Sesquiterpene isocyanides, isothiocyanates, thiocyanates, and formamides from the Thai sponge Halichondria sp.

Prawat, Hunsa; Mahidol, Chulabhorn; Kaweetripob, Wirongrong; Prachyawarakorn, Vilailak; Tuntiwachwuttikul, Pittaya; Ruchirawat, Somsak

doi:10.1016/j.tet.2016.05.060

Cited by 14 publications

(18 citation statements)

References 24 publications

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“…Guided by NMR analysis, the selected terpene-containing fractions were subsequently purified on repeated column chromatography (silica gel, Sephadex LH-20, reversed phase-C18 and RP-HPLC) to afford one new cadinane-type sesquiterpenoid ( 1 ), along with nine known metabolites ( 2 , 3 , 6 – 8 , 12 – 14 , 17 ) (Figure 1). The known compounds were identified as two cadinane-type sesquiterpenoids: halichon G ( 2 ) [35] and 10-isothiocyanato-4-cadinene ( 3 ) [13,28,36,37,38], one eudesmane-type sesquiterpenoid: 11-formamido-7 β H-eudesm-5-ene ( 6 ) [39,40], two bisabolane-type sesquiterpenoids: Δ 7,14 -3-isocyanotheonellin ( 7 ) [1,41] and 3-isocyanotheonellin ( 8 ) [1], two aromadendrane-type sesquiterpenoids: 1-isothiocyanatoaromadendrane ( 12 ) [42] and axamide-2 ( 13 ) [43,44], one mixture of pupukeanane-type sesquiterpenoids: 9-thiocyanatopupukeanane isomers ( 14 ) [6], and one kalihinane-type diterpenoid: kalihinol A ( 17 ) [45].…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge-Prey Acanthella cavernosa

Chen

et al. 2019

Marine Drugs

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A detailed chemical investigation of two South China Sea nudibranchs Phyllidiella pustulosa and Phyllidia coelestis, as well as their possible sponge-prey Acanthella cavernosa, led to the isolation of one new nitrogenous cadinane-type sesquiterpenoid xidaoisocyanate A (1), one new naturally occurring nitrogen-containing kalihinane-type diterpenoid bisformamidokalihinol A (16), along with 17 known nitrogenous terpenoids (2–15, 17–19). The structures of all the isolates were elucidated by detailed spectroscopic analysis and by the comparison of their spectroscopic data with those reported in the literature. In addition, the absolute stereochemistry of the previously reported axiriabiline A (5) was determined by X-ray diffraction (XRD) analysis. In a bioassay, the bisabolane-type sesquiterpenoids 8, 10, and 11 exhibited cytotoxicity against several human cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge-Prey Acanthella cavernosa

Chen

et al. 2019

Marine Drugs

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“…[446][447][448] Only two meroditerpenoids 931 and 932 were reported in 2016, 449 while sesquiterpenoids, their formamides, isocyanides, thiocyanates, isothiocyanates and dimers 933-947 (ref. [450][451][452] were reported from Axinyssa, Dysidea and Halichondria sponges; 944 is a known synthetic compound. 453 A novel taurinated norditerpene geodiataurine 948 was reported from a sample of Geodia macandrewii dredged in both Nordland and Trøndelag, Norway.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2018

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Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) 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 (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

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“…They have been reported to possess many biological activities, such as cytotoxic [3,6,15,16], antibacterial [9,11], antibiotic [17] activities, inhibition of the DNA-relaxing activity of mouse DNA topoisomerase I [12], and enhancement nerve growth factor synthesis in cultured astroglial cells [13]. As a part of our ongoing research program focused on the discovery of cytotoxic compounds from Thai marine sponges [18,19,20], drawing from the previous report, one sesterterpene, erectusolide A, six phenolic alkenes, erectuseneols A–F, together with nine known compounds, were isolated from the EtOAc soluble extract of Hyrtios erectus (Chulabhorn Research Institute (CRI) 588) [3]. Of these, some sesterterpenes exhibited significant cytotoxic activities against the MOLT-3 cell line with an IC 50 values of 3.79–5.82 μM [3].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus

et al. 2018

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Four sesterterpenes, erectusolides B, C, D, and seco-manoalide-25-methyl ether, two 2-furanone derivatives, erectusfuranones A and B, together with thirteen known sesterterpenes, (6Z)-neomanoalide-24-acetate, two diastereomers of 24-O-methylmanoalide, luffariolide B, manoalide, (6E)- and (6Z)-neomanoalide, seco-manoalide, scalarafuran, 12-acetylscalarolide, 12-epi-O-deacetyl-19-deoxyscalarin, 12-epi-scalarin, and 12-O-deacetyl-12-epi-scalarin, three indole alkaloids, 5-hydroxy-1H-indole-3-carbaldehyde, hyrtiosine A, and variabine B, and one norterpene, cavernosine were isolated from the marine sponge Hyrtios erectus. Their structures were determined by means of spectroscopic methods and the absolute configurations of the asymmetric centers were determined using the modified Mosher’s method. The cytotoxic activities for the isolated compounds have been reported.

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Sesquiterpene isocyanides, isothiocyanates, thiocyanates, and formamides from the Thai sponge Halichondria sp.

Cited by 14 publications

References 24 publications

Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge-Prey Acanthella cavernosa

Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge-Prey Acanthella cavernosa

Marine natural products

Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus

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