Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp

Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp

Seven new cembrane-type diterpenes, lobophytolins C–I (3–9), and one new prenylated-guiane-type diterpene, lobophytolin J (10), along with six known related ones (1, 2, 11–14), have been isolated from the soft coral Lobophytum sp. collected off the Xisha Island in the South China Sea. Their structures were elucidated by extensive spectroscopic analysis and quantum mechanical (QM)-NMR methods. The absolute configuration of lobophytolin H (8) was determined by the application of the modified Mosher’s method and chemical transformation. Lobophytolin D (4) exhibited promising cytotoxicities in in vitro bioassays against HT-29, Capan-1, A549, and SNU-398 human cancer cell lines with IC50 values of 4.52, 6.62, 5.17, and 6.15 μM, respectively.

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Bibliographic Details
Main Authors: Li, Song-Wei, Cuadrado, Cristina, Huan, Xia-Juan, Yao, Li-Gong, Miao, Ze-Hong, Hernández Daranas, Antonio, Guo, Yue-Wei
Other Authors: National Natural Science Foundation of China
Format: artículo biblioteca
Language:English
Published: Elsevier 2020-08-25
Subjects:Soft coral, Lobophytum, Cembranoids, Marine natural products, Quantum Mechanical Calculations,
Online Access:http://hdl.handle.net/10261/218930
http://dx.doi.org/10.13039/501100001809
http://dx.doi.org/10.13039/501100003339
http://dx.doi.org/10.13039/501100004837
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spelling dig-ipna-es-10261-2189302022-08-25T04:30:31Z Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp Li, Song-Wei Cuadrado, Cristina Huan, Xia-Juan Yao, Li-Gong Miao, Ze-Hong Hernández Daranas, Antonio Guo, Yue-Wei National Natural Science Foundation of China National Key Research and Development Program (China) Ministerio de Ciencia e Innovación (España) Consejo Superior de Investigaciones Científicas (España) Soft coral Lobophytum Cembranoids Marine natural products Quantum Mechanical Calculations Seven new cembrane-type diterpenes, lobophytolins C–I (3–9), and one new prenylated-guiane-type diterpene, lobophytolin J (10), along with six known related ones (1, 2, 11–14), have been isolated from the soft coral Lobophytum sp. collected off the Xisha Island in the South China Sea. Their structures were elucidated by extensive spectroscopic analysis and quantum mechanical (QM)-NMR methods. The absolute configuration of lobophytolin H (8) was determined by the application of the modified Mosher’s method and chemical transformation. Lobophytolin D (4) exhibited promising cytotoxicities in in vitro bioassays against HT-29, Capan-1, A549, and SNU-398 human cancer cell lines with IC50 values of 4.52, 6.62, 5.17, and 6.15 μM, respectively. This work was financially supported by the Natural Science Foundation of China (Nos. 81991521, 81520108028, 21672230), the National Key Research and Development Program of China (No. 2018YFC0310903), the Drug Innovation Major Project (No. 2018ZX09711-001-001-009), the SKLDR/ SIMM Project (No. SIMM1903ZZ-04) and the Spanish Ministry of Science and Innovation (PID2019-109476RB-C21). A.H.D thanks the CSIC for a JAE-intro grant to C.C.G. This study made use of the SGAI-CSIC supercomputing facilities. Peer reviewed 2020-09-01T09:15:39Z 2020-09-01T09:15:39Z 2020-08-25 artículo http://purl.org/coar/resource_type/c_6501 Bioorganic Chemistry 103, 104223 (2020) 0045-2068 http://hdl.handle.net/10261/218930 10.1016/j.bioorg.2020.104223 http://dx.doi.org/10.13039/501100001809 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/501100004837 en #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-109476RB-C21 PID2019-109476RB-C21/AEI/10.13039/501100011033 Postprint https://doi.org/10.1016/j.bioorg.2020.104223 Sí open Elsevier
institution IPNA ES
collection DSpace
country España
countrycode ES
component Bibliográfico
access En linea
databasecode dig-ipna-es
tag biblioteca
region Europa del Sur
libraryname Biblioteca del IPNA España
language English
topic Soft coral
Lobophytum
Cembranoids
Marine natural products
Quantum Mechanical Calculations
Soft coral
Lobophytum
Cembranoids
Marine natural products
Quantum Mechanical Calculations
spellingShingle Soft coral
Lobophytum
Cembranoids
Marine natural products
Quantum Mechanical Calculations
Soft coral
Lobophytum
Cembranoids
Marine natural products
Quantum Mechanical Calculations
Li, Song-Wei
Cuadrado, Cristina
Huan, Xia-Juan
Yao, Li-Gong
Miao, Ze-Hong
Hernández Daranas, Antonio
Guo, Yue-Wei
Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp
description Seven new cembrane-type diterpenes, lobophytolins C–I (3–9), and one new prenylated-guiane-type diterpene, lobophytolin J (10), along with six known related ones (1, 2, 11–14), have been isolated from the soft coral Lobophytum sp. collected off the Xisha Island in the South China Sea. Their structures were elucidated by extensive spectroscopic analysis and quantum mechanical (QM)-NMR methods. The absolute configuration of lobophytolin H (8) was determined by the application of the modified Mosher’s method and chemical transformation. Lobophytolin D (4) exhibited promising cytotoxicities in in vitro bioassays against HT-29, Capan-1, A549, and SNU-398 human cancer cell lines with IC50 values of 4.52, 6.62, 5.17, and 6.15 μM, respectively.
author2 National Natural Science Foundation of China
author_facet National Natural Science Foundation of China
Li, Song-Wei
Cuadrado, Cristina
Huan, Xia-Juan
Yao, Li-Gong
Miao, Ze-Hong
Hernández Daranas, Antonio
Guo, Yue-Wei
format artículo
topic_facet Soft coral
Lobophytum
Cembranoids
Marine natural products
Quantum Mechanical Calculations
author Li, Song-Wei
Cuadrado, Cristina
Huan, Xia-Juan
Yao, Li-Gong
Miao, Ze-Hong
Hernández Daranas, Antonio
Guo, Yue-Wei
author_sort Li, Song-Wei
title Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp
title_short Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp
title_full Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp
title_fullStr Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp
title_full_unstemmed Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha Soft Coral Lobophytum sp
title_sort rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the xisha soft coral lobophytum sp
publisher Elsevier
publishDate 2020-08-25
url http://hdl.handle.net/10261/218930
http://dx.doi.org/10.13039/501100001809
http://dx.doi.org/10.13039/501100003339
http://dx.doi.org/10.13039/501100004837
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