Sesquiterpenes from the New Zealand Liverwort Lepidolaena hodgsoniae.
NMR studies have shown that seven new sesquiterpenoids, 3, 4, 5a, and 7-10, isolated from dried samples of the New Zealand liverwort Lepidolaena hodgsoniae have the same substituted cyclopentapyran ring system as the previously described insecticidal sesquiterpene diene hodgsonox (1), which has been reported only from this plant. In all but one compound, 10, the 1,1-disubstituted double bond of hodgsonox has migrated into an endocyclic position, but only two, 5a and 9, have the double bonds in conjugation. These seven new compounds represent a variety of different oxidation levels. Two of the new derivatives, 9 and 10, were isolated only from an aged sample and are presumably artifacts. The only other terpenoid isolated in significant quantity was (7R,10R)-calamenene (2).
Barlow
Anna J
AJ
Department of Chemistry, University of Otago, Dunedin, New Zealand.
Compton
Benjamin J
BJ
Hertewich
Ursula
U
Lorimer
Stephen D
SD
Weavers
Rex T
RT
D035926:Hepatophyta / Q000737:chemistry*; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D009520:New Zealand; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification; D014753:Vinyl Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D007306:Insecticides; D000081223:Polycyclic Sesquiterpenes; D011714:Pyrans; D012717:Sesquiterpenes; D013729:Terpenes; D014753:Vinyl Compounds; C502644:calamenene; C500468:hodgsonox