Spirocyclic nortriterpenoids with NGF-potentiating activity from the fruits of Leonurus heterophyllus.
Four new spirocyclic nortriterpenoids, leonurusoleanolide A (1), leonurusoleanolide B (2), leonurusoleanolide C (3), and leonurusoleanolide D (4), were isolated from the MeOH extract of the fruits of Leonurus heterophyllus. Compounds 1 and 2, and compounds 3 and 4, were found to exist as equilibrium mixtures of trans and cis isomers. Mixtures of 1 and 2, and 3 and 4, significantly enhanced the neurite outgrowth of nerve growth factor-treated PC12 cells at concentrations ranging from 1 to 30 μM. Compound 8 was also found to have a neurite outgrowth-promoting effect at concentrations of 1 and 10 μM. The structure-activity relationship of these compounds is discussed.
Pharmaceutical Sciences, Tokushima Bunri University , Tokushima 770-8514, Japan.
Yuhong
Y
Liu
Miwa
M
Kubo
Yoshiyasu
Y
Fukuyama
D000818:Animals; D005638:Fruit / Q000737:chemistry; D019686:Lamiaceae / Q000737:chemistry*; D015394:Molecular Structure; D020932:Nerve Growth Factor / Q000187:drug effects*; D016501:Neurites / Q000502:physiology; D019906:Nuclear Magnetic Resonance, Biomolecular; D016716:PC12 Cells; D051381:Rats; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D013141:Spiro Compounds; D014315:Triterpenes; D020932:Nerve Growth Factor