Saccharoquinoline, a cytotoxic alkaloidal meroterpenoid from marine-derived bacterium Saccharomonospora sp.

Tu Cam Le; Eun Ju Lee; Jihye Lee; Ahreum Hong; Chae Yoon Yim; Inho Yang; Hyukjae Choi; Jungwook Chin; Sung Jin Cho; Jaeyoung Ko; Hayoung Hwang; Sang Jip Nam; William Fenical

doi:10.3390/md17020098

Saccharoquinoline, a cytotoxic alkaloidal meroterpenoid from marine-derived bacterium Saccharomonospora sp.

Tu Cam Le
, Eun Ju Lee
, Jihye Lee
, Ahreum Hong
, Chae Yoon Yim
, Inho Yang
, Hyukjae Choi
, Jungwook Chin
, Sung Jin Cho
, Jaeyoung Ko
, Hayoung Hwang
, Sang Jip Nam
, William Fenical

Department of Chemistry & Nanoscience

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

23 Scopus citations

Abstract

A cytotoxic alkaloidal meroterpenoid, saccharoquinoline (1), has been isolated from the fermentation broth of the marine-derived bacterium Saccharomonospora sp. CNQ-490. The planar structure of 1 was elucidated by 1D, 2D NMR, and MS spectroscopic data analyzes, while the relative configuration of 1 was defined through the interpretation of NOE spectroscopic data. Saccharoquinoline (1) is composed of a drimane-type sesquiterpene unit in combination with an apparent 6,7,8-trihydroxyquinoline-2-carboxylic acid. This combination of biosynthetic pathways was observed for the first time in natural microbial products. Saccharoquinoline (1) was found to have cytotoxicity against the HCT-116 cancer cell line by inducing G1 arrest, which leads to cell growth inhibition.

Original language	English
Article number	98
Journal	Marine Drugs
Volume	17
Issue number	2
DOIs	https://doi.org/10.3390/md17020098
State	Published - 2 Feb 2019

Bibliographical note

Publisher Copyright:
© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

Keywords

Cytotoxicity
Marine natural product
Meroterpenoid
Saccharomonospora sp

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title = "Saccharoquinoline, a cytotoxic alkaloidal meroterpenoid from marine-derived bacterium Saccharomonospora sp.",

abstract = "A cytotoxic alkaloidal meroterpenoid, saccharoquinoline (1), has been isolated from the fermentation broth of the marine-derived bacterium Saccharomonospora sp. CNQ-490. The planar structure of 1 was elucidated by 1D, 2D NMR, and MS spectroscopic data analyzes, while the relative configuration of 1 was defined through the interpretation of NOE spectroscopic data. Saccharoquinoline (1) is composed of a drimane-type sesquiterpene unit in combination with an apparent 6,7,8-trihydroxyquinoline-2-carboxylic acid. This combination of biosynthetic pathways was observed for the first time in natural microbial products. Saccharoquinoline (1) was found to have cytotoxicity against the HCT-116 cancer cell line by inducing G1 arrest, which leads to cell growth inhibition.",

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author = "Le, \{Tu Cam\} and Lee, \{Eun Ju\} and Jihye Lee and Ahreum Hong and Yim, \{Chae Yoon\} and Inho Yang and Hyukjae Choi and Jungwook Chin and Cho, \{Sung Jin\} and Jaeyoung Ko and Hayoung Hwang and Nam, \{Sang Jip\} and William Fenical",

note = "Publisher Copyright: {\textcopyright} 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).",

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doi = "10.3390/md17020098",

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T1 - Saccharoquinoline, a cytotoxic alkaloidal meroterpenoid from marine-derived bacterium Saccharomonospora sp.

AU - Le, Tu Cam

AU - Lee, Eun Ju

AU - Lee, Jihye

AU - Hong, Ahreum

AU - Yim, Chae Yoon

AU - Yang, Inho

AU - Choi, Hyukjae

AU - Chin, Jungwook

AU - Cho, Sung Jin

AU - Ko, Jaeyoung

AU - Hwang, Hayoung

AU - Nam, Sang Jip

AU - Fenical, William

N1 - Publisher Copyright: © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

PY - 2019/2/2

Y1 - 2019/2/2

N2 - A cytotoxic alkaloidal meroterpenoid, saccharoquinoline (1), has been isolated from the fermentation broth of the marine-derived bacterium Saccharomonospora sp. CNQ-490. The planar structure of 1 was elucidated by 1D, 2D NMR, and MS spectroscopic data analyzes, while the relative configuration of 1 was defined through the interpretation of NOE spectroscopic data. Saccharoquinoline (1) is composed of a drimane-type sesquiterpene unit in combination with an apparent 6,7,8-trihydroxyquinoline-2-carboxylic acid. This combination of biosynthetic pathways was observed for the first time in natural microbial products. Saccharoquinoline (1) was found to have cytotoxicity against the HCT-116 cancer cell line by inducing G1 arrest, which leads to cell growth inhibition.

AB - A cytotoxic alkaloidal meroterpenoid, saccharoquinoline (1), has been isolated from the fermentation broth of the marine-derived bacterium Saccharomonospora sp. CNQ-490. The planar structure of 1 was elucidated by 1D, 2D NMR, and MS spectroscopic data analyzes, while the relative configuration of 1 was defined through the interpretation of NOE spectroscopic data. Saccharoquinoline (1) is composed of a drimane-type sesquiterpene unit in combination with an apparent 6,7,8-trihydroxyquinoline-2-carboxylic acid. This combination of biosynthetic pathways was observed for the first time in natural microbial products. Saccharoquinoline (1) was found to have cytotoxicity against the HCT-116 cancer cell line by inducing G1 arrest, which leads to cell growth inhibition.

KW - Cytotoxicity

KW - Marine natural product

KW - Meroterpenoid

KW - Saccharomonospora sp

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DO - 10.3390/md17020098

M3 - Article

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SN - 1660-3397

VL - 17

JO - Marine Drugs

JF - Marine Drugs

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M1 - 98

ER -

Saccharoquinoline, a cytotoxic alkaloidal meroterpenoid from marine-derived bacterium Saccharomonospora sp.

Abstract

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