Prymnesin

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Prymnesin 1
Prymnesin 1.svg
Names
IUPAC name
77‐Amino‐6,35,90‐trichloro‐17,21:22,26:25,29:30,34:33,37:38,42:41,45:46,50:49,53:54,58:57,62:61,65:64,68:67,71‐tetradecaepoxy‐52‐methyl 14‐(5‐hydroxymethyl‐3,4‐dihydroxy‐2‐oxolanyloxy)‐9‐[5‐(1,2‐dihydroxyethyl)‐3,4‐dihydroxy‐2‐oxolanyloxy]‐13‐(3,4,5‐trihydroxytetrahydro‐2H‐pyran‐2‐yloxy)‐72,74,79,81,89‐nonacontapentene‐1,3,83,87‐tetryne‐7,8,10,11,15,18,19,20,23,24,31,39,43,59‐tetradecol
Identifiers
3D model (JSmol)
Properties
C107H154Cl3NO44
Molar mass 2,264.72 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Prymnesin 1 is a chemical with the molecular formula C
107
H
154
Cl
3
NO
44
.

Prymnesins are a class of phycotoxins made by the alga Prymnesium parvum.[1][2] It is known to be toxic to fish, causing mass fish deaths around the world, including in Texas and England.

Structures[edit]

Prymnesins are formed of a large polyether polycyclic core with several conjugate double and triple bonds, chlorine and nitrogen heteroatoms and sugar moieties including L-xylose.[3] There are three forms of prymnesin known, prymnesin 1 and 2, differing in their glycosylation, and prymnesin B1[4] differing in backbone.

References[edit]

  1. ^ Igarashi, Tomoji; Satake, Masayuki; Yasumoto, Takeshi (1999). "Structures and Partial Stereochemical Assignments for Prymnesin-1 and Prymnesin-2: Potent Hemolytic and Ichthyotoxic Glycosides Isolated from the Red Tide Alga Prymnesium parvum". J. Am. Chem. Soc. 121 (37): 8499–8511. doi:10.1021/ja991740e. 
  2. ^ Morohashi, Akio; Satake, Masayuki; Oshima, Yasukatsu; Igarashi, Tomoji; Yasumoto, Takeshi (2001). "Absolute configuration at C14 and C85 in prymnesin-2, a potent hemolytic and ichthyotoxic glycoside isolated from the red tide alga Prymnesium parvum". Chirality. 13 (9): 601–605. doi:10.1002/chir.1184. 
  3. ^ Manning SR, La Claire JW (2010). "Prymnesins: toxic metabolites of the golden alga, Prymnesium parvum carter (Haptophyta)". Marine Drugs. 8 (3): 678–704. doi:10.3390/md8030678. PMC 2857367Freely accessible. PMID 20411121. 
  4. ^ Rasmussen, Silas Anselm; Meier, Sebastian; Andersen, Nikolaj Gedsted; Blossom, Hannah Eva; Duus, Jens Øllgaard; Nielsen, Kristian Fog; Hansen, Per Juel; Larsen, Thomas Ostenfeld (2016). "Chemodiversity of Ladder-Frame Prymnesin Polyethers in Prymnesium parvum". J. Nat. Prod. 79 (9): 2250–2256. doi:10.1021/acs.jnatprod.6b00345.