Ipangulines and minalobines, chemotaxonomic markers of the infrageneric Ipomoea taxon subgenus Quamoclit, section Mina

Jenett‐Siems, Kristina; Ott, Sonja C.; Schimming, Thomas; Siems, Karsten; Müller, Frank; Hilker, Monika; Witte, Ludger; Hartmann, Thomas; Austin, Daniel F.; Eich, Eckart

doi:10.1016/j.phytochem.2004.11.019

Cited by 19 publications

(16 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…1 H and 13 C NMR spectra (Table 1) were similar to those of 1 revealing the presence of a 3β -tropanol moiety esterified to 3-hydroxy-2-methylbutyric acid, whereas no tigloyl residue was observed. We have named compound 2 astrimalvine B. Interestingly, the acyl components of astrimalvine A and B are similar to those occurring as constituents of certain ipangulines, unique pyrrolizidine alkaloids of the Ipomoea section Mina [8].…”

Section: Resultsmentioning

confidence: 96%

Unusual Tropane Alkaloid Pattern in Two African Convolvulaceous Species. Phytochemistry and Chemotaxonomy of the Convolvulaceae, Part 20 [1]

Ott

Tofern-Reblin

Jenett‐Siems

et al. 2007

Zeitschrift Für Naturforschung B

Self Cite

View full text Add to dashboard Cite

An unusual and complex tropane alkaloid pattern has been detected in the root bark of Astripomoea malvacea and in the whole plant of Falkia repens (Convolvulaceae) by GC-MS analysis. The specific profile of both species is characterized by the presence of aliphatic 3-acyloxytropanes/-nortropanes (exclusively in A. malvacea; predominantly in F. repens in cooccurrence with a few aromatic as well as arylalkyl acyl congeners). The principal alkaloid of A. malvacea, astrimalvine A N-oxide [3β -(3-tigloyloxy-2-methylbutyryloxy)tropane N-oxide], isolated and structurally elucidated by detailed spectroscopic analysis, represents the first N-oxide of a 3β -tropanol derivative in the Convolvulaceae. Its minor tertiary congener astrimalvine B [3β -(3-hydroxy-2-methylbutyryloxy)tropane] turned out to be a metabolite of both convolvulaceaous species. This is the first phytochemical report on the African genera Astripomoea and Falkia.

show abstract

Section: Resultsmentioning

confidence: 96%

Unusual Tropane Alkaloid Pattern in Two African Convolvulaceous Species. Phytochemistry and Chemotaxonomy of the Convolvulaceae, Part 20 [1]

Ott

Tofern-Reblin

Jenett‐Siems

et al. 2007

Zeitschrift Für Naturforschung B

Self Cite

View full text Add to dashboard Cite

show abstract

“…The NMR spectra of 4 were very similar to those of 3, but the 1 H NMR data revealed significant differences in the chemical shifts of the protons at positions 5-9 and 13 (Table 1), while in the 13 C NMR spectra such differences occurred at positions 7-9, 12, and 13 (Table 3). Together with this information, an extra signal at δ 51.8 in the 13 C NMR spectrum and a 3H singlet at δ 3.74 in the 1 H NMR spectrum of 4 have led us to propose the methyl ester moiety at C12, which is shown in Figure 1. Confirmation of this was achieved with the aid of HMBC data, which showed the correlations between C12 and H16, as well as C5, C6, and C7 with the hydrogen atom of the C6-hydroxyl group ( Table 2).…”

mentioning

confidence: 73%

“…Nevertheless, additional signals (H2' to H5') that did not correlate with any atom of the eudesmane skeleton suggested an ester of higher complexity at C1. Thus, HMBC and previously published data [12,13] were used for the assignment of all the positions of this ester, as shown in Tables 1, 2, and 3. The HR-ESI-MS data helped us to confirm the structure of 1 as shown in Figure 1.…”

mentioning

confidence: 99%

Eudesmanolides and Methyl Ester Derivatives from Dimerostemma arnottii

Ambrosio

Stefani

et al. 2010

Natural Product Communications

View full text Add to dashboard Cite

The phytochemical investigation of Dimerostemma arnottii (Asteraceae) afforded, in addition to a known eudesmanolide, two unusual eudesmane methyl ester derivatives and a new eudesmanolide. Structural elucidation of the compounds was based on their 1D and 2D NMR spectroscopic as well as HR-ESI-MS data. There is a remarkable similarity between the structures of the eudesmanes from D. arnottii and those previously encountered in other Dimerostemma species, which is in agreement with the results of a previous phylogenetic study based on molecular data. The chemotaxonomic relevance of the isolated compounds is briefly discussed.

show abstract

“…Crotalaria) (Hartmann and Witte 1995;Trigo et al 2003;Jenett-Siems et al 2005;Frölich et al 2006;Brehm et al 2007;Flores et al 2009).…”

Section: Introductionunclassified

Effects of pyrrolizidine alkaloids through different trophic levels

Trigo¹

2010

Phytochem Rev

View full text Add to dashboard Cite

Ipangulines and minalobines, chemotaxonomic markers of the infrageneric Ipomoea taxon subgenus Quamoclit, section Mina

Cited by 19 publications

References 13 publications

Unusual Tropane Alkaloid Pattern in Two African Convolvulaceous Species. Phytochemistry and Chemotaxonomy of the Convolvulaceae, Part 20 [1]

Unusual Tropane Alkaloid Pattern in Two African Convolvulaceous Species. Phytochemistry and Chemotaxonomy of the Convolvulaceae, Part 20 [1]

Eudesmanolides and Methyl Ester Derivatives from Dimerostemma arnottii

Effects of pyrrolizidine alkaloids through different trophic levels

Contact Info

Product

Resources

About