Format

Send to

Choose Destination
Fitoterapia. 2016 Dec;115:1-8. doi: 10.1016/j.fitote.2016.09.009. Epub 2016 Sep 19.

Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8'- and 7,1'-linked metabolites from the Chinese liana Ancistrocladus tectorius.

Author information

1
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. Electronic address: bringman@chemie.uni-wuerzburg.de.
2
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
3
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany; Key Laboratory of Systems Biomedicine, Shanghai Center for Systems Biomedicine, Shanghai Jia Tong University, 800 Dongchuan Road, Shanghai 200240, PR China.
4
Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, PR China.
5
Swiss Tropical and Public Health Institute, Socinstrasse 57, CH-4002 Basel, Switzerland; University of Basel, Petersplatz 1, CH-4003 Basel, Switzerland.
6
Institute of Pharmacy and Biochemistry, Department of Pharmaceutical Biology, University of Mainz, Staudinger Weg 5, D-55128 Mainz, Germany.

Abstract

From the twigs and stems of the Chinese liana Ancistrocladus tectorius (Ancistrocladaceae), two new 5,8'-coupled naphthylisoquinolines, ancistectorine D (5) and its 6-O-demethyl derivative 6, were isolated, along with two new 7,1'-linked alkaloids, 6-O-methylancistectorine B1 (7) and ancistectorine B2 (8). Two further compounds, ancistroealaine A (4) and 6-O-demethyl-8-O-methyl-7-epi-ancistrobrevine D (10), already known from related Asian and African Ancistrocladus species, were discovered for the first time in A. tectorius. The structure elucidation was achieved by spectroscopic analysis including HRESIMS, 1D and 2D NMR, and by chemical (oxidative degradation) and chiroptical (circular dichroism) methods. Chemotaxonomically remarkable, 5,8'-coupled naphthylisoquinolines have as yet been found quite rarely in Asian Ancistrocladus species, where only two examples have so far been detected, while alkaloids with this coupling type represent the by far the largest group of constituents in African taxa. Ancistectorine D (5) shows promising activities against the protozoan parasites Trypanosoma cruzi and Leishmania donovani, and it was likewise found to display strong cytotoxic activities against human leukemia (CCRF-CEM) and multidrug-resistant tumor cells (CEM/ADR5000).

KEYWORDS:

Ancistectorine D; Ancistrocladaceae; Ancistrocladus tectorius; Antileukemic agents; Antiprotozoal agents; Naphthylisoquinoline alkaloids

PMID:
27646602
DOI:
10.1016/j.fitote.2016.09.009
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Elsevier Science
Loading ...
Support Center