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Structures and bioactivities of selected macrocyclic lactones. A, B Structures and bioactivities of stomopnolides A–B. C Structure and bioactivity of stomopneulactone D. D Structure and bioactivity of 16-member macrocyclic lactone isolated from the mollusc Babylonia spirata. E–H Structures and bioactivities of macrocyclic lactones from seafood Amphioctopus neglectus
Source publication
Biochemical investigation of bioactive compounds from the marine demospongiae Clathria (Thalysias) vulpina (Lamarck, 1814) (family Microcionidae) resulted in the isolation of two previously undescribed 22-membered macrocyclic lactone derivatives clathrolide A and B from its organic extract. Structural elucidation of the compounds were carried out u...
Citations
... During the analysis of the constituent amino acid absolute congurations using Marfey's method, racemisation of the terminal Lys residue during derivatisation has led to a cautionary note for assignment of peptides that contain a ureido linkage. 424 Macrolides 991 and 992 have been reported from Clathria vulpina and 993 and 994 from C. procera, although in the latter publication, the authors showed a lack of due diligence and referred to their isolates as procerolides, a name already coined to describe ascidian-derived hydroxy-butenolides. 425,426 Neopetrosiasins A 995 and B 996 are bis-quinolizidine alkaloids from a Neopetrosia, 427 while a series of renierate 997-999 and renieramycin 1000 alkaloids were sourced from a Vietnamese Haliclona. 428 Four new 3-alkylpyridinium dimer alkaloids, neopetrosidines A-D 1001, 1002-1004 were reported from an Indonesian N. chaliniformis. ...
Covering: January to December 2021This review covers the literature published in 2021 for marine natural products (MNPs), with 736 citations (724 for the period January to December 2021) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1425 in 416 papers for 2021), together with the relevant biological activities, source organisms and country of origin. Pertinent reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included. An analysis of the number of authors, their affiliations, domestic and international collection locations, focus of MNP studies, citation metrics and journal choices is discussed.
Two undescribed polyketide type compounds, thalysiaketide A and thalysiaketide B were isolated from a sponge of marine origin Clathria (Thalysias) vulpina (Lamarck, 1814). Thalysiaketide A exhibited significantly greater inhibitory potential against inflammatory 5-lipoxygenase (IC50 0.87 mM) and cyclooxygense-2 (IC50 0.93 mM) compared to those revealed by its thalysiaketide B analogue (IC50 ≥ 1.05 mM). The 5-lipoxygenase inhibitory activity of thalysiaketide A was considerably superior to ibuprofen (standard, IC50 > 4 mM). Higher degree of polar belongings (topological polar surface area 93.06) in conjunction with relatively lower docking parameters of thalysiaketide A with the aminoacyl residues of cyclooxygense-2 and 5-lipoxygenase (docking score -12.99 and -12.27 kcal/mol, respectively) recognized its prospective anti-inflammatory potential.
Intertidal marine brown alga Turbinaria conoides (J.Agardh) Kützing (family Sargassaceae) is considered as one of the largely abundant species, available in the coastal zones of the Indian subcontinent. Bioactivity-guided chromatographic fractionation of the organic extract of T. conoides resulted in three previously undescribed macrocyclic lactone homologues, named as conoidecyclics A-C. Conoidecyclic A displayed greater attenuation potential against cyclooxygenase-2 (IC50 1.75 mM) and 5-lipoxygenase (IC50 4.24 mM) in comparison with other analogues. Conoidecyclic A exhibited higher attenuation potential against 5-lipoxygenase than that displayed by an anti-inflammatory agent, ibuprofen (IC50 4.51 mM). The higher selectivity index of conoidecyclic A (1.79) recognized its selective attenuation potential against the inducible cyclooxygenase-2 enzyme. Inhibition potential of conoidecyclic A against angiotensin converting enzyme-I (IC50 1.23 mM) and protein tyrosine phosphatase-1B (IC50 1.39 mM) were non-competitive, as deduced by kinetic studies. In-silico molecular modeling study of conoidecyclic A with the allosteric sites of the targeted enzymes exhibited least binding energy of −14.51 to −11.27 kcal mol⁻¹ compared to those exhibited by other studied macrolide homologues. Reaction kinetic studies of conoidecyclic A coupled with lesser apparent Vmax inferred that it could efficiently bind with the allosteric site of targeted enzymes in a non-competitive manner to diminish the reaction velocity resulting in enzyme inhibition. Drug-likeness and predictive pharmacokinetic parameters of conoidecyclic A exhibited an acceptable oral bioavailability. These reports inferred that conoidecyclic A encompassing pentacosa macrocyclic moiety could be a promising therapeutic lead to inhibit the enzymes related to the development and progression of pathological conditions leading to inflammation, hypertension and type-2 diabetes.
