Calyculin

Last updated
Calyculins
Calyculin A and C Structure.svg
Calyculins A and C
Names
IUPAC name
((2R,3R,5R,7R,8S,9S)-2-((1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl)-9-((E)-3-(2-((2S)-4-(((2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanoyl)amino)butan-2-yl)-1,3-oxazol-4-yl)prop-2-enyl)-7-hydroxy-4,4,8-trimethyl-1,10-dioxaspiro(4.5)decan-3-yl) dihydrogen phosphate (Calyculin A) [1]
Identifiers
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m1/s1 Yes check.svgY
    Key: FKAWLXNLHHIHLA-LIKMAGLISA-N Yes check.svgY
Properties
C51H83N4O15P (Calyculin C)
Molar mass 1023.2 g/mol (Calyculin C)
Properties
C50H81N4O15P (Calyculin A)
Molar mass 1009.17 g/mol (Calyculin A)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Calyculins are natural products originally isolated from the marine sponge Discodermia calyx. [2] Calyculins have proven to be strong serine/threonine protein phosphatase inhibitors and based on this property, calyculins might be potential tumor-promoting agents.

A laboratory synthesis of calyculin A has been reported. [3]

Biosynthesis

Calyculin A is biosynthesized as a pyrophosphate containing phosphocalyculin A protoxins by a hybrid PKS-NRPS pathway within the sponge bacterial symbiont, "Candidatus Entotheonella" sp. [4]

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Dysidea etheria, commonly known as the ethereal sponge or heavenly sponge, is a species of lobate sponge within the class Demospongiae. This marine sponge is known for its light blue color and can be found in the Caribbean as well as off the coasts of Florida and Georgia. Like all other poriferans, D. etheria is capable of both sexual and asexual reproduction. The use of spicule collection as well as chemical defenses allows D. etheria to protect itself against predators such as the zebra doris and the orange knobby star. D. etheria is also known as a host species of the invasive brittle star Ophiothela mirabilis. Lastly, various molecular biology studies have utilized D. etheria to both study foreign particle transport in sponges and to isolate novel molecules.

References

  1. "Calyculin A" (PDF). Cell Signaling Technology. 2015-01-02.
  2. Suganuma M, Fujiki H, Furuya-Suguri H, Yoshizawa S, Yasumoto S, Kato Y, Fusetani N, Sugimura T (1990). "Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin". Cancer Res. 50 (12): 3521–3525. PMID   2160320.
  3. Tanimoto, Norihiko; Gerritz, Samuel W.; Sawabe, Akiyoshi; Noda, Takeshi; Filla, Sandra A.; Masamune, Satoru (1994-03-17). "Synthese von natürlich vorkommendem (−)‐Calyculin A". Angewandte Chemie. 106 (6): 674–677. doi:10.1002/ange.19941060611. ISSN   0044-8249.
  4. Jomori, Takahiro; Matsuda, Kenichi; Egami, Yoko; Abe, Ikuro; Takai, Akira; Wakimoto, Toshiyuki (2021). "Insights into phosphatase-activated chemical defense in a marine sponge holobiont". RSC Chemical Biology. 2 (6): 1600–1607. doi: 10.1039/D1CB00163A . ISSN   2633-0679. PMC   8637855 . PMID   34977575.