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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)

Author
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: 8/17/2012
Publication Date: 10/7/2012
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: 8/24/2016
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