Studies on indole alkaloid biosynthesis

Kutney, James P.; Beck, John F.; Ehret, Charles F.; Poulton, G. A.; Sood, Rattan; Westcott, Neil D.

doi:10.1016/0045-2068(71)90016-2

Cited by 21 publications

(7 citation statements)

References 27 publications

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“…128 Some of these findings are reviewed in references. [129][130][131][132][133][134][135] More details are known about the six steps that catalyze the elaboration of tabersonine to vindoline (Scheme 8). 6, 136 The cytochrome P450 monooxygenase (tabersonine-16-hydroxylase, T16H) responsible for hydroxylating tabersonine to 16-hydroxytabersonine in the first step of this sequence has been cloned.…”

Section: Strychnos Aspidosperma and Iboga Type: Preakuammicine Vindol...mentioning

confidence: 99%

Chemistry and biology of monoterpene indole alkaloid biosynthesis

2006

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Section: Strychnos Aspidosperma and Iboga Type: Preakuammicine Vindol...mentioning

confidence: 99%

Chemistry and biology of monoterpene indole alkaloid biosynthesis

2006

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“…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.

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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.

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“…l-BenzyI-4aa-ethyl -6 ¡3 -hydroxymethyl -7 -methyl -1,2,3,4,4a,5,6,llca-octahydro-7/7-pyrido[3,2-c]carbazole (8c). In a similar fashion as described (vide supra), 8a was converted to 8c: mp 173-174°; ir (CHC13) 3430-2400 (no shift upon dilution); mass spectrum (70 eV) m/e (rel intensity) 388 (7), 370 (44), 357 (41), 330 (30), 329 (96? ), 210 (40), 194 (30), 182 (37), 181 (34), 146 (50).…”

Section: Methodsmentioning

confidence: 99%

Biogenetically modeled synthesis via an indole acrylic ester. Total synthesis of (+-)-minovine

Ziegler¹,

Spitzner²

1973

J. Am. Chem. Soc.

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The details of a total synthesis of (+)-minovine (3), patterned upon biogenetic considerations, are discussed.n 1962 Wenkert4 postulated that a protonated form I of dihydropyridine acrylic ester 2a might play an integral role in the biosynthesis of Aspidosperma and Zboga alkaloids. In recent years, in citro experiments have been reported with alkaloids of these classes in an attempt to verify the intermediacy of the acrylic esters 2b.j During this period secodine ( l a ) and 16,17dihydrosecodin-17-01 (lb) have been isolated6 and syn-the~ized.",~ Moreover, secodine has been shown to incorporate in Give into the Aspidosperma n u c l e~s .~~~ It was our intention to investigate the viability of the addition of an endocyclic enamine to a 2,2'-indole acrylic ester followed by a Mannich c10sure.~ Although the ultimate test would have been the construction of acrylic ester 2b or 2c, prudence dictated that the manipulation of such a reactive functionality would be best accommodated by isolating the reactive moieties in separate substrates and only at the designated time to allow their chemical union.Whereas an appropriate endocyclic enamine 412 was already at hand from previous work, it was necessary to consider a suitable means of constructing a (1) For a preliminary account of this work, see A considerable amount of controversy has arisen over these results. We leave the reader to formulate his own opinions.(6) (a) G.2,2'-indole acrylic ester. Since it was known13 that N-methylindole is capable of undergoing lithiation at the 2 position, it was an easily accessible method of appropriate functionalization of the indole nucleus which mandated that minovine (3) be a convenient test of the biogenetic-like sequence. la. R = CH. b. R = CH-OH H CO-CH , A s p id o s p e r m a (tabersonine) b.14,15 dehydro; Z = H, 2a.14,15 dehydro: Z = 0 c.14,15 dihydro; Z = H2 3I b o g a ( c a t h a r a n t h i n e ) When ethyl oxalate was added dropwise to an ethereal solution of the lithioindole, only trace amounts of the desired ethyl 1-methyl-2-indole glyoxylic ester 5a could be detected, the two major products being the diketone 6 and the hydroxy ketone 7. Since it was apparent that the glyoxylic ester was undergoing further reactions, the situation was ameliorated by the slow addition of the lithium reagent to an excess of ethyl oxalate in ether. The major product from the inverse addition was the glyoxylate 5a which was directly converted to its crystalline free acid 5b by saponification of the reaction mixture, which served to allow facile chemical separation from both neutral species 6 and 7. Treatment of the glyoxylic acid with ethereal diazomethane provided the methyl ester 5c as a yellow oil whose nuclear magnetic resonance spectrum revealed two three-proton singlets at 6 3.95 and 3.99 (NCHB and (13)

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Studies on indole alkaloid biosynthesis

Cited by 21 publications

References 27 publications

Chemistry and biology of monoterpene indole alkaloid biosynthesis

Chemistry and biology of monoterpene indole alkaloid biosynthesis

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

Biogenetically modeled synthesis via an indole acrylic ester. Total synthesis of (+-)-minovine

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