isotuberculosinol

{{Chembox

| Watchedfields =

| verifiedrevid =

| Name = Isotuberculosinol

| Reference =

| ImageFile = Isotuberculosinol.svg

| ImageName = nosyberkol

| ImageFile1 =

| ImageSize1 =

| ImageName1 =

| IUPACName = (3-Methyl-5-[(1R,2S,8aS)-1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]pent-1-en-3-ol

| OtherNames = Nosyberkol,
edaxadiene

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 26331708

| StdInChIKey = TXBORCBWDUAHAC-AIQOQHTRSA-N

| UNII_Ref =

| UNII =

| ChEMBL_Ref =

| ChEMBL =

| KEGG_Ref =

| KEGG =

| InChI = 1S/C20H34O/c1-7-19(5,21)13-14-20(6)15(2)10-11-16-17(20)9-8-12-18(16,3)4/h7,11,15,17,21H,1,8-10,12-14H2,2-6H3/t15-,17+,19?,20+/m0/s1

| InChIKey = TXBORCBWDUAHAC-AIQOQHTRSA-N

| StdInChI_Ref =

| StdInChI =

| CASNo_Ref =

| CASNo =

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 59685

| SMILES = [H][C@@]12CCCC(C)(C)C1=CC[C@H](C)[C@@]2(C)CCC(C)(O)C=C

| PubChem = 46224604

}}

|Section2={{Chembox Properties

| C=20 | H=34 | O=1

| Density =

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}}

}}

Isotuberculosinol, also called nosyberkol or edaxadiene is a diterpene molecule produced by the bacterium Mycobacterium tuberculosis, the causative agent of TB, which aids in its pathogenesis. Isotuberculosinol functions by preventing maturation of the host-cell phagosome in which the bacterium lives.{{Cite journal

| last1 = Mann | first1 = F. M.

| last2 = Xu | first2 = M.

| last3 = Chen | first3 = X.

| last4 = Fulton | first4 = D. B.

| last5 = Russell | first5 = D. G.

| last6 = Peters | first6 = R. J.

| doi = 10.1021/ja9019287

| title = Edaxadiene: A New Bioactive Diterpene fromMycobacterium tuberculosis

| journal = Journal of the American Chemical Society

| volume = 131

| issue = 48

| pages = 17526–17527

| year = 2009

| pmid = 19583202

| pmc =2787244

}}{{Cite journal

| last1 = Mann | first1 = F. M.

| last2 = Peters | first2 = R. J.

| title = Isotuberculosinol: The unusual case of an immunomodulatory diterpenoid from Mycobacterium tuberculosis.

| journal = MedChemComm

| volume = 3

| issue = 8

| pages = 899–904

| year = 2012

| pmid = 23926455

| pmc = 3733278

| doi=10.1039/c2md20030a

}} Maturation of the phagosome would enable it to kill the bacterium. Mutations in genes involved in the biosynthetic pathway of nosyberkol result in normal development of the phagosome and reduction of mycobacterial infection. These biosynthetic genes include isotuberculosinol synthase.

Nosyberkol was originally isolated in 2004 from a marine sponge in the ocean near island of Nosy Be after which it was named.{{Cite journal

| last1 = Rudi | first1 = A.

| last2 = Aknin | first2 = M.

| last3 = Gaydou | first3 = E.

| last4 = Kashman | first4 = Y.

| title = Asmarines I, J, and K and Nosyberkol: Four New Compounds from the Marine SpongeRaspailiasp

| doi = 10.1021/np049834b

| journal = Journal of Natural Products

| volume = 67

| issue = 11

| pages = 1932–1935

| year = 2004

| pmid = 15568794

| pmc =

}} The molecule was characterised as a triterpene but the structure was revised following its chemical synthesis in 2010.{{Cite journal

| last1 = Spangler | first1 = J. E.

| last2 = Carson | first2 = C. A.

| last3 = Sorensen | first3 = E. J.

| doi = 10.1039/C0SC00284D

| title = Synthesis enables a structural revision of the Mycobacterium tuberculosis-produced diterpene, edaxadiene

| journal = Chemical Science

| volume = 1

| issue = 2

| pages = 202–205

| year = 2010

| pmid = 22114734

| pmc =3221386

}}