Search results for "Indole alkaloid"

Structure-based engineering of strictosidine synthase: auxiliary for alkaloid libraries.

2007

SummaryThe highly substrate-specific strictosidine synthase (EC 4.3.3.2) catalyzes the biological Pictet-Spengler condensation between tryptamine and secologanin, leading to the synthesis of about 2000 monoterpenoid indole alkaloids in higher plants. The crystal structure of Rauvolfia serpentina strictosidine synthase (STR1) in complex with strictosidine has been elucidated here, allowing the rational site-directed mutation of the active center of STR1 and resulting in modulation of its substrate acceptance. Here, we report on the rational redesign of STR1 by generation of a Val208Ala mutant, further describing the influence on substrate acceptance and the enzyme-catalyzed synthesis of 10-m…

Construction and expression of a dual vector for chemo-enzymatic synthesis of plant indole alkaloids inEscherichia coli

2010

A dual vector (pQE-70-STR1-SG) containing coding regions of strictosidine synthase (STR1, EC 4.3.3.2) and strictosidine glucosidase (SG, EC 3.2.1.105) from the Indian medicinal plant Rauvolfia serpentina was constructed. Functional expression of the vector in Escherichia coli cells (M15 strain) was proven by isolation of prepurified enzyme extracts, which show both STR1 and SG activities. Incubation of the enzyme in the presence of tryptamine and secologanin delivered the indole alkaloid cathenamine, demonstrating functional co-expression of both STR1- and SG-cDNAs. Cathenamine reduction by sodium borohydride leading to tetrahydroalstonine revealed the chemo-enzymatic indole alkaloid synthe…

Vomilenine Reductase — a novel Enzyme catalyzing a crucial Step in the Biosynthesis of the Therapeutically applied Antiarrhythmic Alkaloid Ajmaline

2002

Delineation of the biochemical pathway leading to the antiarrhythmic Rauvolfia alkaloid ajmaline has been an important target in biosynthetic research for many years. The biosynthetic sequence starting with tryptamine and the monoterpene secologanin consists of about 10 different steps. Most of the participating enzymes have been detected and characterized previously, except those catalyzing the reduction of the intermediate vomilenine. A novel NADPH-dependent enzyme that reduces the intermediate has been isolated from Rauvolfia serpentina cell suspension cultures. Vomilenine reductase (M(r )43 kDa, temp opt 30 degrees C, pH opt 5.7-6.2), saturates the indolenine double bond of vomilenine w…

ChemInform Abstract: Enzymatic Formation of Raucaffricine, the Major Indole Alkaloid of Rauwolfia serpentina Cell-Suspension Cultures.

2010

Enzymatic Formation of Raucaffricine, the Major Indole Alkaloid ofRauwolfia serpentinaCell-Suspension Cultures

1991

The major alkaloid from Rauwolfia serpentina cell-suspension cultures, the glucoalkaloid raucaffricine (2), was enzymatically formed from vomilenine (1) and UDPG in presence of microsomal-bound enzyme. This glucosyltransferase exhibits a relatively high substrate specificity with strong preference for 1 and UDPG. The apparent Km values for 1 and UDPG were 40 μM and 0.8 mM, respectively, for raucaffricine formation. Optimum transferase activity was observed at 50° and pH 6.3. The taxonomic distribution of this enzyme seems to be very limited because transferase can he exclusively detected in raucaffricine-producing plant cells.

Isolation of Alkaloids from Cultured Hybrid Cells of Rauwolfia serpentina*Rhazya stricta.

1996

Two monoterpenoid indole alkaloids and four β-carbolines were isolated from a hydrid cell suspension culture generated from two Apocynaceous plants, Rauwolfia serpentina Benth. and Rhazya stricta Decaisne. This indicates that the function of alkoloid biosynthesis is retained after hybrid formation and that alkaloids not previously detected in the parental plants or cell cultures are formed.

Erratum to “3D-Structure and function of strictosidine synthase – The key enzyme of monoterpenoid indole alkaloid biosynthesis” [Plant Physiol. Bioch…

2008

Enzymatic biosynthesis of raumacline

1995

Abstract The indole alkaloid, raumacline, is biosynthesized from ajmaline, when the latter was fed to cell suspensions of Rauwolfia serpentina . Formation in catalysed by two enzymes, a cell wall-bound peroxidase followed by a NADPH 2 -dependent reductase. The first enzyme cleaves ajmaline oxidatively leading to a C-21 epimeric mixture of 21-hydroxyraumacline, a novel alkaloid, which, in turn, is reduced under formation of raumacline. The peroxidase reaction is not specific for Rauwolfia cells whereas the reductase is present exclusively in Rauwolfia cell suspensions. The reductase has been purified to homogeneity. The enzyme is highly substrate specific, only accepting 21-hydroxyraumacline…

Biosynthesis of Monoterpenoid Indole Alkaloid Ajmaline Catalyzed by Novel Reductases1

2006

Somatic Hybridization in the Family Apocynaceae (Catharanthus, Rauwolfia, Rhazya, and Vinca Species)

1994

The Apocynaceae family includes about 2000 species belonging to approximately 200 genera (Takhtadjan 1981). The majority of species originate in the tropics, only a few of them are common to Europe (Vinca minor, V. herhaceae, V. major, genus Trachomitum).