120 results on '"Luigi Minale"'
Search Results
2. Unpacking Social Capital
- Author
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Ruben Durante, Nicola Mastrorocco, Luigi Minale, and James M. Snyder
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History ,Polymers and Plastics ,Business and International Management ,Industrial and Manufacturing Engineering - Published
- 2023
3. Risk Attitudes and Household Migration Decisions
- Author
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Luigi Minale, Christian Dustmann, Xin Meng, and Francesco Fasani
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Organizational Behavior and Human Resource Management ,Economics and Econometrics ,050208 finance ,Internal migration ,Risk aversion ,business.industry ,Strategy and Management ,05 social sciences ,Diversification (finance) ,Distribution (economics) ,Left behind ,Emigration ,Family member ,Management of Technology and Innovation ,8. Economic growth ,0502 economics and business ,Demographic economics ,Business ,050207 economics ,050205 econometrics - Abstract
This paper analyses the relation between individual migrations and the risk attitudes of other household members when migration is a household decision. We develop a simple model that implies that which members migrate depends on the distribution of risk attitudes among all household members, and that the risk diversification gain to other household members may induce migrations that would not take place in an individual framework. Using unique data for China on risk attitudes of internal (rural-urban) migrants and the families left behind, we empirically test three key implications of the model: (i) that conditional on migration gains, less risk averse individuals are more likely to migrate; (ii) that within households, the least risk averse individual is more likely to emigrate; and (iii) that across households, the most risk averse households are more likely to send migrants as long as they have at least one family member with sufficiently low risk aversion. Our results not only provide strong evidence that migration decisions are taken on a household level but also that the distribution of risk attitudes within the household affects whether a migration takes place and who will emigrate. JEL classification: J61, 015, R23, D81
- Published
- 2020
4. On the economics and politics of refugee migration
- Author
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Christian Dustmann, Tommaso Frattini, Francesco Fasani, Luigi Minale, and Uta Schönberg
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Market integration ,History ,Economics and Econometrics ,Polymers and Plastics ,Asylum seekers ,Refugee ,Refugee crisis ,Management, Monitoring, Policy and Law ,Asylum policy ,Industrial and Manufacturing Engineering ,Economía ,Convention ,Politics ,Political science ,0502 economics and business ,050602 political science & public administration ,Business and International Management ,050207 economics ,J15 ,Labor mobility ,Interpretation (philosophy) ,Member states ,05 social sciences ,0506 political science ,Political economy ,J61 ,F22 - Abstract
This paper provides a comprehensive analysis of refugee migration, with emphasis on the current refugee crisis. After first reviewing the institutional framework laid out by the Geneva Convention for Refugees, we demonstrate that, despite numerous attempts at developing a common European asylum policy, EU countries continue to differ widely in interpretation and implementation. We then describe key features of the current refugee crisis and document the overall magnitudes and types of refugee movements, illegal border crossings and asylum applications to EU Member States. We next study the labour market integration of past refugee migrants to EU countries and draw conclusions for the current situation. Finally, we turn to the economics of refugee migrations, contrasting economic and refugee migrants, discussing the trade-offs between long-term asylum and temporary protection and highlighting the benefits of well-coordinated national asylum policies. We conclude with several policy recommendations. Luigi Minale gratefully acknowledges support from the Ministerio de Economía y Competitividad (Spain, Maria de Maeztu Grant) and Comunidad de Madrid (MadEco CM S2015/HUM 3444). Christian Dustmann acknowledges funding through the Norface WSF Programme and the DFG (DU1024/1 1) ERC Advanced Grant 323992 DMEA.
- Published
- 2017
5. Agricultural productivity shocks, labour reallocation and rural–urban migration in China
- Author
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Luigi Minale, Ministerio de Economía y Competitividad (España), and Comunidad de Madrid
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China ,Economics and Econometrics ,J22 ,Geography, Planning and Development ,Agricultural productivity ,Labour supply ,R23 ,Economía ,Urbanization ,0502 economics and business ,Economics ,050207 economics ,Land tenure ,Productivity ,Rural-urban migration ,050205 econometrics ,business.industry ,05 social sciences ,Shock (economics) ,Work (electrical) ,Agriculture ,J61 ,Demographic economics ,business - Abstract
This article analyses the way households in rural China use rural-urban migration and off-farm work as a response to negative productivity shocks in agriculture. I employ various waves of a longitudinal survey to construct a panel of individual migration and labour supply histories, and match them to detailed weather information, which I use to instrument agricultural productivity. For identification, I exploit the year-by-county variation in growing season rainfalls to explain within-individual changes in labour allocation. Data on days of work supplied to each sector allow to study the responses to weather shocks along both the participation and the intensive margin. Results suggest that farming is reduced by 4.5% and migration increased by about 5% in response to a 1 standard deviation negative rainfall shock. Increase in rural-urban migration derives from both longer spells in the city and from increment in the likelihood to participate in the urban sector. I find interesting heterogeneous response across generations driven by age-specific productivities in the different sectors and migration costs. Finally, land tenure insecurity seems to partially prevent households from freely reallocating labour away from farming in bad times. I wish to gratefully acknowledge financial support from the Ministerio Economía y Competitividad (Spain), Maria de Maeztu grant (MDM 2014-0431), and the Comunidad de Madrid, MadEco-CM grant (S2015/HUM-3444).
- Published
- 2018
6. News media and crime perceptions: evidence from a natural experiment
- Author
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Luigi Minale, Nicola Mastrorocco, Ministerio de Economía y Competitividad (España), and Comunidad de Madrid
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Economics and Econometrics ,Persuasion ,Natural experiment ,K42 ,media_common.quotation_subject ,Public policy ,Economía ,D72 ,Voting ,Perception ,0502 economics and business ,Economics ,Perceptions ,050207 economics ,News media ,050205 econometrics ,media_common ,business.industry ,05 social sciences ,Advertising ,Audience measurement ,D83 ,L82 ,Digital television ,Crime ,business ,Finance - Abstract
In democracies, voters rely on media outlets to learn about politically salient issues. This raises an important question: how strongly can media affect public perceptions? This paper uses a natural experiment - the staggered introduction of the Digital TV signal in Italy - to measure the effect of media persuasion on the perceptions individuals hold. We focus on crime perceptions and, combining channel-specific viewership and content data, we show that the reduced exposure to channels characterized by high levels of crime reporting decreases individual concerns about crime. The effect is driven by individuals aged 50 and over, who turn out to be more exposed to television while using other sources of information less frequently. Finally, we provide evidence about the effect of the digital introduction on public policies closely related to crime perceptions and on voting behaviour Luigi Minale acknowledges support from the Ministerio Economía y Competitividad (Spain), María de Maeztu grant (MDM 2014-0431), Comunidad de Madrid, MadEco-CM (S2015/HUM-3444), and Fundación Ramón Areces.
- Published
- 2018
7. (The Struggle for) Refugee Integration into the Labour Market: Evidence from Europe
- Author
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Francesco Fasani, Tommaso Frattini, and Luigi Minale
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Economic integration ,Economics and Econometrics ,Market participation ,media_common.quotation_subject ,Refugee ,Geography, Planning and Development ,Immigration ,Differential (mechanical device) ,Eu countries ,Recession ,Political science ,Cohort ,Survey data collection ,Quality (business) ,Demographic economics ,media_common - Abstract
In this paper, we study the labour market performance of refugees vis-A -vis comparable migrants across twenty European countries and over time. In the first part of our analysis, we document that labour market outcomes for refugees are consistently worse than those for other migrants. Refugees are 11.6 percent less likely to have a job and 22.1 percent more likely to be unemployed than migrants with similar characteristics. Moreover, their income, occupational quality and labour market participation are also relatively weaker. The refugee-migrant gap remains sizeable even after controlling for individual characteristics as well as for unobservables using a rich set of fixed effects and interactions between area of origin, entry cohort and destination country. These gaps persist until about 10-15 years after immigration. In the second part of our analysis, we investigate the role of economic and asylum policy conditions at the time of arrival in shaping integration paths of refugees versus migrants. First, we find that immigrating in a recession produces scarring effects for all migrants but no differential effect for forced migrants, leaving little role for this channel to explain observed refugee gaps. Second, we focus on the impact on refugees of being subject to spatial dispersal policies. Our estimates imply that dispersed refugees experience a persistent impact on their residential choices and substantial long run losses in their economic integration with respect to non-dispersed refugees.
- Published
- 2018
8. Risk Attitudes and Household Migration Decisions
- Author
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Christian Dustmann, Xin Meng, Francesco Fasani, and Luigi Minale
- Subjects
Family member ,Labour economics ,Internal migration ,Risk aversion ,Diversification (finance) ,Economics ,Left behind ,Emigration - Abstract
This paper analyses the relation between individual migrations and the risk attitudes of other household members when migration is a household decision. We develop a simple model that implies that which member migrates depends on the distribution of risk attitudes among all household members, and that the risk diversification gain to other household members may induce migrations that would not take place in an individual framework. Using unique data for China on risk attitudes of internal (rural-urban) migrants and the families left behind, we empirically test three key implications of the model: (i) that conditional on migration gains, less risk averse individuals are more likely to migrate; (ii) that within households, the least risk averse individual is more likely to emigrate; and (iii) that across households, the most risk averse households are more likely to send migrants as long as they have at least one family member with sufficiently low risk aversion. Our results not only provide evidence that migration decisions are taken on a household level but also that the distribution of risk attitudes within the household affects whether a migration takes place and who will emigrate.
- Published
- 2017
9. A novel sulphated steroid with a 7-membered 5-oxalactone B-ring from an Antarctic starfish of the family Asteriidae
- Author
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Simona De Marino, Elio Palagiano, Maria Iorizzi, Franco Zollo, Luigi Minale, DE MARINO, Simona, E., Palagiano, Zollo, Franco, L., Minale, and M., Iorizzi
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Sulphated polyhydroxylated steroid ,Chromatography ,biology ,Chemistry ,Stereochemistry ,medicine.medical_treatment ,Organic Chemistry ,Starfish ,biology.organism_classification ,Biochemistry ,High-performance liquid chromatography ,Steroid ,Solvent ,chemistry.chemical_compound ,Sulfation ,Sephadex ,Drug Discovery ,Asterasterols ,medicine ,Acetone ,Asteriidae - Abstract
Three novel sulphated polyhydroxylated steroids, named asterasterols A-C (1-3), have been isolated from an Antarctic starfish of the family Asteriidae and their structures elucidated by spectroscopic studies. Steroid 1 has the seven-membered 5-oxalactone B-ring; 2 and 3 are the corresponding 6-oxo steroids. © 1997 Published by Elsevier Science Ltd. In connection with our systematic investigation of steroid constituents from echinoderms, we examined some Antarctic starfish species, t'2 These studies have led to the isolation of a series of sulfated polyhydroxysteroids and steroidal glycosides structurally very close, some identical, with those found in species collected in warm environments. 3 During the investigation of the polar extracts of an Antarctic starfish of the family Asteriidae, which is the subject of this report, we have isolated a structurally novel steroid exhibiting 7-membered 5- oxalactone B-ring, along with the corresponding 6-oxo steroids. The starfish, Asteriidae family, was collected in Tethis Bay during the Italian-Antarctic expedition in January 1990 at a depth of 50-100 mt. The starfish (500 g fresh) was extracted with water and then with acetone; from the aqueous extract the sulphated steroids and steroidal glycosides were recovered by passing it through a column of Amberlite, washing out salts with distilled water, and eluting the absorbed material with methanol. The acetone extracts were solvent partitioned between water and n-butanol. The combined methanol eluate and n-butanol soluble material, were separated by sequential application of gel permeation on Sephadex LH- 60, DCCC and HPLC, to give the sulphated steroids 1-3, in small amounts, ranging from 7.2 mg of 1 (major) to 3.4 mg of 3 (minor).
- Published
- 1997
10. Downeyoside A and B, Two New Sulphated Steroid Glucuronides from the Starfish Henricia downeyae
- Author
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Thomas S. Hopkins, Maria Iorizzi, Denis Riou, Luigi Minale, Luigi Gomez Paloma, James Mc Clintock, Franco Zollo, Patrick J. Bryan, Christos Roussakis, and Elio Palagiano
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biology ,Stereochemistry ,Chemistry ,medicine.medical_treatment ,Organic Chemistry ,Starfish ,biology.organism_classification ,Biochemistry ,Nmr data ,Henricia downeyae ,Steroid ,Drug Discovery ,Side chain ,medicine ,Spectral analysis ,Epimer ,IC50 - Abstract
Two new sulphated polyhydroxylated steroid glucuronides. downeyoside A and B ( 1, 2 ), C-24 methyl epimers possessing an ethereal ring linking C-16 to C-22 of the steroid, were isolated from the starfish Henricia downeyae collected from the Gulf of Mexico. Their structures were determined by spectral analysis and the stereochemistry of the highly oxygenated steroid side chain was derived from NMR data combined with molecular dynamics calculation. Compounds 1 and 2 were tested against non-small-cell lung human carcinoma cells and found to be cytotoxic with IC50 of 60 μg/ml and 36 μg/ml, respectively.
- Published
- 1995
11. New cytotoxic polyoxygenated steroids from the sponge Dysidea incrustans
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Christos Roussakis, Luigi Minale, Jean François Verbist, Agostino Casapullo, Franco Zollo, A., Casapullo, L., Minale, Zollo, Franco, C., Roussaki, and J. F., Verbist
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biology ,DERIVATIVES ,Chemistry ,Organic Chemistry ,biology.organism_classification ,Biochemistry ,AVAROL ,Sponge ,MARINE NATURAL-PRODUCTS ,Mediterranean sea ,HERBACEA ,Carcinoma Cell ,Drug Discovery ,Cytotoxic T cell ,MOIETY ,Spectral data - Abstract
Two novel polyoxygenated steroids, incrustasterol A ( 1 ) and B ( 2 ), have been isolated from the marine sponge Dysidea incrustans , collected in the Mediterranean sea along the coasts of Tunisia. The structures, which include a rare Δ 8(9) , 11-keto functionality along with other oxygenated functions on the rings A and B, were determined by interpretation of spectral data. These steroids were cytotoxic against human non-small-cell lung, renal and melanoma carcinoma cell lines.
- Published
- 1995
12. On the Composition of Sulfated Polyhydroxysteroids in Some Ophiuroids and the Structure Determination of Six New Constituents
- Author
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Luigi Minale, Raffaele Riccio, Luigi Gomez Paloma, Maria Valeria D'Auria, Angela Zampella, D'Auria, MARIA VALERIA, Gomez Paloma, L., Minale, L., Riccio, R., and Zampella, Angela
- Subjects
Pharmacology ,Sulfation ,Complementary and alternative medicine ,Chemistry ,Organic Chemistry ,Drug Discovery ,Pharmaceutical Science ,Molecular Medicine ,Organic chemistry ,Composition (visual arts) ,Analytical Chemistry - Abstract
Nine ophiuroid species from different geographical areas have been analyzed for their polar steroid content. Six new sulfated polyhydroxysteroids have been isolated, together with six known compounds of this type previously reported from brittle scars. The new steroids possess C-21 and 3 alpha- sulfate groups, which are distinctive features of the steroid sulfates of ophiuroids. Hydroxylation at C-2, C-4, and C-11 and the presence of double bonds at C-5 are further features of the new steroids. The structures of the new compounds were solved by spectroscopic analysis.
- Published
- 1995
13. Four New Dimeric Peptide Alkaloids, Anchinopeptolides B-D, and Cycloanchinopeptolide C, Congeners of Anchinopeptolide A, from the Mediterranean Marine Sponge Anchinoe tenacior
- Author
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Jacques Lavayre, Luigi Minale, Agostino Casapullo, and Franco Zollo
- Subjects
Magnetic Resonance Spectroscopy ,Stereochemistry ,Guinea Pigs ,Molecular Conformation ,Pharmaceutical Science ,Bradykinin ,Peptide ,In Vitro Techniques ,Cell Line ,Analytical Chemistry ,chemistry.chemical_compound ,Alkaloids ,Drug Discovery ,Animals ,Humans ,Receptors, Somatostatin ,Plant Proteins ,Cerebral Cortex ,Pharmacology ,chemistry.chemical_classification ,Membranes ,biology ,Receptors, Bradykinin ,Organic Chemistry ,Anchinoe tenacior ,Neuropeptide Y receptor ,biology.organism_classification ,Porifera ,Rats ,Receptors, Neuropeptide Y ,Sponge ,Somatostatin ,Complementary and alternative medicine ,chemistry ,Intramolecular force ,Molecular Medicine - Abstract
Following the characterization of anchinopeptolide A[1], three new congeneric dimeric peptide alkaloids, named anchinopeptolides B [2], C[3], and D[4], have been isolated from the Mediterranean sponge Anchinoe tenacior. A fourth compound, cycloanchinopeptolide C[5], which is related to anchinopeptolide C[3] by a head-to-head intramolecular [2+2] cyclo-addition reaction, has also been isolated. The structures of these peptide alkaloids have been elucidated on the basis of spectral evidence. Anchinopeptolides bind to the somatostatin, human B2 bradykinin, and neuropeptide Y receptors.
- Published
- 1994
14. Superstolide A: a potent cytotoxic macrolide of a new type from the New Caledonian deep water marine sponge Neosiphonia superstes
- Author
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Luigi Gomez Paloma, Angela Zampella, M. Valeria D'Auria, Luigi Minale, Cécile Debitus, D'Auria, MARIA VALERIA, Debitus, C., Gomez Paloma, L., Minale, L., and Zampella, Angela
- Subjects
chemistry.chemical_classification ,ACTIVITE BIOLOGIQUE ,biology ,CYTOTOXIQUE ,Chemistry ,Stereochemistry ,INVERTEBRE AQUATIQUE ,General Chemistry ,biology.organism_classification ,Biochemistry ,Nmr data ,Catalysis ,STRUCTURE CHIMIQUE ,Deep water ,Sponge ,Colloid and Surface Chemistry ,EPONGE ,SUBSTANCE NATURELLE ,Moiety ,Two-dimensional nuclear magnetic resonance spectroscopy ,SPONGIAIRE ,Lactone ,Neosiphonia - Abstract
A highly cytotoxic macrolide, superstolide A (1), has been isolated from the deep water marine sponge Neosiphonia superstes, collected off New Caledonia. The gross structure was determined by extensive 2D NMR experiments on the lactone 1 and on its opened-ring-derived methyl esters 2 and 3. The relative stereochemistries of the decaline moiety and of the C22-C26 fragment were determined by a combination of NMR data and acetonide analysis on 2. Absolute stereostructure of the decaline portion of 1 has been determined on the basis of GLC-modified Horeau's methodology applied to 4, whereas the results of the application of the modified Mosher's method to 1 and 3 allowed us to propose for the C22-C26 fragment the 22R, 23R, 24R, 25S, 26R configuration. We also propose the solution conformations of superstolide A (1) based on molecular dynamics and mechanics calculations using NMR-derived constraints.
- Published
- 1994
15. Starfish Saponins, Part 2. Steroidal Oligoglycosides from the Starfish Cosmasterias lurida
- Author
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Alejandro J. Roccatagliata, Maria Iorizzi, Luigi Minale, Marta S. Maier, and Alicia M. Seldes
- Subjects
Magnetic Resonance Spectroscopy ,Stereochemistry ,Molecular Sequence Data ,Starfish ,Saponin ,Oligosaccharides ,Pharmaceutical Science ,Asterias forbesi ,Fucose ,Analytical Chemistry ,chemistry.chemical_compound ,Drug Discovery ,Animals ,Monosaccharide ,Glycosides ,Pharmacology ,chemistry.chemical_classification ,biology ,Ovary ,Organic Chemistry ,Glycoside ,Saponins ,Oligosaccharide ,biology.organism_classification ,Aglycone ,Carbohydrate Sequence ,Complementary and alternative medicine ,chemistry ,Molecular Medicine ,Female - Abstract
Four new sulfated asterosaponins, designated as cosmasterosides A [1], B [2], C [4], and D [5], have been isolated from the Atlantic starfish Cosmasterias lurida along with large amounts of the pentaglycoside ophidianoside F [3] and the minor component forbeside H [6], previously isolated from Ophidiaster ophidianus and Asterias forbesi, respectively. Cosmasteroside A [1] contains the same oligosaccharide chain as ophidianoside F [3] and a (20S)-5 alpha-cholesta-9(11),24-diene-3 beta,6 alpha,20-triol-3 beta-sulfated aglycone. Cosmasterosides B [2], C [4], and D [5] are based on the known aglycone, thornasterol A, and differ in the number and type of monosaccharide components of the carbohydrate chain. Cosmasteroside B [2] contains a novel oligosaccharide chain that differs from that of ophidianoside F [3] by the replacement of the quinovose unit attached to C-6 of the steroidal aglycone by glucose. The tetraglycosides cosmasterosides C [4] and D [5] are structurally related to ophidianoside F [3] and cosmasteroside B [2], respectively, by the loss of a terminal fucose unit.
- Published
- 1994
16. A dimeric peptide alkaloid of a completely new type, Anchinopeptolide A, from the marine sponge Anchinoe tenacior
- Author
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Franco Zollo, Agostino Casapullo, Luigi Minale, E. Finamore, A., Casapullo, E., Finamore, L., Minale, and Zollo, Franco
- Subjects
chemistry.chemical_classification ,Peptide alkaloid ,sostanze naturali marine, spugne, isolamento e caratterizzazione ,isolamento e caratterizzazione ,sostanze naturali marine ,biology ,Arginine ,Stereochemistry ,Alkaloid ,Organic Chemistry ,Peptide ,Anchinoe tenacior ,CLIONA-CELATA ,biology.organism_classification ,Biochemistry ,Sponge ,Residue (chemistry) ,Mediterranean sea ,chemistry ,Drug Discovery ,spugne - Abstract
Anchinopeptolide A ( 1 ), a dimeric peptide alkaloid of a completely new type, has been isolated from the marine sponge Anchinoe tenacior collected in the Mediterranean sea along the coasts of Tunisia. The structure elucidation of 1 , which include in each half a C-terminal trans 4-hydroxystirylamino residue linked to L-alanine, which in turn is attached to an arginine derived 5-guanidino-2-hydroxy-pentanoyl residue, is described.
- Published
- 1993
17. Polyoxygenated steroids of marine origin
- Author
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Luigi Minale, Maria Valeria D'Auria, Raffaele Riccio, D'Auria, MARIA VALERIA, Minale, L., and Riccio, R.
- Subjects
Chemistry ,Organic chemistry ,General Chemistry - Abstract
A review, with 386 refs., on polyoxygenated steroids of marine origin, e.g. marine algae, Porifera, Coelenterata, Bryozoa, Mollusca, Echinodermata, Arthropoda, tunicates, and vertebrates (fish).
- Published
- 1993
18. ChemInform Abstract: Polyoxygenated Steroids of Marine Origin
- Author
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Maria Valeria D'Auria, Raffaele Riccio, and Luigi Minale
- Subjects
Chemistry ,Organic chemistry ,General Medicine - Published
- 2010
19. ChemInform Abstract: Steroidal Oligoglycosides and Polyhydroxysteroids from Echinoderms
- Author
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Luigi Minale, Raffaele Riccio, and Franco Zollo
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,Aglycone ,Water soluble ,Triterpenoid ,Phylum Echinodermata ,Steroidal glycosides ,Chemistry ,Botany ,Glycoside ,General Medicine ,Carbohydrate moiety - Abstract
The phylum Echinodermata, which comprises about 6,000 living species distributed in all seas from the tropics to the antarctic zone, is divided into five classes: Crinoidea (sea lilies and feather stars), Holothuroidea (sea cucumbers or holothurians), Echinoidea (sea urchins), Asteroidea (sea stars or starfishes) and Ophiuroidea (brittle stars). Among the echinoderms, sea cucumbers and starfishes invariably contain saponins which are generally responsible for their toxicity. Saponins, complex water soluble compounds composed of a carbohydrate moiety attached to a steroid or triterpenoid aglycone, have been isolated from a great number of terrestrial plants, but are uncommon animal constituents. In the animal kingdom they are almost ubiquitous in sea cucumbers and starfishes (1), while found only rarely in alcyonarians (2), gorgonians (3-5), sponges (6-10) and as potent shark-repelling compounds in fishes (11). Chemically, saponins from sea cucumbers are triterpenoid glycosides whereas those from starfishes are steroidal glycosides.
- Published
- 2010
20. ChemInform Abstract: Callipeltins B and C; Bioactive Peptides from a Marine Lithistida Sponge Callipelta sp
- Author
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L. Gomez Paloma, C. Roussakis, Cécile Debitus, Angela Zampella, V. Le Bert, Luigi Minale, and Maria Valeria D'Auria
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chemistry.chemical_classification ,Sponge ,Callipelta ,biology ,Chemistry ,Stereochemistry ,Callipeltin B ,Lithistida ,Acid hydrolysis ,General Medicine ,Tripeptide ,biology.organism_classification ,Amino acid - Abstract
Following the characterization of callipeltin A (1), two new cytotoxic peptides, callipeltin B (2) and C (3), were isolated from the New Caledonian sponge Callipelta sp.. Callipeltin B (2) possess the same cyclic depsipeptidal structure as in callipeltin A (1) and differs from 1 by having the N-terminal 2,3-dimethylpyroglutamic acid unit instead of the tripeptide chain with the N-terminus blocked by an hydroxyacid. Callipeltin C (3) is simply the acyclic callipeltin A. The structures 2–3 have been determined by NMR experiments, FAB mass spectrometry, evaluation of the aminoacids obtained by acid hydrolysis and by comparison of the data with those of callipeltin A (1). Following the characterization of callipeltin A (1), two new peptides, callipeltin B (2) and C (3), were isolated form Callipelta sp.. Callipeltin B (2) possess the same cyclic depsipeptidal structure as in callipeltin A (1) and differs from 1 by having the N-terminal 2,3-dimethylpyroglutamic acid unit instead of the tripeptide chain with the N-terminus blocked by an hydroxyacid. Callipeltin C (3) is the acyclic callipeltin A. Callipeltins have been found to be cytotoxic against various human carcinoma cells.
- Published
- 2010
21. ChemInform Abstract: Crellastatin A: A Cytotoxic Bis-Steroid Sulfate from the Vanuatu Marine Sponge Crella sp
- Author
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Cécile Debitus, Maria Valeria D'Auria, Luigi Minale, Angela Zampella, Clelia Giannini, and Christos Roussakis
- Subjects
biology ,Chemistry ,Stereochemistry ,medicine.medical_treatment ,General Medicine ,biology.organism_classification ,Molecular mechanics ,In vitro ,Steroid ,Sponge ,Side chain ,medicine ,Cytotoxic T cell ,Steroid sulfate ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
A new nonsymmetric dimeric steroid, crellastatin A (1), was isolated from the Vanuatu Island marine sponge Crella sp. Structural assignment was accomplished through extensive 2D NMR spectroscopy. The stereochemistry of 1 was established from an analysis of ROESY experiments and from molecular mechanics and dynamics calculations. Crellastatin A (1), which possesses an unprecedented connection through the side chains, exhibits in vitro cytotoxic activity against NSCLC-N6 cells (IC50 of 1.5 μg/mL).
- Published
- 2010
22. Starfish Saponins, 48. Isolation of Fifteen Sterol Constituents (Six Glycosides and Nine Polyhydroxysteroids) from the Starfish Solaster borealis
- Author
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Takeshi Yasumoto, Luigi Minale, Raffaele Riccio, and Maria Iorizzi
- Subjects
Asterias amurensis ,Stereochemistry ,Starfish ,Saponin ,Pharmaceutical Science ,Analytical Chemistry ,chemistry.chemical_compound ,Drug Discovery ,Animals ,Steroid sulfate ,Glycosides ,Chromatography, High Pressure Liquid ,Hydroxysteroids ,Pharmacology ,chemistry.chemical_classification ,Molecular Structure ,biology ,Solaster ,Organic Chemistry ,Glycoside ,Saponins ,biology.organism_classification ,Sterol ,Sterols ,Aglycone ,Complementary and alternative medicine ,chemistry ,Biochemistry ,Molecular Medicine - Abstract
This paper reports a complete steroid glycoside and polyhydroxysteroid analysis of the starfish Solaster borealis, collected at Mutsu Bay, Japan. The glycosides include a new pentaglycoside steroid sulfate ("asterosaponin"), designated solasteroside A [1], two new sulfated 24-O-diglycosides, both with the common 5 alpha-cholesta-3 beta,6 alpha,8,15 alpha, 24-pentaol aglycone, borealosides A [2] and B [3], two new 24-O-(3-O-methyl)xylosides, borealosides C [4] and D [5], having the same aglycone with an additional hydroxy group at 4 beta-position in 5, and the known amurensoside B, previously isolated from Asterias amurensis. Among the polyhydroxysteroid constituents, four (7-10) are new, and five (11-15) have previously been isolated from starfishes.
- Published
- 1992
23. The first occurrence of polyhydroxylated steroids with phosphate conjugation from the starfish tremaster novaecaledoniae
- Author
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Raffaele Riccio, Francesco De Riccardis, Maria Iorizzi, Cécile Debitus, and Luigi Minale
- Subjects
chemistry.chemical_classification ,biology ,Stereochemistry ,medicine.medical_treatment ,Organic Chemistry ,Starfish ,Glycoside ,INVERTEBRE AQUATIQUE ,biology.organism_classification ,Phosphate ,Biochemistry ,STRUCTURE CHIMIQUE ,Steroid ,chemistry.chemical_compound ,Residue (chemistry) ,chemistry ,SUBSTANCE NATURELLE ,Drug Discovery ,STEROIDE ,medicine ,ETOILE DE MER - Abstract
Three steroid constituents have been isolated from the starfish Tremaster novaecaledoniae (Jangoux 1982) collected at a depth of 530 m off New Caledonia. Compounds 1 – 3 , designated as tremasterol A – C, are characterized by the presence of 3β-O-sulphated, 6α-O-phosphated and 16β-O-acetylated groupings on a steroidal skeleton. In compound 1 the monophosphate residue is further linked to 1′-glucose (1′-glucose tetracetate in 2 and 1′-glucose-6′-acetate in 3 ).
- Published
- 1992
24. Structure chacterization by two-dimensional NMR spectroscopy, of two marine triterpene oligoglycosides from a pacific sponge of the genusErylus
- Author
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Luigi Minale, Cécile Debitus, Luigi Gomez Paloma, Raffaele Riccio, and M. Valeria D'Auria
- Subjects
chemistry.chemical_classification ,Stereochemistry ,Organic Chemistry ,Saponin ,Glycoside ,Nuclear magnetic resonance spectroscopy ,Biochemistry ,Lanostane ,chemistry.chemical_compound ,Aglycone ,chemistry ,Triterpene ,Drug Discovery ,Side chain ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
The isolation and characterization of two novel triterpene glycosides from a sponge of the genus Erylus , collected at a depth of 500 m in the South of New Caledonia, are described. The structures are characterized by the presence of a branched oligosaccharide chain, composed of three ( 1 ) and four (2) D-galactopyranose units, respectively. Analysis of the oligosaccaride structures was achieved by { 1 H, 1 H} correlation spectroscopy, two-dimensional homonuclear Hartmann-Hahn, and 1 H-detected { 1 H, 13 C} one bond (HMQC) and multiple-bond (HMBC) shift correlation NMR experiments. The novel lanostane derived aglycone features a rare 14-carboxyl group and a 24-methylene, 25-methyl side chain.
- Published
- 1992
25. Petrosaspongiolides M-R: new potent and selective phospholipase A2 inhibitors from the New Caledonian marine sponge Petrosaspongia nigra
- Author
-
Cécile Debitus, Maria J. Alcaraz, Antonio Randazzo, P. García Pastor, Luigi Gomez-Paloma, Luigi Minale, M. Paya, Randazzo, Antonio, Cécile, Debitu, Luigi, Minale, P., GARCIA PASTOR, MARIA J., Alcaraz, Miguel, Paya, and LUIGI GOMEZ, Paloma
- Subjects
Magnetic Resonance Spectroscopy ,Swine ,Pharmaceutical Science ,Spectrometry, Mass, Fast Atom Bombardment ,complex mixtures ,Phospholipases A ,Analytical Chemistry ,Sesterterpenes ,Manoalide ,chemistry.chemical_compound ,Phospholipase A2 ,4-Butyrolactone ,Drug Discovery ,Synovial Fluid ,Animals ,Humans ,Enzyme Inhibitors ,IC50 ,Pancreas ,Pharmacology ,chemistry.chemical_classification ,biology ,Molecular Structure ,Terpenes ,Organic Chemistry ,Biological activity ,In vitro ,Porifera ,Bee Venoms ,Phospholipases A2 ,Enzyme ,Complementary and alternative medicine ,chemistry ,Biochemistry ,Enzyme inhibitor ,biology.protein ,Molecular Medicine ,lipids (amino acids, peptides, and proteins) - Abstract
Five new bioactive sesterterpenes (1-5) have been isolated from the New Caledonian marine sponge Petrosaspongia nigra Bergquist and named petrosaspongiolides M-R. Their chemical structures were determined from 1D and 2D NMR studies and MS data. All compounds inhibited different preparations of phospholipase A(2) (PLA(2)) by irreversibly blocking these enzymes (particularly human synovial and bee venom, see Table 3), with IC50 values in the micromolar range. Interestingly, these compounds displayed a much lower activity (or no activity at all) toward porcine pancreas and Naja naja venom PLA(2) enzymes. The most potent compound, 1 (IC50 1.6 and 0.6 mu M for human synovial and bee venom PLA(2) enzymes, respectively), was slightly more active than manoalide (6) (IC50 3.9 and 7.5 mu M) under our experimental conditions. Compound 3 is more selective, inhibiting-human synovial PLA(2) to a greater extent than bee venom PLA(2).
- Published
- 1998
26. Starfish Saponins, 45. Novel Sulfated Steroidal Glycosides from the Starfish Astropecten scoparius
- Author
-
Raffaele Riccio, Maria Iorizzi, Hisao Kamiya, and Luigi Minale
- Subjects
Pharmacology ,Astropecten scoparius ,biology ,Steroidal glycosides ,Stereochemistry ,Organic Chemistry ,Starfish ,Pharmaceutical Science ,biology.organism_classification ,Animal origin ,Analytical Chemistry ,Sulfation ,Complementary and alternative medicine ,Drug Discovery ,Molecular Medicine - Published
- 1990
27. New Cytotoxic Sesterterpenes From The New Caledonian Marine Sponge Petrosaspongia nigra (Bergquist)
- Author
-
Luigi Gomez Paloma, Luigi Minale, Antonio Randazzo, Christos Roussakis, Cécile Debitus, LUIGI GOMEZ, Paloma, Randazzo, Antonio, Luigi, Minale, Cécile, Debitu, and Christos, Roussakis
- Subjects
ESPECE NOUVELLE ,ACTIVITE BIOLOGIQUE ,biology ,SESTERPENE ,Chemistry ,Stereochemistry ,Organic Chemistry ,INVERTEBRE AQUATIQUE ,biology.organism_classification ,Biochemistry ,STRUCTURE CHIMIQUE ,Sesterterpenes ,Petrosaspongia nigra ,Sponge ,SUBSTANCE NATURELLE ,Genus ,CYTOTOXICITE ,Carcinoma Cell ,ISOLEMENT ,Drug Discovery ,Cytotoxic T cell ,Spectral data ,Two-dimensional nuclear magnetic resonance spectroscopy ,SPONGIAIRE - Abstract
Along with two known cheilanthane sesterterpene lactones, 1 and 2, eight new related sesterterpenes (3–10) and two new nor-sesterterpenes (11 and 12) have been isolated from the New Caledonian marine sponge Petrosaspongia nigra Bergquist 1995 (new genus, new species). Their structures were determined from 1D and 2D NMR studies and mass spectral data. They exhibited cytoxicity against the NSCLC-N6 human bronchopulmunary non-small-cell-lung carcinoma cell lines.
- Published
- 1997
28. Bengamides and Related New Amino Acid Derivatives from the New Caledonian Marine Sponge Jaspis carteri
- Author
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Angela Zampella, Luigi Minale, Maryvonne Frostin, Cécile Debitus, Clelia Giannini, Maria Valeria D'Auria, D'Auria, MARIA VALERIA, Giannini, C., Minale, L., Zampella, Angela, Debitus, C., and Frostin, M.
- Subjects
Pharmacology ,chemistry.chemical_classification ,Formamide ,Stereochemistry ,Organic Chemistry ,Caprolactam ,Pharmaceutical Science ,Biology ,biology.organism_classification ,Animal origin ,Analytical Chemistry ,Amino acid ,chemistry.chemical_compound ,Sponge ,Complementary and alternative medicine ,chemistry ,Drug Discovery ,Lactam ,Molecular Medicine ,Aliphatic compound ,Spectral data - Abstract
Five new amino acid derivs. were isolated from the New Caledonian sponge Jaspis carteri, together with known bengamides A and B. The structures of the new compds. were detd. by interpretation of their spectral data and by comparison with spectral data of known bengamides. Bengamides G (I), and H, I, and J are simply the tridecanoate and pentadecanoate analogs of the original bengamides A and B, whereas bengamide K (II) is a caprolactam formamide deriv. of bengamide B.
- Published
- 1997
29. Crellastatin A: A Cytotoxic Bis-Steroid Sulfate from the Vanuatu Marine Sponge Crella sp
- Author
-
Luigi Minale, Angela Zampella, Maria Valeria D'Auria, Christos Roussakis, Cécile Debitus, Clelia Giannini, D'Auria, MARIA VALERIA, Giannini, C., Zampella, Angela, Minale, L., Debitus, C., and Roussakis, C.
- Subjects
biology ,Stereochemistry ,Chemistry ,medicine.medical_treatment ,Organic Chemistry ,biology.organism_classification ,Molecular mechanics ,In vitro ,Steroid ,Sponge ,medicine ,Side chain ,Cytotoxic T cell ,Steroid sulfate ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
A new nonsymmetric dimeric steroid, crellastatin A (1), was isolated from the Vanuatu Island marine sponge Crella sp. Structural assignment was accomplished through extensive 2D NMR spectroscopy. The stereochemistry of 1 was established from an analysis of ROESY experiments and from molecular mechanics and dynamics calculations. Crellastatin A (1), which possesses an unprecedented connection through the side chains, exhibits in vitro cytotoxic activity against NSCLC-N6 cells (IC(50) of 1.5mgr;g/mL).
- Published
- 2001
30. Isolation, structure elucidation, and biological activity of the steroid oligoglycosides and polyhydroxysteroids from the Antarctic starfish Acodontaster conspicuus
- Author
-
James B. McClintock, B J Baker, Charles D. Amsler, Franco Zollo, Luigi Minale, Maria Iorizzi, S. De Marino, DE MARINO, Simona, M., Iorizzi, Zollo, Franco, L., Minale, C. D., Amsler, B. J., Baker, and J. B., Mcclintock
- Subjects
Magnetic Resonance Spectroscopy ,Stereochemistry ,medicine.medical_treatment ,Starfish ,Saponin ,Pharmaceutical Science ,Microbial Sensitivity Tests ,Spectrometry, Mass, Fast Atom Bombardment ,Analytical Chemistry ,Steroid ,Acodontaster conspicuum ,Marine bacteriophage ,Drug Discovery ,medicine ,Animals ,Antibacterial agent ,Pharmacology ,chemistry.chemical_classification ,biology ,Bacteria ,Organic Chemistry ,Glycoside ,Biological activity ,Marine invertebrates ,biology.organism_classification ,Anti-Bacterial Agents ,Complementary and alternative medicine ,chemistry ,Molecular Medicine ,Steroids ,Steroidal oligoglycosides - Abstract
A total of 19 steroids, of which 13 steroidal oligoglycosides (nine new and four known) and six polyhydroxylated steroids (four new and two known), has been isolated from the Antarctic starfish Acodontaster conspicuus. The mixture is dominated by glycosides composed of steroidal aglycons having the hydroxyl groups typically disposed on one side of the tetracyclic nucleus, i.e., 3 beta,4 beta,6 alpha,8,15 beta-, with some having a sulfate at C-6, and differing in the side chains and/or in the disaccharide moieties that are usually attached at C-26, with some at C-28 and C-29. Those compounds are accompanied by minute amounts of glycosides with a delta 8(14)-double bond in the steroid, which is a structural feature not previously found among polyhydroxysteroids derived from starfish. Small amounts of six related unglycosidated polyhydroxysteroids and three higher-molecular-weight asterosaponins complete the composition of the mixture. The structures of the new compounds were determined by interpretation of their spectral data and by comparison with spectral data of known compounds. Eighteen of these compounds were evaluated for their ability to inhibit growth in Antarctic marine bacteria isolated from either the water column or the surfaces of benthic marine invertebrates. Of these compounds, 50% were active against at least one Antarctic marine bacterium. This suggests that these compounds may play an important role in deterring microbial fouling.
- Published
- 1997
31. Callipeltosides B and C, two novel cytotoxic glycoside macrolides from a marine Lithistida sponge Callipeltasp
- Author
-
Cécile Debitus, M. Valeria D'Auria, Luigi Minale, Angela Zampella, Zampella, Angela, D'Auria, MARIA VALERIA, Minale, L., and Debitus, C.
- Subjects
chemistry.chemical_classification ,biology ,Stereochemistry ,Organic Chemistry ,Glycoside ,biology.organism_classification ,Biochemistry ,Sponge ,Callipeltoside B ,Callipelta ,chemistry ,Callipeltoside A ,Drug Discovery ,Lithistida ,Cytotoxic T cell ,Spectral analysis - Abstract
Following the characterization of callipeltoside A (1), the first member of a novel class of marine glycoside macrolides, two more bioactive constituents, callipeltoside B (2) and C(3), were isolated from Callipelta sp. in very low amounts. The structures, assigned on the basis of spectral analysis, include the same 14-membered macrolide as in callipeltoside A (1) but differed in the saccharide moieties.
- Published
- 1997
32. Isolation of 20 glycosides from the starfish Henricia downeyae, collected in the Gulf of Mexico
- Author
-
Franco Zollo, Luigi Minale, Patrick J. Bryan, Elio Palagiano, James B. McClintock, Thomas S. Hopkins, Maria Iorizzi, E., Palagiano, Zollo, Franco, L., Minale, M., Iorizzi, P., Bryan, J., Mcclintock, and T., Hopkins
- Subjects
Magnetic Resonance Spectroscopy ,Stereochemistry ,medicine.medical_treatment ,Starfish ,Molecular Sequence Data ,Henricia ,Saponin ,Pharmaceutical Science ,Uronic acid ,Spectrometry, Mass, Fast Atom Bombardment ,POLYHYDROXYSTEROIDS ,Analytical Chemistry ,Steroid ,chemistry.chemical_compound ,STEROIDAL GLYCOSIDES ,Drug Discovery ,medicine ,MAGNETIC-RESONANCE SPECTROSCOPY ,SPECTRA ,Animals ,Glycosides ,Echinasteridae ,Pharmacology ,chemistry.chemical_classification ,biology ,Organic Chemistry ,Glycoside ,biology.organism_classification ,Echinaster ,Complementary and alternative medicine ,chemistry ,Biochemistry ,Carbohydrate Sequence ,Molecular Medicine ,Steroids ,ECHINASTER-SEPOSITUS ,SAPONINS - Abstract
Thirteen new (1-13) and seven known (14-20) steroid glycosides were isolated from Henricia downeyae, collected from the offshore waters of the northern Gulf of Mexico. Ethanolic extracts of these starfish caused growth inhibition in bacteria and fungi, potent antifouling activity against barnacle and bryozoan larvae, and feeding deterrent activity against a marine fish. The known compounds are typical glycosides found in several species of the family Echinasteridae, i.e., Echinaster sp. and Henricia Laeviuscola. One of the new compounds belongs to this group, whereas the remaining 12 new compounds represent a novel series of steroid glycosides which have aglycons with structural similarities to the ''asterosaponins''. They possess a Delta(9(11)) 3 beta,6 alpha-dihydroxysteroidal aglycon with 23-oxo or 22,23-epoxy functionalities and often a 20-hydroxyl group in the side chain. The sulfate is located at C-6 and the saccharide moiety at C-3, in contrast with the asterosaponins which have the sulfate at C-3 and the oligosaccaride moiety at C-6. All the new compounds contain a glucuronic acid unit, which is uncommon among steroid glycosides from echinoderms. The structures of the new compounds, isolated in amounts ranging from 3.4 to 0.9 mg, were determined by interpretation of their spectral data and by comparison with spectral data of known compounds.
- Published
- 1996
33. Callipeltins B and C; bioactive peptides from a marine Lithistida sponge Callipelta sp
- Author
-
L. Gomez Paloma, C. Roussakis, Cécile Debitus, Maria Valeria D'Auria, Angela Zampella, Luigi Minale, V. Le Bert, D'Auria, MARIA VALERIA, Zampella, Angela, Gomez Paloma, L., Minale, L., Debitus, C., Roussakis, C., and Le Bert, V.
- Subjects
Sponge ,Callipelta ,biology ,Stereochemistry ,Chemistry ,Organic Chemistry ,Drug Discovery ,Lithistida ,Callipeltin B ,Acid hydrolysis ,Tripeptide ,biology.organism_classification ,Biochemistry - Abstract
Following the characterization of callipeltin A (1), two new cytotoxic peptides, callipeltin B (2) and C (3), were isolated from the New Caledonian sponge Callipelta sp.. Callipeltin B (2) possess the same cyclic depsipeptidal structure as in callipeltin A (1) and differs from 1 by having the N-terminal 2,3-dimethylpyroglutamic acid unit instead of the tripeptide chain with the N-terminus blocked by an hydroxyacid. Callipeltin C (3) is simply the acyclic callipeltin A. The structures 2–3 have been determined by NMR experiments, FAB mass spectrometry, evaluation of the aminoacids obtained by acid hydrolysis and by comparison of the data with those of callipeltin A (1). Following the characterization of callipeltin A (1), two new peptides, callipeltin B (2) and C (3), were isolated form Callipelta sp.. Callipeltin B (2) possess the same cyclic depsipeptidal structure as in callipeltin A (1) and differs from 1 by having the N-terminal 2,3-dimethylpyroglutamic acid unit instead of the tripeptide chain with the N-terminus blocked by an hydroxyacid. Callipeltin C (3) is the acyclic callipeltin A. Callipeltins have been found to be cytotoxic against various human carcinoma cells.
- Published
- 1996
34. Steroid and Triterpenoid Oligoglycosides of Marine Origin
- Author
-
Maria Iorizzi, Luigi Minale, Elio Palagiano, and Raffaele Riccio
- Subjects
Marine sponges ,medicine.medical_treatment ,Molecular Sequence Data ,Pardachirus ,Oligosaccharides ,Zoology ,Biology ,biology.organism_classification ,Triterpenes ,Steroid ,Triterpenoid ,Carbohydrate Sequence ,Phylum Echinodermata ,Genus ,medicine ,Animals ,Humans ,Marine Toxins ,Steroids ,Glycosides ,Marine toxin ,Echinodermata - Abstract
Saponins have been considered for a long time typical metabolites of plant origin. It has been only in the last two decades that the world-wide investigation of marine organisms as sources of new bioactive metabolites disclosed the wide distribution of these molecules also among marine animals. Today saponins are recognized as the most common characteristic metabolites in two classes of the phylum Echinodermata (Holothuroidea and Asteroidea). Furthermore, several steroid and triterpenoid oligoglycosides have been isolated from different species of marine sponges, more rarely Anthozoans, and also from fishes of the genus Pardachirus, where they have been shown to act as shark repellents. This communication offers a general view of the distribution of steroid and triterpenoid oligoglycosides among marine organisms and focuses on a number of recent examples to discuss structural characteristics, biological activities, and methods of investigation.
- Published
- 1996
35. Callipeltin A, an anti-HIV cyclic depsipeptide from the New Caledonian Lithistida sponge Callipelta sp
- Author
-
L. Gomez Paloma, Cécile Debitus, Y. Hénin, Luigi Minale, Angela Zampella, Agostino Casapullo, Maria Valeria D'Auria, Zampella, Angela, D'Auria, MARIA VALERIA, Gomez Paloma, L., Casapullo, A., Minale, L., Debitus, C., and Henin, Y.
- Subjects
chemistry.chemical_classification ,CALLIPELTINE A ,ACTIVITE BIOLOGIQUE ,biology ,SIDA ,Chemistry ,Stereochemistry ,INTERET PHARMACOLOGIQUE ,INVERTEBRE AQUATIQUE ,General Chemistry ,Cyclic depsipeptide ,biology.organism_classification ,Biochemistry ,Catalysis ,Amino acid ,Sponge ,Residue (chemistry) ,Colloid and Surface Chemistry ,Callipelta ,EPONGE ,SUBSTANCE NATURELLE ,Lithistida ,Acid hydrolysis ,Threonine ,SPONGIAIRE - Abstract
Callipeltin A (1) is a cyclic depsidecapeptide from a shallow water sponge of the genus Callipelta (order Lithistida), collected in the waters off New Caledonia. The structure of callipeltin A (1), which possesses the N-terminus blocked with a β-hydroxy acid, and the C-terminus lactonized with a threonine residue, was determined by interpretation of spectral data, chemical degradation, and evaluation of the amino acids obtained by acid hydrolysis. Along with four common l-, one d-, and two N-methyl amino acids, it contains three new amino acid residues: β-methoxytyrosine (βOMeTyr), (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE), and (3S,4R)-3,4-dimethyl-l-glutamine. Callipeltin A (1) has been found to protect cells infected by human immunodeficiency (HIV) virus.
- Published
- 1996
36. Two novel polyhydroxysteroids with a 24-ethyl-25-hydroxy-26-sulfoxy side chain from the deep water starfish Styracaster caroli
- Author
-
Elio Palagiano, Luigi Minale,§ and, Francesco De Riccardis, Maria Iorizzi, Irene Izzo, and Raffaele Riccio
- Subjects
Pharmacology ,Nouvelle caledonie ,Styracaster ,biology ,Stereochemistry ,Chemistry ,Organic Chemistry ,Starfish ,Absolute configuration ,Pharmaceutical Science ,biology.organism_classification ,Animal origin ,Analytical Chemistry ,Deep water ,Complementary and alternative medicine ,Drug Discovery ,Side chain ,Molecular Medicine - Abstract
The structure of two minor polyhydroxysteroids isolated from the deep water starfish Styracaster caroli were determined as (22E,24R,25R)-24-ethyl-5α-cholest-22-en-3β,5,6β,8,15α,25,26-heptol 26-sulf...
- Published
- 1996
37. Investigation of the polar steroids from an Antarctic starfish of the family Echinasteridae: isolation of twenty seven polyhydroxysteroids and steroidal oligoglycosides, structures and biological activities
- Author
-
Valérie Le Bert, Simona De Marino, Franco Zollo, Luigi Minale, Christos Roussakis, Maria Iorizzi, M., Iorizzi, DE MARINO, Simona, L., Minale, Zollo, Franco, V., Le Bert, and C., Roussakis
- Subjects
chemistry.chemical_classification ,biology ,Stereochemistry ,medicine.medical_treatment ,Organic Chemistry ,Starfish ,Glycoside ,biology.organism_classification ,Biochemistry ,Steroid ,chemistry.chemical_compound ,Aglycone ,human non-small-cell lung carcinoma cells ,chemistry ,Drug Discovery ,Glycosides of polyhydroxysteroid ,Side chain ,medicine ,Monosaccharide ,Echinasteridae ,Polyhyoxysteroid - Abstract
An investigation of the extracts from a starfish collected in the Antarctic Sea, Echinasteridae family, has led to the isolation of thirteen glycosides of polyhydroxysteroids (1–13), fourteen polyhydroxysteroids (14–27), which are the subject of this report, and seven asterosaponins (penta-and hexa-saccharides), described in a previous paper. Glycosides 1–13 are composed of the same 3β,4β,6α,8,15β,26-hexahydroxysteroidal aglycone with small variations in the side chains, and a carbohydrate portion made up of one or two monosaccharide units attached at C-26, except 11, which has a steroidal aglycone with a 24,28-dihydroxylated side chain and the monosaccharide unit attached at C-24. The structures of the polyhydroxysteroids (14–27) have the hydroxyl groups typically disposed on one side of the steroid nucleus, i.e. 3β,4β,6β (or α),8,15α (or β) and 16β and the majority of them possess a 26-hydroxyl function. A selection of fifteen compounds were tested against human non-small-cell lung carcinoma cells and found to be moderately cytotoxic.
- Published
- 1996
38. Chemical and biological investigation of the polar constituents of the starfish Luidia clathrata, collected in the Gulf of Mexico
- Author
-
James B. McClintock, Maria Iorizzi, Elio Palagiano, Luigi Minale, Raffaele Riccio, Patrick J. Bryan, Franco Zollo, Stefano Maurelli, M., Iorizzi, P., Bryan, J., Mcclintock, L., Minale, E., Palagiano, S., Maurelli, R., Riccio, and Zollo, Franco
- Subjects
STEREOCHEMICAL ASSIGNMENTS ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Starfish ,Molecular Sequence Data ,Pharmaceutical Science ,ASYMMETRIC DIHYDROXYLATION ,Spectrometry, Mass, Fast Atom Bombardment ,Analytical Chemistry ,chemistry.chemical_compound ,STEROIDAL GLYCOSIDE SULFATES ,Drug Discovery ,Animals ,Spectral data ,Derivatization ,Hydroxysteroids ,Pharmacology ,Larva ,SPECTROSCOPY ,biology ,Molecular Structure ,Chemistry ,Organic Chemistry ,Marine fish ,Nuclear magnetic resonance spectroscopy ,Feeding Behavior ,Saponins ,biology.organism_classification ,Anti-Bacterial Agents ,Fishery ,MARINE POLYHYDROXYLATED STEROIDS ,Complementary and alternative medicine ,Carbohydrate Sequence ,MACULATA ,Molecular Medicine ,Polar ,Luidia clathrata - Abstract
Ten new [1-10] and three known [11-13] polyhydroxysteroids were isolated, along with four known asterosaponins [14-17], from the starfish Luidia clathrata, collected from the offshore waters of the northern Gulf of Mexico. The EtOH extracts of this starfish showed feeding-deterrent properties against marine fish, and inhibited the settlement of larvae of barnacles and bryozoans, as well as the growth of several bacteria. The structures of the new compounds were determined by interpretation of their nmr spectral data and by comparison with the spectral data of known compounds. The assignment of the configurations of the side-chain stereogenic centers of compounds 1 and 3-10 were based on the comparison of their nmr data with those of the stereoisomeric model compounds after derivatization with the chiral auxiliary MTPA reagent. Larval settlement assays conducted on ten isolated compounds revealed they are all potent inhibitors of settlement. Two of these isolated compounds inhibited the growth of several bacteria.
- Published
- 1995
39. Structural studies on chemical constituents of echinoderms
- Author
-
Raffaele Riccio, Luigi Minale, and Franco Zollo
- Subjects
Lower affinity ,Triterpenoid ,Steroidal glycosides ,Phylum Echinodermata ,Membrane cholesterol ,Chemical constituents ,Botany ,Biology ,Haemolysis - Abstract
Publisher Summary This chapter focuses on the more recent developments in the field of natural products from echinoderms. The phylum Echinodermata, which comprises about 6000 living species, is divided into five classes: Crinoidea (sea lilies and feather stars), Holoturoidea (sea cucumbers or holothurians), Echinoidea (sea urchins), Asteroidea (sea stars or starfishes), and Ophiuroidea (brittle stars). Among the echinoderms, starfishes and sea cucumbers usually contain saponins, which are responsible of their general toxicity. Chemically, saponins derived from sea cucumbers are triterpenoid glycosides, whereas those from starfishes are steroidal glycosides. The presence of oligoglycosides in both Holothuroidea and Asteroidea classes gives support to the opinion that sea cucumbers and starfishes are phylogenetically related. In starfishes and sea cucumbers Δ 7 -sterols, which are probably a consequence of the presence of haemolytic saponins, are also predominant, whereas the other three classes contain the usual Δ 5 -sterols. Haemolysis is caused by the abstraction of membrane cholesterol by the saponins. Saponins show a much lower affinity for Δ 7 -sterols and this helps to explain the apparent immunity of starfishes and sea cucumbers to their own saponins.
- Published
- 1995
40. Bioactive Prenylhydroquinone Sulfates and a Novel C31 Furanoterpene Alcohol Sulfate from the Marine Sponge, Ircinia Sp
- Author
-
Aude Vassas, Giuseppe Bifulco, Ines Bruno, Raffaele Riccio, Jacques Lavayre, Genievieve Bourdy, Luigi Minale, and Cécile Debitus
- Subjects
Pharmacology ,biology ,Organic Chemistry ,Pharmaceutical Science ,Alcohol ,biology.organism_classification ,Analytical Chemistry ,chemistry.chemical_compound ,Sponge ,Complementary and alternative medicine ,chemistry ,Drug Discovery ,Molecular Medicine ,Organic chemistry ,Ircinia ,Sulfate - Published
- 1995
41. Reidispongiolide A and B, two new potent cytotoxic macrolides from the New Caledonian sponge Reidispongia coerulea
- Author
-
Cécile Debitus, Christos Roussakis, Angela Zampella, Jean-François Verbist, Luigi Minale, M. Valeria D'Auria, Luigi Gomez Paloma, Josiane Patissou, D'Auria, MARIA VALERIA, Gomez Paloma, L., Minale, L., Zampella, Angela, Verbist, J. F., Roussakis, C., Dibitus, C., and Patissou, J.
- Subjects
biology ,ACTIVITE BIOLOGIQUE ,Stereochemistry ,Chemistry ,CYTOTOXIQUE ,Organic Chemistry ,Nudibranch ,INVERTEBRE AQUATIQUE ,biology.organism_classification ,Biochemistry ,STRUCTURE CHIMIQUE ,Sponge ,EPONGE ,SUBSTANCE NATURELLE ,Drug Discovery ,Cytotoxic T cell ,Reidispongia coerulea ,Cytotoxicity ,SPONGIAIRE ,Neosiphonia - Abstract
Two new 26-membered macrolides, reidispongiolide A (1) and B (2), have been isolated from the New Caledonian marine sponge Redispongia coerulea n.gen.n.sp. Levi and Levi and their structures elucidated. They are related to sphinxolides previously isolated from an unknown nudibranch and later from the sponge Neosiphonia superstes. 1 and 2 co-occurr with sphinxolide B (4) and D (3). These macrolides exhibited potent cytotoxicity against various human carcinoma cells.
- Published
- 1994
42. (+/-)-Gelliusines A and B, two diastereomeric brominated tris-indole alkaloids from a deep water new caledonian marine sponge (Gellius or Orina sp.)
- Author
-
Antonio Calignano, Luigi Minale, Giuseppe Bifulco, Ines Bruno, Raffaele Riccio, Cécile Debitus, G., Bifulco, I., Bruno, L., Minale, R., Riccio, Calignano, Antonio, and C., Debitus
- Subjects
Tris ,Male ,Indoles ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Guinea Pigs ,Pharmaceutical Science ,Stereoisomerism ,Antineoplastic Agents ,KB Cells ,Analytical Chemistry ,chemistry.chemical_compound ,EPONGE ,Drug Discovery ,Animals ,Humans ,Cytotoxicity ,Pharmacology ,Indole test ,TOXICITE ,biology ,Organic Chemistry ,Diastereomer ,Muscle, Smooth ,Nuclear magnetic resonance spectroscopy ,INVERTEBRE AQUATIQUE ,biology.organism_classification ,Parazoa ,Porifera ,Serotonin Receptor Agonists ,Complementary and alternative medicine ,chemistry ,Molecular Medicine ,ALCALOIDE ,Enantiomer ,Drug Screening Assays, Antitumor - Abstract
Two new diastereomeric brominated tris-indole alkaloids occurring as enantiomeric pairs, (+/-)-gelliusines A [1] and B [2], have been isolated from a deep water New Caledonian sponge (Gellius or Orina sp.), whose crude extract exhibited cytotoxicity against KB cells. Their structures were elucidated by spectroscopic methods including one- and two-dimensional nmr spectroscopy. The major compound, (+/-) gelliusine A [1], which showed very weak cytotoxicity, proved to be active at the serotonin receptor.
- Published
- 1994
43. The Unique 6-(p-Hydroxyphenyl)-2H-3,4-Dihydro-1,1-Dioxo-1,4-Thiazine and the New Tripeptide L-Glu-Gly-4-Hydroxystirylamine from the Marine Sponge Anchinoe tenacior
- Author
-
Luigi Minale, Franco Zollo, Agostino Casapullo, A., Casapullo, L., Minale, and Zollo, Franco
- Subjects
chemistry.chemical_classification ,Dipeptide ,sostanze naturali marine ,Stereochemistry ,DERIVATIVES ,Organic Chemistry ,Peptide ,Nuclear magnetic resonance spectroscopy ,Tripeptide ,Biochemistry ,Sulfone ,chemistry.chemical_compound ,Residue (chemistry) ,chemistry ,sostanze naturali marine, siolamento e caratterizzazione ,Thiazine ,Drug Discovery ,Phenols ,siolamento e caratterizzazione - Abstract
6-( p -Hydroxyphenyl)-2H-3,4-dihydro-1,1-dioxo-1,4-thiazine ( 1 ) has been isolated from the marine sponge Anchinoe tenacior , along with a novel tripeptide with a C-terminal trans -4-hydroxystirylamino residue ( 2 ).
- Published
- 1994
44. Paniceins and related sesquiterpenoids from the Mediterranean sponge Reniera fulva
- Author
-
Luigi Minale, Franco Zollo, Agostino Casapullo, A., Casapullo, L., Minale, and Zollo, Franco
- Subjects
Lung Neoplasms ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Cell Survival ,Pharmaceutical Science ,Antineoplastic Agents ,Biology ,Pharmacognosy ,Sesquiterpene ,Analytical Chemistry ,chemistry.chemical_compound ,Carcinoma, Non-Small-Cell Lung ,Drug Discovery ,Tumor Cells, Cultured ,Animals ,Humans ,Cytotoxicity ,SARAI ,Pharmacology ,Hydroquinone ,Organic Chemistry ,ANTIMICROBIAL METABOLITES ,biology.organism_classification ,NMR ,Terpenoid ,Halichondria panicea ,In vitro ,Porifera ,Sponge ,Complementary and alternative medicine ,chemistry ,HETERONUCLEAR SHIFT CORRELATION ,Molecular Medicine ,Sesquiterpenes - Abstract
Two novel sesquiterpenes,fulvanin 1 [1] and fulvanin 2[2], have been isolated from the Mediterranean sponge Reniera fulva. Compound 2 is a sesquiterpenoid linked to a hydroquinone. Also found in Reniera fulva are four known paniceins, a group of aromatic sesquiterpenoids linked to a quinol, isolated previously from Halichondria panicea. The total assignments of C-13-nmr spectra of paniceins have been made with the aid of 2D(HC)-H-1-C-13 correlation techniques, confirming their structures. The paniceins were tested in the in vitro disease-oriented primary antitumor screen at NCI, Bethesda. Paniceins C and B3 showed cytotoxicity against NCI-H522 non-small lung cancer cells and CCRF-CEM leukemia cells, while panicein A hydroquinone revealed more selective cytotoxicity against the latter ones.
- Published
- 1993
45. Starfish saponins, Part 51. Steroidal oligoglycosides from the starfish Distolasterias nipon
- Author
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Maria Iorizzi, Takeshi Yasumoto, Raffaele Riccio, and Luigi Minale
- Subjects
Magnetic Resonance Spectroscopy ,Steroidal glycosides ,Stereochemistry ,Molecular Sequence Data ,Starfish ,Saponin ,Pharmaceutical Science ,Methylation ,Analytical Chemistry ,Distolasterias nipon ,Pycnopodia ,Drug Discovery ,Animals ,Glycosides ,Spectral data ,Pharmacology ,chemistry.chemical_classification ,biology ,Hydrolysis ,Methanol ,Organic Chemistry ,Glycoside ,Saponins ,biology.organism_classification ,Pisaster ochraceus ,Carbohydrate Sequence ,Complementary and alternative medicine ,chemistry ,Molecular Medicine - Abstract
A reinvestigation of the extracts from the starfish Distolasterias nipon, collected at Mutsu Bay, Japan, has led to the isolation of six glycosides of polyhydroxysteroids and six asterosaponins. Four steroidal glycosides have been identified as distolasterosides D1 [1] and D2 [2] (previously isolated from the same organism), and pycnopodioside C [5] and pisasteroside A [6], previously found in the related species Pycnopodia helianthoides and Pisaster ochraceus (family Asteridae), respectively. Two asterosaponins have been identified as the common versicoside A [7] and thornasteroside A [7a]. The two remaining glycosides of polyhydroxysteroids, named distolasterosides D4 [3] and D5 [4], and four asterosaponins designated nipoglycosides A [8], B [9], C [10], and D [11] are new compounds, and their structures have been elucidated mainly by interpretation of spectral data and comparison with known compounds.
- Published
- 1993
46. Isolation and Structure Characterization of Two Novel Bioactive Sulphated Polyhydroxysteroids from the Antarctic OphiuroidOphioderma longicaudum
- Author
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Luigi Gomez Paloma, Luigi Minale, Raffaele Riccio, Mariella Morbidoni, Angela Zampella, and Maria Valeria D'Auria
- Subjects
Stereochemistry ,Molecular Medicine ,Biology ,Ophiosparte gigas ,Isolation (microbiology) - Abstract
Two novel sulphated polyhydroxysteroids, 1, possessing potent cytotoxic activity, and 2, which proved to be cytoprotective against HIV-1, have been isolated from the Antarctic ophiuroid Ophiosparte gigas, together with the known tetrol disulphated 3. The structures of 1 and 2 have been determined to be cholest-5-ene-2α,3α,4β, 21-tetraol 3, 21-disulphate and cholest-5-ene-2β,3α, 21-triol 2, 21-disulphate, respectively.
- Published
- 1993
47. Metabolites of the New Caledonian Sponge Claodocroce incurvata
- Author
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M. Valeria D'Auria, Luigi Gomez Paloma, Luigi Minale, Angela Zampella, Cécile Debitus, Raffaele Riccio, D'Auria, MARIA VALERIA, Gomez Paloma, L., Minale, L., Riccio, R., Zampella, Angela, and Debitus, C.
- Subjects
Stereochemistry ,Carboxylic acid ,Pharmaceutical Science ,Butyrate ,Biology ,Ring (chemistry) ,Analytical Chemistry ,Cyclopropane ,Polyketide ,chemistry.chemical_compound ,EPONGE ,ANALYSE SPECTRALE ,Drug Discovery ,Side chain ,MOLECULE ,Pharmacology ,chemistry.chemical_classification ,Enyne ,Organic Chemistry ,Fatty acid ,INVERTEBRE AQUATIQUE ,CLADOCROCINE ,STRUCTURE CHIMIQUE ,METABOLITE ,Complementary and alternative medicine ,chemistry ,SUBSTANCE NATURELLE ,ACIDE CLADOCROIQUE ,Molecular Medicine - Abstract
The deep-water New Caledonian sponge #Cladocroce incurvata$ contains two "polyketide" metabolites. Cladocrocin A (1) appears to be derived from fatty acid with ethyl side chains, thus incorporating butyrate units. Cladocroic acid (2) is a straight chain fatty acid which incorporates a terminal enyne functionality and a cycloproprane ring directly attached to the carboxylic acid function. The structures were elucidated by interpretation of spectral data, and the cis stereochemistry of the cyclopropane ring in cladocroic acid (2) was derived after the synthesis of cis - and trans - 2, 3 - methanohexanoic acid models and nmr spectral comparisons. (Résumé d'auteur)
- Published
- 1993
48. A novel group of polyhydroxycholanic acid derivatives from the deep water starfish Styracaster caroli
- Author
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Francesco De Riccardis, Cécile Debitus, D. Duhet, Raffaele Riccio, Claude Monniot, Maria Iorizzi, and Luigi Minale
- Subjects
Styracaster ,biology ,Stereochemistry ,Chemistry ,Organic Chemistry ,Starfish ,Nuclear magnetic resonance spectroscopy ,INVERTEBRE AQUATIQUE ,biology.organism_classification ,Biochemistry ,Deep water ,STRUCTURE CHIMIQUE ,ACIDE CYSTEINOLIQUE ,chemistry.chemical_compound ,Group (periodic table) ,SUBSTANCE NATURELLE ,Amide ,Drug Discovery ,Moiety ,POLYHYDROXYSTEROIDE ,ETOILE DE MER ,ACIDE POLYHYDROXYLCHOLANIQUE - Abstract
Three novel polyhydroxysteroid constituents have been isolated from the starfish #Stracaster caroli$ collected at a depht of 2000 m off New Caledonia. These, designated carolisterols A - C (1 - 3), are characterized by a polyhydroxycholanic acid moiety, in which the 24-carboxylic acid function is found as an amide derivative ofD-cysteinolic acid. (Résumé d'auteur)
- Published
- 1993
49. Steroidal oligoglycosides and polyhydroxysteroids from echinoderms
- Author
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Franco Zollo, Raffaele Riccio, and Luigi Minale
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,Triterpenoid ,Aglycone ,Water soluble ,Steroidal glycosides ,chemistry ,Phylum Echinodermata ,Botany ,Glycoside ,Carbohydrate moiety ,Molecular conformation - Abstract
The phylum Echinodermata, which comprises about 6,000 living species distributed in all seas from the tropics to the antarctic zone, is divided into five classes: Crinoidea (sea lilies and feather stars), Holothuroidea (sea cucumbers or holothurians), Echinoidea (sea urchins), Asteroidea (sea stars or starfishes) and Ophiuroidea (brittle stars). Among the echinoderms, sea cucumbers and starfishes invariably contain saponins which are generally responsible for their toxicity. Saponins, complex water soluble compounds composed of a carbohydrate moiety attached to a steroid or triterpenoid aglycone, have been isolated from a great number of terrestrial plants, but are uncommon animal constituents. In the animal kingdom they are almost ubiquitous in sea cucumbers and starfishes (1), while found only rarely in alcyonarians (2), gorgonians (3-5), sponges (6-10) and as potent shark-repelling compounds in fishes (11). Chemically, saponins from sea cucumbers are triterpenoid glycosides whereas those from starfishes are steroidal glycosides.
- Published
- 1993
50. Three new potent cytotoxic macrolides closely related to sphinxolide from the New Caledonian spongeNeosiphonia superstes
- Author
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Luigi Minale, Jean-François Verbist, Cécile Debitus, M. Valeria D'Auria, Luigi Gomez Paloma, Christos Roussakis, Angela Zampella, D'Auria, MARIA VALERIA, Gomez Paloma, L., Minale, L., Zampella, Angela, Verbist, J. F., Roussakis, C., and Debitus, C.
- Subjects
Sponge ,biology ,Stereochemistry ,Chemistry ,Organic Chemistry ,Drug Discovery ,Cytotoxic T cell ,Spectral data ,biology.organism_classification ,Biochemistry ,Neosiphonia - Abstract
Three new macrolides 2–4 have been isolated with sphinxolide 1 from the marine sponge N. superstes collected off New Caledonia. The structures of the new compounds were determined by interpretation of NMR spectral data as well as by comparison of spectral data with those of 1. These compounds were highly cytotoxic against various human carcinoma cells.
- Published
- 1993
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