Ancistrobenomine A, the first naphthylisoquinoline oxygenated at Me-3, and related 5,1'-coupled alkaloids, from the "new" plant species Ancistrocladus benomensis

G. Bringmann (Corresponding Author), M. Dreyer, Heiko Rischer, K. Wolf, H.A. Hadi, R. Brun, H. Meimberg, G. Heubl

Research output: Contribution to journalArticleScientificpeer-review

20 Citations (Scopus)

Abstract

Three new 5,1‘-coupled naphthylisoquinoline alkaloids, ancistrobenomine A (1), 6-O-demethylancistrobenomine A (2), and 5‘-O-demethylancistrocline (3), have been isolated from the stem bark of a botanically as yet undescribed highland liana Ancistrocladus sp., proposed to be named “A. benomensis” according to the region in Peninsular Malaysia where it has been discovered on the mountain of Gunung Benom. Two of the compounds possess an unprecedented structure with a novel hydroxymethylene group at C-3 of the fully dehydrogenated isoquinoline moiety. The structural elucidation was achieved by chemical, spectroscopic, and chiroptical methods. As typical of the so-called Ancistrocladaceae type, all of the compounds isolated bear an oxygen at C-6. Biological activities of these alkaloids against different protozoic pathogens are described.
Original languageEnglish
Pages (from-to)2058 - 2062
Number of pages5
JournalJournal of Natural Products
Volume67
Issue number12
DOIs
Publication statusPublished - 2004
MoE publication typeA1 Journal article-refereed

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Alkaloids
Malaysia
Pathogens
Bioactivity
Oxygen
ancistrobenomine A
isoquinoline
5'-O-demethylancistrocline
6-O-demethylancistrobenomine A

Cite this

Bringmann, G. ; Dreyer, M. ; Rischer, Heiko ; Wolf, K. ; Hadi, H.A. ; Brun, R. ; Meimberg, H. ; Heubl, G. / Ancistrobenomine A, the first naphthylisoquinoline oxygenated at Me-3, and related 5,1'-coupled alkaloids, from the "new" plant species Ancistrocladus benomensis. In: Journal of Natural Products. 2004 ; Vol. 67, No. 12. pp. 2058 - 2062.
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abstract = "Three new 5,1‘-coupled naphthylisoquinoline alkaloids, ancistrobenomine A (1), 6-O-demethylancistrobenomine A (2), and 5‘-O-demethylancistrocline (3), have been isolated from the stem bark of a botanically as yet undescribed highland liana Ancistrocladus sp., proposed to be named “A. benomensis” according to the region in Peninsular Malaysia where it has been discovered on the mountain of Gunung Benom. Two of the compounds possess an unprecedented structure with a novel hydroxymethylene group at C-3 of the fully dehydrogenated isoquinoline moiety. The structural elucidation was achieved by chemical, spectroscopic, and chiroptical methods. As typical of the so-called Ancistrocladaceae type, all of the compounds isolated bear an oxygen at C-6. Biological activities of these alkaloids against different protozoic pathogens are described.",
author = "G. Bringmann and M. Dreyer and Heiko Rischer and K. Wolf and H.A. Hadi and R. Brun and H. Meimberg and G. Heubl",
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Ancistrobenomine A, the first naphthylisoquinoline oxygenated at Me-3, and related 5,1'-coupled alkaloids, from the "new" plant species Ancistrocladus benomensis. / Bringmann, G. (Corresponding Author); Dreyer, M.; Rischer, Heiko; Wolf, K.; Hadi, H.A.; Brun, R.; Meimberg, H.; Heubl, G.

In: Journal of Natural Products, Vol. 67, No. 12, 2004, p. 2058 - 2062.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Ancistrobenomine A, the first naphthylisoquinoline oxygenated at Me-3, and related 5,1'-coupled alkaloids, from the "new" plant species Ancistrocladus benomensis

AU - Bringmann, G.

AU - Dreyer, M.

AU - Rischer, Heiko

AU - Wolf, K.

AU - Hadi, H.A.

AU - Brun, R.

AU - Meimberg, H.

AU - Heubl, G.

PY - 2004

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N2 - Three new 5,1‘-coupled naphthylisoquinoline alkaloids, ancistrobenomine A (1), 6-O-demethylancistrobenomine A (2), and 5‘-O-demethylancistrocline (3), have been isolated from the stem bark of a botanically as yet undescribed highland liana Ancistrocladus sp., proposed to be named “A. benomensis” according to the region in Peninsular Malaysia where it has been discovered on the mountain of Gunung Benom. Two of the compounds possess an unprecedented structure with a novel hydroxymethylene group at C-3 of the fully dehydrogenated isoquinoline moiety. The structural elucidation was achieved by chemical, spectroscopic, and chiroptical methods. As typical of the so-called Ancistrocladaceae type, all of the compounds isolated bear an oxygen at C-6. Biological activities of these alkaloids against different protozoic pathogens are described.

AB - Three new 5,1‘-coupled naphthylisoquinoline alkaloids, ancistrobenomine A (1), 6-O-demethylancistrobenomine A (2), and 5‘-O-demethylancistrocline (3), have been isolated from the stem bark of a botanically as yet undescribed highland liana Ancistrocladus sp., proposed to be named “A. benomensis” according to the region in Peninsular Malaysia where it has been discovered on the mountain of Gunung Benom. Two of the compounds possess an unprecedented structure with a novel hydroxymethylene group at C-3 of the fully dehydrogenated isoquinoline moiety. The structural elucidation was achieved by chemical, spectroscopic, and chiroptical methods. As typical of the so-called Ancistrocladaceae type, all of the compounds isolated bear an oxygen at C-6. Biological activities of these alkaloids against different protozoic pathogens are described.

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