Journal articles on the topic 'Marine polypropionates'

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1

T. Davies-Coleman, Michael, and Mary J. Garson. "Marine polypropionates." Natural Product Reports 15, no. 5 (1998): 477. http://dx.doi.org/10.1039/a815477y.

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2

Davies-Coleman, Michael T., and Mary J. Garson. "ChemInform Abstract: Marine Polypropionates." ChemInform 30, no. 10 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199910319.

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3

Esposito, Germana, Roberta Teta, Gerardo Della Sala, Joseph Pawlik, Alfonso Mangoni, and Valeria Costantino. "Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea." Marine Drugs 16, no. 8 (August 17, 2018): 285. http://dx.doi.org/10.3390/md16080285.

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The organic extract of the Caribbean sponge Smenospongia aurea has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route such as the smenamides. In this paper, we report the presence of a biogenetically different compound known as smenopyrone, which is a polypropionate containing two γ-pyrone rings. The structure of smenopyrone including its relative and absolute stereochemistry was determined by spectroscopic analysis (NMR, MS, ECD) and supported by a comparison with model compounds from research studies. Pyrone polypropionates are unprecedented in marine sponges but are commonly found in marine mollusks where their biosynthesis by symbiotic bacteria has been hypothesized and at least in one case demonstrated. Since pyrones have recently been recognized as bacterial signaling molecules, we speculate that smenopyrone could mediate inter-kingdom chemical communication between S. aurea and its symbiotic bacteria.
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4

Bromley, Candice L., Wendy L. Popplewell, Shirley C. Pinchuck, Alan N. Hodgson, and Michael T. Davies-Coleman. "Polypropionates from the South African Marine Mollusk Siphonaria oculus." Journal of Natural Products 75, no. 3 (January 27, 2012): 497–501. http://dx.doi.org/10.1021/np2009384.

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5

Singh, Keisham S. "Pyrone-derived Marine Natural Products: A Review on Isolation, Bio-activities and Synthesis." Current Organic Chemistry 24, no. 4 (May 9, 2020): 354–401. http://dx.doi.org/10.2174/1385272824666200217101400.

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Marine natural products (MNPs) containing pyrone rings have been isolated from numerous marine organisms, and also produced by marine fungi and bacteria, particularly, actinomycetes. They constitute a versatile structure unit of bioactive natural products that exhibit various biological activities such as antibiotic, antifungal, cytotoxic, neurotoxic, phytotoxic and anti-tyrosinase. The two structure isomers of pyrone ring are γ- pyrone and α-pyrone. In terms of chemical motif, γ-pyrone is the vinologous form of α- pyrone which possesses a lactone ring. Actinomycete bacteria are responsible for the production of several α-pyrone compounds such as elijopyrones A-D, salinipyrones and violapyrones etc. to name a few. A class of pyrone metabolites, polypropionates which have fascinating carbon skeleton, is primarily produced by marine molluscs. Interestingly, some of the pyrone polytketides which are found in cone snails are actually synthesized by actinomycete bacteria. Several pyrone derivatives have been obtained from marine fungi such as Aspergillums flavus, Altenaria sp., etc. The γ-pyrone derivative namely, kojic acid obtained from Aspergillus fungus has high commercial demand and finds various applications. Kojic acid and its derivative displayed inhibition of tyrosinase activity and, it is also extensively used as a ligand in coordination chemistry. Owing to their commercial and biological significance, the synthesis of pyrone containing compounds has been given attention over the past years. Few reviews on the total synthesis of pyrone containing natural products namely, polypropionate metabolites have been reported. However, these reviews skipped other marine pyrone metabolites and also omitted discussion on isolation and detailed biological activities. This review presents a brief account of the isolation of marine metabolites containing a pyrone ring and their reported bio-activities. Further, the review covers the synthesis of marine pyrone metabolites such as cyercene-A, placidenes, onchitriol-I, onchitriol-II, crispatene, photodeoxytrichidione, (-) membrenone-C, lihualide-B, macrocyclic enol ethers and auripyrones-A & B.
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6

Sabitha, Gowravaram, Peddabuddi Gopal, and Jhillu S. Yadav. "Total synthesis of the marine polypropionates, siphonarienal, siphonarienone, and pectinatone." Tetrahedron: Asymmetry 20, no. 19 (October 2009): 2205–10. http://dx.doi.org/10.1016/j.tetasy.2009.08.021.

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7

Beukes, Denzil R., and Michael T. Davies-Coleman. "Novel polypropionates from the South African marine mollusc Siphonaria capensis." Tetrahedron 55, no. 13 (March 1999): 4051–56. http://dx.doi.org/10.1016/s0040-4020(99)00093-9.

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8

Sato, Seizo, Fumie Iwata, Takako Mukai, Shoichi Yamada, Jiro Takeo, Akihisa Abe, and Hiroyuki Kawahara. "Indoxamycins A−F. Cytotoxic Tricycklic Polypropionates from a Marine-Derived Actinomycete." Journal of Organic Chemistry 74, no. 15 (August 7, 2009): 5502–9. http://dx.doi.org/10.1021/jo900667j.

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9

Carbone, Marianna, M. Letizia Ciavatta, Jian-Rong Wang, Ilaria Cirillo, Véronique Mathieu, Robert Kiss, Ernesto Mollo, Yue-Wei Guo, and Margherita Gavagnin. "Extending the Record of Bis-γ-pyrone Polypropionates from Marine Pulmonate Mollusks." Journal of Natural Products 76, no. 11 (November 2013): 2065–73. http://dx.doi.org/10.1021/np400483c.

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10

Ziegler, Frederick E., and Michael R. Becker. "Total synthesis of (-)-denticulatins A and B: marine polypropionates from Siphonaria denticulata." Journal of Organic Chemistry 55, no. 9 (April 1990): 2800–2805. http://dx.doi.org/10.1021/jo00296a044.

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11

Liu, Zhaoming, Hongxin Liu, and Weimin Zhang. "Natural Polypropionates in 1999–2020: An Overview of Chemical and Biological Diversity." Marine Drugs 18, no. 11 (November 19, 2020): 569. http://dx.doi.org/10.3390/md18110569.

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Natural polypropionates (PPs) are a large subgroup of polyketides with diverse structural features and bioactivities. Most of the PPs are discovered from marine organisms including mollusks, fungi and actinomycetes, while some of them are also isolated from terrestrial resources. An increasing number of studies about PPs have been carried out in the past two decades and an updated review is needed. In this current review, we summarize the chemical structures and biological activities of 164 natural PPs reported in 67 research papers from 1999 to 2020. The isolation, structural features and bioactivities of these PPs are discussed in detail. The chemical diversity, bioactive diversity, biodiversity and the relationship between chemical classes and the bioactivities are also concluded.
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12

Wang, Jian-Rong, Marianna Carbone, Margherita Gavagnin, Attila Mándi, Sándor Antus, Li-Gong Yao, Guido Cimino, Tibor Kurtán, and Yue-Wei Guo. "Assignment of Absolute Configuration of Bis-γ-pyrone Polypropionates from Marine Pulmonate Molluscs." European Journal of Organic Chemistry 2012, no. 6 (January 18, 2012): 1107–11. http://dx.doi.org/10.1002/ejoc.201101587.

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13

Brecknell, Douglas J., Lynne A. Collett, Michael T. Davies-Coleman, Mary J. Garson, and David D. Jones. "New Non-Contiguous Polypropionates from Marine Molluscs: A Comment on their Natural Product Status." Tetrahedron 56, no. 16 (April 2000): 2497–502. http://dx.doi.org/10.1016/s0040-4020(00)00095-8.

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14

Guo, Yue-Wei, Margherita Gavagnin, Marianna Carbone, Ernesto Mollo, and Guido Cimino. "Recent Sino-Italian collaborative studies on marine organisms from the South China Sea." Pure and Applied Chemistry 84, no. 6 (March 25, 2012): 1391–405. http://dx.doi.org/10.1351/pac-con-11-09-04.

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In this communication, selected results obtained in the course of a 10-year Sino-Italian collaborative project are presented. During this collaboration, several studies on marine organisms collected in the South China Sea have been conducted, resulting in the characterization of a large number of novel natural products. The main interest has been focused on sponges, cnidarians, and molluscs. Here, the recent research, including some not yet published studies, on cnidarians and molluscs, in particular, opisthobranchs and pulmonates, will be briefly described. The study of cnidarians and pulmonates led to isolate molecules, in particular, biscembranoids and polypropionates, displaying carbon skeletons already described in previous papers. Our studies resulted in their complete structural characterization including the absolute stereochemistry that was clarified by coupling X-ray diffraction to circular dichroism (CD) spectra analysis. Some unique nitrogenous molecules containing either an isonitrile function or an 1,2,4-oxadiazole moiety, this latter found for the first time in a marine organism, as well as known sesterterpenoids and diterpenoids were isolated from opisthobranchs. Owing to their anatomical location, these metabolites should play a relevant role in the protection of the molluscs. Finally, a series of alkaloids structurally related to known anticancer agents were also characterized.
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15

Zhou, Zhen-Fang, Xiao-Lu Li, Li-Gong Yao, Jia Li, Margherita Gavagnin, and Yue-Wei Guo. "Marine bis-γ-pyrone polypropionates of onchidione family and their effects on the XBP1 gene expression." Bioorganic & Medicinal Chemistry Letters 28, no. 6 (April 2018): 1093–96. http://dx.doi.org/10.1016/j.bmcl.2018.02.010.

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16

Jeffery, David W., Michael V. Perkins, and Jonathan M. White. "Synthesis of an Analogue of the Marine Polypropionate Tridachiahydropyrone." Organic Letters 7, no. 3 (February 2005): 407–9. http://dx.doi.org/10.1021/ol0478178.

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17

Paterson, Ian, David Yu-Kai Chen, Jose Luis Acena, and Alison S. Franklin. "ChemInform Abstract: Marine Polypropionate Synthesis: Total Synthesis of (-)-Baconipyrone C." ChemInform 31, no. 37 (September 12, 2000): no. http://dx.doi.org/10.1002/chin.200037232.

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18

Paterson, Ian, David Yu-Kai Chen, José Luis Aceña, and Alison S. Franklin. "Studies in Marine Polypropionate Synthesis: Total Synthesis of (−)-Baconipyrone C." Organic Letters 2, no. 11 (June 2000): 1513–16. http://dx.doi.org/10.1021/ol000027n.

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19

Yamamura, Shosuke, and Shigeru Nishiyama. "Synthetic Studies on Polypropionate-Derived 4-Pyrone-Containing Marine Natural Products." Bulletin of the Chemical Society of Japan 70, no. 9 (September 1997): 2025–37. http://dx.doi.org/10.1246/bcsj.70.2025.

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20

Manker, Denise C., Mary J. Garson, and D. John Faulkner. "De Novo biosynthesis of polypropionate metabolites in the marine pulmonate Siphonaria denticulata." Journal of the Chemical Society, Chemical Communications, no. 16 (1988): 1061. http://dx.doi.org/10.1039/c39880001061.

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21

Paterson, Ian, and Michael V. Perkins. "Total synthesis of the marine polypropionate (+)-muamvatin. A configurational model for siphonariid metabolites." Journal of the American Chemical Society 115, no. 4 (February 1993): 1608–10. http://dx.doi.org/10.1021/ja00057a074.

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22

Carbone, Marianna, Margherita Gavagnin, Carlo A. Mattia, Cinzia Lotti, Francesco Castelluccio, Bruno Pagano, Ernesto Mollo, Yue-Wei Guo, and Guido Cimino. "Structure of onchidione, a bis-γ-pyrone polypropionate from a marine pulmonate mollusk." Tetrahedron 65, no. 22 (May 2009): 4404–9. http://dx.doi.org/10.1016/j.tet.2009.03.052.

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23

Chen, De-Li, Wei Zheng, Jian Feng, Guo-Xu Ma, Yang-Yang Liu, and Xu-Dong Xu. "A new bis-γ-pyrone polypropionate from a marine pulmonate mollusc Onchidium struma." Journal of Asian Natural Products Research 21, no. 4 (January 22, 2018): 384–90. http://dx.doi.org/10.1080/10286020.2018.1427076.

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24

YAMAMURA, S., and S. NISHIYAMA. "ChemInform Abstract: Synthetic Studies on Polypropionate-Derived 4-Pyrone-Containing Marine Natural Products." ChemInform 29, no. 1 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199801278.

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25

Cutignano, Adele, Guido Villani, and Angelo Fontana. "One Metabolite, Two Pathways: Convergence of Polypropionate Biosynthesis in Fungi and Marine Molluscs." Organic Letters 14, no. 4 (February 8, 2012): 992–95. http://dx.doi.org/10.1021/ol2032653.

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26

Li, Song-Wei, Wan-Xiang Cui, Xia-Juan Huan, Margherita Gavagnin, Ernesto Mollo, Ze-Hong Miao, Li-Gong Yao, Xu-Wen Li, and Yue-Wei Guo. "A new bis-γ-pyrone polypropionate of onchidiol family from marine pulmonate mollusk Onchidium sp." Natural Product Research 34, no. 14 (February 5, 2019): 1971–76. http://dx.doi.org/10.1080/14786419.2019.1569010.

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27

PATERSON, I., and M. V. PERKINS. "ChemInform Abstract: Total Synthesis of the Marine Polypropionate (+)-Muamvatin. A Configurational Model for Siphonariid Metabolites." ChemInform 24, no. 27 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199327287.

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28

Cutignano, Adele, Guido Cimino, Guido Villani, and Angelo Fontana. "Origin of the C3-unit in placidenes: further insights into taxa divergence of polypropionate biosynthesis in marine molluscs and fungi." Tetrahedron 65, no. 39 (September 2009): 8161–64. http://dx.doi.org/10.1016/j.tet.2009.07.078.

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29

Garson, Mary J., Christopher J. Small, Brian W. Skelton, Pongchan Thinapong, and Allan H. White. "Structural and stereochemical correlations of polypropionate metabolites from marine pulmonates: revision of the relative stereochemistry of pectinatone by X-ray structure analysis." Journal of the Chemical Society, Perkin Transactions 1, no. 3 (1990): 805. http://dx.doi.org/10.1039/p19900000805.

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30

Sato, Seizo, Fumie Iwata, Takako Mukai, Shoichi Yamada, Jiro Takeo, Akihisa Abe, and Hiroyuki Kawahara. "ChemInform Abstract: Indoxamycins A—F. Cytotoxic Tricyclic Polypropionates from a Marine-Derived Actinomycete." ChemInform 40, no. 52 (December 29, 2009). http://dx.doi.org/10.1002/chin.200952210.

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31

Sabitha, Gowravaram, Peddabuddi Gopal, and Jhillu S. Yadav. "ChemInform Abstract: Total Synthesis of the Marine Polypropionates, Siphonarienal (Ia), Siphonarienone (Ib), and Pectinatone (II)." ChemInform 41, no. 12 (March 23, 2010). http://dx.doi.org/10.1002/chin.201012193.

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32

Chakraborty, Kajal, and Prima Francis. "Callypyrones from marine Callyspongiidae sponge Callyspongia diffusa: antihypertensive bis-γ-pyrone polypropionates attenuate angiotensin-converting enzyme." Natural Product Research, November 2, 2020, 1–12. http://dx.doi.org/10.1080/14786419.2020.1837819.

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33

Jeffery, David W., Michael V. Perkins, and Jonathan M. White. "Synthesis of an Analogue (I) of the Marine Polypropionate Tridachiahydropyrone (II)." ChemInform 36, no. 25 (June 21, 2005). http://dx.doi.org/10.1002/chin.200525206.

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34

Carbone, Marianna, Margherita Gavagnin, Carlo A. Mattia, Cinzia Lotti, Francesco Castelluccio, Bruno Pagano, Ernesto Mollo, Yue-Wei Guo, and Guido Cimino. "ChemInform Abstract: Structure of Onchidione, a Bis-γ-pyrone Polypropionate from a Marine Pulmonate Mollusk." ChemInform 40, no. 38 (September 22, 2009). http://dx.doi.org/10.1002/chin.200938209.

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35

GARSON, M. J., C. J. SMALL, B. W. SKELTON, P. THINAPONG, and A. H. WHITE. "ChemInform Abstract: Structural and Stereochemical Correlations of Polypropionate Metabolites from Marine Pulmonates: Revision of the Relative Stereochemistry of Pectinatone by X-Ray Structure Analysis." ChemInform 21, no. 25 (June 19, 1990). http://dx.doi.org/10.1002/chin.199025276.

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