Acylated pelargonidin glycosides in the red-purple flowers of Pharbitis nil.

Four acylated pelargonidin glycosides and pelargonidin 3-sophoroside-5-glucoside were isolated from 23 red-purple cultivars of Pharbitis nil. The acylated anthocyanins were all based on pelargonidin 3-sophoroside-5-glucoside and were identified as the 3-O-[2-O-(beta-D-glucopyranosyl)-6-O-(trans-caffeyl)-beta-D- glucopyranoside]-5-O-(beta-D-glucopyranoside), the 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta- D-glucopyranosyl)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), the 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta- D-glucopyranosyl)-6-O-(trans-caffeyl)-beta-D-glucopyranoside]-5-O-(beta- D-glucopyranoside); and the 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D- glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-3-O-(beta-D- glucopyranosyl)caffeyl)- beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranoside]-5-O-(beta-D- glucopyranoside). By the analysis of these anthocyanin constituents variously in 23 cultivars, it was found that the red flower colour gradually changed into more bluish colour with increasing numbers of caffeic acid residues in the acylated pelargonidin glycosides. The stabilities of these anthocyanins increased in the order of increasing caffeyl substitution.     

Triacylated cyanidin 3-(3X-glucosylsambubioside)-5-glucosides from the flowers of Malcolmia maritima

Three acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucosides (1-3) and one non-acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucoside (4) were isolated from the purple-violet or violet flowers and purple stems of Malcolmia maritima (L.) R. Br (the Cruciferae), and their structures were determined by chemical and spectroscopic methods. In the flowers of this plant, pigment 1 was determined to be cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-6-O-(trans-p-coumaroyl)-beta-D-glucopyranoside]-5-O-[6-O-(malonyl)-(beta-D-glucopyranoside) as a major pigment, and a minor pigment 2 was determined to be the cis-p-coumaroyl isomer of pigment 1. In the stems, pigment 3 was determined to be cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-6-O-(trans-p-coumaroyl)-beta-d-glucopyranoside]-5-O-(beta-D-glucopyranoside) as a major anthocyanin, and also a non-acylated anthocyanin, cyanidin 3-O-[2-O-(3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside) was determined to be a minor pigment (pigment 4). In this study, it was established that the acylation-enzymes of malonic acid has important roles for the acylation of 5-glucose residues of these anthocyanins in the flower-tissues of M. maritima; however, the similar enzymatic reactions seemed to be inhibited or lacking in the stem-tissues.     

Acylated delphinidin 3-rutinoside-5-glucosides in the flowers of Petunia reitzii

Two acylated anthocyanins were isolated from selected individuals of Petunia reitzii, and identified to be delphinidin 3-O-[6-O-(4-O-(4-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-tr ans-p-coumaroyl)-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside]- 5-O-[beta-D-glucopyranoside] and delphinidin 3-O-[6-O-(4-O-(4-O-(beta-D-glucopyranosyl)-trans-p-coumaroyl)-alph a-L-rhamnopyranosyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside ]. Nine known anthocyanins were also identified.     

Oligosaccharide polyester and triterpenoid saponins from the roots of Polygala japonica

An oligosaccharide polyester, 1-O-(E)-p-coumaroyl-(3-O-benzoyl)-beta-D-fructofuranosyl-(2-->1)-[6-O-(E)-feruloyl-beta-D-glucopyranosyl-(1-->2)]-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)-(4-O-acetyl)-beta-D-glucopyranosyl-(1-->3)]-4-O-[4-O-alpha-L-rhamnopyranosyl-(E)-p-coumaroyl]-alpha-D-glucopyranoside (polygalajaponicose I), and four triterpenoid saponins, 3beta, 23, 27-trihydroxy-29-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-olean-12-en-28-oic acid (polygalasaponin XLVII), 3-O-beta-D-glucopyranosyl presenegenin 28-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (polygalasaponin XLVIII), 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl-(1-->5)-beta-D-apiofuranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester (polygalasaponin XLIX) and 2beta, 27-dihydroxy-3-O-beta-D-glucopyranosyl 11-oxo-olean-12-en-23, 28-dioic acid 28-O-beta-D-galactopyranosyl-(1-->5)-beta-D-apiofuranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (polygalasaponin L), in addition to five known compounds have been isolated from the roots of Polygala japonica.     

Absorption of acylated anthocyanins in rats and humans after ingesting an extract of Ipomoea batatas purple sweet potato tuber

We evaluated the absorbability of anthocyanins in humans and rats administered with a beverage prepared from an extract of the tuber of purple sweet potato (Ipomoea batatas Cultivar Ayamurasaki), or with an anthocyanin concentrate. Two major anthocyanin components, cyanidin 3-O-(2-O-(6-O-(E)-caffeoyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside)-5-O-beta-D-glucopyranoside) and peonidin 3-O-(2-O-(6-O-(E)-caffeoyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside)-5-O-beta-D-glucopyranoside), were detected in the plasma and urine of both rats and humans by HPLC or liquid chromatography/mass spectrometry (LC/MS). The plasma concentration of anthocyanins in humans reached a maximum 90 minutes after ingestion, and the recovery of anthocyanins in the urine was estimated as 0.01-0.03%. These results indicate that acylated anthocyanins could be selectively absorbed after ingesting food.     

6-Hydroxypelargonidin glycosides in the orange-red flowers of Alstroemeria

Two 6-hydroxypelargonidin glycosides were isolated from the orange-red flowers of Alstroemeria cultivars, and determined to be 6-hydroxypelargonidin 3-O-(beta-D-glucopyranoside) and 3-O-[6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside], respectively, by chemical and spectroscopic methods. In addition, five known anthocyanidin glycosides, 6-hydroxycyanidin 3-malonylglucoside, 6-hydroxycyanidin 3-rutinoside, cyanidin 3-malonylglucoside, cyanidin 3-rutinoside and pelargonidin 3-rutinoside were identified in the flowers.     

Steroidal saponins from the fruits of Asparagus racemosus

Three steroidal saponins, racemosides A (1), B (2) and C (3), were isolated from the methanolic extract of the fruits of Asparagus racemosus, and characterized as (25S)-5beta-spirostan-3beta-ol-3-O-{beta-D- glucopyranosyl (1-->6)-[alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->4)]-beta-D-glucopyranoside}, (25S)-5beta-spirostan-3beta-ol-3-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside and (25S)-5beta-spirostan-3beta-ol-3-O-{alpha-L-rhamnopyranosyl-(1-->6)-[alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside}, respectively, by spectrometric analysis and some chemical strategies.     

Bioactive flavonoids and saponins from Climacoptera obtusifolia

Two bidesmosidic saponins were isolated from Climacoptera obtusifolia (Chenopodiaceae) and their structures were determined as gypsogenin 3-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside]-28-O-{beta-D-glucopyranosyl} ester (1) and hederagenin 3-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside]-28-O-[beta-D-glucopyranosyl} ester (2), by spectroscopic methods. Two known compounds, isorhamnetin 3-O-beta-D-glucopyranoside (3), and isorhamnetin 3-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (4) were also isolated for the first time from this plant. Compounds 1-4 were tested in various immunomodulatory assays. Compound 2 suppressed (92%) the reactive oxygen species (ROS) production on mononuclear cells in luminol-based chemiluminescence (CL) assay at a higher concentration (50 microg/mL). Compounds 3 and 4 demonstrated a strong inhibition on ROS production in the oxidative burst activity of whole blood, neutrophils, and mononuclear cells. Additionally compounds 3 and 4 also suppressed PHA T-cell proliferation with no cytotoxic effects.     

Acylated flavonol glycosides as probing stimulants of a bean aphid,Megoura crassicauda,from Vicia angustifolia

A bean aphid, Megoura crassicauda, which feeds selectively on the plant genus Vicia (Fabaceae), was found to be stimulated to probe an extract solution of the host plant, narrowleaf vetch, Vicia angustifolia L., depositing characteristic stylet sheaths on a parafilm membrane. Two acylated flavonol glycosides were isolated as the specific probing stimulants from the extracts and characterized as quercetin 3-O-alpha-L-arabinopyranosyl-(1-->6)-[2"-O-(E)-p-coumaroyl]-beta-D-glucopyranoside and quercetin 3-O-alpha-L-arabinopyranosyl-(1-->6)-[2"-O-(E)-p-coumaroyl]-beta-D-galactopyranoside. A mixture of these compounds in the same equivalency strongly induced the probing response from M. crassicauda, suggesting their kairomonal roles during host recognition.     

Steroidal saponins from the rhizomes of Smilax sieboldii.

Six new steroidal saponins were isolated from the rhizomes of Smilax sieboldii. Their structures were determined by spectroscopic analysis and hydrolysis to be 3 beta-hydroxy-(25R)-5 alpha-spirostan-6-one (laxogenin) 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl-(1- ---6)]-beta-D-glucopyranoside, laxogenin 3-O-alpha-L-arabinopyranosyl-(1----6)-beta-D-glucopyranoside, 3 beta,27-dihydroxy-(25S)-5 alpha-spirostan-6-one 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl-(1- ---6)]- beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-3 beta,22 xi,26-trihydroxy-(25R)-5 alpha-furostan-6-one 3-O-alpha-L-arabinopyranosyl-(1----6)-beta-D-glucopyranoside, 26-O-beta-D-glucopyranosyl-3 beta,22 xi,26-trihydroxy-(25R)-5 alpha-furostan-6- one 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl-(1- ---6)]- beta-D-glucopyranoside and (25R)-5 alpha-spirostan-3 beta-ol (tigogenin) 3-O-beta-D-glucopyranosyl-(1----4)-O-[alpha-L-arabinopyranosyl- (1----6)]-beta-D-glucopyranoside. The inhibition of cAMP phosphodiesterase by the saponins was evaluated.     

Steroidal glycosides from the bulbs of Lilium dauricum.

The bulbs of Lilium dauricum yielded 11 compounds, including six new steroidal glycosides. The structures have been determined by spectral analysis and hydrolysis to be (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L-arabinopyranosyl-( 1----3)]- beta-D-glucopyranoside, (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside, (25R)-spirost-5-en-3 beta-ol (diosgenin) 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L-arabinopyranosyl- (1----3)]-beta-D-glucopyranoside, (25R)-3 beta,17 alpha-dihydroxy-5 alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside, (25R)-3 beta, 17 alpha-dihydroxy-5 alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L- arabinopyranosyl-(1----3)]-beta-D-glucopyranoside and (20R,22R)-3 beta,20,22-trihydroxy-5 alpha-cholestan-6-one (tenuifoliol) 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside. The absolute configurations of C-20 and C-22 of tenuifoliol were further confirmed by detailed analysis of the NOE difference spectrum of the corresponding isopropylidene derivative. Several known compounds were also isolated and identified.     

Phenolic glycosides from Kaempferia parviflora

Three phenolic glycosides were isolated together with two known flavonol glycosides from the H2O-soluble fraction of rhizomes of Kaempferia parviflora. Their structures were determined to be rel-(5aS,10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]indeno[1,2-d]furan-6-one 5a-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-d-glucopyranoside] (1), its rel-5aS,10bR isomer (2), and (2R,3S,4S)-3-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-d-glucopyranosyl]-3'-O-methyl-ent-epicatechin-(2alpha-->O-->3,4alpha-->4)-(5aS,10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]indeno[1,2-d]furan-6-one 5a-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside] (3). The structures were elucidated on the basis of analyses of chemical and spectroscopic evidence.     

Chemistry and antioxidative factors in rosemary and sage

Rosemary and sage are common spices used in food. In our recent search of cancer chemopreventive agents from spices, the alcohol extracts of rosemary and sage showed strong antumorigenic activities. Rosemary and sage extracts contain active antioxidative factors such as phenolic diterpenes, flavonoids and phenolic acids. Here we discuss chromatographic methods used to separate and purify compounds from these spices and MS and NMR spectrometry to identify the isolated compounds. Several new compounds isolated from sage were determined to be 6-O-caffeoyl-beta-D-fructofuranosyl-(2-->1)-beta-glucopyranoside, 1-O-caffeoyl-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, 1-O-p-hydroxybenzoyl-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, 1-O-(3-methyl-2,3,4-trihydroxybutyl)-6-O-feruloyl-beta-D-glucopyranoside, 4-hydroxyacetophenone 4-O-[5-O-(3,5-dimethoxy-4-hydroxybenzoyl)-beta-D-apiofrunosyl]-(1-->2)-beta-D-glucopyranoside and 1-O-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-6-O-trans-caffeoyl-beta-D-glucopyranoside.     

Acylated anthocyanins from the violet-blue flowers of Orychophragonus violaceus

Three acylated cyanidin 3-sambubioside-5-glucosides (1-3) were isolated from the violet-blue flowers of Orychophragonus violaceus, and their structures were determined by chemical and spectroscopic methods. Two of those acylated anthocyanins (1 and 3) were cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-xylopyranosyl)-6-O-(4-O-(beta-D-glucopyranosyl)-trans-acyl)-beta-D-glucopyranoside]-5-O-(6-O-malonyl-beta-D-glucopyranoside)s, in which the acyl groups were p-coumaric acid for 1, and sinapic acid for 3, respectively. The last anthocyanin 2 was cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-xylopyranosyl)-6-O-(4-O-(beta-D-glucopyranosyl)-trans-feruloyl)-beta-D-glucopyranoside]-5-O-beta-D-glucopyranoside. In these flowers, the anthocyanins 2 and 3 were present as dominant pigments, and 1 was obtained in rather small amounts.     

Acylated peonidin glycosides from duskish mutant flowers of Ipomoea nil

Five acylated peonidin glycosides were isolated from the pale gray-purple flowers of a duskish mutant in the Japanese morning glory (Ipomoea nil or Pharbitis nil) as major pigments, along with a known anthocyanin, Heavenly Blue Anthocyanin (HBA). Three of these were based on peonidin 3-sophoroside and two on peonidin 3-sophoroside-5-glucoside as their deacylanthocyanins; both deacylanthocyanins were acylated with caffeic acid and/or glucosylcaffeic acids. By spectroscopic and chemical methods, the structures of the former three pigments were determined to be 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-beta-D-glucopyranoside], 3-O-[2-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-glucopyranoside], and 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside] of peonidin. The structures of the latter two pigments were also confirmed as 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-beta-D-glucopyranoside]-5-O-beta-D-glucopyranoside, and 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside]-5-O-beta-D-glucopyranoside of peonidin. The mutation affecting glycosylation and acylation in anthocyanin biosynthesis of Japanese morning glory was discussed.     

Glucuronide triterpene saponins from Bersama engleriana

Five 3-O-glucuronide triterpene saponins (1-5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-betulinic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl]-oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-xylopyranosyl-(1-->6)-beta-d-glucopyranosyl]-oleanolic acid (3), 3-O-[beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl]-oleanolic acid (4), and 3-O-[beta-d-glucopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-d-xylopyranosyl-(1-->6)-beta-D-glucopyranosyl]-oleanolic acid (5).     

Newbouldiosides A-C, phenylethanoid glycosides from the stem bark of Newbouldia laevis

From the stem bark of Newbouldia laevis three phenylethanoid glycosides, designated as newbouldioside A-C, were isolated together with a sodium salt of analogue B and the known compounds, verbascoside, 5-hydroxydehydro-iso-alpha-lapachone, 3,8-dihydroxydehydro-iso-alpha-lapachone, apigenin and luteolin. The structures of the phenylethanoid glycosides were elucidated by spectroscopic methods as beta-(3,4-dihydroxyphenyl)ethyl 5-O-syringoyl-beta-D-apiofuranosyloxy-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->3)]-beta-D-glucopyranoside, ss-(3,4-dihydroxyphenyl)ethyl 5-O-syringoyl-beta-D-apiofuranosyloxy-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->3)]-6-O-E-feruloyl-beta-D-glucopyranoside, and beta-(3,4-dihydroxyphenyl)ethyl 3-O-E-feruloyl-beta-D-apiofuranosyloxy-(1-->2)-O-alpha-L-rhamnopyranosyl-(1-->2)-6-O-E-sinapoyl-beta-D-glucopyranoside, respectively.     

Triterpenoid saponins from the fruits and galls of Sapindus mukorossi

Six saponins, sapinmusaponin K (1) [hederagenin-3-O-(3-O-acetyl-alpha-L-arabinopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], sapinmusaponin L (2) [hederagenin-3-O-(4-O-acetyl-alpha-L-arabinopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabino-pyranoside], sapinmusaponin M (3) [hederagenin-3-O-(2,3-O-diacetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], sapinmusaponin N (4) [hederagenin-3-O-(2,4-O-diacetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], sapinmusaponin O (5) [3,7,20(S)-trihydroxydammar-24-ene-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside], and sapinmusaponin P (6) [3,7,20(R)-trihydroxydammar-24-ene-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-d-glucopyranoside], along with seven known saponins (7-13), were isolated from fruits and the galls of Sapindus mukorossi. Their structures were elucidated by 1D and 2D NMR spectroscopic techniques and acid hydrolysis. Biological evaluation indicated that saponins 1-4 and 7-13 showed moderate cytotoxicity against several human tumor cell lines.     

Three acylated flavone glycosides from Sideritis ozturkii Aytac & Aksoy

From the aerial parts of Sideritis ozturkii, three new flavonoids, chrysoeriol 7-O-[2'-O-caffeoyl-O-acetyl-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside], chrysoeriol 7-O[2'-O-caffeoyl-beta-D-glucopyranosyl-(1 -->2)-beta-D-glucopyranoside] and chrysoeriol 7-O[2'-O-p-coumaroyl-6'-beta-O-acetyl-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside] named as ozturkosides A, B and C, respectively, were isolated, along with three known phenylethanoid glycosides, verbascoside, leucoseptoside A, martynoside and five known diterpenoids, 7-epicandicandiol, linearol, sidol, sideroxol, epoxyisolinearol. The structures were elucidated mainly by spectroscopic methods.     

Acylated anthocyanins from the blue-violet flowers of Anemone coronaria

Five polyacylated anthocyanins were isolated from blue-violet flowers of Anemone coronaria 'St. Brigid'. They were identified as delphinidin 3-O-[2-O-(2-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(malonyl)-beta-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-beta-D-glucopyranoside]-3'-O-[beta-D-glucuronopyranoside], and its demalonylated form, delphinidin 3-O-[2-O-(2-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(2-O-tartaryl)malonyl)-beta-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-beta-D-glucopyranoside]-3'-O-[beta-D-glucuronopyranoside], and its cyanidin analog as well as delphinidin 3-O-[2-O-(2-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(2-O-(tartaryl)malonyl)-beta-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-beta-D-glucopyranoside].