Meroterpenoids produced by Pseudocosmospora sp. Bm-1-1 isolated from Acanthus ebracteatus Vahl

Tomoki Nakamura; Takuma Suzuki; Nanang Rudianto Ariefta; Takuya Koseki; Takako Aboshi; Tetsuya Murayama; Ari Widiyantoro; Rikhsan Kurniatuhadi; Abdul Malik; Suwardi Annas; Desi Harneti; Rani Maharani; Unang Supratman; Junpei Abe; Naoaki Kurisawa; Ken ich Kimura; Yoshihito Shiono

doi:10.1016/j.phytol.2019.03.014

Meroterpenoids produced by Pseudocosmospora sp. Bm-1-1 isolated from Acanthus ebracteatus Vahl

Tomoki Nakamura, Takuma Suzuki, Nanang Rudianto Ariefta, Takuya Koseki, Takako Aboshi, Tetsuya Murayama, Ari Widiyantoro, Rikhsan Kurniatuhadi, Abdul Malik, Suwardi Annas, Desi Harneti, Rani Maharani, Unang Supratman, Junpei Abe, Naoaki Kurisawa, Ken ich Kimura, Yoshihito Shiono

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

Abstract

Fractionation of ethyl acetate extract obtained by culturing the endophytic fungus Pseudocosmospora sp. Bm-1-1 resulted in the isolation of four new meroterpenoids, cosmosporin A (1), 6-carboxy-cosmosporin A (2), rel-(6aS,10aR)-Δ ⁹ -tetrahydrocannabiorcolic acid B (3) and 8′-hydroxy-cannabiorcichromenic acid (4), in addition to four known compounds 5–8. Structures were elucidated by spectral analysis, as well as by directly comparing the spectral data of new compounds with those of known compounds. Cannabiorcichromenic acid (5), decarboxy-cannabiorcichromenic acid (6), and rel-(6aS,10aR)-decarboxy-Δ ⁹ -tetrahydrocannabiorcolic acid B (8) restored growth of a Saccharomyces cerevisiae mutant strain involving Ca ²⁺ signal transduction. Furthermore, compounds 3 and 8 had cytotoxic activity against HL60 cells (3: IC ₅₀ = 24.1 μM and 8: IC ₅₀ 1.6 μM).

Original language	English
Pages (from-to)	85-91
Number of pages	7
Journal	Phytochemistry Letters
Volume	31
DOIs	https://doi.org/10.1016/j.phytol.2019.03.014
Publication status	Published - 2019 Jun
Externally published	Yes

Keywords

Ca ignaling
Cytotoxicity
Endophyte
Pseudocosmospora sp. Bm-1-1

ASJC Scopus subject areas

Biotechnology
Biochemistry
Agronomy and Crop Science
Plant Science

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10.1016/j.phytol.2019.03.014

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Nakamura, T., Suzuki, T., Rudianto Ariefta, N., Koseki, T., Aboshi, T., Murayama, T., Widiyantoro, A., Kurniatuhadi, R., Malik, A., Annas, S., Harneti, D., Maharani, R., Supratman, U., Abe, J., Kurisawa, N., Kimura, K. I., & Shiono, Y. (2019). Meroterpenoids produced by Pseudocosmospora sp. Bm-1-1 isolated from Acanthus ebracteatus Vahl. Phytochemistry Letters, 31, 85-91. https://doi.org/10.1016/j.phytol.2019.03.014

Nakamura, T, Suzuki, T, Rudianto Ariefta, N, Koseki, T, Aboshi, T, Murayama, T, Widiyantoro, A, Kurniatuhadi, R, Malik, A, Annas, S, Harneti, D, Maharani, R, Supratman, U, Abe, J, Kurisawa, N, Kimura, KI & Shiono, Y 2019, 'Meroterpenoids produced by Pseudocosmospora sp. Bm-1-1 isolated from Acanthus ebracteatus Vahl', Phytochemistry Letters, vol. 31, pp. 85-91. https://doi.org/10.1016/j.phytol.2019.03.014

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title = "Meroterpenoids produced by Pseudocosmospora sp. Bm-1-1 isolated from Acanthus ebracteatus Vahl",

abstract = " Fractionation of ethyl acetate extract obtained by culturing the endophytic fungus Pseudocosmospora sp. Bm-1-1 resulted in the isolation of four new meroterpenoids, cosmosporin A (1), 6-carboxy-cosmosporin A (2), rel-(6aS,10aR)-Δ 9 -tetrahydrocannabiorcolic acid B (3) and 8′-hydroxy-cannabiorcichromenic acid (4), in addition to four known compounds 5–8. Structures were elucidated by spectral analysis, as well as by directly comparing the spectral data of new compounds with those of known compounds. Cannabiorcichromenic acid (5), decarboxy-cannabiorcichromenic acid (6), and rel-(6aS,10aR)-decarboxy-Δ 9 -tetrahydrocannabiorcolic acid B (8) restored growth of a Saccharomyces cerevisiae mutant strain involving Ca 2+ signal transduction. Furthermore, compounds 3 and 8 had cytotoxic activity against HL60 cells (3: IC 50 = 24.1 μM and 8: IC 50 1.6 μM).",

keywords = "Ca ignaling, Cytotoxicity, Endophyte, Pseudocosmospora sp. Bm-1-1",

author = "Tomoki Nakamura and Takuma Suzuki and {Rudianto Ariefta}, Nanang and Takuya Koseki and Takako Aboshi and Tetsuya Murayama and Ari Widiyantoro and Rikhsan Kurniatuhadi and Abdul Malik and Suwardi Annas and Desi Harneti and Rani Maharani and Unang Supratman and Junpei Abe and Naoaki Kurisawa and Kimura, {Ken ich} and Yoshihito Shiono",

note = "Funding Information: This work was partly supported by MEXT KAKENHI Grant Number JP15H05246 . Publisher Copyright: {\textcopyright} 2019 Phytochemical Society of Europe",

year = "2019",

month = jun,

doi = "10.1016/j.phytol.2019.03.014",

language = "English",

volume = "31",

pages = "85--91",

journal = "Phytochemistry Letters",

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T1 - Meroterpenoids produced by Pseudocosmospora sp. Bm-1-1 isolated from Acanthus ebracteatus Vahl

AU - Nakamura, Tomoki

AU - Suzuki, Takuma

AU - Rudianto Ariefta, Nanang

AU - Koseki, Takuya

AU - Aboshi, Takako

AU - Murayama, Tetsuya

AU - Widiyantoro, Ari

AU - Kurniatuhadi, Rikhsan

AU - Malik, Abdul

AU - Annas, Suwardi

AU - Harneti, Desi

AU - Maharani, Rani

AU - Supratman, Unang

AU - Abe, Junpei

AU - Kurisawa, Naoaki

AU - Kimura, Ken ich

AU - Shiono, Yoshihito

PY - 2019/6

Y1 - 2019/6

N2 - Fractionation of ethyl acetate extract obtained by culturing the endophytic fungus Pseudocosmospora sp. Bm-1-1 resulted in the isolation of four new meroterpenoids, cosmosporin A (1), 6-carboxy-cosmosporin A (2), rel-(6aS,10aR)-Δ 9 -tetrahydrocannabiorcolic acid B (3) and 8′-hydroxy-cannabiorcichromenic acid (4), in addition to four known compounds 5–8. Structures were elucidated by spectral analysis, as well as by directly comparing the spectral data of new compounds with those of known compounds. Cannabiorcichromenic acid (5), decarboxy-cannabiorcichromenic acid (6), and rel-(6aS,10aR)-decarboxy-Δ 9 -tetrahydrocannabiorcolic acid B (8) restored growth of a Saccharomyces cerevisiae mutant strain involving Ca 2+ signal transduction. Furthermore, compounds 3 and 8 had cytotoxic activity against HL60 cells (3: IC 50 = 24.1 μM and 8: IC 50 1.6 μM).

AB - Fractionation of ethyl acetate extract obtained by culturing the endophytic fungus Pseudocosmospora sp. Bm-1-1 resulted in the isolation of four new meroterpenoids, cosmosporin A (1), 6-carboxy-cosmosporin A (2), rel-(6aS,10aR)-Δ 9 -tetrahydrocannabiorcolic acid B (3) and 8′-hydroxy-cannabiorcichromenic acid (4), in addition to four known compounds 5–8. Structures were elucidated by spectral analysis, as well as by directly comparing the spectral data of new compounds with those of known compounds. Cannabiorcichromenic acid (5), decarboxy-cannabiorcichromenic acid (6), and rel-(6aS,10aR)-decarboxy-Δ 9 -tetrahydrocannabiorcolic acid B (8) restored growth of a Saccharomyces cerevisiae mutant strain involving Ca 2+ signal transduction. Furthermore, compounds 3 and 8 had cytotoxic activity against HL60 cells (3: IC 50 = 24.1 μM and 8: IC 50 1.6 μM).

KW - Ca ignaling

KW - Cytotoxicity

KW - Endophyte

KW - Pseudocosmospora sp. Bm-1-1

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AN - SCOPUS:85063444143

SN - 1874-3900

VL - 31

SP - 85

EP - 91

JO - Phytochemistry Letters

JF - Phytochemistry Letters

ER -

Meroterpenoids produced by Pseudocosmospora sp. Bm-1-1 isolated from Acanthus ebracteatus Vahl

Abstract

Keywords

ASJC Scopus subject areas

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