Protoberberine Alkaloids as Antimalarials

Jonathan L. Vennerstrom; Daniel L. Klayman

doi:10.1021/jm00401a006

Protoberberine Alkaloids as Antimalarials

Jonathan L. Vennerstrom, Daniel L. Klayman

Research output: Contribution to journal › Article › peer-review

121 Scopus citations

Abstract

The protoberberine alkaloids berberine (1), palmatine (2), jatrorrhizine (3), and several berberine derivatives (4-10) were tested for antimalarial activity in vitro against Plasmodium falciparum and in vivo against Plasmodium berghei. The berberine derivatives 4-10 were designed and synthesized to maximize structural diversity within a modest set of compounds. Palmatine (2) and jatrorrhizine (3) were isolated as their chlorides from Enantia chlorantha. None of the protoberberine alkaloids was active in vivo, although compounds 1, 2, 3, 5, and 6 exhibited a potency comparable to that of quinine in vitro.

Original language	English (US)
Pages (from-to)	1084-1087
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	31
Issue number	6
DOIs	https://doi.org/10.1021/jm00401a006
State	Published - Feb 1 1988
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

Access to Document

10.1021/jm00401a006

Cite this

@article{4e4e84768a844c158c29d6befa878d40,

title = "Protoberberine Alkaloids as Antimalarials",

abstract = "The protoberberine alkaloids berberine (1), palmatine (2), jatrorrhizine (3), and several berberine derivatives (4-10) were tested for antimalarial activity in vitro against Plasmodium falciparum and in vivo against Plasmodium berghei. The berberine derivatives 4-10 were designed and synthesized to maximize structural diversity within a modest set of compounds. Palmatine (2) and jatrorrhizine (3) were isolated as their chlorides from Enantia chlorantha. None of the protoberberine alkaloids was active in vivo, although compounds 1, 2, 3, 5, and 6 exhibited a potency comparable to that of quinine in vitro.",

author = "Vennerstrom, {Jonathan L.} and Klayman, {Daniel L.}",

year = "1988",

month = feb,

day = "1",

doi = "10.1021/jm00401a006",

language = "English (US)",

volume = "31",

pages = "1084--1087",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Protoberberine Alkaloids as Antimalarials

AU - Vennerstrom, Jonathan L.

AU - Klayman, Daniel L.

PY - 1988/2/1

Y1 - 1988/2/1

N2 - The protoberberine alkaloids berberine (1), palmatine (2), jatrorrhizine (3), and several berberine derivatives (4-10) were tested for antimalarial activity in vitro against Plasmodium falciparum and in vivo against Plasmodium berghei. The berberine derivatives 4-10 were designed and synthesized to maximize structural diversity within a modest set of compounds. Palmatine (2) and jatrorrhizine (3) were isolated as their chlorides from Enantia chlorantha. None of the protoberberine alkaloids was active in vivo, although compounds 1, 2, 3, 5, and 6 exhibited a potency comparable to that of quinine in vitro.

AB - The protoberberine alkaloids berberine (1), palmatine (2), jatrorrhizine (3), and several berberine derivatives (4-10) were tested for antimalarial activity in vitro against Plasmodium falciparum and in vivo against Plasmodium berghei. The berberine derivatives 4-10 were designed and synthesized to maximize structural diversity within a modest set of compounds. Palmatine (2) and jatrorrhizine (3) were isolated as their chlorides from Enantia chlorantha. None of the protoberberine alkaloids was active in vivo, although compounds 1, 2, 3, 5, and 6 exhibited a potency comparable to that of quinine in vitro.

UR - http://www.scopus.com/inward/record.url?scp=0023888151&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023888151&partnerID=8YFLogxK

U2 - 10.1021/jm00401a006

DO - 10.1021/jm00401a006

M3 - Article

C2 - 3286870

AN - SCOPUS:0023888151

SN - 0022-2623

VL - 31

SP - 1084

EP - 1087

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 6

ER -

Protoberberine Alkaloids as Antimalarials

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this