Betaenone B

Source: Wikipedia, the free encyclopedia.
Betaenone B
Clinical data
ATC code
  • none
Identifiers
  • (2S,3R,4R,4aS,5R,7R,8aS)-3-sec-butyl-2,7-dihydroxy-4-(3-hydroxypropanoyl)-2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one
JSmol)
Melting point103.5 to 108 °C (218.3 to 226.4 °F)
  • O=C(CCO)[C@]2([C@H]([C@](O)(C(=O)[C@@H]1[C@@H]2[C@@H](C[C@@](O)(C1)C)C)C)[C@H](C)CC)C
  • InChI=1S/C21H36O5/c1-7-12(2)17-20(5,15(23)8-9-22)16-13(3)10-19(4,25)11-14(16)18(24)21(17,6)26/h12-14,16-17,22,25-26H,7-11H2,1-6H3/t12-,13-,14+,16+,17-,19-,20-,21+/m1/s1 checkY
  • Key:PUZNAAVWFXQUDM-HBKHSIGZSA-N checkY
  (verify)

Betaenone B, like other

protein synthesis.[5] Most of the major work on betaenone B, including the initial structure elucidation of betaenone A, B and C as well as the partial elucidation mechanism of biosynthesis, was presented in three short papers published between 1983 and 1988.[1][2][3] The compounds were found to inhibit a variety of protein kinases signifying a possible role in cancer treatment.[6]

Molecular structures of betaenone A, B and C.

The structure of betaenone B was determined via

Bioactivity
of this synthetic product was not tested and no further work on total synthesis of betaenones has been published since.

While a complete de novo synthesis of betaenone B has yet to be reported, Daniel Pratt and Paul Hopkins in 1988 proposed a method for synthesizing a precursor of betaenone B from methoxybenzoquinone and 1,3-butadiene via a Diels–Alder reaction and Claisen chemistry[clarification needed].[7]

Biosynthesis

Very little work has been done to elucidate the biosynthetic pathways of betaenones with almost no literature references published on the subject since 1988. Their low phytotoxicity and lack of biological significance in

cytochrome P-450
is responsible for the oxidation at these three positions since its inhibition produces probetaenone 1, the non-oxidized form of betaenone B.

Biosynthesis of betaenone B as proposed by Oikawa et al.

References

  1. ^
    doi:10.1021/ja00347a070
    .
  2. ^
    doi:10.1039/c39840000814
    .
  3. ^
    doi:10.1039/c39880000600
    .
  4. ^ Afonin AN (2008). "Interactive Agricultural Ecological Atlas of Russia and Neighboring Countries. Economic Plants and their Diseases, Pests and Weeds Online".
  5. ^
    PMID 6402759
    .
  6. doi:10.1016/1359-6446(96)10030-1
    .
  7. ^
    doi:10.1021/jo00260a017
    .
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