ent-dioncophylleine A and related dehydrogenated naphthylisoquinoline alkaloids, the first Asian dioncophyllaceae-type alkaloids, from the “new” plant species Ancistrocladus benomensis

G. Bringmann (Corresponding Author), M. Dreyer, H. Kopff, Heiko Rischer, M. Wohlfarth, H. Hadi, R. Brun, H. Meimberg, G. Heubl

Research output: Contribution to journalArticleScientificpeer-review

30 Citations (Scopus)

Abstract

Three new fully dehydrogenated naphthylisoquinoline alkaloids, the 7,1‘-coupled ent-dioncophylleine A (3a), the likewise 7,1‘-coupled 5‘-O-demethyl-ent-dioncophylleine A (4), and the 7,8‘-linked dioncophylleine D (5), have been isolated from the leaves of the recently described Malaysian highland liana Ancistrocladus benomensis. All of them lack an oxygen function at C-6; this so-called Dioncophyllaceae-type structural subclass had previously been found only in naphthylisoquinoline alkaloids from West and Central African plants. Moreover, compounds 3a and 4 are the first fully dehydrogenated, i.e., only axially chiral, naphthylisoquinoline alkaloids of this type that are optically active; compound 5, by contrast, is fully racemic, due to its configurationally unstable biaryl axis. The structural elucidation was achieved by spectroscopic and chiroptical methods. Biological activities of these alkaloids against different protozoan parasites are described.
Original languageEnglish
Pages (from-to)686 - 690
Number of pages5
JournalJournal of Natural Products
Volume68
Issue number5
DOIs
Publication statusPublished - 2005
MoE publication typeA1 Journal article-refereed

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Dioncophyllaceae
Alkaloids
Bioactivity
Parasites
Oxygen
ent-Dioncophylleine A

Keywords

  • alkaloids
  • Ancistrocladus benomensis
  • liana

Cite this

@article{7fd5e5300ea34c7895ee0b3e139602bd,
title = "ent-dioncophylleine A and related dehydrogenated naphthylisoquinoline alkaloids, the first Asian dioncophyllaceae-type alkaloids, from the “new” plant species Ancistrocladus benomensis",
abstract = "Three new fully dehydrogenated naphthylisoquinoline alkaloids, the 7,1‘-coupled ent-dioncophylleine A (3a), the likewise 7,1‘-coupled 5‘-O-demethyl-ent-dioncophylleine A (4), and the 7,8‘-linked dioncophylleine D (5), have been isolated from the leaves of the recently described Malaysian highland liana Ancistrocladus benomensis. All of them lack an oxygen function at C-6; this so-called Dioncophyllaceae-type structural subclass had previously been found only in naphthylisoquinoline alkaloids from West and Central African plants. Moreover, compounds 3a and 4 are the first fully dehydrogenated, i.e., only axially chiral, naphthylisoquinoline alkaloids of this type that are optically active; compound 5, by contrast, is fully racemic, due to its configurationally unstable biaryl axis. The structural elucidation was achieved by spectroscopic and chiroptical methods. Biological activities of these alkaloids against different protozoan parasites are described.",
keywords = "alkaloids, Ancistrocladus benomensis, liana",
author = "G. Bringmann and M. Dreyer and H. Kopff and Heiko Rischer and M. Wohlfarth and H. Hadi and R. Brun and H. Meimberg and G. Heubl",
year = "2005",
doi = "10.1021/np049626j",
language = "English",
volume = "68",
pages = "686 -- 690",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "5",

}

ent-dioncophylleine A and related dehydrogenated naphthylisoquinoline alkaloids, the first Asian dioncophyllaceae-type alkaloids, from the “new” plant species Ancistrocladus benomensis. / Bringmann, G. (Corresponding Author); Dreyer, M.; Kopff, H.; Rischer, Heiko; Wohlfarth, M.; Hadi, H.; Brun, R.; Meimberg, H.; Heubl, G.

In: Journal of Natural Products, Vol. 68, No. 5, 2005, p. 686 - 690.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - ent-dioncophylleine A and related dehydrogenated naphthylisoquinoline alkaloids, the first Asian dioncophyllaceae-type alkaloids, from the “new” plant species Ancistrocladus benomensis

AU - Bringmann, G.

AU - Dreyer, M.

AU - Kopff, H.

AU - Rischer, Heiko

AU - Wohlfarth, M.

AU - Hadi, H.

AU - Brun, R.

AU - Meimberg, H.

AU - Heubl, G.

PY - 2005

Y1 - 2005

N2 - Three new fully dehydrogenated naphthylisoquinoline alkaloids, the 7,1‘-coupled ent-dioncophylleine A (3a), the likewise 7,1‘-coupled 5‘-O-demethyl-ent-dioncophylleine A (4), and the 7,8‘-linked dioncophylleine D (5), have been isolated from the leaves of the recently described Malaysian highland liana Ancistrocladus benomensis. All of them lack an oxygen function at C-6; this so-called Dioncophyllaceae-type structural subclass had previously been found only in naphthylisoquinoline alkaloids from West and Central African plants. Moreover, compounds 3a and 4 are the first fully dehydrogenated, i.e., only axially chiral, naphthylisoquinoline alkaloids of this type that are optically active; compound 5, by contrast, is fully racemic, due to its configurationally unstable biaryl axis. The structural elucidation was achieved by spectroscopic and chiroptical methods. Biological activities of these alkaloids against different protozoan parasites are described.

AB - Three new fully dehydrogenated naphthylisoquinoline alkaloids, the 7,1‘-coupled ent-dioncophylleine A (3a), the likewise 7,1‘-coupled 5‘-O-demethyl-ent-dioncophylleine A (4), and the 7,8‘-linked dioncophylleine D (5), have been isolated from the leaves of the recently described Malaysian highland liana Ancistrocladus benomensis. All of them lack an oxygen function at C-6; this so-called Dioncophyllaceae-type structural subclass had previously been found only in naphthylisoquinoline alkaloids from West and Central African plants. Moreover, compounds 3a and 4 are the first fully dehydrogenated, i.e., only axially chiral, naphthylisoquinoline alkaloids of this type that are optically active; compound 5, by contrast, is fully racemic, due to its configurationally unstable biaryl axis. The structural elucidation was achieved by spectroscopic and chiroptical methods. Biological activities of these alkaloids against different protozoan parasites are described.

KW - alkaloids

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KW - liana

U2 - 10.1021/np049626j

DO - 10.1021/np049626j

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