, four monoterpene indole alkaloids from Melodinus henryi

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Recent progress in the chemistry of the monoterpenoid indole alkaloids

Cited by 44 publications

References 374 publications

Methyljasmonate Elicitation Increases Terpenoid Indole Alkaloid Accumulation in Rhazya stricta Hairy Root Cultures

Methyljasmonate Elicitation Increases Terpenoid Indole Alkaloid Accumulation in Rhazya stricta Hairy Root Cultures

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

Melodinines Y1–Y4, four monoterpene indole alkaloids from Melodinus henryi

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Melodinines Y₁–Y₄, four monoterpene indole alkaloids from Melodinus henryi