Analysis of indole alkaloids from Rhazya stricta hairy roots by ultra-performance liquid chromatography-mass spectrometry

Amir Akhgari , Into Laakso, Tuulikki Seppänen-Laakso, Teijo Yrjönen, Heikki Vuorela, Kirsi-Marja Oksman-Caldentey, Heiko Rischer

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Rhazya stricta Decne. (Apocynaceae) contains a large number of terpenoid indole alkaloids (TIAs). This study focused on the composition of alkaloids obtained from transformed hairy root cultures of R. stricta employing ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). In the UPLC-MS analyses, a total of 20 TIAs were identified from crude extracts. Eburenine and vincanine were the main alkaloids followed by polar glucoalkaloids, strictosidine lactam and strictosidine. Secodine-type alkaloids, tetrahydrosecodinol, tetrahydro- and dihydrosecodine were detected too. The occurrence of tetrahydrosecodinol was confirmed for the first time for R. stricta. Furthermore, two isomers of yohimbine, serpentine and vallesiachotamine were identified. The study shows that a characteristic pattern of biosynthetically related TIAs can be monitored in Rhazya hairy root crude extract by this chromatographic method.
Original languageEnglish
JournalMolecules
Volume20
Issue number12
Pages (from-to)22621-22634
Number of pages14
ISSN1420-3049
DOIs
Publication statusPublished - 18 Dec 2015
MoE publication typeA1 Journal article-refereed

Fields of Science

  • 317 Pharmacy
  • 116 Chemical sciences
  • Rhazya stricta
  • terpenoid indole alkaloids
  • ultra-performance liquid chromatography-mass spectrometry
  • CATHARANTHUS-ROSEUS
  • CELL-CULTURES
  • ALSTONIA-SCHOLARIS
  • SECODINE-TYPE
  • YOHIMBE BARK
  • BIOSYNTHESIS
  • QUANTIFICATION
  • IDENTIFICATION
  • EXTRACT
  • LINE

Cite this

Akhgari , Amir ; Laakso, Into ; Seppänen-Laakso, Tuulikki ; Yrjönen, Teijo ; Vuorela, Heikki ; Oksman-Caldentey, Kirsi-Marja ; Rischer, Heiko. / Analysis of indole alkaloids from Rhazya stricta hairy roots by ultra-performance liquid chromatography-mass spectrometry. In: Molecules. 2015 ; Vol. 20, No. 12. pp. 22621-22634.
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abstract = "Rhazya stricta Decne. (Apocynaceae) contains a large number of terpenoid indole alkaloids (TIAs). This study focused on the composition of alkaloids obtained from transformed hairy root cultures of R. stricta employing ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). In the UPLC-MS analyses, a total of 20 TIAs were identified from crude extracts. Eburenine and vincanine were the main alkaloids followed by polar glucoalkaloids, strictosidine lactam and strictosidine. Secodine-type alkaloids, tetrahydrosecodinol, tetrahydro- and dihydrosecodine were detected too. The occurrence of tetrahydrosecodinol was confirmed for the first time for R. stricta. Furthermore, two isomers of yohimbine, serpentine and vallesiachotamine were identified. The study shows that a characteristic pattern of biosynthetically related TIAs can be monitored in Rhazya hairy root crude extract by this chromatographic method.",
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author = "Amir Akhgari and Into Laakso and Tuulikki Sepp{\"a}nen-Laakso and Teijo Yrj{\"o}nen and Heikki Vuorela and Kirsi-Marja Oksman-Caldentey and Heiko Rischer",
year = "2015",
month = "12",
day = "18",
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pages = "22621--22634",
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Analysis of indole alkaloids from Rhazya stricta hairy roots by ultra-performance liquid chromatography-mass spectrometry. / Akhgari , Amir ; Laakso, Into ; Seppänen-Laakso, Tuulikki; Yrjönen, Teijo ; Vuorela, Heikki ; Oksman-Caldentey, Kirsi-Marja; Rischer, Heiko.

In: Molecules, Vol. 20, No. 12, 18.12.2015, p. 22621-22634.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Analysis of indole alkaloids from Rhazya stricta hairy roots by ultra-performance liquid chromatography-mass spectrometry

AU - Akhgari , Amir

AU - Laakso, Into

AU - Seppänen-Laakso, Tuulikki

AU - Yrjönen, Teijo

AU - Vuorela, Heikki

AU - Oksman-Caldentey, Kirsi-Marja

AU - Rischer, Heiko

PY - 2015/12/18

Y1 - 2015/12/18

N2 - Rhazya stricta Decne. (Apocynaceae) contains a large number of terpenoid indole alkaloids (TIAs). This study focused on the composition of alkaloids obtained from transformed hairy root cultures of R. stricta employing ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). In the UPLC-MS analyses, a total of 20 TIAs were identified from crude extracts. Eburenine and vincanine were the main alkaloids followed by polar glucoalkaloids, strictosidine lactam and strictosidine. Secodine-type alkaloids, tetrahydrosecodinol, tetrahydro- and dihydrosecodine were detected too. The occurrence of tetrahydrosecodinol was confirmed for the first time for R. stricta. Furthermore, two isomers of yohimbine, serpentine and vallesiachotamine were identified. The study shows that a characteristic pattern of biosynthetically related TIAs can be monitored in Rhazya hairy root crude extract by this chromatographic method.

AB - Rhazya stricta Decne. (Apocynaceae) contains a large number of terpenoid indole alkaloids (TIAs). This study focused on the composition of alkaloids obtained from transformed hairy root cultures of R. stricta employing ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). In the UPLC-MS analyses, a total of 20 TIAs were identified from crude extracts. Eburenine and vincanine were the main alkaloids followed by polar glucoalkaloids, strictosidine lactam and strictosidine. Secodine-type alkaloids, tetrahydrosecodinol, tetrahydro- and dihydrosecodine were detected too. The occurrence of tetrahydrosecodinol was confirmed for the first time for R. stricta. Furthermore, two isomers of yohimbine, serpentine and vallesiachotamine were identified. The study shows that a characteristic pattern of biosynthetically related TIAs can be monitored in Rhazya hairy root crude extract by this chromatographic method.

KW - 317 Pharmacy

KW - 116 Chemical sciences

KW - Rhazya stricta

KW - terpenoid indole alkaloids

KW - ultra-performance liquid chromatography-mass spectrometry

KW - CATHARANTHUS-ROSEUS

KW - CELL-CULTURES

KW - ALSTONIA-SCHOLARIS

KW - SECODINE-TYPE

KW - YOHIMBE BARK

KW - BIOSYNTHESIS

KW - QUANTIFICATION

KW - IDENTIFICATION

KW - EXTRACT

KW - LINE

U2 - 10.3390/molecules201219873

DO - 10.3390/molecules201219873

M3 - Article

VL - 20

SP - 22621

EP - 22634

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 12

ER -