Pyrrole Oligoglycosides from the Starfish <i>Acanthaster planci</i> Suppress Lipopolysaccharide-Induced Nitric Oxide Production in RAW264.7 Macrophages

Abstract

Key words Acanthaster planci; starfish; pyrrole oligoglycoside; isolation; nitric oxide (NO) productionStarfish are benthic widely distributed marine invertebrates found from shallow to deep waters in all the oceans. Starfish have attracted organic chemists, biochemists, and pharmacologists as a fascinating source of bioactive secondary metabolites mainly steroidal and ceramide derivatives. 1-3)Of these, the crown-of-thorns starfish, Acanthaster planci is found throughout the tropical Indo-Pacific region being one of the largest starfish in the world. The adult A. planci is a carnivorous predator that feeds exclusively on coral polyps and is largely responsible for the damage inflicted on the Great Barrier Reef. Steroid and ceramide glycosides are main constituents of this starfish. 3,4)Our previous studies yielded several steroid glycosides from A. planci. [5][6][7] In continuation of our investigations on this species, the current paper deals with the isolation and structure elucidation of two new pyrrole oligoglycosides namely plancipyrrosides A and B (1 and 2, Fig. 1). Their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells were also evaluated. Results and DiscussionUsing various chromatographic procedures, two new pyrrole oligoglycosides were isolated from methanol extract of the Vietnamese starfish A. planci. Plancipyrroside A (1), isolated as a colorless powder revealed a quasi-molecular ion peak at m/z 696.2715 [M+H] +

Anthraquinone and Butenolide Constituents from the Crinoid <i>Capillaster multiradiatus</i>

“…The inhibitory effect on LPS-induced NO production in RAW264.7 cells of compounds 1-8 was evaluated following the previously described protocols. [11][12][13] Among isolates, capillasterquinone A (1) showed strong NO production inhibitory activity with an IC 50 of 5.89±0.11 µM, relative to that of the positive control cardamonin 14) (IC 50 of 2.59±0.18 µM). Compounds 2-5 and 7 showed significant activity with IC 50 values of 12.02±0.45, 20.89±0.76, 13.18±0.15, 19.05±0.32, and 16.98±0.98 µM, respectively, whereas 6 and 8 show less effect (IC 50 >100 µM).…”

Chemical Constituents and Bioactivities of Starfishes: An Update

“…Ten oligoglycosides ( 207 – 216 ; Figure ) were obtained. One ( 207 ) and two ( 208 – 209 ) pyrrole oligoglycosides were isolated from the starfish Asterina bather and Acanthaster planci , respectively . The finding of 208 and 209 represents the third case of pyrrole oligoglycosides reported to date.…”

“…Compound 118 at a dose of 10 μ m exhibited a potential immunomodulatory action, decreasing the intracellular ROS content in RAW 264.7 murine macrophages by 24 % . Compounds 208 and 209 exhibit a potent inhibitory effect on LPS‐induced NO production in RAW264.7 cells with IC 50 values of 5.9 μ m and 16.6 μ m , respectively . Compounds 207 , 211 and 212 moderately inhibited IL‐12 p40 production in LPS‐stimulated bone marrow‐derived dendritic cells (BMDCs) with IC 50 values of 31.6 μ m , 36.4 μ m , and 22.8 μ m , respectively …”

Điểm lại các nghiên cứu hóa học và hoạt tính sinh học một số loài sinh vật biển Việt Nam trong giai đoạn 2013‐2017

“…Hai hợp chất này thể hiện hoạt tính kháng viêm với khả năng ức chế sự sản sinh NO ở đại thực bào RAW264.7 đã được kích thích bằng LPS với giá trị IC 50 tương ứng là 16,61±1,85 và 5,94±0,34 µM. [82] Pyrrole oligoglycosit là một lớp chất có cấu trúc độc đáo và rất hiếm gặp trong thiên nhiên. Cho đến nay, mới chỉ có nhóm nghiên cứu phân lập được các hợp chất 306-308, 310-312 và một số nhà khoa học Trung Quốc phân lập được hợp chất 310 [83] thuộc lớp này từ một số loài sao biển.…”