Anti-Inflammatory Halogenated Monoterpenes from the Red Alga Portieria hornemannii

Author:

Wu Yuan-Jhong1,Huang Tzu-Yin2,Huang Chiung-Yao1,Lin Chi-Chen3ORCID,Wang Wei-Lung4,Huang Hui-Chi5ORCID,Liu Shang-Yin Vanson1,Chao Chih-Hua67ORCID,Sheu Jyh-Horng189

Affiliation:

1. Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan

2. Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan

3. Institute of Biomedical Science, National Chung Hsing University, Taichung 402, Taiwan

4. Department of Biology, National Changhua University of Education, Changhua 500, Taiwan

5. Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan

6. School of Pharmacy, China Medical University, Taichung 404, Taiwan

7. Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan

8. Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 404, Taiwan

9. Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan

Abstract

The chemical investigation of a red alga Portieria hornemannii enabled the identification of three new halogenated monoterpenes (1–3) along with two previously identified metabolites (4 and 5). Their structures were determined by spectroscopic analysis and also by utilizing single-crystal diffraction analysis and quantum chemical calculation, as well as by comparison with literature data. Further corrections for dichloro and dibromo carbons using the sorted training set (STS) method were established in this study to significantly improve the accuracy in GIAO 13C NMR calculation of compounds 1–3. To discover the potential bioactive metabolites from P. hornemannii, the anti-inflammatory activities of all compounds were examined. Compounds 1 and 3–5 showed significant anti-inflammatory activity to inhibit the production of pro-inflammatory cytokines in the LPS-stimulated mature dendritic cells.

Funder

Ministry of Science and Technology of Taiwan

Publisher

MDPI AG

Subject

Drug Discovery,Pharmacology, Toxicology and Pharmaceutics (miscellaneous),Pharmaceutical Science

Reference34 articles.

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3. Chondrocole A and B. Two halogenated dimethyl-hexahydrobenzofurans from the red algae Chondrococcus hornemannii (Mertens) Schmitz;Burreson;Tetrahedron Lett.,1975

4. Apakaochtodenes A and B: Two tetrahalogenated monoterpenes from the red marine alga Portieria hornemannii;Gunatilaka;J. Nat. Prod.,1999

5. Marine natural products: Metabolites of marine algae and herbivorous marine molluscs;Faulkner;Nat. Prod. Rep.,1984

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