Malabaricane Explained

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]}

Notes and References

1. Book: Dictionary of Natural Products . Buckingham J . Macdonald FM . Bradley HM . Cai Y . Munasinghe VRN . Pattenden CF. . 1994–1995 . Chapman & Hall . London . 0-412-46620-1 . 130 . 2010-06-04 . dead . https://web.archive.org/web/20100331171758/http://dnp.chemnetbase.com/intro/DNPIntroduction.pdf . 2010-03-31.
2. Chawla A . Dev S. . 1967. A new class of triterpenoids from Ailanthus malabarica DC derivatives of malabaricane. Tetrahedron Letters. 8. 48. 4837–4843. 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. 10.1021/np000478g. 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. 10.1021/np0104020. 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. 10.1021/np050346t. 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. 10.1021/np970031g. 9170286.