The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis

Jeremy D. Mason, Steven M. Weinreb

Research output: Chapter in Book/Report/Conference proceedingChapter

1 Citation (Scopus)

Abstract

The alstoscholarisines are a small family of biologically and structurally interesting polycyclic monoterpenoid indole alkaloids isolated from the leaf extracts of Alstonia scholaris. The alkaloids can be divided into three different subtypes based upon their structures and putative biogenesis: (1) (−)-alstoscholarisines A–E, (2) (+)-alstoscholarisine G, and (3) (+)-alstoscholarisines H–J. This review discusses the isolation, structure determination, biological activity, and proposed biosynthesis of these metabolites. In addition, synthetic studies on the alkaloids are described including total syntheses of racemic alstoscholarisines A–E, a total synthesis of (−)-alstoscholarisine A, and a synthesis of racemic alstoscholarisine H.

Original languageEnglish (US)
Title of host publicationAlkaloids
Subtitle of host publicationChemistry and Biology
EditorsHans-Joachim Knölker
PublisherAcademic Press Inc.
Pages115-150
Number of pages36
ISBN (Print)9780128171516
DOIs
StatePublished - Jan 1 2019

Publication series

NameAlkaloids: Chemistry and Biology
Volume81
ISSN (Print)1099-4831

Fingerprint

Alkaloids
Alstonia
Secologanin Tryptamine Alkaloids
Biosynthesis
Metabolites
Bioactivity
alstoscholarisine H

All Science Journal Classification (ASJC) codes

  • Biochemistry

Cite this

Mason, J. D., & Weinreb, S. M. (2019). The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis. In H-J. Knölker (Ed.), Alkaloids: Chemistry and Biology (pp. 115-150). (Alkaloids: Chemistry and Biology; Vol. 81). Academic Press Inc.. https://doi.org/10.1016/bs.alkal.2018.09.001
Mason, Jeremy D. ; Weinreb, Steven M. / The Alstoscholarisine Alkaloids : Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis. Alkaloids: Chemistry and Biology. editor / Hans-Joachim Knölker. Academic Press Inc., 2019. pp. 115-150 (Alkaloids: Chemistry and Biology).
@inbook{17fb0c20d8f048c6b27bc6c82750a869,
title = "The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis",
abstract = "The alstoscholarisines are a small family of biologically and structurally interesting polycyclic monoterpenoid indole alkaloids isolated from the leaf extracts of Alstonia scholaris. The alkaloids can be divided into three different subtypes based upon their structures and putative biogenesis: (1) (−)-alstoscholarisines A–E, (2) (+)-alstoscholarisine G, and (3) (+)-alstoscholarisines H–J. This review discusses the isolation, structure determination, biological activity, and proposed biosynthesis of these metabolites. In addition, synthetic studies on the alkaloids are described including total syntheses of racemic alstoscholarisines A–E, a total synthesis of (−)-alstoscholarisine A, and a synthesis of racemic alstoscholarisine H.",
author = "Mason, {Jeremy D.} and Weinreb, {Steven M.}",
year = "2019",
month = "1",
day = "1",
doi = "10.1016/bs.alkal.2018.09.001",
language = "English (US)",
isbn = "9780128171516",
series = "Alkaloids: Chemistry and Biology",
publisher = "Academic Press Inc.",
pages = "115--150",
editor = "Hans-Joachim Kn{\"o}lker",
booktitle = "Alkaloids",
address = "United States",

}

Mason, JD & Weinreb, SM 2019, The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis. in H-J Knölker (ed.), Alkaloids: Chemistry and Biology. Alkaloids: Chemistry and Biology, vol. 81, Academic Press Inc., pp. 115-150. https://doi.org/10.1016/bs.alkal.2018.09.001

The Alstoscholarisine Alkaloids : Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis. / Mason, Jeremy D.; Weinreb, Steven M.

Alkaloids: Chemistry and Biology. ed. / Hans-Joachim Knölker. Academic Press Inc., 2019. p. 115-150 (Alkaloids: Chemistry and Biology; Vol. 81).

Research output: Chapter in Book/Report/Conference proceedingChapter

TY - CHAP

T1 - The Alstoscholarisine Alkaloids

T2 - Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis

AU - Mason, Jeremy D.

AU - Weinreb, Steven M.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The alstoscholarisines are a small family of biologically and structurally interesting polycyclic monoterpenoid indole alkaloids isolated from the leaf extracts of Alstonia scholaris. The alkaloids can be divided into three different subtypes based upon their structures and putative biogenesis: (1) (−)-alstoscholarisines A–E, (2) (+)-alstoscholarisine G, and (3) (+)-alstoscholarisines H–J. This review discusses the isolation, structure determination, biological activity, and proposed biosynthesis of these metabolites. In addition, synthetic studies on the alkaloids are described including total syntheses of racemic alstoscholarisines A–E, a total synthesis of (−)-alstoscholarisine A, and a synthesis of racemic alstoscholarisine H.

AB - The alstoscholarisines are a small family of biologically and structurally interesting polycyclic monoterpenoid indole alkaloids isolated from the leaf extracts of Alstonia scholaris. The alkaloids can be divided into three different subtypes based upon their structures and putative biogenesis: (1) (−)-alstoscholarisines A–E, (2) (+)-alstoscholarisine G, and (3) (+)-alstoscholarisines H–J. This review discusses the isolation, structure determination, biological activity, and proposed biosynthesis of these metabolites. In addition, synthetic studies on the alkaloids are described including total syntheses of racemic alstoscholarisines A–E, a total synthesis of (−)-alstoscholarisine A, and a synthesis of racemic alstoscholarisine H.

UR - http://www.scopus.com/inward/record.url?scp=85056644411&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85056644411&partnerID=8YFLogxK

U2 - 10.1016/bs.alkal.2018.09.001

DO - 10.1016/bs.alkal.2018.09.001

M3 - Chapter

C2 - 30685049

AN - SCOPUS:85056644411

SN - 9780128171516

T3 - Alkaloids: Chemistry and Biology

SP - 115

EP - 150

BT - Alkaloids

A2 - Knölker, Hans-Joachim

PB - Academic Press Inc.

ER -

Mason JD, Weinreb SM. The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis. In Knölker H-J, editor, Alkaloids: Chemistry and Biology. Academic Press Inc. 2019. p. 115-150. (Alkaloids: Chemistry and Biology). https://doi.org/10.1016/bs.alkal.2018.09.001