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Malabaricane

Summary

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]

Malabaricane
Names
IUPAC name
(3S*,3aR*,5aS*,9aS*,9bS*)-3a,6,6,9a-tetramethyl-3-(1,5,9-trimethyldecyl)perhydrobenz[e]indene
Identifiers
  • 81575-65-7 checkY
3D model (JSmol)
  • Interactive image
  • 101786192
  • InChI=1S/C30H56/c1-22(2)12-9-13-23(3)14-10-15-24(4)25-16-17-27-29(25,7)21-18-26-28(5,6)19-11-20-30(26,27)8/h22-27H,9-21H2,1-8H3/t23-,24+,25+,26-,27+,29+,30+/m1/s1
    Key: SGHXJVFMQPUFPZ-LKPKTCMESA-N
  • C[C@@H](CCC[C@H](C)[C@@H]1CC[C@H]2[C@]1(CC[C@H]3[C@@]2(CCCC3(C)C)C)C)CCCC(C)C
Properties
C30H56
Molar mass 416.77
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 edit

  1. ^ Buckingham J; Macdonald FM; Bradley HM; Cai Y; Munasinghe VRN; Pattenden CF. (1994–1995). Dictionary of Natural Products (PDF). London: Chapman & Hall. p. 130. ISBN 0-412-46620-1. Archived from the original (PDF) on 2010-03-31. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)