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Phenylpropanoid-conjugated iridoid glucosides from leaves of Morinda morindoides

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Abstract

Three phenylpropanoid-conjugated iridoid glucosides, acetylgaertneric acid (1), acetyldehydrogaertneroside (2), and dehydrogaertneric acid (10), together with nine known related iridoid glucosides (39, 11, and 12), two coumaroyl alkaloids, one benzenoid, and three flavonoid glucosides were isolated from leaves of Morinda morindoides (Rubiaceae). Structures of these isolated compounds were determined using spectroscopic analysis. Compounds 118 and previously isolated compounds (1929) were evaluated for anti-trypanosomal activity against Trypanosoma cruzi Tulahuen strain (trypomastigote and amastigote) together with cytotoxicity against host cells, new-born mouse heart cells. Among them, molucidin (21) and prismatomerin (22) exhibited good anti-trypanosomal activity (IC50 of 4.67 and 5.70 µM, respectively), together with cytotoxicity (CC50 of 2.76 and 3.22 μM, respectively). Compounds 118 did not show anti-malarial activity against a chloroquine/mefloquine-sensitive strain of Plasmodium falciparum.

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Acknowledgements

The authors would like to thank Mr. Vangu Kilukidi Blaise Van (University Hospital of Kinshasa, Faculty of Medicine, University of Kinshasa) for providing the plant materials. This work was supported by the Joint Usage/Research Center on Tropical Disease, Institute of Tropical Medicine, Nagasaki University (2016-Ippan-20, 2017-Ippan-16, 2018-Ippan-20, and 2019-Ippan-22), a Grant-in-Aid for the Cooperative Research Project from the Institute of Natural Medicine, University of Toyama in 2017, and Kobayashi Foundation. Y.H. is a recipient of a scholarship from Kyoritsu International Foundation.

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Correspondence to Kazufumi Toume or Katsuko Komatsu.

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K. T. has research grant from Kobayashi Foundation.

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Hashim, Y., Toume, K., Mizukami, S. et al. Phenylpropanoid-conjugated iridoid glucosides from leaves of Morinda morindoides. J Nat Med 76, 281–290 (2022). https://doi.org/10.1007/s11418-021-01567-1

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