Furanocembranoid from the Okinawan soft coral Sinularia sp.

One new furanocembranoid diterpene, 11-hydroxy-Δ(12(13))-pukalide (1), along with six known secondary metabolites, 11-acetoxy-Δ(12(13))-pukalide (2), 13α-acetoxypukalide (3), pukalide (4), 3α-methoxyfuranocembranoid (5), Δ(9(15))-africanene (6), and methyl (5′E)-5-(2′,6′-dimethylocta-5′,7′-dienyl)fu...

Descripción completa

Detalles Bibliográficos
Autores principales: Nagasaka, Misaki, Tani, Kazuki, Nishikawa, Keisuke, Kinjo, Riri, Ishii, Takahiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Singapore 2022
Materias:
Original Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8888784/
https://www.ncbi.nlm.nih.gov/pubmed/35233688
http://dx.doi.org/10.1007/s13659-022-00330-7
_version_ 1784661230320877568
author Nagasaka, Misaki
Tani, Kazuki
Nishikawa, Keisuke
Kinjo, Riri
Ishii, Takahiro
author_facet Nagasaka, Misaki
Tani, Kazuki
Nishikawa, Keisuke
Kinjo, Riri
Ishii, Takahiro
author_sort Nagasaka, Misaki
collection PubMed
description One new furanocembranoid diterpene, 11-hydroxy-Δ(12(13))-pukalide (1), along with six known secondary metabolites, 11-acetoxy-Δ(12(13))-pukalide (2), 13α-acetoxypukalide (3), pukalide (4), 3α-methoxyfuranocembranoid (5), Δ(9(15))-africanene (6), and methyl (5′E)-5-(2′,6′-dimethylocta-5′,7′-dienyl)furan-3-carboxylate (7) were isolated from the Okinawan soft coral Sinularia sp. Their chemical structures were elucidated based on spectroscopic analysis (FTIR, NMR, and HRESIMS), and the relative stereochemistry of 1 was determined by NOESY experiments and acetylation, which yielded derivative 2. In addition, compounds 1 and 7 exhibited toxicity in the brine shrimp lethality test. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13659-022-00330-7.
format Online
Article
Text
id pubmed-8888784
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher Springer Singapore
record_format MEDLINE/PubMed
spelling pubmed-88887842022-03-08 Furanocembranoid from the Okinawan soft coral Sinularia sp. Nagasaka, Misaki Tani, Kazuki Nishikawa, Keisuke Kinjo, Riri Ishii, Takahiro Nat Prod Bioprospect Original Article One new furanocembranoid diterpene, 11-hydroxy-Δ(12(13))-pukalide (1), along with six known secondary metabolites, 11-acetoxy-Δ(12(13))-pukalide (2), 13α-acetoxypukalide (3), pukalide (4), 3α-methoxyfuranocembranoid (5), Δ(9(15))-africanene (6), and methyl (5′E)-5-(2′,6′-dimethylocta-5′,7′-dienyl)furan-3-carboxylate (7) were isolated from the Okinawan soft coral Sinularia sp. Their chemical structures were elucidated based on spectroscopic analysis (FTIR, NMR, and HRESIMS), and the relative stereochemistry of 1 was determined by NOESY experiments and acetylation, which yielded derivative 2. In addition, compounds 1 and 7 exhibited toxicity in the brine shrimp lethality test. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13659-022-00330-7. Springer Singapore 2022-03-02 /pmc/articles/PMC8888784/ /pubmed/35233688 http://dx.doi.org/10.1007/s13659-022-00330-7 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Original Article
Nagasaka, Misaki
Tani, Kazuki
Nishikawa, Keisuke
Kinjo, Riri
Ishii, Takahiro
Furanocembranoid from the Okinawan soft coral Sinularia sp.
title Furanocembranoid from the Okinawan soft coral Sinularia sp.
title_full Furanocembranoid from the Okinawan soft coral Sinularia sp.
title_fullStr Furanocembranoid from the Okinawan soft coral Sinularia sp.
title_full_unstemmed Furanocembranoid from the Okinawan soft coral Sinularia sp.
title_short Furanocembranoid from the Okinawan soft coral Sinularia sp.
title_sort furanocembranoid from the okinawan soft coral sinularia sp.
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8888784/
https://www.ncbi.nlm.nih.gov/pubmed/35233688
http://dx.doi.org/10.1007/s13659-022-00330-7
work_keys_str_mv AT nagasakamisaki furanocembranoidfromtheokinawansoftcoralsinulariasp
AT tanikazuki furanocembranoidfromtheokinawansoftcoralsinulariasp
AT nishikawakeisuke furanocembranoidfromtheokinawansoftcoralsinulariasp
AT kinjoriri furanocembranoidfromtheokinawansoftcoralsinulariasp
AT ishiitakahiro furanocembranoidfromtheokinawansoftcoralsinulariasp

Ejemplares similares