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A HEARTWOOD PIGMENT IN DALBERGIA CELL CULTURES. (R827612E02)
Citation:
Czako, M. AND L. Marton. A HEARTWOOD PIGMENT IN DALBERGIA CELL CULTURES. (R827612E02). NATURE. American Chemical Society, Washington, DC, 57(6):1013-1022, (2001).
Description:
In an extensive survey of the genera Baphia, Caesalpinia, Dalbergia, Haematoxylon, and Pterocarpus, we have identified a number of species whose cell cultures accumulated pigments similar to those in heartwood. Thirteen rosewood (Dalbergia) species produced a purple quinonemethide pigment in the callus that was apparently identical between the species. The pigment was first purified from D. retusa cell culture and its structure was elucidated by mass, infrared, and detailed 1H and 13C NMR and NOE spectroscopic studies including 2D experiments (COSY, NOESY, HMQC, and HMBC). Retusapurpurin A (1a) is a C30 isoflavan of novel skeleton whose formation can be rationalized to occur via regioselective oxidative coupling of an isoflavan to 4,4'-dihydroxy-2'-methoxychalcone. Retusapurpurin A was also isolated from D. parviflora heartwood and cell culture indicating that stress metabolism pathways that are shared with heartwood-type secondary metabolism subpathways are initiated in Dalbergia cell cultures. Therefore, Dalbergia cell cultures afford a good model system for studying heartwood-type metabolic differentiation.
Graphical Abstract
A C30 isoflavan, retusapurpurin A, was isolated from Dalbergia cell cultures and heartwood.
Author Keywords: Baphia; Caesalpinia; Dalbergia; Haematoxylon; Pterocarpus; Leguminosae; Cell culture; Heartwood pigment; Isoflavan; Quinonemethide
Abbreviations: APCI, atmospheric pressure chemical ionization; ESI, electrospray ionization; COSY, correlated spectroscopy; DQF-COSY, double-quantum COSY; DMSO, dimethylsulfoxide; HMBC (1H,13C-COSY-nJCH=18 Hz, n=2 and 3), heteronuclear shift correlations via multiple bond connectivities (gradient enhanced); HMQC (1H,13C-COSY-1JCH) heteronuclear multiple quantum coherence; MS, mass spectroscopy; NMR, nuclear magnetic resonance; NOESY, nuclear Overhauser and exchange spectroscopy