Campneoside I

Chemical profiles and metabolite study of raw and processed Cistanche deserticola in rats by UPLC-Q-TOF-MS(E).[Pubmed:34583715]

Chin Med. 2021 Sep 28;16(1):95.

BACKGROUND: Chinese materia medica processing is a distinguished and unique pharmaceutical technique in Traditional Chinese Medicine (TCM) used for reducing side effects, and increasing or even changing therapeutic efficacy of the raw herbs.Changes in the essential components induced by an optimized processing procedure are primarily responsible for the increased efficacy of medicinal plants.The kidney-yang invigorating effect of rice wine-steamed Cistancha deserticola (C. deserticola) was stronger than raw C. deserticola (CD). METHODS: A comparison analysis was carried out using the UPLC-Q-TOF-MS(E) with the UNIFI informatics platform to determine the influence of processing. In vitro studies were performed for the characterization of constituents as well as metabolites in vivo. The chemical components were determined in CD and its processed products. The multivariate statistical analyses were conducted to evaluate variations between them while OPLS-DA was used for pairwise comparison. RESULTS: The results of this study revealed considerable variations in phenylethanoid glycosides (PhGs) and iridoids after processing. A total of 97 compounds were detected in the extracts of CD and its processed product. PhGs having 4'-O-caffeoyl group in the 8-O-beta-D-glucopyranosyl part, like acteoside, cistanoside C, Campneoside II, osmanthuside decreased after being processed, while PhGs with 6'-O-caffeoyl group in the 8-O-beta-D-glucopyranosyl part, such as isoacetoside, isocistanoside C, isoCampneoside I, isomartynoside increased, especially in the CD-NP group. The intensity of echinacoside and cistanoside B whose structure possess 6'-O-beta-D-glucopyranosyl moiety also increased. In in vivo study, 10 prototype components and 44 metabolites were detected in rat plasma, feces, and urine. The obtained results revealed that processing leads to the considerable variation in the chemical constituents of CD and affected the disposition of the compounds in vivo, and phase II metabolic processes are the key cascades of each compound and most of the metabolites are associated with echinacoside or acteoside. CONCLUSIONS: This is the first global comparison research of raw and processed CD. These findings add to our understanding of the impact of CD processing and give important data for future efficacy investigations.

[A new labdane-type diterpenoids from Callicarpa nudiflora].[Pubmed:34467725]

Zhongguo Zhong Yao Za Zhi. 2021 Aug;46(16):4139-4144.

The purpose of the research is to study the bioactive constituents of Callicarpa nudiflora. From the 65% ethanol extract of C. nudiflora leaves, ten compounds were isolated by macroporous adsorption resin, Sephadex LH-20, ODS, silica gel, and preparative HPLC. These compounds were identified as callicapene M6(1), sterebin A(2), isomartynoside(3), crenatoside(4), luteolin-7-O-neohesperidoside(5), apigenin-7-O-beta-D-neohesperidoside(6), isoacteoside(7), acteoside(8),(7R)-Campneoside I(9), and(7S)-Campneoside I(10) on the basis of NMR, HR-ESI-MS, and optical rotation data. Compound 1 was obtained as a new compound. Compounds 2 and 4 were isolated from the genus Callicarpa for the first time. Compounds 9 and 10 were isolated from C. nudiflora for the first time.

Polyphenolic Compounds Extracted and Purified from Buddleja Globosa Hope (Buddlejaceae) Leaves Using Natural Deep Eutectic Solvents and Centrifugal Partition Chromatography.[Pubmed:33920316]

Molecules. 2021 Apr 10;26(8):2192.

Chemical profiling of Buddleja globosa was performed by high-performance liquid chromatography coupled to electrospray ionization (HPLC-DAD-ESI-IT/MS) and quadrupole time-of-flight high-resolution mass spectrometry (HPLC-ESI-QTOF/MS). The identification of 17 main phenolic compounds in B. globosa leaf extracts was achieved. Along with caffeoyl glucoside isomers, caffeoylshikimic acid and several verbascoside derivatives (beta-hydroxyverbascoside and beta-hydroxyisoverbascoside) were identified. Among flavonoid compounds, the presence of 6-hydroxyluteolin-7-O-glucoside, quercetin-3-O-glucoside, luteolin 7-O-glucoside, apigenin 7-O-glucoside was confirmed. Campneoside I, forsythoside B, lipedoside A and forsythoside A were identified along with verbascoside, isoverbascoside, eukovoside and martynoside. The isolation of two bioactive phenolic compounds verbascoside and forsythoside B from Buddleja globosa (Buddlejaceae) was successfully achieved by centrifugal partition chromatography (CPC). Both compounds were obtained in one-step using optimized CPC methodology with the two-phase solvent system comprising ethyl acetate-n-butanol-ethanol-water (0.25:0.75:0.1:1, v/v). Additionally, eight Natural Deep Eutectic Solvents (NADESs) were tested for the extraction of polyphenols and compared with 80% methanol. The contents of verbascoside and luteolin 7-O-glucoside after extraction with 80% methanol were 26.165 and 3.206 mg/g, respectively. Among the NADESs tested in this study, proline- citric acid (1:1) and choline chloride-1, 2- propanediol (1:2) were the most promising solvents. With these NADES, extraction yields for verbascoside and luteolin 7-O-glucoside were 51.045 and 4.387 mg/g, respectively. Taken together, the results of this study confirm that CPC enabled the fast isolation of bioactive polyphenols from B. globosa. NADESs displayed higher extraction efficiency of phenolic and therefore could be used as an ecofriendly alternative to classic organic solvents.

Antioxidant Activity, Enzyme Inhibition Potentials, and Phytochemical Profiling of Premna serratifolia L. Leaf Extracts.[Pubmed:33029485]

Int J Food Sci. 2020 Sep 24;2020:3436940.

Premna serratifolia, commonly known as Arogo in Tentena-Sulawesi, is a popular vegetable. As a promising herbal tea and food ingredient, further investigation is required to find the best knowledge for medicinal use of P. serratifolia leaves. This research investigated the antioxidant activity of the ethanol (EEPS) and water (WEPS) extracts of P. serratifolia leaves, based on their scavenging activities on DPPH radicals and their reducing capacities (CuPRAC, total antioxidant/phosphomolybdenum, and ferric thiocyanate reducing power assays). The DNA-protecting effect by EEPS was tested using pBR322 plasmid DNA against *OH radical-induced damage. The inhibition potentials of both extracts against several enzymes related to metabolic diseases (alpha-glucosidase, alpha-amylase, xanthine oxidase, and protease) were evaluated. The phytochemical analysis was conducted by an LC-QTOF-MS/MS technique. EEPS proved to be a better antioxidant and had higher phenolic content compared to WEPS. EEPS demonstrated a protective effect on DNA with recovery percentage linearly correlated with EEPS concentrations. Strong inhibition on alpha-glucosidase and alpha-amylase was observed for EEPS; however, EEPS and WEPS showed weak inhibitions on xanthine oxidase and protease. LC-QTOF-MS/MS analysis identified seven main components in EEPS, namely scroside E, forsythoside A and forsythoside B, lavandulifolioside, diosmin, nobilin D, Campneoside I, and isoacteoside. These components may be responsible for the observed enzymes inhibitions and antioxidant properties. Premna serratifolia leaves can be an appropriate choice for the development of nutraceutical and drug preparations.

Secoiridoids and other chemotaxonomically relevant compounds in Pedicularis: phytochemical analysis and comparison of Pedicularis rostratocapitata Crantz and Pedicularis verticillata L. from Dolomites.[Pubmed:26828611]

Nat Prod Res. 2016 Aug;30(15):1698-705.

We compared the respective metabolite patterns of two Pedicularis species from Dolomites. Seven phenylethanoid glycosides, i.e., verbascoside (1), echinacoside (2), angoroside A (3), cistantubuloside B1 (4), wiedemannioside C (5), Campneoside II (11) and cistantubuloside C1 (12), together with several iridoid glucosides as aucubin (6), euphroside (7), monomelittoside (8), mussaenosidic acid (9) and 8-epiloganic acid (13) were identified. Pedicularis verticillata showed also the presence of greatly unexpected secoiridoids, ligustroside (14) and excelside B (15), very rare compounds in Lamiales. Both PhGs and iridoids are considered of taxonomical relevance in the Asteridae and their occurrence in Pedicularis was discussed. In particular, the exclusive presence of several compounds such as 8-epiloganic acid (13), Campneoside II (11), cistantubuloside C1 (12), ligustroside (14) and excelside B (15) in Pedicularis rostratocapitata, and angoroside A (3), cistantubuloside B1 (4) and wiedemannioside C (5) in P. verticillata could be considered specific markers for the two botanical entities.

A new phenylethanoid glycoside from Incarvillea compacta.[Pubmed:26630368]

J Asian Nat Prod Res. 2016 Jun;18(6):596-602.

A new phenylethanoid glycoside, 3'''-O-methylCampneoside I (1), was isolated from the 90% ethanolic extract of the roots of Incarvillea compacta, together with three known compounds, Campneoside I (2), ilicifolioside A (3), and Campneoside II (4). Their structures were determined spectroscopically and compared with previously reported spectral data. Compound 1 existed as epimers and displayed better 1,1-diphenyl-2-picrylhydrazyl (DPPH)-free radical scavenging activity using di-tert-butyl-4-methylphenol (BHT) as the positive control. In addition, pretreatment of human HepG2 cells with compound 1 significantly increased the viability on CCl4-induced cell death.

Chemical and genetic discrimination of Cistanches Herba based on UPLC-QTOF/MS and DNA barcoding.[Pubmed:24854031]

PLoS One. 2014 May 22;9(5):e98061.

Cistanches Herba (Rou Cong Rong), known as "Ginseng of the desert", has a striking curative effect on strength and nourishment, especially in kidney reinforcement to strengthen yang. However, the two plant origins of Cistanches Herba, Cistanche deserticola and Cistanche tubulosa, vary in terms of pharmacological action and chemical components. To discriminate the plant origin of Cistanches Herba, a combined method system of chemical and genetic--UPLC-QTOF/MS technology and DNA barcoding--were firstly employed in this study. The results indicated that three potential marker compounds (isomer of Campneoside II, cistanoside C, and cistanoside A) were obtained to discriminate the two origins by PCA and OPLS-DA analyses. DNA barcoding enabled to differentiate two origins accurately. NJ tree showed that two origins clustered into two clades. Our findings demonstrate that the two origins of Cistanches Herba possess different chemical compositions and genetic variation. This is the first reported evaluation of two origins of Cistanches Herba, and the finding will facilitate quality control and its clinical application.

Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice.[Pubmed:24748124]

J Nat Med. 2014 Jul;68(3):561-6.

Acylated phenylethanoid glycosides, echinacoside (1) and acteoside (2), principal constituents in stems of Cistanche tubulosa (Orobanchaceae), inhibited the increase in postprandial blood glucose levels in starch-loaded mice at doses of 250-500 mg/kg p.o. These compounds (1 and 2) also significantly improved glucose tolerance in starch-loaded mice after 2 weeks of continuous administration at doses of 125 and/or 250 mg/kg/day p.o. without producing significant changes in body weight or food intake. In addition, several constituents from C. tubulosa, including 1 (IC50 = 3.1 muM), 2 (1.2 muM), isoacteoside (3, 4.6 muM), 2'-acetylacteoside (4, 0.071 muM), tubulosides A (5, 8.8 muM) and B (9, 4.0 muM), syringalide A 3-O-alpha-L-rhamnopyranoside (10, 1.1 muM), Campneoside I (13, 0.53 muM), and kankanoside J1 (14, 9.3 muM), demonstrated potent rat lens aldose reductase inhibitory activity. In particular, the potency of compound 4 was similar to that of epalrestat (0.072 muM), a clinical aldose reductase inhibitor.

Phenylpropanoid glycosides from plant cell cultures induce heme oxygenase 1 gene expression in a human keratinocyte cell line by affecting the balance of NRF2 and BACH1 transcription factors.[Pubmed:22735309]

Chem Biol Interact. 2012 Aug 30;199(2):87-95.

Phenylpropanoids have several highly significant biological properties in both plants and animals. Four phenylpropanoid glycosides (PPGs), verbascoside (VB), forsythoside B (FB), echinacoside (EC) and Campneoside I (CP), were purified and tested for their capability to activate NRF2 and induce phase II cytoprotective enzymes in a human keratinocyte cell line (HaCaT). All four substances showed similar strong antioxidant and radical-scavenging activities as determined by diphenylpicrylhydrazyl assay. Furthermore, in HaCaT cells, FB and EC are strong activators of NRF2, the nuclear transcription factor regulating many phase II detoxifying and cytoprotective enzymes, such as heme oxygenase 1 (HMOX1). In HaCaT cells, FB and EC (200 muM) induced nuclear translocation of NRF2 protein after 24 h and reduced nuclear protein levels of BACH1, a repressor of the antioxidant response element. FB and EC greatly HMOX1 mRNA levels by more than 40-fold in 72 h. Cytoplasmic HMOX1 protein levels were also increased at 48 h after treatment. VB was less active compared to FB and EC, and CP was slightly active only at later times of treatment. We suggest that hydroxytyrosol (HYD) could be a potential bioactive metabolite of PPGs since HYD, in equimolar amounts to PGGs, is able to both activate HO-1 transcription and modify Nrf2/Bach1 nuclear protein levels. This is in agreement with the poor activity of CP, which contains a HYD moiety modified by an O-methyl group. In conclusion, FB and EC from plant cell cultures may provide long-lasting skin protection by induction of phase II cytoprotective capabilities.

High-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight and ion-trap tandem mass spectrometry to identify phenolic compounds from a lemon verbena extract.[Pubmed:19500792]

J Chromatogr A. 2009 Jul 10;1216(28):5391-7.

High-performance liquid chromatography with diode array and electrospray ionization mass spectrometric detection was used to carry out the comprehensive characterization of a lemon verbena extract with demonstrated antioxidant and antiinflammatory activity. Two different MS techniques have been coupled to HPLC: on one hand, time-of-flight mass spectrometry, and on the other hand, tandem mass spectrometry on an ion-trap. The use of a small particle size C18 column (1.8 microm) provided a great resolution and made possible the separation of several isomers. The UV-visible spectrophotometry was used to delimit the class of phenolic compound and the accurate mass measurements on time-of-flight spectrometer enabled to identify the compounds present in the extract. Finally, the fragmentation pattern obtained in MS-MS experiments confirmed the proposed structures. This procedure was able to determine many well-known phenolic compounds present in lemon verbena such as verbascoside and its derivatives, diglucuronide derivatives of apigenin and luteolin, and eukovoside. Also gardoside, verbasoside, cistanoside F, theveside, Campneoside I, chrysoeriol-7-diglucuronide, forsythoside A and acacetin-7-diglucuronide were found for the first time in lemon verbena.

A new iridoid from Adenosma caeruleum R. Br.[Pubmed:19442709]

Fitoterapia. 2009 Sep;80(6):358-60.

A new iridoid glycoside, adenosmoside, together with five known phenylpropanoids, crenatoside, verbascoside, cistanoside F, Campneoside I, and Campneoside II and two known flavonoids, apigenin 7-O-beta-D-glucuronopyranoside and apigenin 7-O-beta-D-glucopyranoside, were isolated from the aerial parts of Adenosma caeruleum R. Br. Their structures were elucidated by spectral evidence.

Studies on the phenylethanoid glycosides with anti-complement activity from Paulownia tomentosa var. tomentosa wood.[Pubmed:19031237]

J Asian Nat Prod Res. 2008 Nov-Dec;10(11-12):1003-8.

Four epimeric phenylethanoid glycosides, including a new one, R,S-beta-ethoxy-beta-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-rhamnopyranosyl(1-->3)-beta-D-(6-O-E-caffeoyl)-glucopyranoside named isoilicifolioside A (1), and three known compounds, ilicifolioside A (2), Campneoside II (3), and isoCampneoside II (4), were isolated from Paulownia tomentosa var. tomentosa wood. The structures of the four compounds were elucidated by the interpretation of 1D and 2D NMR and MS spectra. This is the first report of the chemical profile of this tree. Compounds 1-4 exhibited excellent anti-complement activity with IC(50) values less than 74 microM, compared with tiliroside (IC(50) = 104 microM) and rosmarinic acid (IC(50) = 182 microM) that were used as positive controls.

Phenylpropanoid glycosides from the leaves of Paulownia coreana.[Pubmed:18266154]

Nat Prod Res. 2008 Feb 15;22(3):241-5.

Study on the water soluble fraction from the leaves of Paulownia coreana led to the isolation of verbascoside (1), isoverbascoside (2), Campneoside II (3), and a new phenylpropanoid glycoside, (R,S)-7-hydroxy-7-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-rhamnopyranosyl(1 --> 3)-beta-d-(6-O-caffeoyl)-glucopyranoside (4). The structures of these compounds were established on the basis of spectroscopic evidence.

[Isolation and characterization of phenylethanoid glycosides from Clerodendron bungei].[Pubmed:16268507]

Yao Xue Xue Bao. 2005 Aug;40(8):722-7.

AIM: To study the chemical constituents from Clerodendron bungei Steud. METHODS: The compounds were isolated and purified by various chromatographic techniques and identified by their physicochemical properties and spectral data. RESULTS: Ten phenylethanoid glycosides were isolated and identified as clerodendronoside (1), acteoside (2), isoacteoside (3), cistanoside C (4), jionoside C (5), leucosceptoside A (6), cistanoside D (7), Campneoside I (8), Campneoside II (9), cistanoside F (10). CONCLUSION: Compound 1 is a new phenylethanoid glycoside, while compounds 4-10 are obtained from this plant for the first time.