Furanocembranoid from the Okinawan soft coral Sinularia sp.

doi:10.1007/s13659-022-00330-7

Natural Products and Bioprospecting ›› 2022, Vol. 12 ›› Issue (1): 1-7.DOI: 10.1007/s13659-022-00330-7

• ORIGINAL ARTICLES •

Furanocembranoid from the Okinawan soft coral Sinularia sp.

Misaki Nagasaka¹, Kazuki Tani¹, Keisuke Nishikawa², Riri Kinjo¹, Takahiro Ishii¹

1 Department of Biosciences and Biotechnology, Faculty of Agriculture, University of the Ryukyus, Senbaru 1, Nishihara, Okinawa 903-0213, Japan;
2 Department of Chemistry, Graduate School of Science, Osaka City University, Osaka 558-8585, Japan

Received:2021-12-20 Revised:2022-02-12 Online:2022-03-12 Published:2022-02-24
Contact: Takahiro Ishii
Supported by:
We are grateful to Mr. Masahiro Wada (Faculty of Agriculture, University of the Ryukyus) for his guidance on the collection site of the soft corals. The authors would also like to thank Mr. Shinichi Gima (Center for Research Advancement and Collaboration, University of the Ryukyus) for the measurement of HRESIMS. Finally, we would like to thank Editage (www.editage.com) for English language editing.

Furanocembranoid from the Okinawan soft coral Sinularia sp.

Misaki Nagasaka¹, Kazuki Tani¹, Keisuke Nishikawa², Riri Kinjo¹, Takahiro Ishii¹

1 Department of Biosciences and Biotechnology, Faculty of Agriculture, University of the Ryukyus, Senbaru 1, Nishihara, Okinawa 903-0213, Japan;
2 Department of Chemistry, Graduate School of Science, Osaka City University, Osaka 558-8585, Japan

通讯作者: Takahiro Ishii
基金资助:
We are grateful to Mr. Masahiro Wada (Faculty of Agriculture, University of the Ryukyus) for his guidance on the collection site of the soft corals. The authors would also like to thank Mr. Shinichi Gima (Center for Research Advancement and Collaboration, University of the Ryukyus) for the measurement of HRESIMS. Finally, we would like to thank Editage (www.editage.com) for English language editing.

Abstract

Abstract: One new furanocembranoid diterpene, 11-hydroxy-Δ¹²⁽¹³⁾-pukalide (1), along with six known secondary metabolites, 11-acetoxy-Δ¹²⁽¹³⁾-pukalide (2), 13α-acetoxypukalide (3), pukalide (4), 3α-methoxyfuranocembranoid (5), Δ⁹⁽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.

Key words: Soft coral, Sinularia sp., Furanocembranoid, Diterpene

摘要： One new furanocembranoid diterpene, 11-hydroxy-Δ¹²⁽¹³⁾-pukalide (1), along with six known secondary metabolites, 11-acetoxy-Δ¹²⁽¹³⁾-pukalide (2), 13α-acetoxypukalide (3), pukalide (4), 3α-methoxyfuranocembranoid (5), Δ⁹⁽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.

关键词: Soft coral, Sinularia sp., Furanocembranoid, Diterpene

Misaki Nagasaka, Kazuki Tani, Keisuke Nishikawa, Riri Kinjo, Takahiro Ishii. Furanocembranoid from the Okinawan soft coral Sinularia sp.[J]. Natural Products and Bioprospecting, 2022, 12(1): 1-7.

Misaki Nagasaka, Kazuki Tani, Keisuke Nishikawa, Riri Kinjo, Takahiro Ishii. Furanocembranoid from the Okinawan soft coral Sinularia sp.[J]. 应用天然产物, 2022, 12(1): 1-7.

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Furanocembranoid from the Okinawan soft coral Sinularia sp.

Furanocembranoid from the Okinawan soft coral Sinularia sp.

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