Scalalactams A–D, scalarane sesterterpenes with a γ-lactam moiety from a Korean Spongia sp. Marine sponge

Inho Yang; Jusung Lee; Jihye Lee; Dongyup Hahn; Jungwook Chin; Dong Hwan Won; Jaeyoung Ko; Hyukjae Choi; Ahreum Hong; Sang Jip Nam; Heonjoong Kang

doi:10.3390/molecules23123187

Scalalactams A–D, scalarane sesterterpenes with a γ-lactam moiety from a Korean Spongia sp. Marine sponge

Inho Yang, Jusung Lee, Jihye Lee, Dongyup Hahn, Jungwook Chin, Dong Hwan Won, Jaeyoung Ko, Hyukjae Choi, Ahreum Hong, Sang Jip Nam, Heonjoong Kang

Department of Chemistry & Nanoscience

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

12 Scopus citations

Abstract

Intensive study on the chemical components of a Korean marine sponge, Spongia sp., has led to the isolation of four new scalarane sesterterpenes, scalalactams A–D (1–4). Their chemical structures were elucidated from the analysis of spectroscopic data including 1D-and 2D-NMR as well as MS data. Scalalactams A–D (1–4) possess a scalarane carbon skeleton with a rare structural feature of a γ-lactam moiety within the molecules. Scalalactams A and B (1 and 2) have an extended isopropanyl chain at the lactam ring, and scalalactams C and D (3 and 4) possess a phenethyl group at the lactam ring moiety. Scalalactams A–D (1–4) did not show FXR antagonistic activity nor cytotoxicity up to 100 μM.

Original language	English
Article number	3187
Journal	Molecules
Volume	23
Issue number	12
DOIs	https://doi.org/10.3390/molecules23123187
State	Published - 3 Dec 2018

Bibliographical note

Funding Information:
Author Contributions: D.H., J.C., and J.K. collected animal sample, prepared extract and fractions, and purified compounds. J.L. (Jusung Lee), J.L. (Jihye Lee), and D.H.W. did bioassays. I.Y., J.L. (Jusung Lee), D.H., and A.H. elucidated the structures, search for the literatures, and prepared original draft. H.C. and S.-J.N. collected spectral data and elucidated the chemical structures. S.-J.N. was the project leader for guiding the experiments of chemical analysis and writing manuscript. H.K. contributed funding sources and supervised the project Funding: The present study was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT NRF-2015M1A5A1037572 and NRF-2016M3A9B8914313).

Funding Information:
The present study was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT NRF-2015M1A5A1037572 and NRF-2016M3A9B8914313).

Publisher Copyright:
© 2018 by the authors.

Keywords

Marine natural products
Marine sponge
Scalalactams
Scalarane sesterterpenes
Spongia sp

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title = "Scalalactams A–D, scalarane sesterterpenes with a γ-lactam moiety from a Korean Spongia sp. Marine sponge",

abstract = "Intensive study on the chemical components of a Korean marine sponge, Spongia sp., has led to the isolation of four new scalarane sesterterpenes, scalalactams A–D (1–4). Their chemical structures were elucidated from the analysis of spectroscopic data including 1D-and 2D-NMR as well as MS data. Scalalactams A–D (1–4) possess a scalarane carbon skeleton with a rare structural feature of a γ-lactam moiety within the molecules. Scalalactams A and B (1 and 2) have an extended isopropanyl chain at the lactam ring, and scalalactams C and D (3 and 4) possess a phenethyl group at the lactam ring moiety. Scalalactams A–D (1–4) did not show FXR antagonistic activity nor cytotoxicity up to 100 μM.",

keywords = "Marine natural products, Marine sponge, Scalalactams, Scalarane sesterterpenes, Spongia sp",

author = "Inho Yang and Jusung Lee and Jihye Lee and Dongyup Hahn and Jungwook Chin and Won, {Dong Hwan} and Jaeyoung Ko and Hyukjae Choi and Ahreum Hong and Nam, {Sang Jip} and Heonjoong Kang",

note = "Funding Information: Author Contributions: D.H., J.C., and J.K. collected animal sample, prepared extract and fractions, and purified compounds. J.L. (Jusung Lee), J.L. (Jihye Lee), and D.H.W. did bioassays. I.Y., J.L. (Jusung Lee), D.H., and A.H. elucidated the structures, search for the literatures, and prepared original draft. H.C. and S.-J.N. collected spectral data and elucidated the chemical structures. S.-J.N. was the project leader for guiding the experiments of chemical analysis and writing manuscript. H.K. contributed funding sources and supervised the project Funding: The present study was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT NRF-2015M1A5A1037572 and NRF-2016M3A9B8914313). Funding Information: The present study was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT NRF-2015M1A5A1037572 and NRF-2016M3A9B8914313). Publisher Copyright: {\textcopyright} 2018 by the authors.",

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day = "3",

doi = "10.3390/molecules23123187",

language = "English",

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AU - Yang, Inho

AU - Lee, Jusung

AU - Lee, Jihye

AU - Hahn, Dongyup

AU - Chin, Jungwook

AU - Won, Dong Hwan

AU - Ko, Jaeyoung

AU - Choi, Hyukjae

AU - Hong, Ahreum

AU - Nam, Sang Jip

AU - Kang, Heonjoong

N1 - Funding Information: Author Contributions: D.H., J.C., and J.K. collected animal sample, prepared extract and fractions, and purified compounds. J.L. (Jusung Lee), J.L. (Jihye Lee), and D.H.W. did bioassays. I.Y., J.L. (Jusung Lee), D.H., and A.H. elucidated the structures, search for the literatures, and prepared original draft. H.C. and S.-J.N. collected spectral data and elucidated the chemical structures. S.-J.N. was the project leader for guiding the experiments of chemical analysis and writing manuscript. H.K. contributed funding sources and supervised the project Funding: The present study was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT NRF-2015M1A5A1037572 and NRF-2016M3A9B8914313). Funding Information: The present study was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT NRF-2015M1A5A1037572 and NRF-2016M3A9B8914313). Publisher Copyright: © 2018 by the authors.

PY - 2018/12/3

Y1 - 2018/12/3

N2 - Intensive study on the chemical components of a Korean marine sponge, Spongia sp., has led to the isolation of four new scalarane sesterterpenes, scalalactams A–D (1–4). Their chemical structures were elucidated from the analysis of spectroscopic data including 1D-and 2D-NMR as well as MS data. Scalalactams A–D (1–4) possess a scalarane carbon skeleton with a rare structural feature of a γ-lactam moiety within the molecules. Scalalactams A and B (1 and 2) have an extended isopropanyl chain at the lactam ring, and scalalactams C and D (3 and 4) possess a phenethyl group at the lactam ring moiety. Scalalactams A–D (1–4) did not show FXR antagonistic activity nor cytotoxicity up to 100 μM.

AB - Intensive study on the chemical components of a Korean marine sponge, Spongia sp., has led to the isolation of four new scalarane sesterterpenes, scalalactams A–D (1–4). Their chemical structures were elucidated from the analysis of spectroscopic data including 1D-and 2D-NMR as well as MS data. Scalalactams A–D (1–4) possess a scalarane carbon skeleton with a rare structural feature of a γ-lactam moiety within the molecules. Scalalactams A and B (1 and 2) have an extended isopropanyl chain at the lactam ring, and scalalactams C and D (3 and 4) possess a phenethyl group at the lactam ring moiety. Scalalactams A–D (1–4) did not show FXR antagonistic activity nor cytotoxicity up to 100 μM.

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KW - Marine sponge

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KW - Scalarane sesterterpenes

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DO - 10.3390/molecules23123187

M3 - Article

C2 - 30513974

AN - SCOPUS:85057589425

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

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M1 - 3187

ER -

Scalalactams A–D, scalarane sesterterpenes with a γ-lactam moiety from a Korean Spongia sp. Marine sponge

Abstract

Bibliographical note

Keywords

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