Isolation of Ciliatamide D from a Marine Sponge <i>Stelletta</i> sp. and a Reinvestigation of the Configuration of Ciliatamide A

Imae, Yasufumi; Takada, Kentaro; Okada, Shigeru; Ise, Yuji; Yoshimura, Hiroshi; Morii, Yasuhiro; Matsunaga, Shigeki

doi:10.1021/np300878b

Cited by 11 publications

(21 citation statements)

References 7 publications

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“…(170 m, Oshimashinsone seamount, Japan). 632 This study also reaffirmed the absolute conguration of ciliatamide A (Aaptos ciliata) as that assigned during the original isolation, 633 and subsequently incorrectly reassigned by synthesis. 634 The sponge Lithoplocamia lithistoides (Madagascar) produced PM050489 619 and PM060184 620, polyketide amides that differ only in the presence of a chlorine atom.…”

Section: Spongessupporting

confidence: 53%

Marine natural products

et al. 2015

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This review covers the literature published in 2013 for marine natural products (MNPs), with 982 citations (644 for the period January to December 2013) 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 (1163 for 2013), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Spongessupporting

confidence: 53%

Marine natural products

et al. 2015

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“…Four synthetic isomers were compared with an authentic natural sample of ciliatamide A, allowing its structure to be revised for the second time, with an (12 R ,22 S ) configuration, highlighting the presence of a d -phenylalanine moiety. Furthermore, the absolute configuration of the methionine sulfoxide residue in ciliatamide D ( 54 ) was also revised to the d form 54 .…”

Section: Structure and Properties Of Mnps From The Stellettmentioning

confidence: 99%

“…Although the HPLC separation of Stelletta ciliatamides was carried out by using a bioassay-guided approach, the purified compounds showed no inhibitory activity on cathepsin B nor cytotoxicity against HeLa cells at 50 μg/mL 54 . Actually, after their first isolation from the sponge Aaptos ciliata in 2008 55 , ciliatamides A and C ( 55 and 57 ) were found to be antileishmanial (50% and 45.5% growth inhibition at 10 µg/mL on Leishmania major , respectively).…”

Section: Structure and Properties Of Mnps From The Stellettmentioning

confidence: 99%

“…In 2013, two uncommon lipopeptides, ciliatamide D ( 54 ) containing a N -methyl- l -methionine sulfone moiety, and ciliatamide A ( 55 ), were isolated from the EtOH extract of a marine sponge Stelletta sp., collected from Oshima-shinsone, southern Japan (Fig. 7) 54 . The absolute configuration of these two peptides were determined by the isolation team by using Marfey׳s analysis, showing that they contained two l -amino acids residues 54 .

Figure 7Chemical structures of compounds 54–57 .…”

Section: Structure and Properties Of Mnps From The Stelletta Genusmentioning

confidence: 99%

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Marine sponges of the genus Stelletta as promising drug sources: chemical and biological aspects

Nay

Yang

et al. 2019

Acta Pharmaceutica Sinica B

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Marine sponges of the genus Stelletta are well known as rich sources of diverse and complex biologically relevant natural products, including alkaloids, terpenoids, peptides, lipids, and steroids. Some of these metabolites, with novel structures and promising biological activities, have attracted a lot of attention from chemists seeking to perform their total synthesis in parallel to intensive biological studies towards new drug leads. In this review, we summarized the distribution of the chemically investigated Stelletta sponges, the isolation, synthesis and biological activities of their secondary metabolites, covering the literature from 1982 to early 2018.

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“…Apart from numerous sulfoxide-containing NPs from allium plants (Nohara et al, 2012(Nohara et al, , 2013Edmands et al, 2013;Radulović et al, 2015;Fukaya et al, 2017), some sulfoxide-containing peptides and β-carboline derivatives, were isolated from marine sponge and ascidian, respectively. The methyl sulfoxide-containing peptides include cytotoxic haligramides A and B (Rashid et al, 2000), hymenamide F (Kobayashi et al, 1996), ciliatamide D (Imae et al, 2013;Takada et al, 2017), waiakeamide (Mau et al, 1996) and its sulfone derivative (Sera et al, 2003), as well as polytheonamides A and B (Hamada et al, 2005). The methyl sulfoxide-containing βcarboline derivatives include eudistomin E (Murata et al, 1991), didemnolines C and D (Schumacher and Davidson, 1995), and eudistomin K sulfoxide with antiviral activity (Lake et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic and Optically Active Pyrisulfoxins From the Endophytic Streptomyces albolongus EA12432

Wang

Cui

et al. 2020

Front. Chem.

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R-Pyrisulfoxin C (1), S-pyrisulfoxin D [(+)-2], R-pyrisulfoxin D [(-)-2], pyrisulfoxin E (13), S-pyrisulfoxin F [(+)-14], and R-pyrisulfoxin F [(-)-14], six new caerulomycin derivatives with a 2,2 ′-bipyridine skeleton, were obtained from the cultures of the endophytic Streptomyces albolongus EA12432 with Aconitum carmichaeli (Ranunculaceae). Additionally, the racemic pyrisulfoxins A [(±)-3] and B [(±)-4] were further purified as optically pure compounds and identified the configurations for the first time. The racemic pyrisulfoxin D [(±)-2] displayed significant cytotoxicity against a series of cancer cell lines with IC 50 values ranging from 0.92 to 9.71 µM. Compounds 7, 8, and (±)-3 showed cytotoxicity against the HCT-116, HT-29, BXPC-3, P6C, and MCF-7 cell lines. Notably, compounds 7 and 8 have a strong inhibition both on the proliferation of human colon cancer cells HCT-116 and HT-29 with IC 50 values ranging from 0.048 to 0.2 µM (doxorubicin, 0.21 and 0.16 µM), and compound 1 showed a selective inhibition on the proliferation of the gastric carcinoma cell lines, N87, with an IC 50 value of 8.09 µM. Optically pure compounds R(-)-14 and S(+)-14 showed weak cytotoxicity against HCT-116 and MCF-7 cell lines with the IC 50 values of 14.7 µM and 10.4 µM, respectively. Interestingly, compounds 1 and (±)-2 didn't show cytotoxic activity against two human normal cell lines, HEK-293F and L02, with IC 50 values >100 µM.

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Isolation of Ciliatamide D from a Marine Sponge Stelletta sp. and a Reinvestigation of the Configuration of Ciliatamide A

Cited by 11 publications

References 7 publications

Marine natural products

Marine natural products

Marine sponges of the genus Stelletta as promising drug sources: chemical and biological aspects

Cytotoxic and Optically Active Pyrisulfoxins From the Endophytic Streptomyces albolongus EA12432

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