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Flavonoids from the root and stem of Sophora tomentos
Abstract
From the root and the stem of Sophora tomentosa, five new flavonoids, tomentosanols A-E, were isolated in addition to 15 known flavonoids. The structures were determined by spectral analysis including 2D-NMR techniques.
... This was confirmed by HMBC correlations between H-10 (1.79 ppm) and C-3 (122.9 ppm), C-4 (135.5 ppm) and C-5 (40.2 ppm) on one hand, and between H-8 and H-9 and the similar carbons C-6 (125.1 ppm) and C-7 (131.6 ppm) on the other ( Figure 2). The 13 C NMR spectrum displayed characteristic signals of a kaempferol derivative at δ C 138.2 (C-3), 156.0 (C-5), 131.1 (C-2 /C-6 ), 115.4 (C-3 /C-5 ), and 163.0 (C-7) [36,37]. The HMBC correlation from H-6 (6.74 ppm) and the aromatic carbons at 156.0 (C-5), 163.0 (C-7) and 113.0 (C-8) allowed us to suggest that the geranyl was located at position 8. ...
... This was further confirmed by the HMBC correlation between proton H-2 (3.38 ppm) and carbons at 113.0 (C-8), 163.0 (C-7), and 158.6 (C-8a). All of these data were superimposable on those of isomacarangin (6) [36]. Careful examination of the remaining signals of 1 H and 13 163.0 ...
... This is the case for β-sitosterol (1), stigmasterol (2), and β-sitosterol-3-O-β-D-glucopyranoside (3) isolated from M. magna [14]; lupeol (4), evidenced from M. balansae [16]; schweinfurthins O and B (9 and 10), previously found in M. tanarius, and M. schweinfurthii [8,19]. Isomacarangin (6) was found in M. barteri [6] and M. schweinfurthii [36]; kaempferol (7) and quercetin (8) were isolated from M. indica [18]; ellagic acid (11) was found in M. barteri [11]. Nevertheless, this work reports, for the first time, the isolation of the glycosylated flavonoid apigenin-7-O-β-D-glycoside (5) from the Macaranga genus. ...
Citation: Kamso, V.F.K.; Simo Fotso, C.C.; Kanko Mbekou, I.M.; Tousssie, B.T.; Ndjakou Lenta, B.; Boyom, F.F.; Sewald, N.; Frese, M.; Ngadjui, B.T.; Wabo Fotso, G. Chemical Constituents of Macaranga occidentalis, Antimicrobial and Chemophenetic Studies. Molecules 2022, 27, 8820.
... Tanaka et al., 1997 leachianone A, ophoraflavanones G,H and I, miyabenol C, α-viniferin, ε-viniferin, davidols A-C (stilbene oligomers) ...
... Tanaka et al., 1997 flavonol tetraglycoside S. japonica Seeds Wang et al., 2003 sophorabioside, sophoraflavonoloside, genistein 7,4'-di-O-β-D- glucopyranoside S. japonica Seeds Watanabe et al., 1993 1,6-di-O-β-D-glucose S. japonica Seeds Kashiwada et al., 1988 isoscutellarein S. japonica Seeds Terashina et al., 1991 sissotrin, tectoridin S. japonica Seeds Xu et al., 1999 7-O-α-L-rhamnopyranoside S. japonica Seeds Liu et al., 1994. sophororicoside S. japonica Seeds Wang et al., 2003. ...
... S. tomentosa Root Tanaka et al., 1997 ...
Sophora is a genus of the Fabaceae family, contains about 52 species, nineteen varieties, and seven forms that are widely distributed in Asia, Oceanica, and the Pacific islands, in the family Fabaceae of herbaceous (Sophora flavescens Aiton) to trees (Sophora japonica L.). More than fifteen species in this genus have a long history of use in traditional Chinese medicines. In the last decades the use of this genus in traditional Chinese drugs has led to rapid increase in the information available on active components and reported to posses various pharmacological/ therapeutic properties. The paper reviews the ethnopharmacology, the biological activities and the correlated chemical compounds of genus Sophora, Fabaceae. More than 300 compounds has been isolated, among them major are quinolizidine alkaloids particularly matrine and oxymatrine and flavonoids particularly prenylated and isoprenylated flavonoids. Modern pharmacological studies and clinical studies demonstrated that these chemical constituens possess wide reaching pharmacological actions like anti oxidant, anticancer, anti-asthamatic, anti-neoplastic, antimicrobial, antiviral, antidote, anti pyretic, cardiotonic, antinflammatory, diuretic and in the treatment of skin diseases like eczema, colitis and psoriasis.
... With the exception of compounds 12 and 13, all known compounds were isolated for the first time from D. melanoxylon. For tomentosanol B (9) so far only the planar structure based on 1 H NMR data was described [18]. Herein we report its 13 C ( Table 2) and 2D NMR data ( Figures S9_3 and S9_4, Table S9). ...
... The substitution at C-8 is further supported by the chemical shift of the H-bonded OH at position 5 (δ H 12.21), which is shifted downfield to 12.41-12.43 ppm in compounds 2-4 bearing a prenyl chain at C-6 [18,46]. Hence, compound 6 was characterized as (Z)-2 ,4 ,5,7-tetrahydroxyl-8-(3,7-dimethylocta-2,6-dienyl)-isoflavanone. ...
Dalbergia melanoxylon Guill. & Perr (Fabaceae) is widely utilized in the traditional medicine of East Africa, showing effects against a variety of ailments including microbial infections. Phytochemical investigation of the root bark led to the isolation of six previously undescribed prenylated isoflavanones together with eight known secondary metabolites comprising isoflavanoids, neoflavones and an alkyl hydroxylcinnamate. Structures were elucidated based on HR-ESI-MS, 1- and 2-D NMR and ECD spectra. The crude extract and the isolated compounds of D. melanoxylon were tested for their antibacterial, antifungal, anthelmintic and cytotoxic properties, applying established model organisms non-pathogenic to humans. The crude extract exhibited significant antibacterial activity against Gram-positive Bacillus subtilis (97% inhibition at 50 μg/mL) and antifungal activity against the phytopathogens Phytophthora infestans, Botrytis cinerea and Septoria tritici (96, 89 and 73% at 125 μg/mL, respectively). Among the pure compounds tested, kenusanone H and (3R)-tomentosanol B exhibited, in a panel of partially human pathogenic bacteria and fungi, promising antibacterial activity against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and Mycobacterium showing MIC values between 0.8 and 6.2 μg/mL. The observed biological effects support the traditional use of D. melanoxylon and warrant detailed investigations of its prenylated isoflavanones as antibacterial lead compounds.
... Yields of compounds 1 and 2 were found to be 0.027% and 0.033% of dry weight of plant material respectively. The compounds were authenticated by comparing their spectral data with that available in the literature (Wollenweber et al., 2003;Tanaka et al., 1997). The structures of these compounds are given in Fig. 1. ...
The immunomodulatory activities of two isoflavones, 5,7-dihydroxy-6,4'-dimethoxyisoflavone (irisolidone) (1) and 5,4'-dihydroxy-6,7-methylenedioxyisoflavone (irilone) (2) isolated from Iris germanica (Iridaceae) is reported. Their influence on production of T-lymphocytes (CD4+ and CD8+ cells) and T-cell cytokines, namely Th1: IL-2, IFN-gamma and Th2: IL-4 and IL-5 in a dose-dependent manner was studied by flow cytometric method in Balb/c mice. Oral administration of drugs at doses of 0.1-0.8 mg/kg per oral dose showed 1 to possess stimulatory activity on T-cells and Th1 cytokine production, while as 2 acted as an immunosuppressant for both cells and cytokines. The methylated products of 1 and 2 showed a similar trend to that of their parent compounds but their activity was drastically decreased revealing the importance of free phenolic groups for their immunomodulating activities.
In the ongoing investigation of bioactive compounds from the roots of Sophora flavescens, six prenylflavanones, including two new ones, sophoraflavanones M (1) and N (2), were isolated. The structures of the new compounds were elucidated on the basis of their spectroscopic data. In addition, compound 5 exhibited moderate anti-influenza virus activity, with EC50 value of 43.9 μM.
Twenty-seven compounds, including a new diarypropane and two new lignans were isolated from the twigs and leaves of Endocomia macrocoma. Their structures were elucidated by spectroscopic analysis. Cytotoxicity evaluation of the new compounds against five human tumor lines showed no inhibitory effects.
Two new isoflavanones, erybrucein A and B (1, 2), together with nineteen known compounds are reported herein from the stem and root bark of the Ethiopian medicinal plant, Erythrina brucei. All known compounds, except erythraline (19), have been isolated for the first time from E. brucei. Their structures were established on the basis of extensive spectroscopic and spectrometric analyses (1D and 2D NMR, CD, IR and ESI-HRMS n) and confirmed by comparison with reported-and DFT-calculated data. The absolute configuration of kenusanone F (3) and the 7-methyl ether (4) were determined in the same way. Antibacterial properties as well as DPPH radical scavenging activities of the new isoflavanones and selected known compounds were evaluated. Although most tested compounds showed weak activity against the tested organisms, erybrucein B (2) showed moderate activity (MIC = 0.062 mg/mL) against Bacillus cereus. In the DPPH radical scavenging assays, compounds 1, 2, and 3 showed moderate activity whereas two other compounds showed high activity.
Seventy-five compounds, including 21 new compounds (1-21), were isolated from the root bark of Cudrania tricuspidata. The structures of the isolated compounds were elucidated by interpretation of their spectroscopic data. All isolated compounds were evaluated for their neuroprotective effects against 6-hydroxydopamine (6-OHDA)-induced cell death, and nine compounds had activities with EC50 values of 1.9-30.2 μM. The 75 isolated compounds along with 34 previously reported xanthones were tested also for neuroprotective effects against the 1-methyl-4-phenylpyridinium ion (MPP(+)) and oxygen glucose deprivation (OGD)-induced cell death. Three compounds were active against MPP(+)-induced cell death with EC50 values of 0.2-10.3 μM, and 23 compounds were active in the OGD model with EC50 values of 2.9-35.5 μM.
Two new flavanones, puguflavanone A [5,4′-dihydroxy-6-(1″, 1″-dimethylprop-2-enyl)-2‴,2‴-dimethylpyrano-(5‴, 6‴:7,8)flavanone] (1) and puguflavanone B [5,7,4′-trihydroxy-6- (1″,1″-dimethylprop-2-enyl)-8-(3-methylbut-2-enyl)flavanone] (2) were isolated from the ethyl acetate extract of the root bark of Baphia puguensis, together with four known compounds, erythrisenegalone (3), 3-methoxy-8,9-methylenedioxypterocarpene, alkyl trans-4-hydroxy-3- methoxycinnamate, and stigmasterol. Structures were established using NMR and MS techniques.
Objective: To investigate the flavonoids in the roots of Glycyrrhiza uralensis from Hangjinqi, Inner Mongolia. Methods: The 95% and 70% ethanol extracts from the roots of G. uralensis were separated and purified by column chromatography over silica gel, polyamide, MCI, ODS, Sephadex LH-20, and RP-HPLC. Their chemical structures were identified on the basis of physicochemical characteristics and spectral analyses. Results: Nineteen compounds were isolated and identified as 3-methylkaempherol (1), genistein (2), naringenin (3), licoisoflavone A (4), licoricone (5), isoformononetin (6), semilicoisoflavone B (7), 3'-isoprenylgenistein (8), lupiwighteone (9), licoflavonol (10), topazolin (11), licoisoflavone B (12), isolicoflavonol(13), gancaonin H (14), glyasperin A (15), licoricidin (16), glyasperin D (17), orobol (18), and 7-methyl-luteone (19). Conclusion: Compounds 1, 6, 8, 18, and 19 are isolated from the genus Glycyrrhiza Linn. and compounds 2-4, 12, 14, and 15 are isolated from this plant for the first time.
Sophora pachycarpa Schrenk ex C.A.Mey. belongs to the family Fabaceae. Some species of the genus Sophora have shown to possess anti-proliferative and apoptosis-inducing activities in cancer cells. However, there is no available information addressing this effect in S. pachycarpa. Here, we investigated the cytotoxic effects of methanol extract and different fractions obtained from S. pachycarpa root on different cancer cell lines including A549, HeLa, HL-60, MCF-7, and PC3 cell lines and leukocytes as non-malignant cells. Apoptotic cells were determined using PI staining of DNA fragmentation by flow cytometry (sub-G1 peak). S. pachycarpa inhibited the growth of malignant cells in a dose-dependent manner. CH2Cl2 and EtOAc fractions showed the lowest IC50 values ranging from 6 to 50 μg/mL in various cancer cell lines. HeLa cells as the most sensitive cells were chosen for further mechanistic studies. The sub-G1 peak in flow cytometry histogram of S. pachycarpa treated HeLa cells indicates apoptotic cell death in S. pachycarpa-induced toxicity. In conclusion, S. pachycarpa exerts cytotoxic effects in different cancer cell lines in which apoptosis plays an important role. Thus, S. pachycarpa could be considered as a potential chemotherapeutic agent in cancer treatment.
8-Prenylnaringenin (8PN) is a naturally occurring bioactive chiral prenylflavonoid found most commonly in the female flowers of hops (Humulus lupulus L.). A stereospecific method of analysis for 8PN in biological fluids is necessary to study the pharmacokinetic disposition of each enantiomer. A novel and simple liquid chromatographic-electrospray ionization-mass spectrometry (LC-ESI-MS) method was developed for the simultaneous determination of R- and S-8PN in rat serum and urine. Carbamazepine was used as the internal standard (IS). Enantiomeric resolution of 8PN was achieved on a Chiralpak(®) AD-RH column with an isocratic mobile phase consisting of 2-propanol and 10 mM ammonium formate (pH 8.5) (40:60, v/v) and a flow rate of 0.7 mL/min. Detection was achieved using negative selective ion monitoring (SIM) of 8PN at m/z 339.15 for both enantiomers and positive SIM m/z at 237.15 for the IS. The calibration curves for urine were linear over a range of 0.01-75 µg/mL and 0.05-75 µg/mL for serum with a limit of quantification of 0.05 µg/mL in serum and 0.01 µg/mL in urine. The method was successfully validated showing that it was sensitive, reproducible, and accurate for enantiospecific quantification of 8PN in biological matrices. The assay was successfully applied to a preliminary study of 8PN enantiomers in rat. Chirality 00:000-000, 2014. © 2014 Wiley Periodicals, Inc.
New potential treatments for disseminated fungal infections are needed, especially for infections caused by the commonly drug-resistant pathogens Candida albicans and C. glabrata. These pathogens cause systemic candidiasis, a significant cause of mortality in immune-compromised patients. ABC transporters of the pleiotropic drug resistance subfamily, such as Cdr1p of C. albicans, play an important role in antifungal resistance and are potential bioassay targets for antifungal therapies against drug-resistant pathogens. We observed strong antifungal growth inhibitory activity in the methanol extract of Dalea formosa roots. This extract afforded six new isoflavonoids, sedonans A-F (1-6), a new but-2-enolide, 4'-O-methylpuerol A (7), and the new pterocarpan ent-sandwicensin (8). The structures and absolute configurations of these compounds were assigned using spectroscopic and chiroptical techniques. The direct antifungal activity of 1 against C. glabrata (MIC = 20 μM) was higher than that of fluconazole. Sedonans A-F and ent-sandwicensin were also active against Saccharomyces cerevisiae strains that express differing ABC transporter-associated resistance mechanisms but differed in their susceptibility to Cdr1p-mediated detoxification. A sedonan A (1)/ent-sandwicensin (8) combination exhibited synergistic growth inhibition. The results demonstrate that multiple crude extract compounds are differentially affected by efflux-mediated resistance and are collectively responsible for the observed bioactivity.
Seven known compounds including three prenylated flavonoids (sophoraisoflavanone A, sophoraflavanone G, and 3′-isoprenylgenistein), two flavonostilbenes (alopecurone A and alopecurone B), in addition to two steroid glucosides (sitosterol 3-O.-glucoside and stigmasterol 3-O.-glucoside), were isolated using silica gel column chromatography and preparative thin layer chromatography from the roots of Sophora pachycarpa. C. A. Mey. (Papilionaceae) for the first time. The structures were characterized by 1D and 2D NMR experiments.
Prenylated flavonoids and isoflavonoids are widely distributed throughout the plant kingdom, with many biological effects. Psoralea corylifolia, which contains many kinds of prenylated components, has been widely used as a medicinal plant in Asia and India for thousands of years. The goal of this study was to characterize the components in P. corylifolia using a liquid chromatography with diode-array detection and quadrupole time-of-flight mass spectrometry (LC-DAD/Q-TOF-MS) method, and to elucidate the fragmentation behavior of the different prenyl substituent groups and their appropriate characteristic pathways in positive ion mode.
The calculated accurate masses of the protonated molecules, the fragment ions, the retention behavior, and the data from UV spectra were used for identification of the components in P. corylifolia.
A total of 45 compounds, including 43 prenylated components, were identified or tentatively identified in P. corylifolia. Different diagnostic fragment ions and neutral losses were observed in different prenyl substructures: neutral loss of 56 Da (C(4) H(8) ) and a fragment ion at m/z 69 (C(5) H(9) (+) ) were generated by a prenyl chain; neutral losses of 42 Da (C(3) H(6) ), 54 Da (C(4) H(6) ), 15 Da (CH(3) •) and 16 Da (CH(4) ) were observed in a ring-closed prenyl group; neutral losses of 72 Da (C(4) H(8) O), 60 Da (C(2) H(4) O(2) ), 58 Da (C(3) H(6) O) and 18 Da (H(2) O) were detected in a 2,2-dimethyl-3,4-dihydroxydihydropyran ring; neutral losses of 72 Da (C(4) H(8) O), 60 Da (C(3) H(8) O) and 18 Da (H(2) O) were yielded from a 2,2-dimethyl-3-hydroxydihydropyran ring, a 2-(1-hydroxy-1-methylethyl)dihydrofuran ring or a 1-hydroxy-3-methylbut-3-enyl chain.
This method can be applied for analysis of prenylated components in P. corylifolia and other herbal medicines. Copyright © 2012 John Wiley & Sons, Ltd.
Isoflavonoids are found predominantly in subfamily Papilionoideae of the Leguminosae. This review describes more than 420 new examples of Leguminosae isoflavonoids, giving details of their source, identification, biological activity, synthesis, and ecological or chemosystematic significance. Other topics addressed include the application of hyphenated analytical techniques to the characterisation of legume-derived isoflavonoids, and advances made in biosynthetic studies. A checklist of new compounds by species is given, and 404 references are cited.
In the course of our program to search for protein tyrosine phosphatase 1B (PTPB) inhibitors, five new 5-deoxyflavonoids along with eight known derivatives were isolated from EtOAc layer of the root bark of Erythrina abyssinica. Their structures were elucidated on the basis of spectroscopic (IR, UV, MS, CD, 1D- and 2D-NMR) and physicochemical analyses. All isolates exhibited moderate inhibitory effects on the enzyme assay with IC₅₀ values ranging from 14.9 ± 1.6 to 98.1 ± 11.3 μM. Compounds with prenyl and methoxy groups in the B ring (1, 2, 4, 8, and 13) possessed strong activity (IC(50) 14.9 ± 1.6 to 19.2 ± 1.1 μM), while compounds (3, 5, and 9) with 2,2-dimethylpyrano ring showed less inhibitory effect (IC₅₀ 22.6 ± 2.3 to 72.9 ± 9.7 μM). These results suggest that prenyl and methoxy groups may be responsible for the increase on the activity of 5-deoxyflavonoids against PTP1B, but the presence of 2,2-dimethylpyrano ring on the B ring may be induced the decrease of PTP1B inhibitory activity.
Phytochemical investigation on the root bark of Garcinia edulis (Clusiaceae) gave a new isoprenylated xanthone, 1,4,6-trihydroxy-3-methoxy-2-(3-methyl-2-butenyl)-5-(1,1-dimethyl-prop-2-enyl)xanthone (1), a known xanthone, forbexanthone (2) together with three known pentacyclic triterpenoids, friedelin, lupeol and lupeol acetate. The structure of the new compound was fully characterised by NMR spectroscopic analysis. Compound 1 showed significant anti-HIV-1 protease activity with IC(50) value of 11.3 microg/mL. Furthermore, compound 1 showed potent cytotoxic activity with LC(50) value of 2.36 microg/mL against brine shrimp larva in vitro.
Six new prenylated isoflavanones named sophoronols A-F (1-6), together with eight phenolic constituents, were isolated from the roots of Sophora mollis. Their structures and stereochemistry were established by 1D and 2D NMR techniques, especially HMBC and NOESY as well as CD results. Componds 3 and 5 exhibited moderate anitplasmodial activity against the CQS D10 strain of Plasmodium falciparum, with IC50 values of 12.9 and 12.8 μM, respectively. © 2009 American Chemical Society and American Society of Pharmacognosy.
Phytochemical investigation of the rhizomes of Iris kashmiriana (Iridaceae) led to the isolation of three isoflavones characterized by 1D and 2D NMR, IR, UV, and MS as 4'-hydroxy-8-methoxy-6,7-methylenedioxyisoflavone (isonigricin, 1), 5,6-dihydroxy-4',7-dimethoxyisoflavone (isoirisolidone, 2), and 5,7-dihydroxy-4',6-dimethoxyisoflavone (irisolidone, 3). Compound 1 is a new isoflavone, while 2 is reported for the first time from a natural source.
Covering: January 1998 to December 2000. Previous review: 1998, 15, 631.
Bioassay-guided fractionation of the ethyl acetate extract of the roots of Dalea scandens (Miller) R. Clausen var. paucifolia led to the isolation of new flavonoids, 2( S)-5'-(-1"',1"'-dimethylallyl)-8-(3",3"-dimethylallyl)-2',4',5,7-tetrahydroxyflavanone, 2( S)-5'-(1"',1"'-dimethylallyl)-8-(3",3"-dimethylallyl)-2'-methoxy-4',5,7-trihydroxyflavanone and 5'-(1"',1"'-dimethylallyl)-8-(3",3"-dimethylallyl)-2',4',5,7-tetrahydroxyflavone. Structure elucidation was carried out by spectroscopic methods. All three compounds showed significant activity against both methicillin-susceptible and methicillin-resistant Staphylococcus aureus.
Two prenylated flavonoid derivatives, 5-hydroxy-4'-methoxy-2",2"-dimethylpyrano-(7,8:6",5")flavanone (1) and 5,4'-dihydroxy-[2"-(1-hydroxy-1-methylethyl)dihydrofurano]-(7,8:5",4")flavanone (2), were isolated from an ethyl acetate-soluble extract of the leaves of Macaranga conifera using an in vitro activity-guided fractionation procedure based on the inhibition of cyclooxygenase-2. Also obtained were eight known compounds, 5,7-dihydroxy-4'-methoxy-8-(3-methylbut-2-enyl)flavanone (3), lonchocarpol A (4), sophoraflavanone B (5), 5,7-dihydroxy-4'-methoxy-8-(2-hydroxy-3-methylbut-3-enyl)flavanone (6), tomentosanol D (7), lupinifolinol (8), isolicoflavonol (9), and 20-epibryonolic acid (10). The structures of compounds 1 and 2 were determined using spectroscopic methods. All isolates were tested for their inhibitory effects against both cyclooxygenases-1 and -2, and selected compounds were evaluated in a mouse mammary organ culture assay.
A new flavonoid (1) was isolated from organic extracts of Dalea versicolor, along with six known phenolic compounds (2-7). The structures of the seven compounds were determined by NMR and HRMS methods. These compounds were evaluated for direct activity against a variety of organisms in vitro, including the Gram-positive bacteria Staphylococcus aureus and Bacillus cereus. In addition, the compounds were evaluated for their ability to potentiate the activity of known antimicrobials through inhibition of multidrug-resistance (MDR) pumps. Compounds 1, 2, 4, and 7 exhibited direct or synergistic activity toward the human pathogen S. aureus and the opportunistic pathogen B. cereus. Compounds 4 and 7 were also found to potentiate the activity of berberine and of prescribed antibiotics, with 4 demonstrating a mode of action consistent with inhibition of the NorA MDR efflux pump in S. aureus.
A new isoflavone 5,7,4'-trihydroxy-3'-(3-hydroxy-3-methylbutyl)isoflavone (isowigtheone hydrate) (1), together with six known isoflavones 2-7 and (-)epicatechin, were isolated from the root barks of Brosimum utile. Their structures were established on the basis of spectroscopic evidence. The in vitro cytotoxic activity of the new compound 1 was evaluated against cell lines MCF7 (human breast carcinoma), PC3 (human prostate carcinoma), HT29 (human colon cancer) and human dermis fibroblasts.
Two new benzofuran derivatives [I], mp 235—237°, C15H10O5and [II], mp 179—181°, C16H1205, together with l-maackiain, stigmasterol, medicagol, formononetin and 2',4’,4-trihydroxychalone (isoliquiritigenin) were isolated from the aerial parts of Sophora tomentosa L., and the structures of I and II were established to be 2-(2,4'-dihydroxyphenyl)-5,6-methylenedioxybenzofuran and 2-(2'-hydroxy-4’-methoxyphenyl)-5,6-methylenedioxybenzofuran on the bases of chemical and spectral evidence, respectively. © 1978, The Pharmaceutical Society of Japan. All rights reserved.
By further investigation on the constituents of roots of Echinosophora koreensis, three novel flavanones with a 2',4',6'-trioxygenated B ring were isolated. These structures were determined to be (2R,3R)-8-gamma,gamma-dimethylallyl-6-geranyl-5,7,2',6'-tetrahydroxy-4'-methoxyflavanone (kenusanone C), (2S)-8-gamma,gamma-dimethylallyl-5,7,2',6'-tetrahydroxy-4'-methoxyflavanone (kenusanone D) and (2S)-8-gamma,gamma-dimethylallyl-5,2',6'-trihydroxy-7,4'-dimethoxyflavanone (kenusanone E), respectively, by spectroscopic analysis. The characteristic behaviour of H-2 and H-3 in a 2',6'-dioxygenated flavanone or flavanonol is also discussed.
Two novel flavonoid compounds, tetrapterols A and B, in which a geranyl group is dehydrogenated and isomerized to forma new aromatic ring, were isolated from the roots of Sophora tetraptera (Leguminosae). The structures were established by means of 2D NMR spectroscopy.
Two new isoflavonoids were isolated from the underground part of Echinosophora koreensis Nakai (Leguminosae) and their structures were determined by spectroscopic analysis to be 4',5-dihydroxy-2',7-dimethoxy-5'- (α,α-dimethylallyl)isoflavanone and 2',4'-dimethoxy-3'-(γ, γ-dimethy1allyl)- 3,5,7-trihydroxyisoflavanone. The structure of a known 3-hydroxyflavanone, sophoronol, which was isolated as another component of the plant, should be revised as having a 3-hydroxyisoflavanone skeleton instead of 3-hydroxy- flavanone.
C-6 or C-8 substituted flavanones were determined by methods of chemical and/or 1H-NMR spectral analysis. We report a very convenient method for determining the substituted position of these flavanones using 13C-1H long range coupling. In connection with this study, we revised some structures of flavanones using this technique.
Two novel resveratrol trimers, named leachianols A (1) and B (2), were isolated from the roots of Sophora leachiana. Their structures were determined by spectroscopy using correlation spectroscopy involving long range coupling and nuclear Overhauser effect experiments. The resveratrol trimers 1 and 2, which are formed by characteristic oligomerization via a pallidol (3), are the first naturally occurring oligostilbenes to be reported.
Kanzakiflavone-1 (III), C17H12O7, mp 291-293°, a new flavone, has been isolated from the rhizomes of Iris unguicularis POIR. (Japanese name : Kanzakiayame) together with irigenin (I) and iristectorigenin A (II). The structure of kanzakiflavone-1 (III) has been determined as 5, 8-dihydroxy-4'-methoxy-6, 7-methylenedioxyflavone by chemical and spectral means.
In addition to known phenolic compounds, medicarpin, maackiain, echinoisoflavanone and echinoisosophoranone, a new isoflavanone named kenusanone A was isolated from the roots of Echinosophora koreensis. The structure was determined to be 5′-geranyl-5,7,2′,4′-tetrahydroxyisoflavanone by means of spectroscopic analysis.
In our continued study on phenolic compounds in the root of Sophora exigua, seven further new prenylated flavanones (exiguaflavanones G-M) and a new benzochromone (exiguachromone B) were isolated. These structures were determined by the analysis of spectral data and chemical transformation.
In addition to two known compounds (5,7,2′-trihydroxy-8-lavandulylflavanone and maackiain), four new flavanones and a novel benzochromone were isolated from the roots of Sophora exigua. By means of spectral analysis, the structures were elucidated to be (2S)-5,7,2′,4′,6′- pentahydroxy-6-lavandulylflavanone (exiguaflavanone C), (2S)-6-γ,γ-dimethylallyl-5,7,2′, 6′-tetrahydroxy-8-lavandulylflavanone (exiguaflavanone D), (2S)-5,2′,4′-trihydroxy-8- lavandulyl-7,5′-dimethoxyflavanone (exiguaflavanone E), 5,2′,5′-trihydroxy-8-lavandulyl-7- methoxyflavanone (exiguaflavanone F) and 5,7-dihydroxy-8-lavandulylbenzochromone (exiguachromone A), respectively.
Further investigation of the phenolic compound in the roots and stems of Echinosophora koreensis led to the isolation of three new isoflavanones from the roots and 14 compounds, including two new flavanones, from the stems. Their structures were determined by means of spectral analysis to be 3,5,7,4′-tetrahydroxy-2′-methoxy-3′-γ,γ-dimethylallylisoflavanone (kenusanone F), 5,7,3′-trihydroxy-4′-methoxyisoflavanone (kenusanone G) and 8-geranyl-5, 7,2′,4′-tetrahydroxyisoflavanone (kenusanone H) as root constituents, and 5,2′,4′-trihydroxy-7-methoxy-8-γ,γ-dimethylallylflavanone (kenusanone I), 5,2′,4′-trihydroxy-6″,6″-dimethyldihydropyrano [2″,3″: 7,8] flavanone (kenusanone J), sophoraflavanones C and D, sophoronol, echinoisosophoranone, scopoletin, scoparone, liquilitigenin, genistein, licoisoflavone A, 2-(2′,4′-dihydroxyphenyl)-5, 6-methylenedioxybenzofuran, caffeic acid ester and sophoracarpan B as stem constituents.
Two novel flavonoid compounds, an isoflavanone, tetrapterol A, and a pterocarpan, tetrapterol B, and three new isoflavanones, tetrapterols C-E, were isolated from the roots of Sophora tetraptera, in addition to eight known phenolic compounds (kenusanone A, lespedeol B, euchenone a9, lonchocarpol A, cajanone, (−)-maackiain, isoneorautenol and pentacosanyl caffeate). The two novel compounds had a common characteristic partial structure which is derived from a geranyl group which forms a new aromatic ring after cyclization with a hydroxyl group located at a side ring in a flavonoid framework and dehydrogenation. The new isoflavanones had a geranyl or an isoprenyl group on their A or B ring. The structures were determined by analysis of spectral data, in particular, 2D-NMR.
From the roots of Sophora secundiflora, three new isoflavonoids, secundiflorols A-C, were isolated in addition to 10 known flavonoids. The structures were determined by spectral analysis including 2D-NMR techniques.
Five novel oligostilbenes, named leachianols C-G, were isolated from the roots of Sophora leachiana. Their structures were established by means of 2D NMR spectroscopic analysis, including HMBC, COLOC and PSNOESY, to be a resveratrol tetramer with a 2-cyclohexen-4-one ring (leachianol C), a resveratrol trimer with a dihydrobenzofuran ring (leachianol D), a regioisomer of leachianol D (leachianol E), a resveratrol dimer (leachianol F) and a stereoisomer of leachianol F (leachianol G), respectively. These oligostilbenes in S. leachiana derived from pallidol are different from those in S. moorcroftiana, which are derived from ε-viniferin.
Three new isoflavanones, named prostratols A–C, were isolated from the roots ofSophora prostrata. The structures were confirmed by means of spec
Two new flavanones, leachianones D and E, were isolated from the roots of Sophora leachiana together with maackiain and a caffeic acid ester. The structures of new flavanones were characterized as 8-(5-hydroxy-5-methyl2-isopropenyl-trans-hex-3-enyl)-5,7,4′-trihydroxy-2′-methoxyflavanone (leachianone D) and 5,7,4′-trihydroxy-8-lavandulyl flavanone (leachianone E) by means of spectral data.
By further investigation on the constituents of roots of Echinosophora koreensis, three novel flavanones with a 2′,4′,6′-trioxygenated B ring were isolated. These structures were determined to be (2R,3R)-8-γ,γ-dimethylallyl-6 -geranyl-5,7,2′,6′-tetrahydroxy-4′-methoxyflavanone (kenusanone C), (2S)-8-γ,γ-dimethylallyl-5,7,2′,6′-tetrahydroxy-4′ -methoxyflavanone (kenusanone D) and (2S)-8-γ,γ-dimethylallyl-5,2′,6′-trihydroxy-7,4′-dimethoxyflavanone (kenusanone E), respectively, by spectroscopic analysis. The characteristic behaviour of H-2 and H-3 in a 2′,6′-dioxygenated flavanone or flavanonol is also discussed.
A novel flavanone, leachianone A, with a lavandulyl residue was isolated from the roots of Sophora leachiano in addition to sophoraflavanone G. The structure was determined to be 5,7,4′-trihydroxy-8-lavandulyl-2′-methoxyflavanone by means of NMR (1H-1H and 1H-13C COSY) spectral analysis. The structural relationships of leachianone A with isokurarinone and vexibidin, and of sophoraflavanone G and kushenol F with nor-kurarinone and vexibinol are also discussed.
Two new complicated flavanone derivatives containing stilbenoid nuclei were isolated from the roots ofSophora leachiana. The structures of leachianones B and C were established by means of spectroscopic analysis.
The proton signal of the hydrogen-bonded hydroxyl group of the 6-isoprenoid substituted flavanone was shifted more downfield than that of 6-nonsubstituted flavanone. By comparison of the chemical shifts of the hydrogen-bonded hydroxyl groups of 8-(3″,3″-dimethylallyl)-5,7,3′,4′-tetrahydroxyflavanone (3) and its 6-isomer (4) isolated from Wyethia helenioides, the proposed structures 3 and 4 were reversed each other. Comparison of the chemical shift of the hydroxyl group is a facile method to discriminate the 6-isoprenoid substituted flavanone and the 6-nonsubstituted one.
A novel resveratrol tetramer, leachianol C, composed of a pallidol and two resveratrol units was isolated from the roots of Sophora leachiana. The structure and the relative stereochemistry were determined by means of 2D NMR spectroscopy including PSNOESY.
Six novel flavonostilbenes, alopecurones A-F, were isolated from the roots of Sophora alopecuroides, in addition to a new 5-deoxyflavanone with a lavandulyl group, alopecurone G. The structures of alopecurones A-F, which are flavonostilbenes composed of a flavanone [5,7,2′,4′-tetrahydroxy-8-lavandulylfavanone (sophoraflavanone G) or its 2′-methyl ether (leachianone A)] condensed with a stilbene [3,5,4′-trihydroxystilbene (resveratrol)] through the A ring of the flavanone skeleton, were established by spectroscopic analysis. Chemical relationships between S. alopecuroides, S. leachiana and S. moorcroftiana are discussed on the basis of their phenolic components.
Two novel flavanones with a lavandulyl residue, exiguaflavanones A and B, were isolated from the roots of Sophora exigua in addition to a known flavanone (sophoraflavanone G). The structure of the new flavanones was determined to be 5,7,2′,6′-tetrahydroxy-8-lavandulyl- (exiguaflavanone A) and 5,2′,6′-trihydroxy-8-lavandulyl-7-methoxyflavanone (exiguaflavanone B) by means of 2D NMR spectral analysis.
Six known phenolic compounds [ sophoronol, sophoraisoflavanone A, maackiain, sophoracarpan B, calycosin and 2-(2′,4′-dihydroxyphenyl)- 5,6 -methylenedioxybenzofuran], and a new isoflavanone were isolated from the roots of Sophora fraserii. The structure of the new compound, named fraserinone A, was shown to be 5,7,4′ -trihydroxy- 5′-(1,1-dimethylallyl)- 2′-methoxyisoflavanone by means of spectroscopic analysis.
Further investigation of the phenolic constituents in the roots of Sophora prostrata gave 14 phenolic compounds, including four new ones, prostratols D-G. Structures were characterized by means of spectral data involving 2D NMR techniques.
Two new benzofuran derivatives [I], mp 235-237°, C15H10O5 and [II], mp 179-181°, C16H12O5, together with l-maackiain, stigmasterol, medicagol, formononetin and 2', 4', 4-trihydroxychalone (isoliquirtigenin) were isolated from the aerial parts of Sophora tomentosa L., and the structures of I and II were established to be 2-(2', 4'-dihydroxyphenyl)-5, 6-methylenedioxybenzofuran and 2-(2'-hydroxy-4'-methoxyphenyl)-5, 6-methylenedioxybenzofuran on the bases of chemical and spectral evidence, respectively.
Three phytochemical compounds (alopecurone A-C), flavanostilbenes which are produced by condensation between a hydroxyflavanone and a hydroxystilbene, were isolated as major components from the root of Sophora alopecuroides. They uniformly inhibited the growth of 21 strains of methicillin-resistant Staphylococcus aureus with minimum inhibitory concentrations of 3.13-6.25 micrograms ml-1.
- Komatsu
- Komastu