Campneoside II

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.

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.

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.

Phenylpropanoid glycosides from Orobanche caerulescens.[Pubmed:14765293]

Planta Med. 2004 Jan;70(1):50-3.

Two new phenylpropanoid glycosides, caerulescenoside ( 1), and 3'-methyl crenatoside ( 2), as well as five known phenylpropanoid glycosides [acteoside ( 3), isoacteoside ( 4), Campneoside II ( 5), crenatoside ( 6), and desrhamnosyl acteoside ( 7)] were isolated from the whole plant of Orobanche caerulescens. The antioxidative effects of compounds 1 - 7 on human low-density lipoprotein were evaluated. All these compounds suppress concentration-dependently conjugated diene formation with IC (50) values of 1.25 +/- 0.06, 2.97 +/- 0.31, 0.31 +/- 0.01, 1.01 +/- 0.05, 1.15 +/- 0.04, 1.69 +/- 0.15, and 0.64 +/- 0.03 microM, respectively. Comparison of their antioxidative activities with that of resveratrol (IC (50) : 6.75 +/- 1.05 microM), a natural phenolic antioxidant isolated from grape, demonstrated that the prolonged effect on lag-time and the damping effect on oxidative rate by compounds 1 - 7 were all more potent.