Synthesis of [2H]gibberellins from steviol using the fungus Gibberella fujikuroi

Thomas Gianfagna; Jan A.D. Zeevaart; William J. Lusk

doi:10.1016/0031-9422(83)83017-9

Synthesis of [²H]gibberellins from steviol using the fungus Gibberella fujikuroi

Thomas Gianfagna, Jan A.D. Zeevaart, William J. Lusk

School of Environmental and Biological Sciences, Plant Biology

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

[²H]Steviol (ent-13-hydroxykaur-16-en-19-oic acid) was synthesized from steviol acetate norketone (ent-13-acetoxy-16-oxo-17-norkauran-19-oic acid) by the Wittig reaction using (methyl-d₃)triphenylphosphonium bromide. A mixture of steviol analogs was produced containing from one to four ²H/molecule. [²H]Steviol was fed to strain LM-45-399 of the fungus Gibberella fujikuroi which was grown on synthetic medium (ICI, 0% N) in the presence of the growth retardant CCC. [²H]GA₁, [²H]GA₁₈, [²H]GA₂₃ and [²H]GA₅₃ were isolated from the fungal medium after 4 days. This strain converted steviol to 13-hydroxy GAs in the highest yields of the four Gibberella strains tested, and in amounts suitable for metabolic studies with higher plants.

Original language	English (US)
Pages (from-to)	427-430
Number of pages	4
Journal	Phytochemistry
Volume	22
Issue number	2
DOIs	https://doi.org/10.1016/0031-9422(83)83017-9
State	Published - 1983

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Biology
Plant Science
Horticulture

Keywords

GA
GA
GA
GA
GC/MS
Gibberella fujikuroi
H-labelled
fungi
gibberellin biosynthesis
steviol

Access to Document

10.1016/0031-9422(83)83017-9

Cite this

@article{031b836ac7bd4600a31e4acb9c1e91b2,

title = "Synthesis of [2H]gibberellins from steviol using the fungus Gibberella fujikuroi",

abstract = "[2H]Steviol (ent-13-hydroxykaur-16-en-19-oic acid) was synthesized from steviol acetate norketone (ent-13-acetoxy-16-oxo-17-norkauran-19-oic acid) by the Wittig reaction using (methyl-d3)triphenylphosphonium bromide. A mixture of steviol analogs was produced containing from one to four 2H/molecule. [2H]Steviol was fed to strain LM-45-399 of the fungus Gibberella fujikuroi which was grown on synthetic medium (ICI, 0% N) in the presence of the growth retardant CCC. [2H]GA1, [2H]GA18, [2H]GA23 and [2H]GA53 were isolated from the fungal medium after 4 days. This strain converted steviol to 13-hydroxy GAs in the highest yields of the four Gibberella strains tested, and in amounts suitable for metabolic studies with higher plants.",

keywords = "GA, GA, GA, GA, GC/MS, Gibberella fujikuroi, H-labelled, fungi, gibberellin biosynthesis, steviol",

author = "Thomas Gianfagna and Zeevaart, {Jan A.D.} and Lusk, {William J.}",

note = "Funding Information: Acknowledyemmr~ This work was supported by the United States Department of Energy under Contract No. DE-ACO2-76ER0133X. We also acknowledge the use of CC, MS equipment rn the MSU-NIH Mass Spectrometry Facility (RROO480). We thank Dr. James Metzger for preliminary feedmg studies wtth steviol, Dr. Maria Tanis for advice with the Witttg reaction and Dr. Gregory Boyer for helpful discussions throughout the course of this work.",

year = "1983",

doi = "10.1016/0031-9422(83)83017-9",

language = "English (US)",

volume = "22",

pages = "427--430",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd",

number = "2",

}

TY - JOUR

T1 - Synthesis of [2H]gibberellins from steviol using the fungus Gibberella fujikuroi

AU - Gianfagna, Thomas

AU - Zeevaart, Jan A.D.

AU - Lusk, William J.

N1 - Funding Information: Acknowledyemmr~ This work was supported by the United States Department of Energy under Contract No. DE-ACO2-76ER0133X. We also acknowledge the use of CC, MS equipment rn the MSU-NIH Mass Spectrometry Facility (RROO480). We thank Dr. James Metzger for preliminary feedmg studies wtth steviol, Dr. Maria Tanis for advice with the Witttg reaction and Dr. Gregory Boyer for helpful discussions throughout the course of this work.

PY - 1983

Y1 - 1983

N2 - [2H]Steviol (ent-13-hydroxykaur-16-en-19-oic acid) was synthesized from steviol acetate norketone (ent-13-acetoxy-16-oxo-17-norkauran-19-oic acid) by the Wittig reaction using (methyl-d3)triphenylphosphonium bromide. A mixture of steviol analogs was produced containing from one to four 2H/molecule. [2H]Steviol was fed to strain LM-45-399 of the fungus Gibberella fujikuroi which was grown on synthetic medium (ICI, 0% N) in the presence of the growth retardant CCC. [2H]GA1, [2H]GA18, [2H]GA23 and [2H]GA53 were isolated from the fungal medium after 4 days. This strain converted steviol to 13-hydroxy GAs in the highest yields of the four Gibberella strains tested, and in amounts suitable for metabolic studies with higher plants.

AB - [2H]Steviol (ent-13-hydroxykaur-16-en-19-oic acid) was synthesized from steviol acetate norketone (ent-13-acetoxy-16-oxo-17-norkauran-19-oic acid) by the Wittig reaction using (methyl-d3)triphenylphosphonium bromide. A mixture of steviol analogs was produced containing from one to four 2H/molecule. [2H]Steviol was fed to strain LM-45-399 of the fungus Gibberella fujikuroi which was grown on synthetic medium (ICI, 0% N) in the presence of the growth retardant CCC. [2H]GA1, [2H]GA18, [2H]GA23 and [2H]GA53 were isolated from the fungal medium after 4 days. This strain converted steviol to 13-hydroxy GAs in the highest yields of the four Gibberella strains tested, and in amounts suitable for metabolic studies with higher plants.

KW - GA

KW - GC/MS

KW - Gibberella fujikuroi

KW - H-labelled

KW - fungi

KW - gibberellin biosynthesis

KW - steviol

UR - http://www.scopus.com/inward/record.url?scp=0142129178&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0142129178&partnerID=8YFLogxK

U2 - 10.1016/0031-9422(83)83017-9

DO - 10.1016/0031-9422(83)83017-9

M3 - Article

AN - SCOPUS:0142129178

SN - 0031-9422

VL - 22

SP - 427

EP - 430

JO - Phytochemistry

JF - Phytochemistry

IS - 2

ER -