Steroid glycosides of the roots ofCapsicum annuum. I. The structure of capsicosides A1, B1, and C1

Three new steroid glycosides of the spirostan series — capsicosides A₁, B₁, and C₁ — have been isolated from a methanolic extract of the roots of red pepper. In an investigation of the products of complete acid hydrolysis of these glycosides, a single aglycon — gitogenin — was identified. The complete chemical structure of each of the capsicosides has been shown with the aid of complete and partial acid hydrolysis, methylation and methanolysis, and periodate oxidation, and also by physicochemical methods of investigation.     

Triterpene glycosides ofCaltha polypetala glycosides A,B, D,E, and F

Five individual triterpene glycosides — A, B, D, E, and F — which are hederagen-in mono- and biosides, have been isolated from the roots ofCaltha polypetala (Great Marsh Marigold), familyRanunculaceae. Glycosides E and F proved to be new compounds for which, on the basis of the results of acid and alkaline hydrolyses, methylation, methanolysis, and physicochemical methods of investigation, the following structures are proposed: E — hederagenin 3-0-D-glucopyranoside, 28-O-L-rhamnopyranoside; and F — heteragenin 28-O-[O-L-rhamnopyranosyl-(1→ 6)-D-glucopyranoside].     

Triterpene and steroid glycosides of theMelilotus genus and their genins I. Melilotosides A,B, and C from the roots ofMelilotus albus

Three new triterpene glycosides of the oleanane series — melilotosides A, B, and C — and the nonglycosylated soyasapogenol B have been isolated from the roots of the plant Melilotus albus Medik. (Leguminosae). The structures of the glycosides have been shown on the basis of chemical transformations and spectral results. Melilotoside A has the structure of soyasapogenol B 3-O-α-L-arabinopyranoside, melilotoside B that of soyasapogenol B 3-O-[O-β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside], and melilotoside C that of soyasapogenol B 3-O-[O-α-L-rhamnopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside.     

Triterpene glycosides ofScabiosa soongorica

Partial syntheses of glycosides of oleanolic acid — the 3-0-β-D-xylopyranoside (songoroside A), the 3,28-bis-0-β-D-xylopyranoside, and the 28-0-β-gentiobioside-3-0-β-D-xylopyranoside — and also the formation of 3-0-β-D-xylopyranosyloleanolic acid 13,28-lactone are described.     

Steroids of the spirostan and furostan series of plants of the Allium genus. XXIII. Structure of cepagenin and of alliospirosides C and D from Allium cepa

Two new steroid glycosides of the spirostan series have been isolated from the fruit ofAllium cepa L. (family Liliaceae): alliospirosides C and D. On the basis of chemical transformations and spectral characteristics it has been established that the aglycon of both glycosides is a new steroid sapogenin — cepagenin — having the structure of (24S,25R)-spirost-5-ene-1β,3β,24-triol. Alliospirosides C and D are cepagenin 1-O-[O-α-L-rhamnopyranosyl-(1→2)α-L-arabinopyranoside] and 1-O-[O-α-L-rhamnopyranosyl-(1→2)-O-β-D-galactopyranoside], respectively.     

Glycosides of marine invertegrates. XI. Two new triterpene glycosides from holothurians of the familyStichopadidae

By repeated column chromatography on silica gel new glycosides have been isolated from the holothuriansAstichopus multifidus andStichopus chloronotus — astichoposide C and stichoposide C (I and II, respectively). Their structures have been studied with the aid of chemical and physicochemical methods. The complete structures of the glycosides have been established as 23(S)-acetoxy-3β-{4′-O-[O-(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl]-2′-O-[O-(3-O-methyl-β-D-glucopyranosyl)-(1→3)-O-β-D-xylopyranosyl-(1→4)-β-D-quinovopyranosyl]-β-D-xylopyranosyloxy}holosta-7,25-diene and -holost-7-ene.     

Tripenoid glycosides of alfalfa. VII. Medicosides E and F

Two hederagenin glycosides — medicosides E and F — have been isolated from the roots ofMedicago sativa L. (Leguminosae). Medicoside E has the structure of hederagenin 28-O-β-D-glucopyranoside 3-O-[O-β-G-glucopyranosyl-(1→3)-β-D-xylopyranoside]. Medicoside F has the structure of hederagenin 28-O-β-D-glucopyranoside 3-O-[O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside].     

Glycosides of cinnamyl alcohol from the rhizomes ofRhodiola rosea

Three new cinnamyl alcohol glycosides have been isolated for the first time from the rhizomes of roseroot stonecropRhodiola rosea L. (Sedum rosea). On the basis of chemical transformations and the results of UV, IR, PMR, and mass spectroscopy the following structures are proposed for the compounds isolated: rozin — trans-cinnamyl O-β-D-glucopyranoside; rozavin — transcinnamyl O-(6′-O-α-L-arabinopyranosyl-β-D-glucopyranoside); and rozarin — trans-cinnamyl O-(6′-O-α-L-arabinofuranosyl-β-glucopyranoside).     

Steroid glycosides ofNicotiana tabacum seeds I. The structures of nicotianosides A,B, and E

Two steroid glycosides of the spirostan series — nicotianosides A and B — and one glycoside of the furostan series — nicotianoside E — have been isolated from the seeds ofNicotiana tabacum L. Nicotianoside A is (25S)-5α-spirostan-3β-ol 3-O-β-D-glucopyranoside, nicotianoside B is (25S)-5β-spirostan-3β-ol 3-O-[O-α-L-rhamnopyranosyl-(1→2)-gb-D-glucopyranoside], and nicotianoside E is (25S)-5α-furostan-3β,22α,26-triol 26-O-β-glucopyranoside 3-O-[O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside].     

High-Performance Thin-Layer Chromatography Combined with Densitometry for Quantitative Analysis of Phenolic Acids in Complex Mixtures

JPC – Journal of Planar Chromatography – Modern TLC - Protocatechuic acid and caffeic acid in plant extracts, both free and bound as glycosides and ester derivatives, have been...     

Synthesis of glycosidic analogues of N-acetylneuramoyl-L-alanyl-D-isoglutamine

β-Heptyl and β-hexadecyl glycosides of N-acetylglucosamine have been obtained by the oxazoline method followed by deacetylation. Via a benzylidenation stage, the glycosides have been converted into the corresponding N-acetylmuramic acid derivatives and from these compounds glycosidic analogues of N-acetylmuramoyl-L-alanyl-D-isoglutamine have been synthesized.     

Triterpene glycosides ofHedera colchica. Structure of hederacolchisides E and F

The leaves of Colchis ivy (family Araliaceae) have yielded polar glycosides — hederacolchisides E and F — and their structures have been established. It has been shown on the basis of the results of methylation and of acid and alkaline hydrolysis that these glycosides are hexaosides of oleanolic acid and of hederagenin.I. G. Kutateladze Institute of Pharmacochemistry, Academy of Sciences of the Georgian SSR, Tbilisi. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 747–750, November–December, 1984.     

Phenolics from Acalypha indica

Two novel hydrolysable tannins, potassium brevifolincarboxylate and acaindinin, together with eight known tannins—1-O-galloyl-β-D -glucose, 1,2,3,6-tetra-D -galloyl-β-D -glucose, corilagin, geraniin, acetonylgeraniin A, euphormisin M₂, repandusinic acid A, and chebulagic acid, as well as two flavonoid glycosides — quercetin 3-O-β-D -glucoside and rutin, were isolated from Acalypha indica. Their structures were elucidated on the basis of chemical and spectroscopic evidence.     

The glycosides of the roots from Gongronema taylorii (Schltr. & Rendle) Bullock)

The roots of Gongronema taylorii are rich in glycosides. These glycosides form a complex mixture of substances, of which some are closely related. From this mixture, six more or less pure but amorphous glycosides could be separated. Mild acid hydrolysis followed by alkaline hydrolysis led to the isolation of 5α-dihydrosarcostin ( 1 ) and some tayloron ( 3 ), whose probable structures have been reported earlier. In the original mixture, these genins are esterified predominantly with benzoic and cinnamic acids, and are also bound through glycosidic linkages to a series of sugars of which the following four could be identified by paper and thin layer chromatography: cymarose, digitoxose, oleandrose and pachybiose. Pachybiose and its two anomeric methyl glycosides have been isolated for the first time in a cristalline state.     

Qualitative and quantitative analysis of phenolic acid glycosides in Ginkgo biloba L. leaf,G. biloba leaf extract and its injection

Ginkgo biloba L. leaf (GBL) is one of the most commonly used medicinal plants in the world. Phenolic acids with biological activities have a relatively high content in G. biloba leaf extracts (GBE); therefore they are of great significance for the quality control of GBL, GBE and its preparations. However, there have been few studies focused on their analysis. In this work, 12 phenolic acids, including 11 phenolic acid glycosides, were identified by liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (LC–Q-TOF/MS). Then, a method combining enzymolysis with HPLC was established for quantification of phenolic acid glycosides. It was found that the aglycones of phenolic acid glycosides mainly comprised five phenolic acids: 2,4,6-trihydroxybenzoic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid and p-coumaric acid. The quantitative method was validated, and the correlation coefficient (0.9993–0.9999), recovery (≥88.4%), repeatability (≤0.8%), and inter-day precision (≤5.5%) were satisfactory. Finally, the contents of glycosides of five phenolic acids in GBL, GBE and GBE injection from different sources were determined by the developed method. The method was accurate, repeatable and practicable, which could be helpful for the quantification of phenolic acid glycosides in other products containing GBL or GBE.     

Structures of cucumariosides C1 and C2 — Two new triterpene glycosides from the holothurian Eupentacta fraudatrix

Two new triterpene glycosides — cucmariosides C₁ and C₂ — have been isolated from the Far Eastern holothurianEupentacta (=Cucumaria)fraudatrix Djakonov et Baranova. Their structures have been established with the aid of¹³C NMR and PMR spectroscopy, partial acid hydrolysis, periodate oxidation, and methylation as 16β-acetoxy-3-{[3-O-methyl-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)] [β-D-xylopyranosyl-(1→2)]-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyloxy}holosta-7,23,24(cis)-triene and 16β-acetoxy-3-{[3-O-methyl-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)] [β-D-xylopyranosyl-(1→2)]-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyloxy}holosta-7,22,24(trans)-triene, respectively.     

Resin glycosides. XV. Simonins I-V, ether-soluble resin glycosides (jalapins) from the roots of Ipomoea batatas (cv. Simon).

Five new ether-soluble resin glycosides (jalapins), simonins I-V, have been isolated from the roots of Ipomoea batatas and characterized on the bases of chemical and spectral data. Simonin I is the first example of resin glycoside with aromatic acid (trans-cinnamic acid) as a component organic acid.     

Triterpene glycosides of Astragalus and their genins XLIV. Structure of cyclocarposides A and C

The structures of two new cycloartane glycosides — cyclocarposides A and C, isolated from the herbAstragalus coluteocarpus Boiss. — have been established on the basis of spectral characteristics and chemical transformations. Cyclocarposides A and C are: 204R,24S-epoxycycloartane-3β,6α,17β,25-tetraol 3-O-(2-O-acetyl-β-D-xylopyranoside)6-O-(2-O-acetyl-α-L-rhamnopyranoside) and 20R,24S-epoxycyloartane-3β,6α,16β,25-tetraol 3-O-(2-O-acetyl-β-D-xylopyranoside) 6-O-α-L-rhamnopyranoside, respectively.     

Studies of iridoid glycosides using liquid chromatography/electrospray ionization tandem mass spectrometry

Fragmentation pathways of five iridoid glycosides have been studied by using electrospray ionization multi-stage tandem mass spectrometry (ESI-MS(n)). The first-stage MS data of the five iridoid glycosides were compared. The MS spectra showed that the adduct ions of iridoid glycosides and the formate anion were diagnostic ions to distinguish iridoid glycosides with a carboxyl group at the C-4 position or an ester group at the C-4 position. The MS fragmentation pathways of the five iridoid glycosides were also studied. Analyzing the product ion spectra of iridoid glycosides, some neutral losses were observed, such as H(2)O, CO(2) and glucose residues, which were very useful for the identification of the functional groups in the structures of iridoid glycosides. Furthermore, specific loss of one molecule of methyl 3-oxopropanoate or 3-oxopropanic acid was firstly discussed, which corresponded to the isomerization of the hemiacetal group in the structure of iridoid aglycone. According to the fragmentation mechanisms and HPLC/MS(n) data, the structures of five iridoid glycosides in a crude extract of Gardenia jasminoisdes fruit have been identified. Three compounds were compared with standards and the other two were identified as shanzhiside and genipin gentibioside by their MS(n) data without standard compounds. In order to further validate the veracity of the deduction, genipin gentiobioside was isolated from the extract of Gardenia jasminoisdes fruit using Purification Factory and was further identified by C- and H-NMR.     

Identification of flavonoids and their glycosides by high-performance liquid chromatography with electrospray ionization mass spectrometry and with diode array ultraviolet detection

Identification of flavonoids and flavonoid glycosides was carried out on Psidium guajava Linn leaves by means of high-performance liquid chromatography ultraviolet (HPLC-UV) analysis and HPLC mass spectrometry. By using HPLC-UV, two known phenolics (gallic acid and quercetin) and five newly reported ones (procatechuic acid, chlorogenic acid, caffeic acid, kaempferol and ferulic acid) were identified in alcohol guava leaf extract. Structural information about the compounds was obtained from the retention times, the UV spectra and mass spectra without the need to isolate the individual compounds. Two flavonoids (quercetin and kaempferol) and four flavonoid glycosides (three known components, quercetin 3-O-alpha-L-arabinoside, quercetin 3-O-beta-D-glucoside and quercetin 3-O-beta-D-galactoside, along with one novel compound, kaempferol-glycoside) and three other unknown compounds have been identified in the fractions.