Minor Steroidal Triglycoside Planciside D from the Tropical Starfish Acanthaster planci

Abstract

A new steroidal glycoside called planciside D was isolated from the tropical starfish Acanthaster planci and assigned the structure (. Planciside D was a triglycoside containing two carbohydrate chains, which are rarely found in starfish. Its structure was established using 2D NMR spectroscopy and tandem mass spectrometry with electrospray ionization (ESI).Keywords: starfish, Acanthaster planci, glycoside, steroidal aglycon, NMR spectroscopy.Glycosides of polyhydroxysteroids and asterosaponins are the most common structural groups of starfish steroidal metabolites [1-6]. Glycosides of polyhydroxysteroids contain a highly oxidized aglycon with 3-10 hydroxyls and one, two, or rarely three monosaccharide residues located on C-3 (or C-15) of the steroid core and/or in the C-24 or C-26, C-28, and C-29 positions of the aglycon side chain. Asterosaponins are oligoglycosides containing, as a rule, a 3-O-sulfated ' 9(11) -3E,6D-dihydroxysteroidal aglycon and a carbohydrate chain of 5-6 monosaccharide residues located on C-6 of the aglycon. Starfish steroidal glycosides are usually found in extracts as complicated mixtures that are difficult to separate into the pure compounds. The majority of the minor components of these fractions are unstudied although certain biosynthesis features of them or other metabolites are related to their formation. Starfish steroidal glycosides are interesting not only because of their unusual chemical structures but also because of their broad spectra of biological properties, including embryotoxic, antifungal, antiviral, antibacterial, neuroprotective, and other types of activity [1-6].The starfish Acanthaster planci L. 1758 (Order Valvatida, Family Acanthasteridae) is distributed in tropical waters of the Indian and Pacific Oceans and preys primarily on reef-forming coral polyps. A. planci is one of the largest starfish and is known also by the name "crown of thorns" because its body is covered with numerous long sharp needles. The toxic properties of needles from this starfish are often associated with the presence of polar steroidal glycosides, mainly asterosaponins, in its tissues [1]. Polar steroidal compounds from A. planci were studied earlier by Japanese and Italian researchers.

Chemical Constituents and Bioactivities of Starfishes: An Update

“…The unsubstituted β ‐ d ‐galactofuranose residue at C‐28 ( 164 ) or C‐29 ( 163 ) of the side chains was found in starfish steroidal glycosides for the first time. Compounds 165 and 166 were generated by the starfish Choriaster granulatus and Acanthaster planci , respectively. Compound 166 was a triglycoside containing two carbohydrate chains, which are rarely found in starfish .…”

“…Compounds 165 and 166 were generated by the starfish Choriaster granulatus and Acanthaster planci , respectively. Compound 166 was a triglycoside containing two carbohydrate chains, which are rarely found in starfish . The starfish Lethasterias fusca yielded compounds 167 – 168 and they were a rather scarce structural group of natural glycosylated steroidal polyols containing monosaccharide residues attached to both O‐3 and O‐24 atoms of the aglycon .…”

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

“…Sáu steroit glycosit mới là planciside A F (177 182) cùng với echinasterioside C (183), linkoside L4 (184), attenuatoside B-I (185), halityloside D (186) và culcitoside C 2 (187) đã được phân lập từ loài sao biển gai Acanthaster planci. [51][52][53][54] Gần đây, nhóm nghiên cứu đã phân lập được một steroit glycosit mới là polyacanthoside A (188) từ loài sao biển Astropecten polyacanthus; [7] hai steroit glycosit mới từ loài Pentaceraster gracilis là pentaceroside A (189) và pentaceroside B (190) cùng với nodososide (191) và (5α,25S)-cholestane-3β,6α,8,15β,16β,26-hexol 3-O-[(2-O-methyl)-β-Dxylopyranoside] (192). [10] Hợp chất 191 cũng được nhóm nghiên cứu phân lập được từ loài sao biển Protoreaster nodosus và có hoạt tính ức chế sự tạo thành cytokin tiền viêm IL-12 p40 và IL-6 ở tế bào BMDCs được kích thích bằng LPS với giá trị IC 50 tương ứng là 12,47±0,38 và 23,18±0,46 M. [47] Ngoài ra, granulatoside A được phân lập từ loài sao biển Linckia laevigata; [55] linckoside B (193), halityloside A (194), halityloside B (195) và culcitoside C 5 (196) được phân lập từ loài sao biển Culcita novaeguineae.…”

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

“…[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).…”