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United States Department of Agriculture

Agricultural Research Service

Research Project: Discovery and Development of Natural Product-Based Weed Management Methods

Location: Natural Products Utilization Research

Title: Pentacyclic ingamine-type alkaloids, a new antiplasmodial pharmacophore from the marine sponge petrosid Ng5 Sp5

Authors
item Muhammad, Ilias -
item Ibrahim, Mohamed -
item Khan, Shabana -
item Jacob, Melissa -
item Tekwani, Babu -
item Walker, Larry -
item Sameylenko, Vladimir -

Submitted to: Planta Medica
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: August 17, 2012
Publication Date: October 7, 2012
Citation: Muhammad, I., Ibrahim, M.A., Khan, S.I., Jacob, M.R., Tekwani, B.L., Walker, L.A., Sameylenko, V. 2012. Pentacyclic ingamine-type alkaloids, a new antiplasmodial pharmacophore from the marine sponge petrosid Ng5 Sp5. Planta Medica. 78(15):1690-1697.

Interpretive Summary: Two new pentacyclic ingamine- type alkaloids, namely 22(S)-hydroxyingamine A and dihydroingenamine D, together with the known ingamine A have been isolated from a marine sponge obtained from the open repository of National Cancer Institute, USA. The structures of compounds 1-3 were determined. Compounds 1 and 3 showed strong antiplasmodial activity against chloroquine-sensitive and -resistant strains of the malaria pathogen Plasmodium falciparum. The compounds were found to be devoid of in vitro cytotoxicity against human or animal cells.

Technical Abstract: Two new pentacyclic ingamine- type alkaloids, namely 22(S)-hydroxyingamine A (2) and dihydroingenamine D (3), together with the known ingamine A (1) have been isolated from marine sponge Petrosid Ng5 Sp5 (Family: Petrosiidae) obtained from the open repository of National Cancer Institute, USA. The structures of compounds 1-3 were determined using 1D and 2D NMR, and MS techniques. The absolute configuration of both the hydroxyl groups at C9 and C22 of 2 was determined as (S) using a modified Mosher esterification method. Compounds 1 and 3 showed strong antiplasmodial activity against chloroquine-sensitive (D6) and -resistant (W2) strains of Plasmodium falciparum with IC50 values of 90 and 78 ng/mL, and 72 and 57 ng/mL, respectively, while 2 was found to be less active (IC50 values of 200 and 140 ng/mL, respectively). The compounds were found to be devoid of in vitro cytotoxicity against human solid tumor cells of ductal (BT-549), ovary (SK-OV-3) and epidermoid (KB) carcinomas and skin melanoma (SK-MEL), as well as against non-cancerous monkey kidney fibroblasts (VERO) and pig kidney epithelial (LLC-PK11) cells, up to a maximum concentration of 10 µg/mL.

Last Modified: 10/31/2014
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