Malabaricane

Malabaricane
IUPAC name

(3S*,3aR*,5aS*,9aS*,9bS*)-3a,6,6,9a-tetramethyl-3-(1,5,9-trimethyldecyl)perhydrobenz[e]indene
Identifiers
CAS number 81575-65-7 Y
Properties
Molecular formula C30H56
Molar mass 416.77
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

The molecule malabaricane and its derivatives, the malabaricanes, are triterpene and triterpenoid compounds found in various organisms.[1] They are named after the rain forest tree Ailanthus malabarica (Ailanthus triphysa), from which they were first isolated in 1967 by scientists at the National Chemical Laboratory in Pune, India.[2] Later, great varieties of malabaricanes were discovered in other organisms, mostly in marine sponges such as Rhabdastrella globostellata.[3][4]

Isomalabaricanes are malabaricanes in which the three carbon rings of the molecule are connected in trans−syn−trans conformation, as opposed to other malabaricanes, where the rings are connected in trans−anti−trans conformation. They are of particular research interest because many of them have been reported to show anti-tumour activity in cell culture.[5][6]

References

  1. ^ Buckingham J, Macdonald FM, Bradley HM, Cai Y, Munasinghe VRN, Pattenden CF. (1994-1995) (PDF). Dictionary of Natural Products. London: Chapman & Hall. p. 130. ISBN 0412466201. http://dnp.chemnetbase.com/intro/DNPIntroduction.pdf. Retrieved 2010-06-04. 
  2. ^ Chawla A, Dev S. (1967). "A new class of triterpenoids from Ailanthus malabarica DC derivatives of malabaricane". Tetrahedron Letters 8 (48): 4837–4843. doi:10.1016/S0040-4039(01)89615-5. 
  3. ^ Meragelman KM, McKee TC, Boyd MR. (March 2001). "New Cytotoxic Isomalabaricane Triterpenes from the Sponge Jaspis Species". Journal of Natural Products 64 (3): 389–392. doi:10.1021/np000478g. PMID 11277766. 
  4. ^ Tasdemir D, Mangalindan GC, Concepción GP, Verbitski SM, Rabindran S, Miranda M, Greenstein M, Hooper JN, Harper MK, Ireland CM. (February 2002). "Bioactive Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata". Journal of Natural Products 65 (2): 210–214. doi:10.1021/np0104020. PMID 11858759. 
  5. ^ Fouad M, Edrada RA, Ebel R, Wray V, Müller WE, Lin WH, Proksch P. (February 2006). "Cytotoxic Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata". Journal of Natural Products 69 (2): 211–218. doi:10.1021/np050346t. PMID 16499318. 
  6. ^ McKee TC, Bokesch HR, McCormick JL, Rashid MA, Spielvogel D, Gustafson KR, Alavanja MM, Cardelline JH 2nd, Boyd MR. (May 1997). "Isolation and Characterization of New Anti-HIV and Cytotoxic Leads from Plants, Marine, and Microbial Organisms". Journal of Natural Products 60 (5): 431–438. doi:10.1021/np970031g. PMID 9170286.