Anditomin

Anditomin is an oxygenated meroterpenoid produced by Aspergillus stellatus[1] or Aspergillus variecolor.[2]

Anditomin
Names
IUPAC name
(2S,3R,9R,12S,14R,16S,20S)-3,8,8,14-tetramethyl-21-methylidene-7,18-dioxahexacyclo[12.7.1.02,12.03,9.012,20.016,20]docos-4-ene-6,17,22-trione
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C25H30O5/c1-13-17-18-23(5)8-7-16(26)30-21(2,3)15(23)6-9-24(18)11-22(4,19(17)27)10-14-20(28)29-12-25(13,14)24/h7-8,14-15,17-18H,1,6,9-12H2,2-5H3/t14-,15+,17?,18+,22-,23+,24+,25+/m1/s1
    Key: HWLYZRWDCDSFFO-VIJQBOBYSA-N
  • C[C@]12C[C@@H]3C(=O)OC[C@]34C(=C)C(C1=O)[C@@H]5[C@@]4(C2)CC[C@@H]6[C@@]5(C=CC(=O)OC6(C)C)C
Properties
C25H30O5
Molar mass 410.510 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

Aspergillus variecolor produces anditomin from 3,5-dimethylorsellinic acid and farnesyl pyrophosphate using 12 enzymes.[3] The enzyme AndA firstly dehydrogenates one ring of preandiloid B to make preaniloid C. Next it causes a complex ring isomerisation to make anditomin.[4]

Properties

Anditomin can dissolve in ethyl acetate or chloroform. Anditomin forms tetragonal crystals with space group P41 (No. 76), with unit cell dimensions a = 9.310 and c = 24.84 Å, and unit cell volume = 2153 Å3 with Z = 4, and density = 1.27 gcm−3.[2]

References
  1. Chen, A.J.; Frisvad, J.C.; Sun, B.D.; Varga, J.; Kocsubé, S.; Dijksterhuis, J.; Kim, D.H.; Hong, S.-B.; Houbraken, J.; Samson, R.A. (1 June 2016). "Aspergillus section Nidulantes (formerly Emericella): Polyphasic taxonomy, chemistry and biology". Studies in Mycology. 84 (1): 1–118. doi:10.1016/j.simyco.2016.10.001. PMC 5198626. PMID 28050053.
  2. Simpson, Thomas J.; Walkinshaw, Malcolm D. (1981). "Anditomin, a new C25 metabolite from Aspergillus variecolor". Journal of the Chemical Society, Chemical Communications (17): 914. doi:10.1039/C39810000914.
  3. Matsuda, Yudai; Wakimoto, Toshiyuki; Mori, Takahiro; Awakawa, Takayoshi; Abe, Ikuro (29 October 2014). "Complete Biosynthetic Pathway of Anditomin: Nature's Sophisticated Synthetic Route to a Complex Fungal Meroterpenoid". Journal of the American Chemical Society. 136 (43): 15326–15336. doi:10.1021/ja508127q. PMID 25216349.
  4. Nakashima, Yu; Mitsuhashi, Takaaki; Matsuda, Yudai; Senda, Miki; Sato, Hajime; Yamazaki, Mami; Uchiyama, Masanobu; Senda, Toshiya; Abe, Ikuro (1 August 2018). "Structural and Computational Bases for Dramatic Skeletal Rearrangement in Anditomin Biosynthesis". Journal of the American Chemical Society. 140 (30): 9743–9750. doi:10.1021/jacs.8b06084. PMID 29972643. S2CID 207192801.
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