Spongenolactones A-C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge Spongia sp

Chi-Jen Tai; Atallah F Ahmed; Chih-Hua Chao; Chia-Hung Yen; Tsong-Long Hwang; Fang-Rong Chang; Yusheng M Huang; Jyh-Horng Sheu

doi:10.3390/md20080498

Spongenolactones A-C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge Spongia sp

Mar Drugs. 2022 Aug 1;20(8):498. doi: 10.3390/md20080498.

Authors

Chi-Jen Tai¹, Atallah F Ahmed^{2

3}, Chih-Hua Chao^{4

5}, Chia-Hung Yen^{6

7}, Tsong-Long Hwang^{8

9

10}, Fang-Rong Chang⁶, Yusheng M Huang^{11

12}, Jyh-Horng Sheu^{1

6

13

14}

Affiliations

¹ Doctoral Degree Program in Marine Biotechnology, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
² Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.
³ Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.
⁴ School of Pharmacy, China Medical University, Taichung 40604, Taiwan.
⁵ Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40604, Taiwan.
⁶ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁷ National Natural Product Libraries and High-Throughput Screening Core Facility, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁸ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan.
⁹ Research Center for Chinese Herbal Medicine, Graduate Institute of Healthy Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 33303, Taiwan.
¹⁰ Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 333423, Taiwan.
¹¹ Department of Marine Recreation, National Penghu University of Science and Technology, Magong, Penghu 88046, Taiwan.
¹² Tropical Island Sustainable Development Research Center, National Penghu University of Science and Technology, Magong, Penghu 88046, Taiwan.
¹³ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
¹⁴ Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 404333, Taiwan.

Abstract

Three new 5,5,6,6,5-pentacyclic spongian diterpenes, spongenolactones A-C (1-3), were isolated from a Red Sea sponge Spongia sp. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and the absolute configurations of 1-3 were determined on the basis of comparison of the experimental circular dichroism (CD) and calculated electronic circular dichroism (ECD) spectra. Compounds 1-3 are the first 5,5,6,6,5-pentacyclic spongian diterpenes bearing an β-hydroxy group at C-1. These metabolites were assayed for their cytotoxic, antibacterial, and anti-inflammatory activities. All three compounds were found to exert inhibitory activity against superoxide anion generation in fMLF/CB-stimulated human neutrophils. Furthermore, 1 showed a higher activity against the growth of Staphylococcus aureus in comparison to 2.

Keywords: 5,5,6,6,5-pentacyclic spongian diterpenes; Red Sea sponge; Spongia sp.; anti-inflammatory assay; antibacterial assay.

MeSH terms

Animals
Diterpenes* / chemistry
Humans
Indian Ocean
Molecular Structure
Porifera*
Staphylococcus aureus

Substances

Diterpenes

Abstract

MeSH terms

Substances

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