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New anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth

[Display omitted] Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the v... Full description

Journal Title: Bioorganic & medicinal chemistry letters 2015-08-01, Vol.25 (15), p.3030-3033
Main Author: Suzuki, Mitsuko
Other Authors: Tung, Nguyen Huu , Kwofie, Kofi D , Adegle, Richard , Amoa-Bosompem, Michael , Sakyiamah, Maxwell , Ayertey, Frederick , Owusu, Kofi Baffour-Awuah , Tuffour, Isaac , Atchoglo, Philip , Frempong, Kwadwo Kyereme , Anyan, William K , Uto, Takuhiro , Morinaga, Osamu , Yamashita, Taizo , Aboagye, Frederic , Appiah, Alfred Ampomah , Appiah-Opong, Regina , Nyarko, Alexander K , Yamaoka, Shoji , Yamaguchi, Yasuchika , Edoh, Dominic , Koram, Kwadwo , Ohta, Nobuo , Boakye, Daniel A , Ayi, Irene , Shoyama, Yukihiro
Format: Electronic Article Electronic Article
Language: English
Subjects:
Publisher: England: Elsevier Ltd
ID: ISSN: 0960-894X
Link: https://www.ncbi.nlm.nih.gov/pubmed/26048790
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title: New anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth
format: Article
creator:
  • Suzuki, Mitsuko
  • Tung, Nguyen Huu
  • Kwofie, Kofi D
  • Adegle, Richard
  • Amoa-Bosompem, Michael
  • Sakyiamah, Maxwell
  • Ayertey, Frederick
  • Owusu, Kofi Baffour-Awuah
  • Tuffour, Isaac
  • Atchoglo, Philip
  • Frempong, Kwadwo Kyereme
  • Anyan, William K
  • Uto, Takuhiro
  • Morinaga, Osamu
  • Yamashita, Taizo
  • Aboagye, Frederic
  • Appiah, Alfred Ampomah
  • Appiah-Opong, Regina
  • Nyarko, Alexander K
  • Yamaoka, Shoji
  • Yamaguchi, Yasuchika
  • Edoh, Dominic
  • Koram, Kwadwo
  • Ohta, Nobuo
  • Boakye, Daniel A
  • Ayi, Irene
  • Shoyama, Yukihiro
subjects:
  • Animals
  • Anti-trypanosomal activity
  • Cell Line
  • Cell Line, Tumor
  • Humans
  • Iridoids - chemistry
  • Iridoids - isolation & purification
  • Iridoids - pharmacology
  • Medicinal plants
  • Models, Molecular
  • Molucidin
  • Morinda - chemistry
  • Morinda lucida
  • Plant Extracts - chemistry
  • Plant Extracts - pharmacology
  • Structure-Activity Relationship
  • Tetracyclic iridoid
  • Trypanocidal Agents - chemistry
  • Trypanocidal Agents - pharmacology
  • Trypanosoma - drug effects
  • Trypanosomiasis, African - drug therapy
ispartof: Bioorganic & medicinal chemistry letters, 2015-08-01, Vol.25 (15), p.3030-3033
description: [Display omitted] Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the viewpoints of toxicity and drug resistance issues. Recently, there have been a lot of emphases on the use of medicinal plants world-wide. Morinda lucida Benth. is one of the most popular medicinal plants widely distributed in Africa and several groups have reported on its anti-protozoa activities. In this study, we have isolated one novel tetracyclic iridoid, named as molucidin, from the CHCl3 fraction of the M. lucida leaves by bioassay-guided fractionation and purification. Molucidin was structurally elucidated by 1H and 13C NMR including HMQC, HMBC, H–H COSY and NOESY resulting in tetracyclic iridoid skeleton, and its absolute configuration was determined. We have further demonstrated that molucidin presented a strong anti-trypanosomal activity, indicating an IC50 value of 1.27μM. The cytotoxicity study using human normal and cancer cell lines indicated that molucidin exhibited selectivity index (SI) against two normal fibroblasts greater than 4.73. Furthermore, structure–activity relationship (SAR) study was undertaken with molucidin and oregonin, which is identical to anti-trypanosomal active components of Alnus japonica. Overlapping analysis of the lowest energy conformation of molucidin with oregonin suggested a certain similarities of aromatic rings of both oregonin and molucidin. These results contribute to the future drug design studies for HAT.
language: eng
source:
identifier: ISSN: 0960-894X
fulltext: no_fulltext
issn:
  • 0960-894X
  • 1464-3405
url: Link


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titleNew anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth
creatorSuzuki, Mitsuko ; Tung, Nguyen Huu ; Kwofie, Kofi D ; Adegle, Richard ; Amoa-Bosompem, Michael ; Sakyiamah, Maxwell ; Ayertey, Frederick ; Owusu, Kofi Baffour-Awuah ; Tuffour, Isaac ; Atchoglo, Philip ; Frempong, Kwadwo Kyereme ; Anyan, William K ; Uto, Takuhiro ; Morinaga, Osamu ; Yamashita, Taizo ; Aboagye, Frederic ; Appiah, Alfred Ampomah ; Appiah-Opong, Regina ; Nyarko, Alexander K ; Yamaoka, Shoji ; Yamaguchi, Yasuchika ; Edoh, Dominic ; Koram, Kwadwo ; Ohta, Nobuo ; Boakye, Daniel A ; Ayi, Irene ; Shoyama, Yukihiro
creatorcontribSuzuki, Mitsuko ; Tung, Nguyen Huu ; Kwofie, Kofi D ; Adegle, Richard ; Amoa-Bosompem, Michael ; Sakyiamah, Maxwell ; Ayertey, Frederick ; Owusu, Kofi Baffour-Awuah ; Tuffour, Isaac ; Atchoglo, Philip ; Frempong, Kwadwo Kyereme ; Anyan, William K ; Uto, Takuhiro ; Morinaga, Osamu ; Yamashita, Taizo ; Aboagye, Frederic ; Appiah, Alfred Ampomah ; Appiah-Opong, Regina ; Nyarko, Alexander K ; Yamaoka, Shoji ; Yamaguchi, Yasuchika ; Edoh, Dominic ; Koram, Kwadwo ; Ohta, Nobuo ; Boakye, Daniel A ; Ayi, Irene ; Shoyama, Yukihiro
description[Display omitted] Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the viewpoints of toxicity and drug resistance issues. Recently, there have been a lot of emphases on the use of medicinal plants world-wide. Morinda lucida Benth. is one of the most popular medicinal plants widely distributed in Africa and several groups have reported on its anti-protozoa activities. In this study, we have isolated one novel tetracyclic iridoid, named as molucidin, from the CHCl3 fraction of the M. lucida leaves by bioassay-guided fractionation and purification. Molucidin was structurally elucidated by 1H and 13C NMR including HMQC, HMBC, H–H COSY and NOESY resulting in tetracyclic iridoid skeleton, and its absolute configuration was determined. We have further demonstrated that molucidin presented a strong anti-trypanosomal activity, indicating an IC50 value of 1.27μM. The cytotoxicity study using human normal and cancer cell lines indicated that molucidin exhibited selectivity index (SI) against two normal fibroblasts greater than 4.73. Furthermore, structure–activity relationship (SAR) study was undertaken with molucidin and oregonin, which is identical to anti-trypanosomal active components of Alnus japonica. Overlapping analysis of the lowest energy conformation of molucidin with oregonin suggested a certain similarities of aromatic rings of both oregonin and molucidin. These results contribute to the future drug design studies for HAT.
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languageeng
publisherEngland: Elsevier Ltd
subjectAnimals ; Anti-trypanosomal activity ; Cell Line ; Cell Line, Tumor ; Humans ; Iridoids - chemistry ; Iridoids - isolation & purification ; Iridoids - pharmacology ; Medicinal plants ; Models, Molecular ; Molucidin ; Morinda - chemistry ; Morinda lucida ; Plant Extracts - chemistry ; Plant Extracts - pharmacology ; Structure-Activity Relationship ; Tetracyclic iridoid ; Trypanocidal Agents - chemistry ; Trypanocidal Agents - pharmacology ; Trypanosoma - drug effects ; Trypanosomiasis, African - drug therapy
ispartofBioorganic & medicinal chemistry letters, 2015-08-01, Vol.25 (15), p.3030-3033
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1Tung, Nguyen Huu
2Kwofie, Kofi D
3Adegle, Richard
4Amoa-Bosompem, Michael
5Sakyiamah, Maxwell
6Ayertey, Frederick
7Owusu, Kofi Baffour-Awuah
8Tuffour, Isaac
9Atchoglo, Philip
10Frempong, Kwadwo Kyereme
11Anyan, William K
12Uto, Takuhiro
13Morinaga, Osamu
14Yamashita, Taizo
15Aboagye, Frederic
16Appiah, Alfred Ampomah
17Appiah-Opong, Regina
18Nyarko, Alexander K
19Yamaoka, Shoji
20Yamaguchi, Yasuchika
21Edoh, Dominic
22Koram, Kwadwo
23Ohta, Nobuo
24Boakye, Daniel A
25Ayi, Irene
26Shoyama, Yukihiro
title
0New anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth
1Bioorganic & medicinal chemistry letters
addtitleBioorg Med Chem Lett
description[Display omitted] Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the viewpoints of toxicity and drug resistance issues. Recently, there have been a lot of emphases on the use of medicinal plants world-wide. Morinda lucida Benth. is one of the most popular medicinal plants widely distributed in Africa and several groups have reported on its anti-protozoa activities. In this study, we have isolated one novel tetracyclic iridoid, named as molucidin, from the CHCl3 fraction of the M. lucida leaves by bioassay-guided fractionation and purification. Molucidin was structurally elucidated by 1H and 13C NMR including HMQC, HMBC, H–H COSY and NOESY resulting in tetracyclic iridoid skeleton, and its absolute configuration was determined. We have further demonstrated that molucidin presented a strong anti-trypanosomal activity, indicating an IC50 value of 1.27μM. The cytotoxicity study using human normal and cancer cell lines indicated that molucidin exhibited selectivity index (SI) against two normal fibroblasts greater than 4.73. Furthermore, structure–activity relationship (SAR) study was undertaken with molucidin and oregonin, which is identical to anti-trypanosomal active components of Alnus japonica. Overlapping analysis of the lowest energy conformation of molucidin with oregonin suggested a certain similarities of aromatic rings of both oregonin and molucidin. These results contribute to the future drug design studies for HAT.
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1Anti-trypanosomal activity
2Cell Line
3Cell Line, Tumor
4Humans
5Iridoids - chemistry
6Iridoids - isolation & purification
7Iridoids - pharmacology
8Medicinal plants
9Models, Molecular
10Molucidin
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12Morinda lucida
13Plant Extracts - chemistry
14Plant Extracts - pharmacology
15Structure-Activity Relationship
16Tetracyclic iridoid
17Trypanocidal Agents - chemistry
18Trypanocidal Agents - pharmacology
19Trypanosoma - drug effects
20Trypanosomiasis, African - drug therapy
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5Sakyiamah, Maxwell
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7Owusu, Kofi Baffour-Awuah
8Tuffour, Isaac
9Atchoglo, Philip
10Frempong, Kwadwo Kyereme
11Anyan, William K
12Uto, Takuhiro
13Morinaga, Osamu
14Yamashita, Taizo
15Aboagye, Frederic
16Appiah, Alfred Ampomah
17Appiah-Opong, Regina
18Nyarko, Alexander K
19Yamaoka, Shoji
20Yamaguchi, Yasuchika
21Edoh, Dominic
22Koram, Kwadwo
23Ohta, Nobuo
24Boakye, Daniel A
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titleNew anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth
authorSuzuki, Mitsuko ; Tung, Nguyen Huu ; Kwofie, Kofi D ; Adegle, Richard ; Amoa-Bosompem, Michael ; Sakyiamah, Maxwell ; Ayertey, Frederick ; Owusu, Kofi Baffour-Awuah ; Tuffour, Isaac ; Atchoglo, Philip ; Frempong, Kwadwo Kyereme ; Anyan, William K ; Uto, Takuhiro ; Morinaga, Osamu ; Yamashita, Taizo ; Aboagye, Frederic ; Appiah, Alfred Ampomah ; Appiah-Opong, Regina ; Nyarko, Alexander K ; Yamaoka, Shoji ; Yamaguchi, Yasuchika ; Edoh, Dominic ; Koram, Kwadwo ; Ohta, Nobuo ; Boakye, Daniel A ; Ayi, Irene ; Shoyama, Yukihiro
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0Animals
1Anti-trypanosomal activity
2Cell Line
3Cell Line, Tumor
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5Iridoids - chemistry
6Iridoids - isolation & purification
7Iridoids - pharmacology
8Medicinal plants
9Models, Molecular
10Molucidin
11Morinda - chemistry
12Morinda lucida
13Plant Extracts - chemistry
14Plant Extracts - pharmacology
15Structure-Activity Relationship
16Tetracyclic iridoid
17Trypanocidal Agents - chemistry
18Trypanocidal Agents - pharmacology
19Trypanosoma - drug effects
20Trypanosomiasis, African - drug therapy
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6Ayertey, Frederick
7Owusu, Kofi Baffour-Awuah
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7Owusu, Kofi Baffour-Awuah
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22Koram, Kwadwo
23Ohta, Nobuo
24Boakye, Daniel A
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atitleNew anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth
jtitleBioorganic & medicinal chemistry letters
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issue15
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pages3030-3033
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abstract[Display omitted] Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the viewpoints of toxicity and drug resistance issues. Recently, there have been a lot of emphases on the use of medicinal plants world-wide. Morinda lucida Benth. is one of the most popular medicinal plants widely distributed in Africa and several groups have reported on its anti-protozoa activities. In this study, we have isolated one novel tetracyclic iridoid, named as molucidin, from the CHCl3 fraction of the M. lucida leaves by bioassay-guided fractionation and purification. Molucidin was structurally elucidated by 1H and 13C NMR including HMQC, HMBC, H–H COSY and NOESY resulting in tetracyclic iridoid skeleton, and its absolute configuration was determined. We have further demonstrated that molucidin presented a strong anti-trypanosomal activity, indicating an IC50 value of 1.27μM. The cytotoxicity study using human normal and cancer cell lines indicated that molucidin exhibited selectivity index (SI) against two normal fibroblasts greater than 4.73. Furthermore, structure–activity relationship (SAR) study was undertaken with molucidin and oregonin, which is identical to anti-trypanosomal active components of Alnus japonica. Overlapping analysis of the lowest energy conformation of molucidin with oregonin suggested a certain similarities of aromatic rings of both oregonin and molucidin. These results contribute to the future drug design studies for HAT.
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