Catalpalactone

Environ Toxicol Pharmacol. 2008 Jul;26(1):86-91.

Effects of catalpalactone on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells.[Pubmed: 21783893]

The effects of Catalpalactone on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells were investigated.
METHODS AND RESULTS:
Catalpalactone at 5-30μM decreased intracellular dopamine content with the IC(50) value of 22.1μM. Catalpalactone at 5-20μM, but not 30μM, did not alter cell viability. Catalpalactone at 20μM inhibited tyrosine hydroxylase (TH) and aromatic-l-amino acid decarboxylase (AADC) activities. Catalpalactone also decreased cyclic AMP levels and inhibited TH phosphorylation. In addition, Catalpalactone at 20μM reduced the increases in dopamine levels induced by L-DOPA (20-50μM). Catalpalactone (5-30μM) associated with L-DOPA (50-100μM) enhanced L-DOPA-induced cytotoxicity at 48h, which was prevented by N-acetyl-l-cysteine.
CONCLUSIONS:
These results suggest that Catalpalactone inhibited dopamine biosynthesis by reducing TH and AADC activities and enhanced L-DOPA-induced cytotoxiciy in PC12 cells.

Arch Pharm Res. 2010 Mar;33(3):381-5.

Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide.[Pubmed: 20361302]

METHODS AND RESULTS:
Bioassay-guided fractionation of a CH2Cl2-soluble fraction of the stems of Catalpa ovata led to isolation of a new naphthoquinone, 4-hydroxy-2-(2-methoxy-3-hydroxy-3-methyl-but-1-enyl)-4-hydro-1H-naphthalen-1-one (10), together with nine known compounds, catalponol (1), catalponone (2), Catalpalactone (3), alpha-lapachone (4), 9-hydroxy-alpha-lapachone (5), 4,9-dihydroxy-alpha-lapachone (6), 9-methoxy-alpha-lapachone (7), 4-oxo-alpha-lapachone (8), and 9-methoxy-4-oxo-alpha-lapachone (9). The structures were elucidated on the basis of spectroscopic analyses. The inhibitory effects of these isolates on lipopolysaccharide-induced NO synthesis in RAW 264.7 cells were evaluated.
CONCLUSIONS:
Among them, catapalactone (3), 9-hydroxy-alpha-lapachone (5) and 4,9-dihydroxy-alpha-lapachone (6) exhibited potent inhibitory effects, with IC(50) values of 9.80, 4.64 and 2.73 microM, respectively.

J Chem Ecol. 1992 Mar;18(3):359-69.

Major antitermitic components of the heartwood of southern catalpa.[Pubmed: 24254942]

METHODS AND RESULTS:
A structurally related ketone, catalponone (1%); and the phthalide, Catalpalactone (25%). Pure compounds were isolated by semipreparative scale reversed-phase HPLC and identified by GC-MS and UV spectroscopy. The structure of catalponol was further confirmed by the formation of derivatives.
CONCLUSIONS:
Bioassays indicated that catalponol had the greatest toxicity in cellulose pad tests, but in tests using vacuum impregnation of these compounds into termite-susceptible wood blocks at levels approximating those found in catalpa heartwood, Catalpalactone exhibited the highest antitermitic activity.

J Nat Prod. 1998 May;61(5):629-32.

Antitumor-promoting naphthoquinones from Catalpa ovata.[Pubmed: 9599262]

METHODS AND RESULTS:
Bioassay-directed fractionation of an extract of the stem-bark of Catalpa ovata led to the isolation of three new naphthoquinones: 8-methoxydehydroiso-alpha-lapachone (1), 9-methoxy-4-oxo-alpha-lapachone (2), and (4S,4aR,10R,10aR)-4, 10-dihydroxy-2,2-dimethyl-2,3,4,4alpha,10, 10alpha-hexahydrobenzo[g]chromen-5-one (3), which is a 1,4-reductive form of 6. The known compounds 3-hydroxydehydroiso-alpha-lapachone (4), 4,9-dihydroxy-alpha-lapachone (5), 4-hydroxy-alpha-lapachone (6), and 9-methoxy-alpha-lapachone (7), and Catalpalactone (8) were also isolated. Their structures were elucidated by spectral methods.
CONCLUSIONS:
These compounds all exhibited significant inhibitory activity against 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells.

Periodical of Ocean University of China, 2012, 42: 127-45.

An Improved Synthesis and Cytotoxicity Activities of Catalpalactone[Reference: WebLink]

METHODS AND RESULTS:
An improved synthesis of Catalpalactone was carried out with a total yield of 18% by using 2-formylbenzoic acid as the starting material followed by a four-steps procedure including Wittig reaction,lactonization,retro-Michael addition and a one-pot manipulation to introduce the double bond.The structures of all of the intermediates as well as the stereo-configurations of double bond in compounds 11,12a and 12b were determined by 1H NMR,13C NMR,MS,1H-1H COSY and NOE techniques.This improved synthetic method provides several advantages such as inexpensive and easily available reagents,mild reaction conditions,simple operations,and high yields.
CONCLUSIONS:
Through being evaluated in vitro against a panel of two human tumor cell lines(MCF-7,BxPC3) which were determined by the SRB assays, Catalpalactone displayed good activities against MCF-7 and BxPC3.