Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography

Lars P. Christensen*, Kell Kristiansen

*Kontaktforfatter for dette arbejde

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

The content of tuliposides and tulipalins were determined in Tulipa species and cultivars by reversed-phase high-performance liquid chromatography (RP-HPLC), using a water:methanol gradient as mobile phase. The compounds were detected by a diode array detector employed at 208 nm. The investigation revealed, in addition to 1- and 6-tuliposide A, tuliposide D and the lactonized aglycones tulipalin A and (-)-tulipalin B, the new tuliposide F and 6-tuliposide B, the latter being a new acyl derivative of the known 1-tuliposide B. All compounds were isolated by preparative RP-HPLC and identified by NMR and mass spectroscopy. The predominant compounds were 6-tuliposide A and B present in amounts up to 1.5% and 1.3% of fresh weight, respectively. 6-Tuliposide A and tulipalin A seem to be the major allergens in tulips, although tuliposide D and F may also contribute to the allergenic properties. Tulipalin A and (-)-tulipalin B occur in intact tulips and are not only produced in response to fungal attack or after excision of the plants. A few species were found to have very low allergen content and a relatively high level of tuliposide B indicating it should be possible to breed non-allergenic and disease-resistant tulips.

OriginalsprogEngelsk
TidsskriftContact Dermatitis
Vol/bind40
Udgave nummer6
Sider (fra-til)300-309
Antal sider10
ISSN0105-1873
DOI
StatusUdgivet - 1999
Udgivet eksterntJa

Fingeraftryk

Tulipa
High Pressure Liquid Chromatography
Reverse-Phase Chromatography
Allergens
Methanol
Weights and Measures
alpha-methylene gamma-butyrolactone
6-tuliposide A

Citer dette

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title = "Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography",
abstract = "The content of tuliposides and tulipalins were determined in Tulipa species and cultivars by reversed-phase high-performance liquid chromatography (RP-HPLC), using a water:methanol gradient as mobile phase. The compounds were detected by a diode array detector employed at 208 nm. The investigation revealed, in addition to 1- and 6-tuliposide A, tuliposide D and the lactonized aglycones tulipalin A and (-)-tulipalin B, the new tuliposide F and 6-tuliposide B, the latter being a new acyl derivative of the known 1-tuliposide B. All compounds were isolated by preparative RP-HPLC and identified by NMR and mass spectroscopy. The predominant compounds were 6-tuliposide A and B present in amounts up to 1.5{\%} and 1.3{\%} of fresh weight, respectively. 6-Tuliposide A and tulipalin A seem to be the major allergens in tulips, although tuliposide D and F may also contribute to the allergenic properties. Tulipalin A and (-)-tulipalin B occur in intact tulips and are not only produced in response to fungal attack or after excision of the plants. A few species were found to have very low allergen content and a relatively high level of tuliposide B indicating it should be possible to breed non-allergenic and disease-resistant tulips.",
keywords = "Allergen isolation by HPLC, Allergens, Allergic contact dermatitis, Biosynthesis, Chemosystematics, Liliaceae, Plants, Prevention, Tulipa, Tulipalins, Tuliposides",
author = "Christensen, {Lars P.} and Kell Kristiansen",
year = "1999",
doi = "10.1111/j.1600-0536.1999.tb06080.x",
language = "English",
volume = "40",
pages = "300--309",
journal = "Contact Dermatitis",
issn = "0105-1873",
publisher = "Wiley-Blackwell",
number = "6",

}

Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography. / Christensen, Lars P.; Kristiansen, Kell.

I: Contact Dermatitis, Bind 40, Nr. 6, 1999, s. 300-309.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography

AU - Christensen, Lars P.

AU - Kristiansen, Kell

PY - 1999

Y1 - 1999

N2 - The content of tuliposides and tulipalins were determined in Tulipa species and cultivars by reversed-phase high-performance liquid chromatography (RP-HPLC), using a water:methanol gradient as mobile phase. The compounds were detected by a diode array detector employed at 208 nm. The investigation revealed, in addition to 1- and 6-tuliposide A, tuliposide D and the lactonized aglycones tulipalin A and (-)-tulipalin B, the new tuliposide F and 6-tuliposide B, the latter being a new acyl derivative of the known 1-tuliposide B. All compounds were isolated by preparative RP-HPLC and identified by NMR and mass spectroscopy. The predominant compounds were 6-tuliposide A and B present in amounts up to 1.5% and 1.3% of fresh weight, respectively. 6-Tuliposide A and tulipalin A seem to be the major allergens in tulips, although tuliposide D and F may also contribute to the allergenic properties. Tulipalin A and (-)-tulipalin B occur in intact tulips and are not only produced in response to fungal attack or after excision of the plants. A few species were found to have very low allergen content and a relatively high level of tuliposide B indicating it should be possible to breed non-allergenic and disease-resistant tulips.

AB - The content of tuliposides and tulipalins were determined in Tulipa species and cultivars by reversed-phase high-performance liquid chromatography (RP-HPLC), using a water:methanol gradient as mobile phase. The compounds were detected by a diode array detector employed at 208 nm. The investigation revealed, in addition to 1- and 6-tuliposide A, tuliposide D and the lactonized aglycones tulipalin A and (-)-tulipalin B, the new tuliposide F and 6-tuliposide B, the latter being a new acyl derivative of the known 1-tuliposide B. All compounds were isolated by preparative RP-HPLC and identified by NMR and mass spectroscopy. The predominant compounds were 6-tuliposide A and B present in amounts up to 1.5% and 1.3% of fresh weight, respectively. 6-Tuliposide A and tulipalin A seem to be the major allergens in tulips, although tuliposide D and F may also contribute to the allergenic properties. Tulipalin A and (-)-tulipalin B occur in intact tulips and are not only produced in response to fungal attack or after excision of the plants. A few species were found to have very low allergen content and a relatively high level of tuliposide B indicating it should be possible to breed non-allergenic and disease-resistant tulips.

KW - Allergen isolation by HPLC

KW - Allergens

KW - Allergic contact dermatitis

KW - Biosynthesis

KW - Chemosystematics

KW - Liliaceae

KW - Plants

KW - Prevention

KW - Tulipa

KW - Tulipalins

KW - Tuliposides

UR - http://www.scopus.com/inward/record.url?scp=0032976703&partnerID=8YFLogxK

U2 - 10.1111/j.1600-0536.1999.tb06080.x

DO - 10.1111/j.1600-0536.1999.tb06080.x

M3 - Journal article

VL - 40

SP - 300

EP - 309

JO - Contact Dermatitis

JF - Contact Dermatitis

SN - 0105-1873

IS - 6

ER -