Pharmacology, Biochemistry, and Clinical Applications of the Monoterpenoid Alkaloids

Creasey, William A.

doi:10.1002/9780470186954.ch14

Cited by 13 publications

(6 citation statements)

References 137 publications

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“…Although macroline 19 has not been isolated as an alkaloid itself, it is believed to be a biogenetic precursor for numerous alkaloids in this class. (+)-Ajmaline 26 , a clinically and historically important alkaloid [20,50,51,52], is structurally related to the sarpagine alkaloids. These three major types of indole alkaloids are inter-related through their biogenetic origin.…”

Section: Biogenetic Relationship Between Sarpagine/macroline/ajmalmentioning

confidence: 99%

Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

2016

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Bisindole natural products consist of two monomeric indole alkaloid units as their obligate constituents. Bisindoles are more potent with respect to their biological activity than their corresponding monomeric units. In addition, the synthesis of bisindoles are far more challenging than the synthesis of monomeric indole alkaloids. Herein is reviewed the enantiospecific total and partial synthesis of bisindole alkaloids isolated primarily from the Alstonia genus of the Apocynaceae family. The monomeric units belong to the sarpagine, ajmaline, macroline, vobasine, and pleiocarpamine series. An up-to-date discussion of their isolation, characterization, biological activity as well as approaches to their partial and total synthesis by means of both synthetic and biosynthetic strategies are presented.

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Section: Biogenetic Relationship Between Sarpagine/macroline/ajmalmentioning

confidence: 99%

Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

2016

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“…Tryptamine is an b-arylethylamine whereas secologanin is a monoterpenoid aldehyde. Such a condensation of an amine and aldehyde is called a Pictet-Spengler type reaction (Pictet and Spengler 1911), it is completely stereo-selective and functions as the (Creasey 1994) discussed here. In conclusion, STR1 and the enzyme which follows STR1 in the pathway, strictosidine glucosidase (SG), occupy key positions in all the pathways leading to all these therapeutic agents.…”

Section: Introductionmentioning

confidence: 97%

The molecular architecture of major enzymes from ajmaline biosynthetic pathway

et al. 2007

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The biosynthetic pathway leading to the monoterpenoid indole alkaloid ajmaline in Rauvolfia serpentiin serpentina is one of the most studied in the field of natural product biosynthesis. Ajmaline has a complex structure which is based on a six-membered ring system harbouring nine chiral carbon atoms. There are about fifteen enzymes involved, including some involving the side reactions of the ajmaline biosynthetic pathway. All enzymes exhibit pronounced substrate specificity. In the recent years isolation and sequencing of their cDNAs has allowed a detailed sequence analysis and comparison with functionally related and occasionally un-related enzymes. Site-directed mutations of several of the ajmaline-synthesizing enzymes have been performed and their catalytic residues have been identified. Success with overexpression of the enzymes was an important step for their crystallization and structural analysis by X-ray crystallography. Crystals with sufficient resolution were obtained from the major enzymes of the pathway. Strictosidine synthase has a 3D-structure with a six-bladed bpropeller fold the first time such a fold found in the plant kingdom. Its ligand complexes with tryptamine and secologanin, as well as structure-based sequence alignment, indicate a possible evolutionary relationship to several primary sequence-unrelated structures with this fold. The structure of strictosidine glucosidase was determined and its structure has as a (b/a) 8 barrel fold. Vinorine synthase provides the first 3D structure of a member of BAHD enzyme super-family. Raucaffricine glucosidase involved in a side-route of ajmaline biosynthesis has been crystallized. The ajmaline biosynthetic pathway is an outstanding example where many enzymes 3D-structure have been known and where there is a real potential for protein engineering to yield new alkaloid.

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“…Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties [ 3 ]. The spirooxindole system is the core structure of many pharmacological agents and natural alkaloids [ 4 , 5 , 6 ]. The key structural characteristic of these compounds is the spiro ring fused at the 3-carbon position of the oxindole core with varied heterocyclic motifs.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Spiro[indoline-3,9′-xanthene]trione Derivatives Catalyzed by Magnesium Perchlorate

Chen

Liang

et al. 2017

Molecules

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A simple and efficient method for the synthesis of spiro[indoline-3,9′-xanthene]trione derivatives by means of condensation between isatins and 1,3-cyclohexanedione in the presence of a catalytic amount of magnesium perchlorate at 80 °C in 50% aqueous ethanol medium has been described. Notably, the present method offers desirable advantages of good yields, simplicity of workup procedure, easy purification, and reduced reaction times.

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Pharmacology, Biochemistry, and Clinical Applications of the Monoterpenoid Alkaloids

Cited by 13 publications

References 137 publications

Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

The molecular architecture of major enzymes from ajmaline biosynthetic pathway

An Efficient Synthesis of Spiro[indoline-3,9′-xanthene]trione Derivatives Catalyzed by Magnesium Perchlorate

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