Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis (original) (raw)
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Biochimica et Biophysica Acta (BBA) - General Subjects, 2007
Chemical transformation studies of the marine sesquiterpene phenol (S)-(+)-curcuphenol (1) isolated from the Jamaican sponges, Didiscus oxeata and Myrmekioderma styx, were accomplished. In order to optimize the activity and better understand the SAR of (S)-(+)-curcuphenol, nineteen semisynthetic analogs were prepared and evaluated for activity against infectious diseases. A number of analogs showed significant activity against Mtb and Leishmania donovani, while showing good to moderate activities in antibacterial and antifungal assays as well as against P. falciparium (D6 clone) and (W2 clone). The analogs a, c, h, and r exhibited Mtb activity with MICs of 24.6, 41.2, 6.90, and 50.5 μM, respectively. Analog f shows enhanced activity against L. donovani with an IC 50 of 0.6 μM and IC 90 of 40 μM respectively.
Bioactive Semisynthetic Derivatives of (S)-(+)-Curcuphenol
Natural Product Communications
New semisynthetic sesquiterpene derivatives (3-7, 10), together with two known ones (8-9) were prepared from (S)-(+)curcuphenol (1), isolated from the Caribbean sponge Didiscus oxeata. The natural sesquiterpenes 1 and (S)-(+)-curcudiol (2), as well as semisynthetic derivatives 3-10, were evaluated against the herbivorous insect species Spodoptera littoralis, Leptinotarsa decemlineata and Rhopalosiphum padi. All compounds had an antifeedant effect on L. decemlineata. With R. padi, a structure-dependent antifeedant response was observed, with 1 being the most active, followed by 4 and 5. Furthermore, compounds 1, 4, 5, 7, 8 and 10 reduced S. littoralis larval weight, with 10 also reducing ingestion by S. littoralis larvae. Of the derivatives studied here, none showed stronger effects (either antifeedant or postingestive) than the parent compound 1. It can, therefore, be concluded that the structure of the side chain and the presence of the phenol ring of curcuphenol are important structural requirements for its insect antifeedant and growth regulation effects.
Isolation and Structure Elucidation of Bioactive Secondary Metabolites from Marine Sponges
docserv.uni-duesseldorf.de
Cytotoxic cyclic peptide……………………………………………………..….170 Biosynthesis of peptides………………………………………………………...171 Relationship between structures and cytotoxic activities of callyaerins …….....174 4.2. Metabolites isolated from the sponge Diacarnus megaspinorhabdosa…...…174 Cytotoxic norterpene peroxides…………………………………………………174 Proposed biosynthesis of terpene peroxides……………………..…………...…175 Mechanism of the antimalarial activity of cyclic peroxides…………………….177 Structure activity relationship of norterpene cyclic peroxides…………….……178 Indole, phenolic and nucleoside derivatives.………………………………...…179 Mechanism of action of nucleoside analogs.
Bioactive Semisynthetic Dervatives of (S)-(+)-Curcuphenol
2008
8 pages, figures, and tables statistics.New semisynthetic sesquiterpene derivatives (3-7, 10), together with two known ones (8-9) were prepared from (S)-(+)- curcuphenol (1), isolated from the Caribbean sponge Didiscus oxeata. The natural sesquiterpenes 1 and (S)-(+)-curcudiol (2), as well as semisynthetic derivatives 3-10, were evaluated against the herbivorous insect species Spodoptera littoralis, Leptinotarsa decemlineata and Rhopalosiphum padi. All compounds had an antifeedant effect on L. decemlineata. With R. padi, a structure-dependent antifeedant response was observed, with 1 being the most active, followed by 4 and 5. Furthermore, compounds 1, 4, 5, 7, 8 and 10 reduced S. littoralis larval weight, with 10 also reducing ingestion by S. littoralis larvae. Of the derivatives studied here, none showed stronger effects (either antifeedant or postingestive) than the parent compound 1. It can, therefore, be concluded that the structure of the side chain and the presence of the phe...
New Δ 8(14) -3β, 7α-Dihydroxysterols from the Marine Sponge Pellina semitubulosa
Journal of Natural Products, 1992
ABsmcT.-T'he marine sponge Pellina smitubulosa was examined for polyoxygenated sterols. The sponge contained six new 3P,7a-diols, (22E)-5a-cholesta-S( 14),22diene-3P,7adiol [2], (22E,24R)-24-methyl-5a-cholesta-8(14~,22-diene-3~,7adiol [3f, (22E,24S)-24methyl-5a-cholesta-8(14),22-diene-3P,7a-diol [4), 24-methyl-5a-cholesta-S(14),24(28)diene-3P,7a-diol [SI, (242)-24-ethyl-5a-cholesta-8( 14),24(28)-diene-3f3,7a-diol 161, and (24E)-24+xhyl-5a-cholesta-8( 14),24(28)-diene-3f3,7a-diol 17, along with the previously synthesized 5a-cholest-8( 14)-ene-38,7adiol [I]. The structure of the new natural products was determined by interpretation of spectral data and secured by synthesis of 1 starting from 5acholest-7-en-3 8-01, R Journal of Natural Products Wol. 55, No. 6 RESULTS AND DISCUSSION The Et,O-soluble material from Me,CO and CHC1,-MeOH (1: 1) extracts of the sponge was chromatographed over Si gel using CHCI,/MeOH mixtures as eluent. The fractions eluted with CHCl,-MeOH (9: 1) were subjected to hplc separation on Si gel columns. The fraction containing 8( 14)-ene-3P,7a-dihydroxysterols was then subjected to reversed-phase hplc [MeOH-H,O (88: 12)) in order to separate the individual compounds. The major component 5 of the sterol mixture gave a molecular ion peak in the hrms at mlz 4 14.3486, corresponding to a molecular formula of C2*H4602 requiring six sites of unsaturation, and other significant peaks at m h 396.3358 EM -H 2 0 ) + , 363.3028 EM -2 H 2 0 -Me)+, 289.2143 EM -C9H17)+, 271.2068 -%Hi7 -H20}+, and 253.1954 EM -C9H17 -2H207+ that indicated the presence of two hydroxyl
Journal of the Marine Biological Association of India, 2016
A variety of biologically active compounds with unique structures and pharmacological properties have been reported to occur in marine organisms. Demospongiae, an important class of marine sponge is known for producing the largest number and diversity of secondary metabolites isolated till recent times. The review covers the diverse class of bioactive compounds isolated for therapeutic drug applications from different marine organisms. It is an attempt to update the marine research community with results of our ongoing search for bioactive secondary metabolites from marine sponge Spongosorites halichondriodes which has exhibited antibacterial, antifungal, cytotoxic, anti-inflammatory and immunomodulatory activity in our studies. Spongosorites halichondriodes (order Halichondrida, family Halichondriidae) is a predominant marine sponge collected from west coast of Mumbai, India. The sponge S. halichondriodes has shown presence of Octadecadienoic acid (Linoleic acid), ergostan tetraen-ol, dihydroxy cholanoic-methyl esters,C 28 saturated and unsaturated esters like 3β, 4β, 7α, 12α-tetrahydroxy-5β-cholan-24-oic acid methyl ester, 7α, 12β-dihydroxy-5β-cholan24-oic acid methyl ester, novel isocoumarin citrinolactone A, a triterpenoid glycyrrhetinic acid as well as other unknown compounds such as nucleoside inosine.
Bioactive Metabolites from the Caribbean Sponge Aka coralliphagum
Journal of Natural Products, 2007
The chemistry of the burrowing sponge Aka coralliphagum was investigated to identify chemically labile secondary metabolites. The HPLC-MS analysis of the two growth forms typica and incrustans revealed different metabolites. The previously unknown sulfated compounds siphonodictyals B1 to B3 (6-8), corallidictyals C (9) and D (10), and siphonodictyal G (11) were isolated, and their structures were elucidated by NMR and MS experiments. The compounds were tested in a DPPH assay, in antimicrobial assays against bacteria, yeasts, and fungi, and in antiproliferation assays using cultures of mouse fibroblasts. The biological activity was linked to the presence of the ortho-hydroquinone moiety.