High-Performance Liquid Chromatography On-Line Coupled to High-Field NMR and Mass Spectrometry for Structure Elucidation of Constituents of <i>Hypericum perforatum</i> L.

Hansen, Steen Honoré; Jensen, Anette Gemal; Cornett, Claus; Bjørnsdottir, Inga; Taylor, Steven; Wright, and Brian; Wilson, Ian D.

doi:10.1021/ac990598x

Cited by 126 publications

(68 citation statements)

References 15 publications

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“…The presence of an HMBC (heteronuclear shift correlations via multiple bond connectivities) correlation between H-1ЈЈ and C-3 allowed the pigment's complete assignment as quercetin 3-O-␤-D-glucoronide (1). The second pigment to elute showed mass spectra and 1 H NMR spectra in accord with those reported for the dimeric flavonoid, I3-II8-biapigenin (2) (19). Both of these flavonoids have been reported to occur in other species of Hypericum (19,20).…”

Section: Uv Patternsupporting

confidence: 75%

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Attractive and defensive functions of the ultraviolet pigments of a flower ( Hypericum calycinum )

Gronquist

Bezzerides

Attygalle

et al. 2001

Proc. Natl. Acad. Sci. U.S.A.

146

104

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The flower of Hypericum calycinum, which appears uniformly yellow to humans, bears a UV pattern, presumably visible to insects. Two categories of pigments, flavonoids and dearomatized isoprenylated phloroglucinols (DIPs), are responsible for the UV demarcations of this flower. Flavonoids had been shown previously to function as floral UV pigments, but DIPs had not been demonstrated to serve in that capacity. We found the DIPs to be present in high concentration in the anthers and ovarian wall of the flower, suggesting that the compounds also serve in defense. Indeed, feeding tests done with one of the DIPs (hypercalin A) showed the compound to be deterrent and toxic to a caterpillar (Utetheisa ornatrix). The possibility that floral UV pigments fulfill both a visual and a defensive function had not previously been contemplated. DIPs may also serve for protection of female reproductive structures in other plants, for example in hops (Humulus lupulus). The DIPs of hops are put to human use as bitter flavoring agents and preservatives in beer.nectar guides ͉ pollination ͉ plant defense ͉ dearomatized phloroglucinols ͉ flavonoids

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Section: Uv Patternsupporting

confidence: 75%

“…The second pigment to elute showed mass spectra and 1 H NMR spectra in accord with those reported for the dimeric flavonoid, I3-II8-biapigenin (2) (19). Both of these flavonoids have been reported to occur in other species of Hypericum (19,20).…”

Section: Uv Patternsupporting

confidence: 75%

Attractive and defensive functions of the ultraviolet pigments of a flower ( Hypericum calycinum )

Gronquist

Bezzerides

Attygalle

et al. 2001

Proc. Natl. Acad. Sci. U.S.A.

146

104

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“…Biological activities were previously reported for the isolated triterpenes: anti-AIDS for betulinic acid, herbicid for lupenone and fibrinolytic for betulin (Connolly & Hill, 2010). The flavonoids 7-9 were identified based on NMR data (Hansen et al, 1999;Galotta et al, 2008) and typical fragmentation by CID experiments with ESI-MS (Fabre et al, 2001). Some biological activities reported for the isolated flavonoids are: antidepressant for rutin (Nolder & Schotz, 2002), anti-inflammatory for rutin and quercetin (Afanaseva et al, 2001) and antioxidant for all of them (Galotta et al, 2008).…”

Section: Resultsmentioning

confidence: 99%

Triterpenes and flavonoids from the roots of Mauritia flexuosa

Koolen¹,

Soares²,

Silva³

et al. 2012

Rev. bras. farmacogn.

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Mauritia flexuosa L. f., Arecaceae, is an endemic species of South America. This species was studied with the intent to isolate the constituents of its roots. After the fractionation of the n-hexane and methanolic extracts from the roots of M. flexuosa, six triterpenes were obtained: friedelin, taraxerone, lupenyl acetate, lupenone, betulin and betulinic acid, along with three flavonoids: rutin, quercitrin and quercetin. All the compounds were identified by analysis of NMR and MS data and comparison with the literature. All those compounds are been reported for the first time in Mauritia, and the chemosystematic significance of the flavonoids isolated in this genus is discussed.

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“…Another natural products application of HPLC/NMR/ MS has identified compounds in extracts of Hypericum preforatum L (17). Among the compounds characterized were the arabinoside and galacturonide of quercetin, which had not previously been described for this species.…”

Section: Although Superheated Watermentioning

confidence: 99%

“…Not long afterward, an HPLC/ NMR instrument with an ion trap mass spectrometer was described for the identification of the urinary-excreted metabolites of acetaminophen (6). Numerous applications have followed rapidly, which now include a range of analytes from such areas as pharmaceuticals, natural products, and drug metabolites (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20).…”

mentioning

confidence: 99%