New 3,4- seco-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge Spongia sp

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

doi:10.3390/ijms24021252

New 3,4- seco-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge Spongia sp

Int J Mol Sci. 2023 Jan 8;24(2):1252. doi: 10.3390/ijms24021252.

Authors

Chi-Jen Tai^{1

2}, Chih-Hua Chao^{3

4}, Atallah F Ahmed^{5

6}, Chia-Hung Yen^{7

8}, Tsong-Long Hwang^{9

10

11}, Fang-Rong Chang⁷, Yusheng M Huang^{12

13}, Jyh-Horng Sheu^{1

7

14}

Affiliations

¹ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
² National Museum of Marine Biology and Aquarium, Pingtung 944401, Taiwan.
³ School of Pharmacy, China Medical University, Taichung 40604, Taiwan.
⁴ Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40604, Taiwan.
⁵ Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.
⁶ Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.
⁷ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁸ National Natural Product Libraries and High-Throughput Screening Core Facility, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁹ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan.
¹⁰ 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.
¹¹ Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 333423, Taiwan.
¹² Department of Marine Recreation, National Penghu University of Science and Technology, Magong 88046, Taiwan.
¹³ Tropical Island Sustainable Development Research Center, National Penghu University of Science and Technology, Magong 88046, Taiwan.
¹⁴ Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 404333, Taiwan.

Abstract

Continuing chemical investigation of the Red Sea sponge Spongia sp. led to the isolation of four new 3,4-seco-3,19-dinorspongian diterpenoid lactones, secodinorspongins A-D (1-4), along with a classical spongian diterpenoid lactone, sponginolide (5). The chemical structures, including the absolute configurations of these compounds, were elucidated using the extensive spectroscopic study composed of 1D and 2D NMR data analyses, and a comparison between calculated-electronic-circular-dichroism (ECD) and experimental-circular-dichroism (CD) spectra. A plausible biosynthetic pathway of 1-4 was also proposed. Furthermore, the cytotoxicity, antibacterial and anti-inflammatory activities of 1-5 were evaluated. Compound 1 was found to exhibit inhibitory activity against the growth of Staphylococcus aureus (S. aureus), and 4 and 5 exhibited suppression of superoxide-anion generation and elastase release in fMLF/CB-induced human neutrophils.

Keywords: 3,4-seco-3,19-dinorspongian diterpenoid lactones; Red Sea sponge; Spongia sp.; anti-inflammatory; antibacterial assay; secodinorspongins A−D; spongian diterpene.

MeSH terms

Animals
Diterpenes* / chemistry
Humans
Lactones
Molecular Structure
Porifera* / chemistry
Staphylococcus aureus

Substances

Lactones
Diterpenes

Abstract

MeSH terms

Substances

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