A pyrrocidine derivative produced by fungus Neonectria ramulariae In-2 isolated from a Beetle Holotrichia picea

Yoshihito Shiono; Mariko Furukawa; Takuya Koseki; Eunsang Kwon; Andreas Hendracipta Kurniawan; Satoru Sato; Desi Harneti; Rani Maharani; Unang Supratman; Shota Uesugi; Ken ichi Kimura

doi:10.1016/j.phytol.2018.05.030

A pyrrocidine derivative produced by fungus Neonectria ramulariae In-2 isolated from a Beetle Holotrichia picea

Yoshihito Shiono, Mariko Furukawa, Takuya Koseki, Eunsang Kwon, Andreas Hendracipta Kurniawan, Satoru Sato, Desi Harneti, Rani Maharani, Unang Supratman, Shota Uesugi, Ken ichi Kimura

SCI - Research and Analytical Center for Giant Molecules

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

6 Citations (Scopus)

Abstract

A new pyrrocidine A derivative, 19-epi-pyrrocidine A (1) was isolated from the insect–derived fungus Neonectria ramulariae In-2, together with known pyrrocidine A (2). The structure of 1 was determined by extensive 1D- and 2D-NMR, and MS spectral analyses. The absolute configuration of 2 was confirmed for the first time by X-ray crystallography. Compound 1 exhibited cytotoxicity against human acute promyelocytic leukemia HL60 cells (IC₅₀ 2.05 μM). In addition, semi-synthetic compounds 19-O-methyl-pyrrocidine A (3), 19-O-acetyl-pyrrocidine A (4), and 1,2-4,5-17,18-triepoxy-pyrrocidine A (5) were found to possess significant cytotoxicity, with IC₅₀ values of 0.66 μM, 0.19 μM, and 2.00 μM, respectively.

Original language	English
Pages (from-to)	120-124
Number of pages	5
Journal	Phytochemistry Letters
Volume	26
DOIs	https://doi.org/10.1016/j.phytol.2018.05.030
Publication status	Published - 2018 Aug

Keywords

19-epi-Pyrrocidine A
HL60
Holotrichia picea
Neonectria ramulariae
Pyrrocidine A

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10.1016/j.phytol.2018.05.030

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@article{ccc871bd466848b9a9912d1ff6017c98,

title = "A pyrrocidine derivative produced by fungus Neonectria ramulariae In-2 isolated from a Beetle Holotrichia picea",

abstract = "A new pyrrocidine A derivative, 19-epi-pyrrocidine A (1) was isolated from the insect–derived fungus Neonectria ramulariae In-2, together with known pyrrocidine A (2). The structure of 1 was determined by extensive 1D- and 2D-NMR, and MS spectral analyses. The absolute configuration of 2 was confirmed for the first time by X-ray crystallography. Compound 1 exhibited cytotoxicity against human acute promyelocytic leukemia HL60 cells (IC50 2.05 μM). In addition, semi-synthetic compounds 19-O-methyl-pyrrocidine A (3), 19-O-acetyl-pyrrocidine A (4), and 1,2-4,5-17,18-triepoxy-pyrrocidine A (5) were found to possess significant cytotoxicity, with IC50 values of 0.66 μM, 0.19 μM, and 2.00 μM, respectively.",

keywords = "19-epi-Pyrrocidine A, HL60, Holotrichia picea, Neonectria ramulariae, Pyrrocidine A",

author = "Yoshihito Shiono and Mariko Furukawa and Takuya Koseki and Eunsang Kwon and Kurniawan, {Andreas Hendracipta} and Satoru Sato and Desi Harneti and Rani Maharani and Unang Supratman and Shota Uesugi and Kimura, {Ken ichi}",

note = "Publisher Copyright: {\textcopyright} 2018 Phytochemical Society of Europe",

year = "2018",

month = aug,

doi = "10.1016/j.phytol.2018.05.030",

language = "English",

volume = "26",

pages = "120--124",

journal = "Phytochemistry Letters",

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publisher = "Elsevier BV",

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TY - JOUR

T1 - A pyrrocidine derivative produced by fungus Neonectria ramulariae In-2 isolated from a Beetle Holotrichia picea

AU - Shiono, Yoshihito

AU - Furukawa, Mariko

AU - Koseki, Takuya

AU - Kwon, Eunsang

AU - Kurniawan, Andreas Hendracipta

AU - Sato, Satoru

AU - Harneti, Desi

AU - Maharani, Rani

AU - Supratman, Unang

AU - Uesugi, Shota

AU - Kimura, Ken ichi

PY - 2018/8

Y1 - 2018/8

N2 - A new pyrrocidine A derivative, 19-epi-pyrrocidine A (1) was isolated from the insect–derived fungus Neonectria ramulariae In-2, together with known pyrrocidine A (2). The structure of 1 was determined by extensive 1D- and 2D-NMR, and MS spectral analyses. The absolute configuration of 2 was confirmed for the first time by X-ray crystallography. Compound 1 exhibited cytotoxicity against human acute promyelocytic leukemia HL60 cells (IC50 2.05 μM). In addition, semi-synthetic compounds 19-O-methyl-pyrrocidine A (3), 19-O-acetyl-pyrrocidine A (4), and 1,2-4,5-17,18-triepoxy-pyrrocidine A (5) were found to possess significant cytotoxicity, with IC50 values of 0.66 μM, 0.19 μM, and 2.00 μM, respectively.

AB - A new pyrrocidine A derivative, 19-epi-pyrrocidine A (1) was isolated from the insect–derived fungus Neonectria ramulariae In-2, together with known pyrrocidine A (2). The structure of 1 was determined by extensive 1D- and 2D-NMR, and MS spectral analyses. The absolute configuration of 2 was confirmed for the first time by X-ray crystallography. Compound 1 exhibited cytotoxicity against human acute promyelocytic leukemia HL60 cells (IC50 2.05 μM). In addition, semi-synthetic compounds 19-O-methyl-pyrrocidine A (3), 19-O-acetyl-pyrrocidine A (4), and 1,2-4,5-17,18-triepoxy-pyrrocidine A (5) were found to possess significant cytotoxicity, with IC50 values of 0.66 μM, 0.19 μM, and 2.00 μM, respectively.

KW - 19-epi-Pyrrocidine A

KW - HL60

KW - Holotrichia picea

KW - Neonectria ramulariae

KW - Pyrrocidine A

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AN - SCOPUS:85047405146

SN - 1874-3900

VL - 26

SP - 120

EP - 124

JO - Phytochemistry Letters

JF - Phytochemistry Letters

ER -

A pyrrocidine derivative produced by fungus Neonectria ramulariae In-2 isolated from a Beetle Holotrichia picea

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Keywords

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