Prymnesin-B1

Last updated
Prymnesin-B1
Prymnesin-B1.svg
Names
IUPAC name
1-((2R,3S,4R,5S,6R)-6-((2R,2'S,3'R,4aS,4'aR,6S,6'S,7R,8S,8aR,8'S,8'aS)-6'-(2-((2R,4aS,6S,7R,8aR)-6-((2S,4aR,5aS,6aR,7aS,10R,11aR,12aS,13aR,15S,15aS)-10-((1E,3E,8E,10E,18E)-6-amino-19-chlorononadeca-1,3,8,10,18-pentaen-12,16-diyn-1-yl)-15-hydroxyoctadecahydropyrano[3,2-b]pyrano[2,3:5',6']pyrano[2',3':5,6]pyrano[2,3-f]oxepin-2-yl)-7-methyloctahydropyrano[3,2-b]pyran-2-yl)-2-hydroxyethyl)-3',7,8,8'-tetrahydroxyhexadecahydro-[2,2'-bipyrano[3,2-b]pyran]-6-yl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexadeca-13,15-diyne-2,4,6,7,8,9,10-heptaol
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C91H132ClNO34/c1-3-4-5-19-24-48(95)72(103)76(107)73(104)50(97)37-52(99)84(127-91-82(113)78(109)75(106)71(43-94)125-91)53(100)39-69-74(105)77(108)79(110)89(124-69)90-81(112)80(111)88-62(123-90)32-31-61(122-88)86-55(102)40-70-87(126-86)51(98)36-47(115-70)35-49(96)56-27-28-58-63(116-56)34-44(2)83(120-58)59-29-30-60-85(121-59)54(101)38-64-66(118-60)42-67-68(119-64)41-65-57(117-67)26-25-46(114-65)23-18-15-17-22-45(93)21-16-13-11-9-7-6-8-10-12-14-20-33-92/h1,9,11,13,15-18,20,23,33,44-91,94-113H,8,10,19,21-22,24-32,34-43,93H2,2H3/b11-9+,16-13+,17-15+,23-18+,33-20+/t44-,45?,46+,47+,48?,49?,50?,51+,52?,53?,54+,55-,56-,57+,58+,59+,60-,61-,62+,63-,64-,65-,66+,67-,68+,69-,70-,71-,72?,73?,74-,75+,76?,77-,78+,79+,80+,81-,82-,83+,84?,85+,86+,87+,88+,89-,90+,91-/m1/s1
  • [H][C@@]([C@@]1([H])[C@@H](O)[C@@H]([C@H](O)[C@](CC(O)C(O[C@@H]2[C@H](O)[C@H]([C@@H](O)[C@@H](CO)O2)O)C(O)CC(O)C(O)C(O)C(O)C(O)CCC#CC#C)([H])O1)O)([C@@H]([C@@H]([C@]3(O[C@]([C@](O4)([H])[C@H](O)C[C@]5([H])[C@]4([H])[C@@H](O)C[C@@](CC([C@@]([H])(CC[C@](O[C@@]6([C@@](O[C@]7([C@H](C8)O)[H])(CC[C@@]7([H])O[C@](C[C@]([H])9O[C@]%10(CC[C@@]%11(/C=C/C=C/CC(C/C=C/C=C/C#CCCC#C/C=C/Cl)N)[H])[H])([H])[C@]8([H])O[C@]9(C[C@@](O%11)%10[H])[H])[H])[H])%12[H])O[C@@]%12(C[C@H]6C)[H])O)([H])O5)([H])CC%13)[H])O)O)O[C@]3%13[H]
Properties
C91H132ClNO34
Molar mass 1819.48 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Prymnesin-B1 is a chemical with the molecular formula C
91
H
132
ClNO
34
. It is a member of the prymnesins, a class of ladder-frame polyether phycotoxins made by the alga Prymnesium parvum . It is known to be toxic to fish. It is a so called "Type-B" prymnesin, which differ in the number of backbone cycles when compared to Type-A prymnesins like prymnesin-2. [1]

Contents

Structures

Prymnesins-B1 is formed of a large polyether polycyclic core with several conjugate double and triple bonds, chlorine and nitrogen heteroatoms and a single sugar moiety consisting of α-D-galactopyranose.

See also

Related Research Articles

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R−O−R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<span class="mw-page-title-main">Polyurethane</span> Polymer composed of a chain of organic units joined by carbamate (urethane) links

Polyurethane refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from a wide range of starting materials. This chemical variety produces polyurethanes with different chemical structures leading to many different applications. These include rigid and flexible foams, varnishes and coatings, adhesives, electrical potting compounds, and fibers such as spandex and polyurethane laminate (PUL). Foams are the largest application accounting for 67% of all polyurethane produced in 2016.

Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest. Total synthesis targets can also be organometallic or inorganic, though these are rarely encountered. Total synthesis projects often require a wide diversity of reactions and reagents, and subsequently requires broad chemical knowledge and training to be successful.

<span class="mw-page-title-main">Crown ether</span> Ring molecules with several ether (–O–) groups

In organic chemistry, crown ethers are cyclic chemical compounds that consist of a ring containing several ether groups (R−O−R’). The most common crown ethers are cyclic oligomers of ethylene oxide, the repeating unit being ethyleneoxy, i.e., −CH2CH2O−. Important members of this series are the tetramer (n = 4), the pentamer (n = 5), and the hexamer (n = 6). The term "crown" refers to the resemblance between the structure of a crown ether bound to a cation, and a crown sitting on a person's head. The first number in a crown ether's name refers to the number of atoms in the cycle, and the second number refers to the number of those atoms that are oxygen. Crown ethers are much broader than the oligomers of ethylene oxide; an important group are derived from catechol.

Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynthesis, and application of polyketides has evolved. It is a large and diverse group of secondary metabolites caused by its complex biosynthesis which resembles that of fatty acid synthesis. Because of this diversity, polyketides can have various medicinal, agricultural, and industrial applications. Many polyketides are medicinal or exhibit acute toxicity. Biotechnology has enabled discovery of more naturally-occurring polyketides and evolution of new polyketides with novel or improved bioactivity.

In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups. The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, three and four hydroxyl groups are diols, triols, and tetrols, respectively.

<span class="mw-page-title-main">Macrocycle</span> Molecule with a large ring structure

Macrocycles are often described as molecules and ions containing a ring of twelve or more atoms. Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins. Macrocycles describe a large, mature area of chemistry.

Prymnesium parvum is a species of haptophytes. The species is of concern because of its ability to produce the phycotoxin prymnesin. It is a flagellated alga that is normally found suspended in the water column. It was first identified in North America in 1985, but it is not known if it was introduced artificially or missed in previous surveys. Toxin production mainly kills fish and appears to have little effect on cattle or humans. This distinguishes it from a red tide, which is an algal bloom whose toxins lead to harmful effects in people. Although no harmful effects are known, it is recommended not to consume dead or dying fish exposed to a P. parvum bloom.

Carl Shipp "Speed" Marvel was an American chemist who specialized in polymer chemistry. He made important contributions to U.S. synthetic rubber program during World War II, and later worked at developing polybenzimidazoles, temperature-resistant polymers that are used in the aerospace industry, in fire-fighting equipment, and as a replacement for asbestos. He has been described as "one of the world's outstanding organic chemists" and received numerous awards, including the 1956 Priestley Medal and the 1986 National Medal of Science, presented by President Ronald Reagan.

<i>Prymnesium</i> Genus of single-celled organisms

Prymnesium is a genus of haptophytes, including the species Prymnesium parvum. The genus is a unicellular motile alga. It is ellipsoidal in shape one flagellum is straight and there are two longer ones which enable movement.

<span class="mw-page-title-main">Halichondrin B</span> Chemical compound

Halichondrin B is a polyether macrolide originally isolated from the marine sponge Halichondria okadai by Hirata and Uemura in 1986. In the same report, these authors also reported the exquisite anticancer activity of halichondrin B against murine cancer cells both in culture and in in vivo studies. Halichondrin B was highly prioritized for development as a novel anticancer therapeutic by the United States National Cancer Institute and, in 1991, was the original test case for identification of mechanism of action by NCI's then-brand-new "60-cell line screen" The complete chemical synthesis of halichondrin B was achieved by Yoshito Kishi and colleagues at Harvard University in 1992, an achievement that ultimately enabled the discovery and development of the structurally simplified and pharmaceutically optimized analog eribulin. Eribulin was approved by the U.S. Food and Drug Administration on November 15, 2010, to treat patients with metastatic breast cancer who have received at least two prior chemotherapy regimens for late-stage disease, including both anthracycline- and taxane-based chemotherapies. Eribulin is marketed by Eisai Co. under the tradename Halaven.

Poly(<i>p</i>-phenylene oxide) Chemical compound

Poly(p-phenylene oxide) (PPO), poly(p-phenylene ether) (PPE), often referred to simply as polyphenylene oxide, is a high-temperature thermoplastic. It is rarely used in its pure form due to difficulties in processing. It is mainly used as blend with polystyrene, high impact styrene-butadiene copolymer or polyamide. PPO is a registered trademark of SABIC Innovative Plastics B.V. under which various polyphenylene ether resins are sold.

<span class="mw-page-title-main">Prymnesin-1</span> Chemical compound

Prymnesin-1 is a chemical with the molecular formula C
107
H
154
Cl
3
NO
44
. It is a member of the prymnesins, a class of hemolytic phycotoxins made by the alga Prymnesium parvum. It is known to be toxic to fish, causing mass fish deaths around the world, including in Texas and England, or in 2022 in the border region of Germany and Poland (Oder).

Ichthyotoxins are compounds which are either toxic to fish, or are toxins produced by fish. The former include the algae-produced euglenophycin and prymnesins, which can cause large-scale fish deaths. The latter includes ostracitoxin, produced by boxfish. Many toxin-producing algal species can be found both in marine and fresh water environments when the algae are in bloom. Ichthyotoxic poisoning in humans can cause symptoms ranging in severity dependent on how much toxin was consumed. The symptoms of an ichthyotoxin poisoning from fish venoms can include headache, vomiting, diarrhea, dizziness, and drop in blood pressure.

<span class="mw-page-title-main">Charles C. Price</span> American chemist (1913–2001)

Charles C. Price was an American chemist and president of the American Chemical Society (1965). He taught at the University of Illinois at Chicago, the University of Notre Dame, and the University of Pennsylvania.

Prymnesin-2 is an organic compound that is secreted by the haptophyte Prymnesium parvum. It belongs to the prymnesin family and has potent hemolytic and ichthyotoxic properties. In a purified form it appears as a pale yellow solid. P. parvum is responsible for red harmful algal blooms worldwide, causing massive fish killings. When these algal blooms occur, this compound poses a threat to the local fishing industry. This is especially true for brackish water, as the compound can reach critical concentrations more easily.

Prymnesin may refer to:

Rappephyceae, or Rappemonads, are a small family of protists first described in 2011, of uncertain phylogenic affinity. It has been discussed as a possible member of a larger clade Haptophyta. This newly identified taxonomic class of phytoplankton are named after a professor from the Hawai’i institute of marine biology, known as Michael Rappé. Rappé discovered these phytoplankton in the Atlantic Ocean and published his findings on their DNA in 1998. Current research has shown that these organisms provide an immense amount of nutritional organic molecules, such as oxygen, for other organisms using biochemical processes like photosynthesis and carbon fixation.

<span class="mw-page-title-main">Transition metal ether complex</span>

In chemistry, a transition metal ether complex is a coordination complex consisting of a transition metal bonded to one or more ether ligand. The inventory of complexes is extensive. Common ether ligands are diethyl ether and tetrahydrofuran. Common chelating ether ligands include the glymes, dimethoxyethane (dme) and diglyme, and the crown ethers. Being lipophilic, metal-ether complexes often exhibit solubility in organic solvents, a property of interest in synthetic chemistry. In contrast, the di-ether 1,4-dioxane is generally a bridging ligand.

<span class="mw-page-title-main">Karmitoxin</span> Chemical compound

Karmitoxin is an amine-containing polyhydroxy-polyene toxin isolated from Karlodinium armiger strain K-0668. It is structurally related to amphidinols, luteophanols, lingshuiols, carteraols, and karlotoxins.

References

  1. Rasmussen, Silas Anselm; Meier, Sebastian; Andersen, Nikolaj Gedsted; Blossom, Hannah Eva; Duus, Jens Øllgaard; Nielsen, Kristian Fog; Hansen, Per Juel; Larsen, Thomas Ostenfeld (2016-08-23). "Chemodiversity of Ladder-Frame Prymnesin Polyethers in Prymnesium parvum". Journal of Natural Products. American Chemical Society (ACS). 79 (9): 2250–2256. doi: 10.1021/acs.jnatprod.6b00345 . ISSN   0163-3864. PMID   27550620.