Phenylpropanoid-conjugated iridoid glucosides from leaves of Morinda morindoides

Yasinjan Hashim; Kazufumi Toume; Shusaku Mizukami; Toshinori Kitami; Mayumi Taniguchi; Awet Alem Teklemichael; Yuki Tayama; Nguyen Tien Huy; José Nzunzu Lami; Joseph M. Bodi; Kenji Hirayama; Katsuko Komatsu

doi:10.1007/s11418-021-01567-1

Phenylpropanoid-conjugated iridoid glucosides from leaves of Morinda morindoides

Yasinjan Hashim, Kazufumi Toume^*, Shusaku Mizukami, Toshinori Kitami, Mayumi Taniguchi, Awet Alem Teklemichael, Yuki Tayama, Nguyen Tien Huy, José Nzunzu Lami, Joseph M. Bodi, Kenji Hirayama, Katsuko Komatsu^*

^*Corresponding author for this work

Department of Medicinal Resources Management, Institute of Natural Medicine
Section of Pharmacognosy, Division of Medicinal Resources, Institute of Natural Medicine

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Three phenylpropanoid-conjugated iridoid glucosides, acetylgaertneric acid (1), acetyldehydrogaertneroside (2), and dehydrogaertneric acid (10), together with nine known related iridoid glucosides (3–9, 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 1–18 and previously isolated compounds (19–29) 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 1–18 did not show anti-malarial activity against a chloroquine/mefloquine-sensitive strain of Plasmodium falciparum.

Original language	English
Pages (from-to)	281-290
Number of pages	10
Journal	Natural Medicines
Volume	76
Issue number	1
DOIs	https://doi.org/10.1007/s11418-021-01567-1
State	Published - 2022/01

Keywords

Iridoid
Morinda morindoides
Phenylpropanoid-conjugated iridoid glucosides
Trypanosoma
Trypanosoma cruzi

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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title = "Phenylpropanoid-conjugated iridoid glucosides from leaves of Morinda morindoides",

abstract = "Three phenylpropanoid-conjugated iridoid glucosides, acetylgaertneric acid (1), acetyldehydrogaertneroside (2), and dehydrogaertneric acid (10), together with nine known related iridoid glucosides (3–9, 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 1–18 and previously isolated compounds (19–29) 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 1–18 did not show anti-malarial activity against a chloroquine/mefloquine-sensitive strain of Plasmodium falciparum.",

keywords = "Iridoid, Morinda morindoides, Phenylpropanoid-conjugated iridoid glucosides, Trypanosoma, Trypanosoma cruzi",

author = "Yasinjan Hashim and Kazufumi Toume and Shusaku Mizukami and Toshinori Kitami and Mayumi Taniguchi and Teklemichael, {Awet Alem} and Yuki Tayama and Huy, {Nguyen Tien} and Lami, {Jos{\'e} Nzunzu} and Bodi, {Joseph M.} and Kenji Hirayama and Katsuko Komatsu",

note = "Publisher Copyright: {\textcopyright} 2021, The Japanese Society of Pharmacognosy.",

year = "2022",

month = jan,

doi = "10.1007/s11418-021-01567-1",

language = "英語",

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pages = "281--290",

journal = "Natural Medicines",

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number = "1",

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TY - JOUR

T1 - Phenylpropanoid-conjugated iridoid glucosides from leaves of Morinda morindoides

AU - Hashim, Yasinjan

AU - Toume, Kazufumi

AU - Mizukami, Shusaku

AU - Kitami, Toshinori

AU - Taniguchi, Mayumi

AU - Teklemichael, Awet Alem

AU - Tayama, Yuki

AU - Huy, Nguyen Tien

AU - Lami, José Nzunzu

AU - Bodi, Joseph M.

AU - Hirayama, Kenji

AU - Komatsu, Katsuko

PY - 2022/1

Y1 - 2022/1

N2 - Three phenylpropanoid-conjugated iridoid glucosides, acetylgaertneric acid (1), acetyldehydrogaertneroside (2), and dehydrogaertneric acid (10), together with nine known related iridoid glucosides (3–9, 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 1–18 and previously isolated compounds (19–29) 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 1–18 did not show anti-malarial activity against a chloroquine/mefloquine-sensitive strain of Plasmodium falciparum.

AB - Three phenylpropanoid-conjugated iridoid glucosides, acetylgaertneric acid (1), acetyldehydrogaertneroside (2), and dehydrogaertneric acid (10), together with nine known related iridoid glucosides (3–9, 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 1–18 and previously isolated compounds (19–29) 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 1–18 did not show anti-malarial activity against a chloroquine/mefloquine-sensitive strain of Plasmodium falciparum.

KW - Iridoid

KW - Morinda morindoides

KW - Phenylpropanoid-conjugated iridoid glucosides

KW - Trypanosoma

KW - Trypanosoma cruzi

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DO - 10.1007/s11418-021-01567-1

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AN - SCOPUS:85115073494

SN - 1340-3443

VL - 76

SP - 281

EP - 290

JO - Natural Medicines

JF - Natural Medicines

IS - 1

ER -

Phenylpropanoid-conjugated iridoid glucosides from leaves of Morinda morindoides

Abstract

Keywords

ASJC Scopus subject areas

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