:Malabaricane
{{Chembox
| verifiedrevid = 452848750
| ImageFile = Malabaricane Structure.svg
| ImageSize =
| ImageAlt =
| IUPACName = (3S,3aS,5aS,9aS,9bS)-Dodecahydro-3a,6,6,9a-tetramethyl-3-[(5R)-1,5,9-trimethyldecyl]-1H-benz[e]indene
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|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 81575-65-7
| ChemSpiderID = 95601981
| PubChem = 101786192
| StdInChI=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
| StdInChIKey = SGHXJVFMQPUFPZ-LKPKTCMESA-N
| SMILES = 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
}}
|Section2={{Chembox Properties
| C=30 | H=56
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|Section3={{Chembox Hazards
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The molecule malabaricane and its derivatives, the malabaricanes, are triterpene and triterpenoid compounds found in various organisms.
{{cite book
|title = Dictionary of Natural Products
|author1 = Buckingham J
|author2 = Macdonald FM
|author3 = Bradley HM
|author4 = Cai Y
|author5 = Munasinghe VRN
|author6 = Pattenden CF.
|year = 1994–1995
|publisher = Chapman & Hall
|location = London
|isbn = 0-412-46620-1
|page = 130
|url = http://dnp.chemnetbase.com/intro/DNPIntroduction.pdf
|access-date = 2010-06-04
|url-status = dead
|archive-url = https://web.archive.org/web/20100331171758/http://dnp.chemnetbase.com/intro/DNPIntroduction.pdf
|archive-date = 2010-03-31
}} 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.
{{cite journal
|author1=Chawla A |author2=Dev S. | year = 1967
| title = A new class of triterpenoids from Ailanthus malabarica DC derivatives of malabaricane
| journal = Tetrahedron Letters
| volume = 8
| issue = 48
| pages = 4837–4843
| doi = 10.1016/S0040-4039(01)89615-5
}} Later, great varieties of malabaricanes were discovered in other organisms, mostly in marine sponges such as Rhabdastrella globostellata.
{{cite journal
|author1=Meragelman KM |author2=McKee TC |author3=Boyd MR. | date = March 2001
| title = New Cytotoxic Isomalabaricane Triterpenes from the Sponge Jaspis Species
| journal = Journal of Natural Products
| volume = 64
| issue = 3
| pages = 389–392
| doi = 10.1021/np000478g
| pmid = 11277766
{{cite journal
|author1=Tasdemir D |author2=Mangalindan GC |author3=Concepción GP |author4=Verbitski SM |author5=Rabindran S |author6=Miranda M |author7=Greenstein M |author8=Hooper JN |author9=Harper MK |author10=Ireland CM. | date = February 2002
| title = Bioactive Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata
| journal = Journal of Natural Products
| volume = 65
| issue = 2
| pages = 210–214
| doi = 10.1021/np0104020
| pmid = 11858759
}}
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.
{{cite journal
|author1=Fouad M |author2=Edrada RA |author3=Ebel R |author4=Wray V |author5=Müller WE |author6=Lin WH |author7=Proksch P. | date = February 2006
| title = Cytotoxic Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata
| journal = Journal of Natural Products
| volume = 69
| issue = 2
| pages = 211–218
| doi = 10.1021/np050346t
| pmid = 16499318
{{cite journal
| author = McKee TC, Bokesch HR, McCormick JL, Rashid MA, Spielvogel D, Gustafson KR, Alavanja MM, Cardelline JH 2nd, Boyd MR.
| date = May 1997
| title = Isolation and Characterization of New Anti-HIV and Cytotoxic Leads from Plants, Marine, and Microbial Organisms
| journal = Journal of Natural Products
| volume = 60
| issue = 5
| pages = 431–438
| doi = 10.1021/np970031g
| pmid = 9170286
}}