Bioactive Bis(indole) Alkaloids from a <i>Spongosorites</i> sp. Sponge

Six new bis(indole) alkaloids (<b>1</b>–<b>6</b>) along with eight known ones of the topsentin class were isolated from a <i>Spongosorites</i> sp. sponge of Korea. Based on the results of combined spectroscopic analyses, the structures of spongosoritins A–D (<b...

Full description

Bibliographic Details
Main Authors: Jae Sung Park, Eunji Cho, Ji-Yeon Hwang, Sung Chul Park, Beomkoo Chung, Oh-Seok Kwon, Chung J. Sim, Dong-Chan Oh, Ki-Bong Oh, Jongheon Shin
Format: Article
Language:English
Published: MDPI AG 2020-12-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/19/1/3
_version_ 1797543696227368960
author Jae Sung Park
Eunji Cho
Ji-Yeon Hwang
Sung Chul Park
Beomkoo Chung
Oh-Seok Kwon
Chung J. Sim
Dong-Chan Oh
Ki-Bong Oh
Jongheon Shin
author_facet Jae Sung Park
Eunji Cho
Ji-Yeon Hwang
Sung Chul Park
Beomkoo Chung
Oh-Seok Kwon
Chung J. Sim
Dong-Chan Oh
Ki-Bong Oh
Jongheon Shin
author_sort Jae Sung Park
collection DOAJ
description Six new bis(indole) alkaloids (<b>1</b>–<b>6</b>) along with eight known ones of the topsentin class were isolated from a <i>Spongosorites</i> sp. sponge of Korea. Based on the results of combined spectroscopic analyses, the structures of spongosoritins A–D (<b>1</b>–<b>4</b>) were determined to possess a 2-methoxy-1-imidazole-5-one core connecting the indole moieties, and these were linked by a linear urea bridge for spongocarbamides A (<b>5</b>) and B (<b>6</b>). The absolute configurations of spongosoritins were assigned by electronic circular dichroism (ECD) computation. The new compounds exhibited moderate inhibition against transpeptidase sortase A and weak inhibition against human pathogenic bacteria and A549 and K562 cancer cell lines.
first_indexed 2024-03-10T13:49:20Z
format Article
id doaj.art-50dd476b98c84b9e9ada57c134b898c5
institution Directory Open Access Journal
issn 1660-3397
language English
last_indexed 2024-03-10T13:49:20Z
publishDate 2020-12-01
publisher MDPI AG
record_format Article
series Marine Drugs
spelling doaj.art-50dd476b98c84b9e9ada57c134b898c52023-11-21T02:15:45ZengMDPI AGMarine Drugs1660-33972020-12-01191310.3390/md19010003Bioactive Bis(indole) Alkaloids from a <i>Spongosorites</i> sp. SpongeJae Sung Park0Eunji Cho1Ji-Yeon Hwang2Sung Chul Park3Beomkoo Chung4Oh-Seok Kwon5Chung J. Sim6Dong-Chan Oh7Ki-Bong Oh8Jongheon Shin9Natural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, KoreaDepartment of Agricultural Biotechnology, College of Agriculture and Life Sciences, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, KoreaDepartment of Agricultural Biotechnology, College of Agriculture and Life Sciences, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, KoreaDepartment of Biological Sciences, College of Life Science and Nano Technology, Hannam University, 461-6 Jeonmin, Yuseong, Daejeon 305-811, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, KoreaDepartment of Agricultural Biotechnology, College of Agriculture and Life Sciences, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, KoreaSix new bis(indole) alkaloids (<b>1</b>–<b>6</b>) along with eight known ones of the topsentin class were isolated from a <i>Spongosorites</i> sp. sponge of Korea. Based on the results of combined spectroscopic analyses, the structures of spongosoritins A–D (<b>1</b>–<b>4</b>) were determined to possess a 2-methoxy-1-imidazole-5-one core connecting the indole moieties, and these were linked by a linear urea bridge for spongocarbamides A (<b>5</b>) and B (<b>6</b>). The absolute configurations of spongosoritins were assigned by electronic circular dichroism (ECD) computation. The new compounds exhibited moderate inhibition against transpeptidase sortase A and weak inhibition against human pathogenic bacteria and A549 and K562 cancer cell lines.https://www.mdpi.com/1660-3397/19/1/3<i>Spongosorites</i> sp. spongebis(indole) alkaloidsspongosoritinsspongocarbamidestopsentinsortase A inhibition
spellingShingle Jae Sung Park
Eunji Cho
Ji-Yeon Hwang
Sung Chul Park
Beomkoo Chung
Oh-Seok Kwon
Chung J. Sim
Dong-Chan Oh
Ki-Bong Oh
Jongheon Shin
Bioactive Bis(indole) Alkaloids from a <i>Spongosorites</i> sp. Sponge
Marine Drugs
<i>Spongosorites</i> sp. sponge
bis(indole) alkaloids
spongosoritins
spongocarbamides
topsentin
sortase A inhibition
title Bioactive Bis(indole) Alkaloids from a <i>Spongosorites</i> sp. Sponge
title_full Bioactive Bis(indole) Alkaloids from a <i>Spongosorites</i> sp. Sponge
title_fullStr Bioactive Bis(indole) Alkaloids from a <i>Spongosorites</i> sp. Sponge
title_full_unstemmed Bioactive Bis(indole) Alkaloids from a <i>Spongosorites</i> sp. Sponge
title_short Bioactive Bis(indole) Alkaloids from a <i>Spongosorites</i> sp. Sponge
title_sort bioactive bis indole alkaloids from a i spongosorites i sp sponge
topic <i>Spongosorites</i> sp. sponge
bis(indole) alkaloids
spongosoritins
spongocarbamides
topsentin
sortase A inhibition
url https://www.mdpi.com/1660-3397/19/1/3
work_keys_str_mv AT jaesungpark bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT eunjicho bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT jiyeonhwang bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT sungchulpark bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT beomkoochung bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT ohseokkwon bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT chungjsim bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT dongchanoh bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT kibongoh bioactivebisindolealkaloidsfromaispongosoritesispsponge
AT jongheonshin bioactivebisindolealkaloidsfromaispongosoritesispsponge