Biotransformation of Cyclodextrine-Complexed Semisynthetic Betulin Derivatives by Plant Cells

Suvi T. Häkkinen, Heli Nygren, Natalia Maiorova, Raisa Haavikko, Sami Alakurtti, Jari Yli-Kauhaluoma, Heiko Rischer, Kirsi Marja Oksman-Caldentey

Research output: Contribution to journalArticleScientificpeer-review

Abstract

In this study, three semisynthetic betulonic acid-based compounds, 20(29)-dihydrolup-2-en[2,3- d ]isoxazol-28-oic acid, 1-betulonoylpyrrolidine, and lupa-2,20(29)-dieno[2,3- b ]pyrazin-28-oic acid, were studied in biotransformation experiments using Nicotiana tabacum and Catharanthus roseus cell suspension cultures. Biotransformation was performed using cyclodextrin to aid dissolving poorly water-soluble substrates. Several new derivatives were found, consisting of oxidized and glycosylated (pentose- and hexose-conjugated) products.

Original languageEnglish
Pages (from-to)743-748
Number of pages6
JournalPlanta Medica
Volume84
Issue number9-10
DOIs
Publication statusPublished - 1 Jul 2018
MoE publication typeA1 Journal article-refereed

Fingerprint

Plant Cells
Biotransformation
Catharanthus
Derivatives
Pentoses
Acids
Hexoses
Cyclodextrins
Tobacco
Suspensions
Cell Culture Techniques
Water
Substrates
Experiments
betulin
azastene
betulonic acid
compound 20

Keywords

  • Apocynaceae
  • betulinic acid
  • biotransformation
  • Catharanthus roseus
  • Nicotiana tabacum
  • Solanaceae

Cite this

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title = "Biotransformation of Cyclodextrine-Complexed Semisynthetic Betulin Derivatives by Plant Cells",
abstract = "In this study, three semisynthetic betulonic acid-based compounds, 20(29)-dihydrolup-2-en[2,3- d ]isoxazol-28-oic acid, 1-betulonoylpyrrolidine, and lupa-2,20(29)-dieno[2,3- b ]pyrazin-28-oic acid, were studied in biotransformation experiments using Nicotiana tabacum and Catharanthus roseus cell suspension cultures. Biotransformation was performed using cyclodextrin to aid dissolving poorly water-soluble substrates. Several new derivatives were found, consisting of oxidized and glycosylated (pentose- and hexose-conjugated) products.",
keywords = "Apocynaceae, betulinic acid, biotransformation, Catharanthus roseus, Nicotiana tabacum, Solanaceae",
author = "H{\"a}kkinen, {Suvi T.} and Heli Nygren and Natalia Maiorova and Raisa Haavikko and Sami Alakurtti and Jari Yli-Kauhaluoma and Heiko Rischer and Oksman-Caldentey, {Kirsi Marja}",
year = "2018",
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language = "English",
volume = "84",
pages = "743--748",
journal = "Planta Medica",
issn = "0032-0943",
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Biotransformation of Cyclodextrine-Complexed Semisynthetic Betulin Derivatives by Plant Cells. / Häkkinen, Suvi T.; Nygren, Heli; Maiorova, Natalia; Haavikko, Raisa; Alakurtti, Sami; Yli-Kauhaluoma, Jari; Rischer, Heiko; Oksman-Caldentey, Kirsi Marja.

In: Planta Medica, Vol. 84, No. 9-10, 01.07.2018, p. 743-748.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Biotransformation of Cyclodextrine-Complexed Semisynthetic Betulin Derivatives by Plant Cells

AU - Häkkinen, Suvi T.

AU - Nygren, Heli

AU - Maiorova, Natalia

AU - Haavikko, Raisa

AU - Alakurtti, Sami

AU - Yli-Kauhaluoma, Jari

AU - Rischer, Heiko

AU - Oksman-Caldentey, Kirsi Marja

PY - 2018/7/1

Y1 - 2018/7/1

N2 - In this study, three semisynthetic betulonic acid-based compounds, 20(29)-dihydrolup-2-en[2,3- d ]isoxazol-28-oic acid, 1-betulonoylpyrrolidine, and lupa-2,20(29)-dieno[2,3- b ]pyrazin-28-oic acid, were studied in biotransformation experiments using Nicotiana tabacum and Catharanthus roseus cell suspension cultures. Biotransformation was performed using cyclodextrin to aid dissolving poorly water-soluble substrates. Several new derivatives were found, consisting of oxidized and glycosylated (pentose- and hexose-conjugated) products.

AB - In this study, three semisynthetic betulonic acid-based compounds, 20(29)-dihydrolup-2-en[2,3- d ]isoxazol-28-oic acid, 1-betulonoylpyrrolidine, and lupa-2,20(29)-dieno[2,3- b ]pyrazin-28-oic acid, were studied in biotransformation experiments using Nicotiana tabacum and Catharanthus roseus cell suspension cultures. Biotransformation was performed using cyclodextrin to aid dissolving poorly water-soluble substrates. Several new derivatives were found, consisting of oxidized and glycosylated (pentose- and hexose-conjugated) products.

KW - Apocynaceae

KW - betulinic acid

KW - biotransformation

KW - Catharanthus roseus

KW - Nicotiana tabacum

KW - Solanaceae

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