MOLECULE

7-Hydroxy-5-methoxyindan-1-spiro-cyclohexane

7-hydroxy-5-methoxyindan-1-spiro-cyclohexane, belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Indanes are compounds which consist of a cyclopentane fused to a benzene ring. 7-hydroxy-5-methoxyindan-1-spiro-cyclohexane is also classified as a phenol. It is one of the spiroindane compounds that have been identified in cannabis (DOI: 10.1016/S0031-9422(00)81194-2; PMID: 6924596). Spiroindanes are cyclic compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane. Spiroindane compounds were first isolated and identified as cannabis constituents in 1976. 7-hydroxy-5-methoxyindan-1-spiro-cyclohexane is one of the 19 stilbenoids detected in cannabis (DOI: 10.1007/s11101-008-9094-4). The stilbenoids are phenolic compounds that are widely distributed throughout the plant kingdom. Their functions in plants include constitutive and inducible defense mechanisms (PMID: 11027734; PMID: 11982391), plant growth inhibitors and dormancy factors (DOI: 10.1007/s11101-008-9094-4). Frequently, the stilbenoids are constituents of heartwood or roots, and have antifungal and antibacterial activities (PMID: 10691624; PMID: 14697275) or they are repellent towards insects (DOI:10.1016/S0031-9422(00)88199-6). The biosynthesis of 7-hydroxy-5-methoxyindan-1-spiro-cyclohexane was proposed as the following: The first step could be the formation of bibenzyl compounds from the condensation of one molecule of dihydro-pcoumaroyl-CoA and 3 molecules of malonyl-CoA to dihydroresveratrol, which is converted to 3,4'-dihydroxy-5-methoxybibenzyl by O-methyltransferase. Cannabispiradienone is subsequently formed and reduced to α-cannabispiranol, which yields 7-hydroxy-5-methoxyindan-1-spiro-cyclohexane (DOI: 10.1007/s11101-008-9094-4).