Triterpene Saponins from Calendula arvensis (original) (raw)

A Novel Eudesmane Glycosides Sesquiterpene from Calendula officinalis L

International Journal of Pharmacology, Phytochemistry and Ethnomedicine, 2016

The chromatographic separation of aqueous methanolic extract of Calendula officinalis led to the isolation of a new eudesmane sesquiterpene glycoside (1), together with tow known compounds, a lupane ester (2) and flavonoide gulcoside (3). Their structures were characterized to be 1β,3β,6α,8α,tetrahydroxyeudesm-4-ene 11-O-β-D-glucopyrnoside (1), 3β-E-caffoeyl lupeol (2), kaempferol-3-O-gulcoside (3) by spectroscopic means.

A New Monodesmosidic Triterpenoid Saponin from the Seeds of Vigna unguiculata subsp. unguiculata

1995

Phytochemical investigation of the leaves of Pometia pinnata resulted in the isolation of a new triterpenoid saponin (1), together with a known compound, kaemferol 3-O-α-L-rhamnopyranoside (2). The structure of 1 was established as 3-O-[α-L-arabinofuranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranosyl]-hederagenin. The structure elucidation of the isolated compounds was based primarily on 1D-and 2D-NMR techniques, including 1 H and 13 C NMR spectra, DEPT, and by 2D COSY, HMQC, HMBC and TOCSY experiments.

A New Triterpene Saponin from Chenopodium ficifolium

The new triterpene saponin 3-O--d-glucopyranoside, 28--d-glucopyranosyl-(1 5 2)--d-glucopyranosiduronic acid oleanolate was isolated from the roots of Chenopodium ficifolium. The known compounds stigmasterol-3-O-glucoside and 3-O--d-glucopyranosiduronic acid, 28--d-glucopyranosyl oleanolate were also isolated. The latter compound, oleanolic acid, -sitosterol and its glucoside were isolated from the aerial parts. The identity of these compounds was verified through different chemical and physico-chemical evidences including different 1D and 2D NMR experiments.

Characterization of Three New Triterpenoid Saponins from Ardisia japonica

Journal of Natural Products, 1993

h m m . -T h e isolation and characterization of three novel triterpene glycosides 1-3 from the medicinal plant Ardisia japonica (Myrsinaceae) are described. The compounds are characterized by a branched oligosaccharide chain, composed of four sugar units. The oligosaccharide structures were determined by 'H-'H correlation spectroscopy (COSY, HOHAHA, ROESY) and 'H-I3C heteronuclear correlation (HETCOR) nmr experiments. The aglycone moieties are the oleane-type triterpenes cyclamiretin A for 1 and the new 13,28-epoxy-30,30dimethoxyolean-3P,lba-dioland 3~,16a-dihydroxy-13,28-epxyolean-294cacidfor2and 3, respectively. In China a decoction ofArdisia japonica (Thunb.) BI. (Myrsinaceae) is taken to stop cough and uterine bleeding (1). Roots of Ardisia crispa (Thunb.) A. DC. are, in

Triterpene glycosides from Agrostemma gracilis

Phytochemistry, 2010

Four triterpene saponins, agrostemmosides A-D were isolated from the methanol extract of Agrostemma gracilis. The structures of the compounds were determined as 3-O-beta-D-xylopyranosyloleanolic acid 28-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyloleanolic acid 28-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-beta-D-xylopyranosylechinocystic acid 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-beta-D-xylopyranosylechinocystic acid 28-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->6)]-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. To the best of our knowledge this is the first phytochemical report on A. gracilis, and echinocystic acid saponins were encountered for the first time in Caryophyllaceae family.

Triterpenoid Saponins from the Roots of Glycyrrhiza Glabra

Natural Product Communications, 2019

Seven new oleanane-type triterpenoid saponins (glabasaponin A-G) were isolated from the roots of Glycyrrhiza glabra together with a known compound macedonoside A. The structures of compounds 1-7 were determined on the basis of 1D and 2D NMR as well as the MS data analyses. The sugar moieties of compound 5 were confirmed by gas chromatography after hydrolysis.

Saponins in Calendula officinalis L. – Structure, Biosynthesis, Transport and Biological Activity

Phytochemistry Reviews, 2005

Trends in research on Calendula officinalis L. saponins performed in Department of Plant Biochemistry at Warsaw University are reviewed. Calendula officinalis, a well known medicinal plant, contains significant amounts of oleanane saponins, which form two distinct series of related compounds, called ''glucosides'' and ''glucuronides'' according to the structure of the respective precursor. Both series differ in the pathway of their biosynthesis and further metabolism, i.e. the rate of formation and stages of possible degradation; distribution in the single cell and in the whole plant, including accumulation sites; and the possible physiological role played in the plant according to appropriate biological activities.

Structural studies of triterpenoid saponins with new acyl components from Quillaja saponaria Molina

Eight new triterpenoid saponins were isolated from a bark extract of Quillaja saponaria Molina by silica and reverse phase chromatography. The saponins were characterized by spectroscopic data and chemical methods as phytolaccagenic acid, 22bhydroxy-quillaic acid, and echinocystic acid substituted with dierent oligosaccharides at C-3 and C-28. The O-4 of the fucosyl residue in the 28-O-oligosaccharide was substituted with either acetyl, (S)-2-methylbutanoyl, or (3S,4S)-3-hydroxy-4-methylhexanoyl groups. #