Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) Papenfuss

Gerwick, William H.; Fenical, William

doi:10.1021/jo00314a005

Cited by 144Seaweed-derived Bioactive CompoundsMarine Sponges and Natural ProductsMicrobial Natural Products and Biosynthesis

The DOI matches its Crossref record.

Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) Papenfuss

Gerwick, William H., Fenical, William·1981·The Journal of Organic Chemistry

DOI 10.1021/jo00314a005

Open this paper in CoChat — free account

Abstract

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIchthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) PapenfussWilliam H. Gerwick and William FenicalCite this: J. Org. Chem. 1981, 46, 1, 22–27Publication Date (Print):January 1, 1981Publication History Published online1 May 2002Published inissue 1 January 1981https://pubs.acs.org/doi/10.1021/jo00314a005https://doi.org/10.1021/jo00314a005research-articleACS PublicationsRequest reuse permissionsArticle Views606Altmetric-Citations126LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Integrity signals

Registry

Crossref · 10.1021/jo00314a005

Cites

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Still being checked.

Sorted by citations

Tubulin as a target for anticancer drugs: Agents which interact with the mitotic spindle
Jordan, A. M., Hadfield, J. A., Lawrence, N. J., & McGown, A. T. (1998) · Medicinal Research Reviews · doi:10.1002/(sici)1098-1128(199807)18:4 · Cited by 678
Marine Natural Products: A Source of Novel Anticancer Drugs
Khalifa, S. A. M., Elias, N., Farag, M. A., Chen, L., Saeed, A., Hegazy, M.-E. F., Moustafa, M. S., Abd El-Wahed, A., Al-Mousawi, S. M., Musharraf, S. G., et al. (2019) · Marine Drugs · doi:10.3390/md17090491 · Cited by 555
“1 μg/mL, and to inhibit cells cleavage via inhibition of tubulin polymerization [85].”
Background
Biological importance of marine algae
El‐Gamal, A. A. (2010) · Saudi Pharmaceutical Journal · doi:10.1016/j.jsps.2009.12.001 · Cited by 547
Marine natural products
Blunt, J. W., Copp, B. R., Hu, W.-P., Munro, M. H. G., Northcote, P. T., & Prinsep, M. R. (2009) · Natural Product Reports · doi:10.1039/b805113p · Cited by 520
Marine natural products
Blunt, J. W., Copp, B. R., Keyzers, R. A., Munro, M. H. G., & Prinsep, M. R. (2014) · Natural Product Reports · doi:10.1039/c3np70117d · Cited by 496
Anticancer Drugs from Marine Flora: An Overview
Boopathy, N. S., & Kathiresan, K. (2010) · Journal of Oncology · doi:10.1155/2010/214186 · Cited by 415
Biomedical Compounds from Marine organisms
Jha, R. K., & Zi-rong, X. (2004) · Marine Drugs · doi:10.3390/md203123 · Cited by 324
Retracted
Seaweed susceptibility to herbivory: chemical and morphological correlates
Paul, V. J., & Hay, M. E. (1986) · Marine Ecology Progress Series · doi:10.3354/meps033255 · Cited by 261
Intramolecular Palladium-Catalyzed Alkane C−H Arylation from Aryl Chlorides
Rousseaux, S. A. L., Davi, M., Sofack‐Kreutzer, J., Pierre, C., Kefalidis, C. E., Clot, E., Fagnou, K., & Baudoin, O. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1048847 · Cited by 249
Biomedical Potential of Marine Natural Products
Ireland, C. M., Copp, B. R., Foster, M. P., McDonald, L. A., Radisky, D. C., & Swersey, J. C. (1993) · Springer eBooks · doi:10.1007/978-1-4899-2391-2_1 · Cited by 240
Biomedical potential of marine natural products
(1996) · BioScience · doi:10.2307/1312834 · Cited by 238
Chemical ecology of marine organisms: An overview
Bakus, G. J., Targett, N. M., & Schulte, B. A. (1986) · Journal of Chemical Ecology · doi:10.1007/bf01638991 · Cited by 211
Predictable spatial escapes from herbivory: how do these affect the evolution of herbivore resistance in tropical marine communities?
Hay, M. E. (1984) · Oecologia · doi:10.1007/bf00379139 · Cited by 190
Marine natural products
Faulkner, D. J. (1997) · Natural Product Reports · doi:10.1039/np9971400259 · Cited by 186
Cytotoxic and antioxidant marine prenylated quinones and hydroquinones
Sunassee, S. N., & Davies‐Coleman, M. T. (2012) · Natural Product Reports · doi:10.1039/c2np00086e · Cited by 163
Biogeographical variation in brown algal polyphenolics and other secondary metabolites: comparison between temperate Australasia and North America
Steinberg, P. D. (1989) · Oecologia · doi:10.1007/bf00379112 · Cited by 146
Biogeographic comparisons of marine algal polyphenolics: evidence against a latitudinal trend
Targett, N. M., Coen, L. D., Boettcher, A. A., & Tanner, C. E. (1992) · Oecologia · doi:10.1007/bf00317150 · Cited by 134
Merging chemoenzymatic and radical-based retrosynthetic logic for rapid and modular synthesis of oxidized meroterpenoids
Li, J., Li, F., King‐Smith, E., & Renata, H. (2020) · Nature Chemistry · doi:10.1038/s41557-019-0407-6 · Cited by 126
The Antioxidant Properties of Brown Seaweed ( Sargassum siliquastrum ) Extracts
Cho, S.-H., Kang, S.-E., Cho, J.-Y., Kim, A.-R., Park, S., Hong, Y., & Ahn, D.-H. (2007) · Journal of Medicinal Food · doi:10.1089/jmf.2006.099 · Cited by 126
Some pharmacological observations on marine natural products
Jacobs, R. S., Culver, P., Langdon, R. B., O'Brien, T., & White, S. (1985) · Tetrahedron · doi:10.1016/s0040-4020(01)96465-8 · Cited by 117
The Effects of Seaweed Secondary Metabolites on Biofouling
da Gama, B. A. P., Pereira, R. C., Carvalho, A. G. V., Coutinho, R., & Yoneshigue‐Valentin, Y. (2002) · Biofouling · doi:10.1080/08927010290017680 · Cited by 106
Macroalgal palatability and the flux of ciguatera toxins through marine food webs
Cruz‐Rivera, E., & Villareal, T. A. (2005) · Harmful Algae · doi:10.1016/j.hal.2005.09.003 · Cited by 95
Effects of secondary metabolites from marine algae on feeding by the sea urchin,Lytechinus variegatus
McConnell, O. J., Hughes, P. A., Targett, N. M., & Daley, J. (1982) · Journal of Chemical Ecology · doi:10.1007/bf00989101 · Cited by 87
Meroditerpenoids from the southern Australian marine brown alga Sargassum fallax
Reddy, P., & Urban, S. (2009) · Phytochemistry · doi:10.1016/j.phytochem.2008.12.007 · Cited by 85
Plant defense associations in the marine environment
Littler, M. M., Taylor, P. R., & Littler, D. S. (1986) · Coral Reefs · doi:10.1007/bf00270354 · Cited by 81
Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications
Birringer, M., Siems, K., Maxones, A., Frank, J., & Lorkowski, S. (2018) · RSC Advances · doi:10.1039/c7ra11819h · Cited by 76
What are and where are the bioactive terpenoids metabolites from Dictyotaceae (Phaeophyceae)
De‐Paula, J. C., Vallim, M. A., & Teixeira, V. L. (2011) · Revista Brasileira de Farmacognosia · doi:10.1590/s0102-695x2011005000079 · Cited by 75
The Search for Antiviral and Anticancer Compounds from Marine Organisms
Munro, M. H. G., Luibrand, R. T., & Blunt, J. W. (1987) · Bioorganic marine chemistry · doi:10.1007/978-3-642-72726-9_4 · Cited by 75
Breviane Spiroditerpenoids from an Extreme-Tolerant Penicillium sp. Isolated from a Deep Sea Sediment Sample
Li, Y., Ye, D., Chen, X., Lu, X., Shao, Z., Zhang, H., & Che, Y. (2009) · Journal of Natural Products · doi:10.1021/np900116m · Cited by 74
Anti-Proliferative Activity of Meroditerpenoids Isolated from the Brown Alga Stypopodium flabelliforme against Several Cancer Cell Lines
Pereira, D. M., Cheel, J., Areche, C., San-Martı́n, A., Rovirosa, J., Silva, L. R., Valentão, P., & Andrade, P. B. (2011) · Marine Drugs · doi:10.3390/md9050852 · Cited by 70
Antifouling Activity of Meroditerpenoids from the Marine Brown Alga Halidrys siliquosa
Culioli, G., Ortalo-Magné, A., Valls, R., Hellio, C., Clare, A. S., & Piovetti, L. (2008) · Journal of Natural Products · doi:10.1021/np070110k · Cited by 69
Radical-scavenging activity of Aegean Sea marine algae
Nahas, R., Abatis, D., ANAGNOSTOPOULOU, M., Kefalas, P., Vagias, C., & Roussis, V. (2006) · Food Chemistry · doi:10.1016/j.foodchem.2006.05.036 · Cited by 69
The major bioactive components of seaweeds and their mosquitocidal potential
Yu, K.-X., Jantan, I., Ahmad, R., & Wong, C.-L. (2014) · Parasitology Research · doi:10.1007/s00436-014-4068-5 · Cited by 67
Food choice inSiganus fuscescens: influence of macrophyte nutrient content and availability
Pillans, R. D., Franklin, C. E., & Tibbetts, I. R. (2004) · Journal of Fish Biology · doi:10.1111/j.0022-1112.2004.00261.x · Cited by 66
Lipophyllic antioxidants from Iryanthera juruensis fruits
Silva, D. H. S., Pereira, F. C., Zanoni, M. V. B., & Yoshida, M. (2001) · Phytochemistry · doi:10.1016/s0031-9422(00)00477-5 · Cited by 66
Integration of LC/MS-based molecular networking and classical phytochemical approach allows in-depth annotation of the metabolome of non-model organisms - The case study of the brown seaweed Taonia atomaria
Carriot, N., Paix, B., Greff, S., Viguier, B., Briand, J., & Culioli, G. (2020) · Talanta · doi:10.1016/j.talanta.2020.121925 · Cited by 63
Allelochemistry in marine macroalgae
Harlin, M. M., & Rice, E. L. (1987) · Critical Reviews in Plant Sciences · doi:10.1080/07352688709382241 · Cited by 62
SHORT COMMUNICATION. Antimicrobial and Antineoplastic Activity in Some South Florida Seaweeds
Hodgson, L. M. (1984) · Botanica Marina · doi:10.1515/botm.1984.27.8.387 · Cited by 55
Bioactivity of the red algae Asparagopsis taxiformis collected from the Southwestern coast of India
Manilal, A., Sujith, S., Balu, S., Kiran, G. S., Selvin, J., Shakir, C., & Lipton, A. P. (2010) · Ocean and Coastal Research · doi:10.1590/s1679-87592010000200002 · Cited by 54
The chemistry of the cystoseiraceae (Fucales: Pheophyceae): Chemotaxonomic relationships
Valls, R., & Piovetti, L. (1995) · Biochemical Systematics and Ecology · doi:10.1016/0305-1978(95)00068-2 · Cited by 53
Phospholipase A2 inhibitors from marine algae
Mayer, A. M. S., Paul, V. J., Fenical, W., Norris, J. N., de Carvalho, M. S., & Jacobs, R. S. (1993) · Springer eBooks · doi:10.1007/978-94-011-1998-6_69 · Cited by 51
Self-citation
Phospholipase A2 inhibitors from marine algae
Mayer, A. M. S., Paul, V. J., Fenical, W., Norris, J. N., de Carvalho, M. S., & Jacobs, R. S. (1993) · Hydrobiologia · doi:10.1007/bf00049065 · Cited by 51
Self-citation
Isoepitaondiol, a diterpenoid of Stypopodium flabelliforme and the insecticidal activity of stypotriol, epitaondiol and derivatives
Rovirosa, J., Sepulveda, M., Quezada, E., & San-Martı́n, A. (1992) · Phytochemistry · doi:10.1016/0031-9422(92)83610-b · Cited by 51
Evaluation of Cancer-Preventive Activity and Structure–Activity Relationships of 3-Demethylubiquinone Q2, Isolated from the Ascidian Aplidium glabrum, and its Synthetic Analogs
Fedorov, S. N., Radchenko, O. S., Shubina, L. K., Balaneva, N. N., Bode, A. M., Stonik, V. A., & Dong, Z. (2005) · Pharmaceutical Research · doi:10.1007/s11095-005-8813-4 · Cited by 47
The adaptive significance of life history characters in selectedorders of marine brown maeroalgae
Clayton, M. N. (1990) · Australian Journal of Ecology · doi:10.1111/j.1442-9993.1990.tb01469.x · Cited by 47
Herbivory by Caribbean majid crabs: feeding ecology and plant susceptibility
Coen, L. D. (1988) · Journal of Experimental Marine Biology and Ecology · doi:10.1016/0022-0981(88)90127-x · Cited by 47
Obionin A: A new polyketide metabolite from the marine fungus leptosphaeria obiones
Poch, G. K., & Gloer, J. B. (1989) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)99419-x · Cited by 47
Marine Metabolites Which Inhibit Development of Echinoderm Embryos
Fusetani, N. (1987) · Bioorganic marine chemistry · doi:10.1007/978-3-642-72726-9_3 · Cited by 44
Marine Polyprenylated Hydroquinones, Quinones, and Chromenols with Inhibitory Effects on Leukotriene Formation
Tziveleka, L., Abatis, D., Paulus, K., Bauer, R., Vagias, C., & Roussis, V. (2005) · Chemistry & Biodiversity · doi:10.1002/cbdv.200590066 · Cited by 41
Cytotoxic meroterpenoids from brown alga Stypopodium schimperi (Kützing) Verlaque & Boudouresque with comprehensive molecular docking & dynamics and ADME studies
Demirkıran, Ö., Erol, E., Şenol, H., Kesdi, İ. M., Toraman, G. Ö. A., Okudan, E. Ş., & Topçu, G. (2023) · Process Biochemistry · doi:10.1016/j.procbio.2023.11.029 · Cited by 40
Atomarianones A and B: two cytotoxic meroditerpenes from the brown alga Taonia atomaria
Abatis, D., Vagias, C., Galanakis, D., Norris, J. N., Moreau, D., Roussakis, C., & Roussis, V. (2005) · Tetrahedron Letters · doi:10.1016/j.tetlet.2005.10.007 · Cited by 40
Ichtyotoxic activity of extracts from Mexican marine macroalgae
Lara-Isassi, G. D., Álvarez-Hernández, S., & Collado‐Vides, L. (2000) · Journal of Applied Phycology · doi:10.1023/a:1008103609841 · Cited by 39
Stereostructure Reassignment and Absolute Configuration of Isoepitaondiol, a Meroditerpenoid from Stypopodium flabelliforme
Areche, C., San-Martı́n, A., Rovirosa, J., Muñoz, M. A., Hernandez-Barragan, A., Bucio, M. A., & Joseph‐Nathan, P. (2009) · Journal of Natural Products · doi:10.1021/np900553p · Cited by 35
Chemical Diversity of Headspace and Volatile Oil Composition of Two Brown Algae (Taonia atomaria and Padina pavonica) from the Adriatic Sea
Jerković, I., Kranjac, M., Marijanović, Z., Roje, M., & Jokić, S. (2019) · Molecules · doi:10.3390/molecules24030495 · Cited by 35
Macroalgal Defense against Competitors and Herbivores
Budzałek, G., Śliwińska‐Wilczewska, S., Wiśniewska, K. A., Wochna, A., Bubak, I., Latała, A., & Wiktor, J. M. (2021) · International Journal of Molecular Sciences · doi:10.3390/ijms22157865 · Cited by 35
Variation in chemical defenses against herbivory in southwestern Atlantic Stypopodium zonale (Phaeophyta)
Pereira, R. C., Soares, A. R., Teixeira, V. L., Villaça, R. C., & da Gama, B. A. P. (2004) · Botanica Marina · doi:10.1515/bot.2004.020 · Cited by 35
Antibacterial Quinone Metabolites from the Brown Alga, Sargassum sagamianum
Horie, S., Tsutsumi, S., Takada, Y., & Kimura, J. (2008) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.81.1125 · Cited by 35
Escapes from herbivory in relation to the structure of mangrove island macroalgal communities
Taylor, P. R., Littler, M. M., & Littler, D. S. (1986) · Oecologia · doi:10.1007/bf00410352 · Cited by 34
Total Synthesis of Terpenes and Their Biological Significance: A Critical Review
Kanwal, A., Bılal, M., Rasool, N., Zubaır, M., Shah, S. A. A., & Zakaria, Z. A. (2022) · Pharmaceuticals · doi:10.3390/ph15111392 · Cited by 33
Fibrinolytic Compounds Isolated from a Brown Alga, Sargassum fulvellum
Wu, W., Hasumi, K., Peng, H., Hu, X., Wang, X., & Bao, B. (2009) · Marine Drugs · doi:10.3390/md7020085 · Cited by 32
Biological Importance of Marine Algae
El‐Gamal, A. A. (2011) · Wiley eBooks · doi:10.1002/9781119977087.ch1 · Cited by 32
An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: Studies by NMR spectroscopic and computational methods
Areche, C., San-Martı́n, A., Rovirosa, J., Soto‐Delgado, J., & Contreras, R. R. (2009) · Phytochemistry · doi:10.1016/j.phytochem.2009.07.017 · Cited by 32
Stypolactone, an interesting diterpenoid from the brown alga Stypopodium zonale
Dorta, E., Cueto, M., Díaz‐Marrero, A. R., & Dárias, J. (2002) · Tetrahedron Letters · doi:10.1016/s0040-4039(02)02279-7 · Cited by 30
An Efficient Stereoselective Synthesis of Stypodiol and Epistypodiol
Abad‐Somovilla, A., Agulló, C., Arnó, M., Cuñat, A. C., Meseguer, B., & Zaragoza, R. J. (1998) · The Journal of Organic Chemistry · doi:10.1021/jo980311g · Cited by 30
The compound 14-keto-stypodiol diacetate from the algae Stypopodium flabelliforme inhibits microtubules and cell proliferation in DU-145 human prostatic cells
Depix, M., Martı́nez, J., Santibañez, F., Rovirosa, J., Martín, A. S., & Maccioni, R. B. (1998) · Molecular and Cellular Biochemistry · doi:10.1023/a:1006879308861 · Cited by 27
Sesquiterpenes and geranylgeranylglycerol from the brown algae Taonia lacheana and Taonia atomaria f. ciliata: their chemotaxonomic significance
Tringali, C., Piattelli, M., & Spatafora, C. (1995) · Phytochemistry · doi:10.1016/0031-9422(95)00357-d · Cited by 27
A quinone-hydroquinone couple from the Brown alga Cystoseira stricta
Amico, V., Oriente, G., Piattelli, M., Ruberto, G., & Tringali, C. (1982) · Phytochemistry · doi:10.1016/s0031-9422(00)95280-4 · Cited by 27
Enantioselective Total Synthesis and Assignment of the Absolute Configuration of the Meroterpenoid (+)-Taondiol
Dethe, D. H., Mahapatra, S., & Sau, S. K. (2018) · Organic Letters · doi:10.1021/acs.orglett.8b00997 · Cited by 25
Induction of Attachment of the Mussel Perna perna by Natural Products from the Brown Seaweed Stypopodium zonale
Soares, A. R., da Gama, B. A. P., da Cunha, A. P., Teixeira, V. L., & Pereira, R. C. (2007) · Marine Biotechnology · doi:10.1007/s10126-007-9048-7 · Cited by 24
Antiproliferative activity and absolute configuration of zonaquinone acetate from the Jamaican alga Stypopodium zonale
Penicooke, N., Walford, K., Badal, S. A. M., Delgoda, R., Williams, L. A. D., Joseph‐Nathan, P., Gordillo-Román, B., & Gallimore, W. A. (2012) · Phytochemistry · doi:10.1016/j.phytochem.2012.11.014 · Cited by 24
Diastereoisomers of cyclocymopol and cyclocymopol monomethyl ether from Cymopolia barbata
McConnell, O. J., Hughes, P. A., & Targett, N. M. (1982) · Phytochemistry · doi:10.1016/0031-9422(82)83071-9 · Cited by 24
Diterpenoids of mixed biogenesis in phaeophyta biogenetic-type interconversions
González, A. G., Alvarez, M. A., Martı́n, J. D., Norte, M., Pérez, C., & Rovirosa, J. (1982) · Tetrahedron · doi:10.1016/0040-4020(82)80215-9 · Cited by 24
Algae-Based Biologically Active Compounds
Ibrahim, M., Salman, M., Kamal, S., Rehman, S., Razzaq, A., & Akash, M. S. H. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-812360-7.00006-9 · Cited by 23
Seven new meroditerpenoids, from the marine spongeStrongylophora strongylata, that inhibited the maturation of starfish oocytes
Liu, H., Namikoshi, M., Akano, K., Kobayashi, H., Nagai, H., & Yao, X. (2005) · Journal of Asian Natural Products Research · doi:10.1080/1028602032000169604 · Cited by 23
Synthesis and absolute configuration of (−)-stypoldione
Mori, K., & Koga, Y. (1992) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(00)80153-5 · Cited by 23
The Chemistry of Marine Algae and Cyanobacteria
Choi, H., Pereira, A. R., & Gerwick, W. H. (2012) · Springer eBooks · doi:10.1007/978-90-481-3834-0_2 · Cited by 22
Self-citation
Anti-bacterial activity of extracts from the brown seaweed Stoechospermum marginatum
Silva, S. S. M. D., Gamage, S. K. T., Kumar, N. S., & Balasubramaniam, S. (1982) · Phytochemistry · doi:10.1016/0031-9422(82)80100-3 · Cited by 22
Marine Resource
Gupta, A. P., Pandotra, P., Sharma, R. B., Kushwaha, M., & Gupta, S. (2013) · Studies in natural products chemistry · doi:10.1016/b978-0-444-59603-1.00008-4 · Cited by 22
Rogiolol Acetate: A Novel β‐Chamigrene‐Type Sesquiterpene Isolated from a Marine Sponge
Guella, G., Mancini, I., Chiasera, G., & Pietra, F. (1990) · Helvetica Chimica Acta · doi:10.1002/hlca.19900730606 · Cited by 20
Pharmacological properties of a marine natural product, stypoldione, obtained from the brown alga Stypopodium zonale
O’Brien, E. T., White, S., Jacobs, R. S., Boder, G. B., & Wilson, L. (1984) · Hydrobiologia · doi:10.1007/bf00027652 · Cited by 19
Synthesis of 3H-spiro[benzofuran-2,1′-cyclohexane] derivatives from naturally occurring filifolinol and their classical complement pathway inhibitory activity
Useglio, M., Castellano, P. M., Operto, M. A., Torres, R., & Kaufman, T. S. (2006) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2006.07.029 · Cited by 17
Bioinspired synthesis of pentacyclic onocerane triterpenoids
Bartels, F., Hong, Y. J., Ueda, D., Weber, M., Sato, T., Tantillo, D. J., & Christmann, M. (2017) · Chemical Science · doi:10.1039/c7sc03903d · Cited by 17
Brevianes Revisited
Macías, F. A., Carrera, C., & Galindo, J. C. G. (2013) · Chemical Reviews · doi:10.1021/cr300048m · Cited by 17
Application of Photoinduced Biomimetic Cascade Cyclizations of Terpenoid Polyalkenes for the Synthesis of (±)-Stypoldione
Xing, X., & Demuth, M. (2001) · European Journal of Organic Chemistry · doi:10.1002/1099-0690(200102)2001:3 · Cited by 17
Towards the in vivo production of tocotrienol compounds: Engineering of a plasmid-free Escherichia coli strain for the heterologous synthesis of 2-methyl-6-geranylgeranyl-benzoquinol
Ghanegaonkar, S., Conrad, J., Beifuß, U., Sprenger, G. A., & Albermann, C. (2012) · Journal of Biotechnology · doi:10.1016/j.jbiotec.2012.08.010 · Cited by 16
Synthesis of terpenophenols via direct alkylation of phenols by terpenes
Kuzakov, E. V., & Shmidt, E. N. (2000) · Chemistry of Natural Compounds · doi:10.1007/bf02238328 · Cited by 16
Diterpenoid total synthesis, XXXI. Synthesis and absolute configuration of (−)‐stypoldione, a metabolite of Stypopodium zonale
Mori, K., & Koga, Y. (1995) · Liebigs Annalen · doi:10.1002/jlac.1995199510246 · Cited by 16
Pharmacological properties of a marine natural product, stypoldione, obtained from the brown alga Stypopodium zonale
O’Brien, E. T., White, S., Jacobs, R. S., Boder, G. B., & Wilson, L. (1984) · Springer eBooks · doi:10.1007/978-94-009-6560-7_21 · Cited by 16
Seco-Taondiol, an Unusual Meroterpenoid from the Chilean Seaweed Stypopodium flabelliforme and Its Gastroprotective Effect in Mouse Model
Areche, C., Benites, J. F., Cornejo, A., Ruíz, L. M., García‐Beltrán, O., Simirgiotis, M. J., & Sepúlveda, B. (2015) · Marine Drugs · doi:10.3390/md13041726 · Cited by 15
Bioactive Marine Prenylated Quinones/Quinols
(2012) · Studies in natural products chemistry · doi:10.1016/b978-0-444-53836-9.00023-2 · Cited by 15
Aplysia sea hare assimilation of secondary metabolites from brown seaweed,Stypopodium zonale
Gerwick, W. H., & Whatley, G. G. (1989) · Journal of Chemical Ecology · doi:10.1007/bf01014710 · Cited by 15
Self-citation
Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]
Huang, Y., Tan, M., Wang, N., Zhang, Y., Yao, H. Q., Xiao, X., Huang, N., & Zou, K. (2023) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.3c01154 · Cited by 13
Intraspecific variation of meroditerpenoids in the brown alga Stypopodium zonale guiding the isolation of new compounds
Soares, A. R., Duarte, H. M., Tinoco, L. W., Pereira, R. C., & Teixeira, V. L. (2015) · Revista Brasileira de Farmacognosia · doi:10.1016/j.bjp.2015.09.006 · Cited by 13
New Meroditerpenoids from a Taiwanese Marine Sponge Strongylophora Durissima
Shen, Y., Hung, M., Prakash, C. V. S., & Wang, J. (2000) · Journal of the Chinese Chemical Society · doi:10.1002/jccs.200000076 · Cited by 13
Antiproliferative effect and apoptotic activity of linear geranylphenol derivatives from phloroglucinol and orcinol
Taborga, L., Espinoza, L., Moller, A., Carrasco, H., Cuéllar, M., & Villena, J. (2016) · Chemico-Biological Interactions · doi:10.1016/j.cbi.2016.01.016 · Cited by 13
Effects of ocean acidification and contact with the brown alga Stypopodium zonale on the settlement and early survival of the coral Porites astreoides
Campbell, J., Sneed, J. M., Johnston, L., & Paul, V. J. (2017) · Marine Ecology Progress Series · doi:10.3354/meps12249 · Cited by 13
Diterpenoid total synthesis, XXIX. Synthesis of (±)‐14‐deoxystypoldione, an analogue of the marine natural product stypoldione
Mori, K., & Koga, Y. (1991) · Liebigs Annalen der Chemie · doi:10.1002/jlac.1991199101132 · Cited by 13
Robinson Annulation Applied to the Total Synthesis of Natural Products
Heravi, M. M., Alipour, B., Zadsirjan, V., & Malmir, M. (2022) · Asian Journal of Organic Chemistry · doi:10.1002/ajoc.202200668 · Cited by 12
On the relative stereochemistry of atomaric acid and related compounds
Dorta, E., Díaz‐Marrero, A. R., Cueto, M., & Dárias, J. (2003) · Tetrahedron · doi:10.1016/s0040-4020(03)00215-1 · Cited by 12
VCD Determination of the Absolute Configuration of Stypotriol
Muñoz, M. A., Areche, C., San-Martı́n, A., Rovirosa, J., & Joseph‐Nathan, P. (2009) · Natural Product Communications · doi:10.1177/1934578x0900400804 · Cited by 12

ChemInform Abstract: ICHTHYOTOXIC AND CYTOTOXIC METABOLITES OF THE TROPICAL BROWN ALGA STYPOPODIUM ZONALE (LAMOUROUX) PAPENFUSS
Gerwick, W. H., & Fenical, W. (1981) · ChemInform · doi:10.1002/chin.198124214
Self-citation
Stypolactone, an Interesting Diterpenoid from the Brown Alga Stypopodium zonale
Dorta, E., Cueto, M., Diaz‐Merrero, A. R., & Dárias, J. (2003) · ChemInform · doi:10.1002/chin.200311184
Pharmacological properties of a marine natural product, stypoldione, obtained from the brown alga Stypopodium zonale
O’Brien, E. T., White, S., Jacobs, R. S., Boder, G. B., & Wilson, L. (1984) · Springer eBooks · doi:10.1007/978-94-009-6560-7_21 · Cited by 16
Stypotriol and stypoldione; ichthyotoxins of mixed biogenesis from the marine alga
Gerwick, W. H., Fenical, W., Fritsch, N., & Clardy, J. (1979) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)85907-4 · Cited by 63
Self-citation
Chemical variation in the tropical seaweed Stypopodium zonale (dictyotaceae)
Gerwick, W. H. (1985) · Phytochemistry · doi:10.1016/s0031-9422(00)81115-2 · Cited by 60
Self-citation

Authors: Gerwick, W. H., & Fenical, W.
ORCID: Gerwick, William H.
Fenical, William
Venue: The Journal of Organic Chemistry
Publisher: American Chemical Society (ACS)
Published: 1981-01
Volume: 46
Issue: 1
Pages: 22-27
ISSN: 0022-3263 (ISSN-L)
1520-6904
DOI: 10.1021/jo00314a005
OpenAlex: W2949267956
Cited by: 142
References: 0
Citations by year: 2026: 2 · 2025: 3 · 2024: 1 · 2023: 2 · 2022: 4 · 2021: 2 · 2020: 5 · 2019: 4 · 2018: 4 · 2017: 5 · 2016: 2 · 2015: 2 · 2014: 4 · 2013: 4 · 2012: 7
FWCI: 8.82
Type: journal article
Language: en
Open access: closed
Locations: The Journal of Organic Chemistry (publishedVersion)
Topics: Life Sciences › Agricultural and Biological Sciences › Aquatic Science › Seaweed-derived Bioactive Compounds
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Marine Sponges and Natural Products
Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Microbial Natural Products and Biosynthesis
Keywords: Stypopodium zonale, brown algae, cytotoxic metabolites, marine natural products, fish toxicity, algal toxins

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) Papenfuss

Abstract

Overview

Integrity signals

Verification

Claims the paper makes

Citations

Cites

Cited by

Related

Metadata

Record

About these checks