Prev. Article Next Article Table of Contents

Note

Anthelmintic Macrolactams from Nonomuraea turkmeniaca MA7364

Sloan Ayers,^† Deborah L. Zink,^† Kenneth Mohn,^‡ Joanne Staats Powell,^‡ Christine M. Brown,^‡ Terry Murphy,^‡ Alan Grund,^§ Olga Genilloud, Oscar Salazar, Donald Thompson,^‡ and Sheo B. Singh*^†

Natural Products Chemistry, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, Merck and Co., Inc., Branchburg Farm, 203 River Road, Somerville, New Jersey 08876, Bio-Technical Resources, 1035 South 7th Street, Manitowoc, Wisconsin 54220, and Centro de Investigacin Bsica, Merck, Sharp & Dohme de Espana, S.A., Josefa Valcarcel 38, 28027 Madrid, Spain

J. Nat. Prod., 2007, 70 (8), pp 1371–1373

DOI: 10.1021/np070131e

Publication Date (Web): July 18, 2007

†

Natural Products Chemistry, MRL.

‡

Branchburg Farm.

Bio-Technical Resources.

CIBE.

To whom correspondence should be addressed. Tel: (732) 594-3222. Fax: (732) 594-6880. E-mail: sheo_singh@merck.com.

Abstract

Two new macrolactams, 6-desmethyl-N-methylfluvirucin A₁ (1) and N-methylfluvirucin A₁ (2), have been isolated from the acetone extract of Nonomuraea turkmeniaca MA7364. These compounds were isolated by bioassay-guided fractionation as part of our search for new anthelmintics. The structures of these compounds were elucidated by comparison of their NMR and MS data to those of previously reported fluvirucins and confirmed by 2D NMR. Compound 1 exhibited in vitro activity (EC₉₀ 15 ± 5 μg/mL) against Haemonchus contortus larvae, whereas compound 2, while a bit less active in vitro (EC₉₀ 29 ± 8 μg/mL), showed modest in vivo activity against a surrogate organism, Heligmosomoides polygyrus in mice, at 50 mg/kg.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue August 24, 2007
Received March 26, 2007

Recommend & Share

Related Content

Serinocyclins A and B, Cyclic Heptapeptides from Metarhizium anisopliaeJournal of Natural Products
- Serinocyclins A and B, Cyclic Heptapeptides from Metarhizium anisopliae
  Stuart B. Krasnoff, Ivan Keresztes, Richard E. Gillilan, Doletha M. E. Szebenyi, Bruno G. G. Donzelli, Alice C. L. Churchill and Donna M. Gibson
  Journal of Natural Products 2007 70 (12), pp 1919–1924
  Abstract: Two new cyclic heptapeptides, serinocyclins A (1) and B (2), were isolated from conidia of the entomopathogenic fungus Metarhizium anisopliae. Structures were elucidated by a combination of mass spectrometric, NMR, and X-ray diffraction techniques. ...
  Abstract | Full Text HTML | Hi-Res PDF
A Dimeric Lactone from Ardisia japonica with Inhibitory Activity for HIV-1 and HIV-2 Ribonuclease HJournal of Natural Products
- A Dimeric Lactone from Ardisia japonica with Inhibitory Activity for HIV-1 and HIV-2 Ribonuclease H
  Nguyen Tien Dat, KiHwan Bae, Antony Wamiru, James B. McMahon, Stuart F. J. Le Grice, Marion Bona, John A. Beutler, and Young Ho Kim
  Journal of Natural Products 2007 70 (5), pp 839–841
  Abstract: A new dimeric lactone, ardimerin digallate (1), was isolated from the whole plants of Ardisia japonica, along with six known constituents. The structure of 1 was established on the basis of spectroscopic analysis including 1D- and 2D-NMR techniques. ...
  Abstract | Full Text HTML | Hi-Res PDF
Habbemines A and B, Pyrrolidine Alkaloids with Human δ-Opioid Receptor Binding Affinity from the Leaves of Elaeocarpus habbemensisJournal of Natural Products
- Habbemines A and B, Pyrrolidine Alkaloids with Human δ-Opioid Receptor Binding Affinity from the Leaves of Elaeocarpus habbemensis
  Peter L. Katavic, Debra A. Venables, Topul Rali, and Anthony R. Carroll
  Journal of Natural Products 2007 70 (5), pp 866–868
  Abstract: The first phytochemical investigation of the Papua New Guinean plant Elaeocarpus habbemensis resulted in the isolation of two new pyrrolidine alkaloids, habbemines A (2) and B (3), as a 1:1 mixture of inseparable diastereomers. The structures of these ...
  Abstract | Full Text HTML | Hi-Res PDF

Note

Anthelmintic Macrolactams from Nonomuraea turkmeniaca MA7364

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Serinocyclins A and B, Cyclic Heptapeptides from Metarhizium anisopliae

A Dimeric Lactone from Ardisia japonica with Inhibitory Activity for HIV-1 and HIV-2 Ribonuclease H

Habbemines A and B, Pyrrolidine Alkaloids with Human δ-Opioid Receptor Binding Affinity from the Leaves of Elaeocarpus habbemensis

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES