Trinor-Guaiane-Type Sesquiterpenes with Unusual Skeletons from the Okinawan Soft Coral Clavularia viridis
6 affiliations
- 1University of the Ryukyus , , 1 Senbaru, Nishihara , ,
- 2Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi-ku, ,
- 3Hirosaki University , , 3-Bunkyo-cho , ,
- 4Kindai University , , 3-4-1 Kowakae , , ,
- 5Kagoshima University , , 4-50-20 Shimoarata , ,
- 6Kagoshima University , , 1-21-24 Korimoto , ,
Abstract
Four new trinor-guaiane sesquiterpenes, clavuridin C (1), clavuridin D (2), 5-methoxyclavuridin B (3), and 5-epi-clavuridin B (4), together with three known compounds, clavuridin B (6), clavularin A (7), and clavularin B (8), were isolated from the soft coral Clavularia viridis collected from the coast of Cape Kyan, Okinawa Prefecture, Japan. The structures of the newly isolated compounds 1–4, including their relative configurations, were elucidated through detailed analysis of spectroscopic data, such as IR, NMR, MS, and density functional theory (DFT)-based DP4 analysis, as well as by comparison with previously reported related compounds. The absolute configurations of 2 and 3 were additionally investigated through electronic circular dichroism (ECD) calculations. The absolute configuration of 4 was determined through benzoylation, followed by application of the allylic benzoate rule. Furthermore, structural differences between 4 and antheliol (4a) were addressed through detailed comparison of experimental and calculated NMR data, including DP4 and CP3 analyses, leading to a revision of the previously proposed structure. These results highlight the importance of integrated spectroscopic and computational approaches for accurate structure determination of closely related sesquiterpenes. In addition, isolated compounds 1–4 and 6–8 were evaluated for their antibacterial and antifungal activities.
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BibTeX
@article{tani2026trinorguaianetype,
title = {{Trinor-Guaiane-Type Sesquiterpenes with Unusual Skeletons from the Okinawan Soft Coral Clavularia viridis}},
author = {Kazuki Tani and Misaki Nagasaka and Tomoki Tsuruta and Ayaka Fukushige and Ayari Hojo and Matsumi Doe and Hiroyuki Miyake and Yoshiki Morimoto and Masaru Hashimoto and Shinsuke Marumoto and Michihiro Ito and Momochika Kumagai and Keisuke Nishikawa and Takahiro Ishii},
journal = {ACS Omega},
year = {2026},
month = oct,
doi = {10.1021/acsomega.6c08064},
url = {https://pubs.acs.org/acsodf/article/11/42/65432/5452765/Trinor-Guaiane-Type-Sesquiterpenes-with-Unusual},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Trinor-Guaiane-Type Sesquiterpenes with Unusual Skeletons from the Okinawan Soft Coral Clavularia viridis
AU - Kazuki Tani
AU - Misaki Nagasaka
AU - Tomoki Tsuruta
AU - Ayaka Fukushige
AU - Ayari Hojo
AU - Matsumi Doe
AU - Hiroyuki Miyake
AU - Yoshiki Morimoto
AU - Masaru Hashimoto
AU - Shinsuke Marumoto
AU - Michihiro Ito
AU - Momochika Kumagai
AU - Keisuke Nishikawa
AU - Takahiro Ishii
PY - 2026
DA - 2026/10/16
JO - ACS Omega
DO - 10.1021/acsomega.6c08064
UR - https://pubs.acs.org/acsodf/article/11/42/65432/5452765/Trinor-Guaiane-Type-Sesquiterpenes-with-Unusual
AB - Four new trinor-guaiane sesquiterpenes, clavuridin C (1), clavuridin D (2), 5-methoxyclavuridin B (3), and 5-epi-clavuridin B (4), together with three known compounds, clavuridin B (6), clavularin A (7), and clavularin B (8), were isolated from the soft coral Clavularia viridis collected from the coast of Cape Kyan, Okinawa Prefecture, Japan. The structures of the newly isolated compounds 1–4, including their relative configurations, were elucidated through detailed analysis of spectroscopic data, such as IR, NMR, MS, and density functional theory (DFT)-based DP4 analysis, as well as by comparison with previously reported related compounds. The absolute configurations of 2 and 3 were additionally investigated through electronic circular dichroism (ECD) calculations. The absolute configuration of 4 was determined through benzoylation, followed by application of the allylic benzoate rule. Furthermore, structural differences between 4 and antheliol (4a) were addressed through detailed comparison of experimental and calculated NMR data, including DP4 and CP3 analyses, leading to a revision of the previously proposed structure. These results highlight the importance of integrated spectroscopic and computational approaches for accurate structure determination of closely related sesquiterpenes. In addition, isolated compounds 1–4 and 6–8 were evaluated for their antibacterial and antifungal activities.
SN - 2470-1343
ER -