New anticancer bastadin alkaloids from the sponge Dendrilla cactos

Reddy, A. Vijender; Kodela, Ravinder; Narasimhulu, M.; Sridevi, A.; Satyanarayana, N.; Kondapi, Anand K.; Venkateswarlu, Y.

doi:10.1016/j.bmc.2006.02.033

Cited by 33 publications

(30 citation statements)

References 24 publications

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“…This formula provided a match to four previously reported bastadins: 5 ( 6 ), 9, 14, 15, 22, 24, 26, 27 15, 16, 28 16 29 and 19 ( 1a ), 24, 26 while also ruling out the presence of benzene rings coded as 3 and 6 in Table 1. The constitutions of the four aryl rings, containing nine protons as three distinct two-spin systems and one ABX pattern, were established using the Table 1 database plus g COSY NMR data.…”

Section: Resultssupporting

confidence: 78%

“…Many exhibit cytotoxic activity against cancer cells and some are still under evaluation as potential therapeutic leads. 9–16 Somewhat unusual are the additional reports of bastadins from two other sponges including a Verongid of the genus Psammaplysilla 15 and the Dendroceratid Dendrilla . 16 …”

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confidence: 96%

“…Finally, using the bastadin NMR database, we were able to propose 1 H NMR data revisions for bastadin 23. 16 …”

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confidence: 99%

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Additional Insights on the Bastadins: Isolation of Analogues from the Sponge Ianthella cf. reticulata and Exploration of the Oxime Configurations

et al. 2010

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The focus of this study was on the bastadin class of bromotyrosine derivatives, commonly isolated from Ianthella marine sponges, and is the first report on the secondary metabolites from Ianthella cf. reticulata. Two new bastadins were isolated, (E,Z)-bastadin 19 (1b), a diastereoisomer of the known (E,E)-bastadin 19 (1a), and dioxepine bastadin 3 (2), an unusual dibenzo-1,3-dioxepine. A bastadin NMR database was created and assisted in the structure determination of 1b, 2 and the rapid dereplication of ten other known compounds including bastadins 2–9 (3-10), 13 (11) and 19 (1a). The geometry of the 2-(hydroxyimino)-N-alkylamide chains, a chemical feature present in all bastadins, was further probed and new insights regarding the natural oxime configuration are discussed. Bastadins possessing (E,Z), (Z,E) or (E,E)-dioxime configurations could be artifacts of isolation or storage in solution. Therefore, this point was explored by photochemical and thermal isomerization studies, as well as molecular mechanics calculations. Bastadins 13 (11) and 19 (1a) exhibited moderate inhibition against Trypanosoma brucei and bastadin 4 (5) was cytotoxic to HCT-116 colon cancer cells.

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Section: Resultssupporting

confidence: 78%

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confidence: 96%

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Additional Insights on the Bastadins: Isolation of Analogues from the Sponge Ianthella cf. reticulata and Exploration of the Oxime Configurations

et al. 2010

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“…[9][10][11][12][13][14][15][16][17][18][19][20][21] More than twenty bastadins have been identified so far from marine sponges of Ianthella sp., Psammaplysilla sp. and Dendrilla sp., and they have been known to exhibit some interesting biological activities, such as antibacterial 9) and cytotoxic [10][11][12][13] activities, enzyme inhibitory activities against inositol-5′-phosphate dehydrogenase, 14) topoisomerase II and dihydrofolate reductase, 12) selective inhibitory activity toward δ-opioid receptors, 13) and interaction with the intracellular ryanodine receptor-1 (RyR-1) calcium channel complex. 15,16) Based on a growth inhibitory assay using HUVECs and KB3-1 cells, we have identified bastadins as selective antiproliferative substances from the Indonesian marine sponge of Ianthella basta (Fig.…”

Section: Bastadins From the Marine Sponge Ianthella Bastamentioning

confidence: 99%

Search for Anti-angiogenic Substances from Natural Sources

Kotoku

Arai

Kobayashi

2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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As angiogenesis is critical for tumor growth and metastasis, potent and selective anti-angiogenic agents with novel modes of action are highly needed for anti-cancer drug discovery. In this review, our studies focusing on the search for anti-angiogenic substances from natural sources, such as bastadins, globostellatic acid X methyl esters and cortistatins from marine sponges, and pyripyropenes from marine-derived fungus, together with senegasaponins from medicinal plant, are summarized.

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“…As a part of our ongoing research on the biologically active substances from marine organisms, 14) we have investigated the sponge Phycopsis sp. collected from Mandapam coast, India.…”

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confidence: 99%

Chemical Examination of the Sponge Phycopsis sp.

Kondempudi

Rajaram

Narasimhulu

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two new compounds 7a a,8a a-epoxy theonellin isothiocyanate (1) and 5a a,8a a-epidioxyergosta-6Z,22Z,25-trien3b b-ol (2) along with two known compounds, theonellin isothiocyanate (3) and theonellin formamide (4) have been isolated from the sponge Phycopsis sp. Compound 2 showed cytotoxic activity against HL-60 and U937 human cancer cell lines with IC 50 values of 5.96؎0.02 and 31.72؎0.55 m mg/ml, respectively.Key words 7a,8a-epoxy theonellin isothiocyanate; cytotoxic activity; Phycopsis sp.; 5a,8a-epidioxyergosta-6Z,22Z,25-trien3b-ol Chem. Pharm. Bull. 57(9) 990-992 (2009)

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New anticancer bastadin alkaloids from the sponge Dendrilla cactos

Cited by 33 publications

References 24 publications

Additional Insights on the Bastadins: Isolation of Analogues from the Sponge Ianthella cf. reticulata and Exploration of the Oxime Configurations

Additional Insights on the Bastadins: Isolation of Analogues from the Sponge Ianthella cf. reticulata and Exploration of the Oxime Configurations

Search for Anti-angiogenic Substances from Natural Sources

Chemical Examination of the Sponge Phycopsis sp.

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