Role of loganin in the biosynthesis of indole alkaloids

Battersby, Alan R.; Brown, Ros; Kapil, R. S.; Martin, J. A.; Plunkett, Andrew

doi:10.1039/c19660000890

Cited by 20 publications

(11 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tryptophan (28,24,23), tryptamine (24,9,5), mevalonate (30,34,7,21,35), geraniol (21,8,33,29,16), loganin (11,6), intermediates to understand the biosynthetic pathway in this particular fungus have already been initiated by our group (Fig. 6).…”

Section: Discussionmentioning

confidence: 99%

Effect of precursors feeding and media manipulation on production of novel anticancer pro-drug camptothecin from endophytic fungus

Amna¹,

Amina²,

Sharma³

et al. 2012

Braz. J. Microbiol.

View full text Add to dashboard Cite

We have established methodology for the isolation and characterization of a novel endophytic fungus from the inner bark of medicinal plant Nothapodytes foetida, which produced camptothecin in Sabouraud broth (SB) under shake flask conditions. Camptothecin and its related compounds are at present obtained by extraction from intact plants, but fungal endopytes may be an alternative source of production. In present study we have observed the effect of different nutrient combinations and precursors (tryptophan, tryptamine, geraniol, citral, mevalonic acid and leucine) on the accumulation of camptothecin by endophytic fungus Entrophospora infrequens. The precursors were fed either alone or in combinations (tryptophan and geraniol, tryptophan and citral, tryptophan and mevalonic acid, tryptophan and leucine). The highest camptothecin content was observed in the range of 503 ± 25µg/100g dry cell mass in Sabouraud medium.Camptothecin content in the medium was increased by 2.5 folds by the presence of tryptophan and leucine whereas the production with trytophan was also significantly different from other treatments. Furthermore, the effect of fungal camptothecin on the morphology of human cancer cell lines was also studied. The treated cells showed reduction in size, condensation of nucleus and the protoplasmic extensions were reduced. All these characteristics are found in apoptotic cells.

show abstract

Section: Discussionmentioning

confidence: 99%

Effect of precursors feeding and media manipulation on production of novel anticancer pro-drug camptothecin from endophytic fungus

Amna¹,

Amina²,

Sharma³

et al. 2012

Braz. J. Microbiol.

View full text Add to dashboard Cite

show abstract

“…Consideration of later steps in the biosynthetic sequence led Battersby to test several natural cy clopentanomonoterpenes as precursors of the Vinca rosea alkaloids (19,265). Verbenalin, genepin, monotropeine methyl ester, and loganin (Fig.…”

Section: Ipecoside Perivinementioning

confidence: 99%

“…Negligible activity was detected at N-methyl groups or aryl methoxy groups, indicating that there had been no significant transfer of methyl groups. The presence of loganin in Vinca rosea plants was established by radiochemical dilution (265). Plants fed gerani~l-l-~H were extracted in the presence of nonradioactive loganin.…”

Section: Ipecoside Perivinementioning

confidence: 99%

Alkaloid Biosynthesis

Leete¹

1969

Advances in Enzymology - And Related Areas of Molecular Biology

View full text Add to dashboard Cite

“…In the biosynthesis of monoterpene indole alkaloids, the "monoterpene portion" of the alkaloids has been shown to arise from the seco-iridoid glucoside secologanin (1) [1,2] which in turn arises, via the cyclopentanoid derivative loganin (2) [3], from the acy-…”

Section: Introductionmentioning

confidence: 99%

The Role of 9- and/or 10-oxygenated Derivatives of Geraniol, Geranial, Nerol, and Neral in the Biosynthesis of Loganin and Ajmalicine

Balsevich¹,

Kurz²

1983

Planta Med

View full text Add to dashboard Cite

A number of deuterium labelled 9- and/or 10-oxygenated derivatives of geraniol, geranial, nerol, and neral were used as substrates in feeding experiments with a cell suspension culture of CATHARANTHUS ROSEUS. The 9- and 10-oxo derivatives of geraniol, geranial, nerol, and neral as well as 9,10-dihydroxygeraniol, 9-oxo-10-hydroxygeraniol, and 9,9,10,10-tetraethoxygeranial were found to be good precursors of the indole alkaloid ajmalicine. The compounds 9-hydroxygeraniol, 9-hydroxynerol, 9,10-dihydroxynerol, 9-oxo-10-hydroxynerol, 9-hydroxy-10-oxonerol, 9-hydroxy-10-oxogeraniol, 9,9,10,10-tetraethoxynerol, and 9,9,10,10-tetraethoxygeraniol were relatively poor precursors. Competitive feeding experiments, employing mixtures of unlabelled citral and labelled 9-oxogeranial, 10-oxonerol, 10-oxoneral, or 9,10-dihydroxygeraniol were also carried out. The incorporation of 9,10-dihydroxygeraniol into ajmalicine was not significantly affected by the presence of citral, while the incorporations of the other labelled substrates were greatly reduced.

show abstract

Role of loganin in the biosynthesis of indole alkaloids

Cited by 20 publications

References 0 publications

Effect of precursors feeding and media manipulation on production of novel anticancer pro-drug camptothecin from endophytic fungus

Effect of precursors feeding and media manipulation on production of novel anticancer pro-drug camptothecin from endophytic fungus

Alkaloid Biosynthesis

The Role of 9- and/or 10-oxygenated Derivatives of Geraniol, Geranial, Nerol, and Neral in the Biosynthesis of Loganin and Ajmalicine

Contact Info

Product

Resources

About