No full-text available
To read the full-text of this research,
you can request a copy directly from the authors.
Constituents of Viscum ovalifolium DC(II)
Abstract
OBJECTIVE: To study the chemical constituents of Viscum oralifolium DC, further. METHODS: Chemical constituents were isolated from the title plant by various chromatographic methods such as silica gel medium pressure column, sephadex LH-20 column chromatography, et al. Their structures were elucidated by physiochemical and spectral analysis. RESULTS: Eight triterpenoids and triterpenoid saponins were isolated and identified as lupeol stearate (I), lupeol palmitate (II), β-amyrin acetate (III), hederagenin (IV), gypsogenic acid (V), hederagenin-3-O-α-L-arabinopyranoside (VI), hederagenin-3-O-α-L-arabinopyranoyl-(2→ 1)-O-β-D-glucopyranoside (VII), 3-O-α-L-arabinopyranoyl- hederagenin-28-O-β-D-glucopyranosyl- (1→6)-β-D-glucopyranoside (VIII). CONCLUSION: Compound I-VIII were isolated from this plant for the first time, compound IV-VIII were isolated from Viscum for the first time.
... 2S)-5,3,4-trihydroxyflavanone 7-O-β-D-glucoside 790, (2S)-homoeriodictyol 791, (2S)-homoeriodictyol 7-O-β-D-glucoside 792, (2S)-naringenin 7-O-β-D-glucoside 793, (2S)-pinocembrin 7-O-[cinnamoyl(15)-β-D-apiosyl(12)]-β-D-glucoside 794, (2S)-pinocembrin 7-O-[β-D-apiosyl(12)]β-D-glucoside (1) 795, (2S)-pinocembrin 7-O-β-D-glucoside 796, (4′-hydroxy-2′,3′,6′,3′′-tetramethoxy-1,3-diphenylpropane)-4′′-O-β-Dglucopyranoside 797, 1-O-benzyl-[5-O-benzoyl-β-Dapiofuranosyl(12)]-β-D-glucopyranoside 798, 2-deoxy-epi-inositol 799, 2-phenylethanol 800, 4-β-D-glucosyloxy-3-hydroxy-benzoic acid 801, 4′-hydroxy-7,3′-dimethoxyflavan-5-O-β-D-glucopyranoside 802, 4-O-cinnamoyl quinic acid 803, 5,3′,4′-trihydroxyflavanone-7-O-β-D-glucopyranoside 804, 5,4′-dihydroxyflavanone-7-O-β-D-lucopyranoside 805, 7-O-β-D-glucopyranoside 806, botulin 807, betulin 808, betulinic acid 809, cinnamic acid methyl ester 810, diphenylpropane glycoside 811, eriodictyol 7-O-β-Dglucopyranoside 812, homoeriodictyol 7-O-β-D-glucopyranoside 813, homoeriodictyol-7-O-β-D-glucopyranoside 814, homoeriodictyol-7-O-β-Dglucopyranoside-4′-O-β-D-(5′′′-cinnamoyl)apiofuranoside 815, homoeriodictyol-7-O-β-D-glucopyranoside-4′-O-β-D-apiofuranoside 816, lupenyl acetate 817, lupeol 247, lupeol acetate 818, lupeol palmitate 819, lupeol stearate 820, lycorin 821, methylparaben 822, naringenin 7-O-β-Dglucopyranoside 823, Oleanolic acid 127, p-hydroxybenzaldehyde 432, p-hydroxy-benzoic acid 824, pinocembrin 825, pinocembrin 7-O-β-Dglucopyranoside 826, pinocembrin-7-O-[cinnamoyl (15)-β-D-apiofuranosyl (1→2)]-β-D-glucopyranoside 827, pinocembrin-7-O-β-D-apio furanosyl(12)-β-D-glucopyranoside 828, pinocembrin-7-O-β-D-apiofuranosyl-(1→5)-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside 829, protocatechuic acid 189, vanillin 293, visartisides A-C 830, 831, 832, visartisides D-F (4-6) 833, 834, 835, viscumitol 836, α-amyrin 342, β-amyrin acetate 837, β-sitosterol 11 [343-347,455-457] 69 Viscum ovalifolium DC 3-O-α-L-arabinopyranoyl-hederagenin-28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside 838, gypsogenic acid 839, hederagenin 840, hederagenin-3-O-α-L-arabinopyranoside 841, hederagenin-3-O-α-L-arabinopyranoyl-(2→1)-O-β-D-glucopyranoside 842, lupeol acetate 818, lupeol palmitate 819, oleanolic acid 127, lupeol stearate 820, β-amyrin 198, β-amyrin acetate 344[458,459] ...
This is an extensive review on epiphytic plants that have been used traditionally as medicines. It provides information on 185 epiphytes and their traditional medicinal uses, regions where Indigenous people use the plants, parts of the plants used as medicines and their preparation, and their reported phytochemical properties and pharmacological properties aligned with their traditional uses. These epiphytic medicinal plants are able to produce a range of secondary metabolites, including alkaloids, and a total of 842 phytochemicals have been identified to date. As many as 71 epiphytic medicinal plants were studied for their biological activities, showing promising pharmacological activities, including as anti-inflammatory, antimicrobial, and anticancer agents. There are several species that were not investigated for their activities and are worthy of exploration. These epipythes have the potential to furnish drug lead compounds, especially for treating cancers, and thus warrant indepth investigations.
... Gypsogenic acid (8) was detected in bAS, CPR, CYP716A12 and CYP72A68v2-expressing yeast. This compound was previously reported in Astrantia major (Apiaceae), Gardenia turgida (Rubiaceae), Hedyotis diffusa (Rubiaceae) and Viscum ovalifolium (Santalaceae; Hiller et al. 1973, Reddy et al. 1973, Huang et al. 2009, Yang et al. 2011. Additionally, gypsogenic acid glycosides were reported in Caryophyllaceae (Dianthus deltoides, D. superbus, Gypsophila trichomata, G. pacifica and Saponaria officinalis), Fabaceae (Vigna angularis and Swartzia simplex) and Chenopodiaceae (Climacoptera transoxana; Kochetkov et al. 1964, Bukharov and Shcherbak 1969, Bukharov and Shcherbak 1971, Luchanskaya et al. 1971, Kitagawa et al. 1983, Annaev and Abubakirov 1984, Oshima et al. 1984a, Oshima et al. 1984b, Borel et al. 1987, Hostettmann and Marston 2005. ...
... Gypsogenic acid (8) was detected in bAS, CPR, CYP716A12 and CYP72A68v2-expressing yeast. This compound was previously reported in Astrantia major (Apiaceae), Gardenia turgida (Rubiaceae), Hedyotis diffusa (Rubiaceae) and Viscum ovalifolium (Santalaceae; Hiller et al. 1973, Reddy et al. 1973, Huang et al. 2009, Yang et al. 2011 ). Additionally, gypsogenic acid glycosides were reported in Caryophyllaceae (Dianthus deltoides, D. superbus, Gypsophila trichomata, G. pacifica and Saponaria officinalis ), Fabaceae (Vigna angularis and Swartzia simplex) and Chenopodiaceae (Climacoptera transoxana; Kochetkov et al. 1964, Bukharov and Shcherbak 1969, Bukharov and Shcherbak 1971, Luchanskaya et al. 1971, Kitagawa et al. 1983, Annaev and Abubakirov 1984, Oshima et al. 1984a, Oshima et al. 1984b, Borel et al. 1987, Hostettmann and Marston 2005). ...
... Gypsogenic acid (8) was detected in bAS, CPR, CYP716A12 and CYP72A68v2-expressing yeast. This compound was previously reported in Astrantia major (Apiaceae), Gardenia turgida (Rubiaceae), Hedyotis diffusa (Rubiaceae) and Viscum ovalifolium (Santalaceae; Hiller et al. 1973, Reddy et al. 1973, Huang et al. 2009, Yang et al. 2011. Additionally, gypsogenic acid glycosides were reported in Caryophyllaceae (Dianthus deltoides, D. superbus, Gypsophila trichomata, G. pacifica and Saponaria officinalis), Fabaceae (Vigna angularis and Swartzia simplex) and Chenopodiaceae (Climacoptera transoxana; Kochetkov et al. 1964, Bukharov and Shcherbak 1969, Bukharov and Shcherbak 1971, Luchanskaya et al. 1971, Kitagawa et al. 1983, Annaev and Abubakirov 1984, Oshima et al. 1984a, Oshima et al. 1984b, Borel et al. 1987, Hostettmann and Marston 2005. ...
Triterpenoid saponins are a diverse group of specialized (secondary) metabolites with many biological properties. The model
legume Medicago truncatula has an interesting profile of triterpenoid saponins from which sapogenins are differentiated into hemolytic and non-hemolytic
types according to the position of their functional groups and hemolytic properties. Gene co-expression analysis confirmed
the presence of candidate P450s whose gene expression correlated highly with that of β-amyrin synthase (bAS). Among these,
we identified CYP716A12 and CYP93E2 as key enzymes in hemolytic and non-hemolytic sapogenin biosynthetic pathways. The other
candidate P450s showed no β-amyrin oxidation activity. However, among the remaining candidate P450s, CYP72A61v2 expression highly correlated with that of CYP93E2, and CYP72A68v2 expression highly correlated with that of CYP716A12. These correlation values were higher than occurred with bAS expression. We generated yeast strains expressing bAS, CPR, CYP93E2 and CYP72A61v2, and bAS, CPR, CYP716A12 and CYP72A68v2. These transgenic yeast strains produced soyasapogenol B and gypsogenic acid, respectively. We were therefore able to identify
two CYP72A subfamily enzymes: CYP72A61v2, which modifies 24-OH-β-amyrin, and CYP72A68v2, which modifies oleanolic acid. Additionally,
P450s that seemed not to work together in planta were combinatorially expressed in transgenic yeast. The yeast strains (expressing
bAS, CPR, CYP72A63 and CYP93E2 or CYP716A12) produced rare triterpenoids that do not occur in M. truncatula. These results show the potential for combinatorial synthesis of diverse triterpenoid structures and enable identification
of the enzymes involved in their biosynthesis.
Ethnopharmacological relevance
The genus Viscum comprises approximately 100 species that are mainly distributed across Africa, Asia and Europe. The extracts and preparations of Viscum species are widely used as common complementary and alternative medicines in the treatment of rheumatism and cancer.
Aim of the review
This review aims to explore the medicinal properties of twelve species belonging to the genus Viscum for potential therapeutic applications.
Materials and methods
We collected online information (including PubMed, CNKI, Google Scholar, and Web of Science) from January 1915 to April 2021 and knowledge from classical books on Chinese herbal medicines available for 12 species of the genus Viscum, including Viscum coloratum (Kom.) Nakai, Viscum album L., Viscum articulatum Burm. f., Viscum liquidambaricola Hayata, Viscum ovalifolium DC., Viscum capitellatum Sm., Viscum cruciatum Sieber ex Boiss., Viscum nudum Danser, Viscum angulatum B.Heyne ex DC., Viscum tuberculatum A.Rich., Viscum multinerve Hayata, and Viscum diospyrosicola Hayata.
Results
At least 250 different compounds have been reported across twelve Viscum species, including amino acid and peptides, alkaloids, phenolic acids, flavonoids, terpenoids, carbohydrates, fatty acids, lipids, and other types of compounds. In particular, for Viscum coloratum (Kom.) Nakai and Viscum album L., the plants, preparations, and bioactive components have been thoroughly reviewed. This has allowed to elucidate the role of active components, including lectins, viscotoxins, flavonoids, terpenoids, phenolic acids, and polysaccharides, in multiple bioactivities, such as anti-cancer, anti-rheumatism arthralgia, anti-inflammation, anti-cardiovascular diseases, enhancing immunity, and anti-chemotherapy side effects. We also evaluated quality control methods based on active compounds, in vivo exposure compounds, and discriminated chemical markers.
Conclusions
This is the first report to systematically review the pharmaceutical development history, chemical composition, clinical evidence, pharmacological activity, discriminated chemical markers, in vivo exposure, and quality control on twelve distinct species of Viscum plants with medicinal properties. The significant safety and efficacy, along with the minor side effects are constantly confirmed in clinics. The genus Viscum is thus an important medicinal resource that is worth exploring and developing in future pharmacological and chemical studies.
In order to understand the nature of surface patterns on silicon melt in industrial Czochralski furnaces, we conducted a series of unsteady three-dimensional numerical simulations of thermocapillary flow in thin silicon melt pools in annular containers under microgravity. The pool is heated from the outer cylindrical wall and cooled at the inner wall. Bottom and top surfaces either are adiabatic or allow heat transfer in the vertical direction. With large temperature difference in the radial direction, the simulation can predict two types of oscillatory convections. One is characterized by spoke patterns traveling in the azimuthal direction. The other one is characterized by radially extended roll cells periodically alternating the azimuthal flow directions but are stationary. The small vertical heat flux (3W/cm2) does not have significant effects on the characteristics of those oscillatory flows. Details of the flow and temperature disturbances are discussed and the critical conditions for the incipience of the oscillatory flow are determined.
OBJECTIVE: To study the chemical constituents in fruit of Akebia trifoliata. METHODS: The compounds were isolated and purified by recrystallization and columnchromatography with silica gel and ODS. Their structures were elucidated on the basis of physico chemical properties and spectral analysis. RESULTS: Seven compounds were identified as hederagenin-3-O-α-L-rhamnopyranosyl-(1→2)-α-L- arabinopyranoside(I), hederagenin-3-O-α-L-arabinopyranoside(II),3-O- α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin-28- O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6) -β-D-gluco pyranoside(III), 3-O-α-L-arabinopyranosyl-hederagenin-28- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (IV), hederagenin-28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (V), 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-30-nor- olean-12,20(29)- dien-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-β- D-glucopyranosyl-(1→6)-β-D-gluco pyranosyl ester(VI), daucosterol(VII). CONCLUSION: Compound II, III and IV were isolated from A. trifoliata (Thunb.) Koidz. for the first time and compounds V and VI were isolated from Akebia genus for the first time.
Aim: To investigate the chemical constituents in flower bud of Lonicera macranthoides. Methods: The constituents were isolated and purified by means of various chromatographic methods, and spectroscopic methods were used to identify their structures. Results: Eleven compounds were obtained and identified as 1-O-caffeoylquinic acid (I), 4-O-caffeoylquinic acid (II) 5-O-caffeoylquinic acid butyl ester (III), quercetin (IV), tricin-7-O-β-D-glucopyranoside (V), quercetin-7-O-β-D-glucopyranoside (VI), luteolin-7-O-β-D-galactoside (VII), inositol (VIII), β-sitosterol (IX), nonadecanol (X) and glucose (XI). Conclusion: Compounds I, II were first isolated from Genus Lonicera, while compounds III-XI were isolated from the plant for the first time.
To investigate the chemical constituents from roots of Boehmeria nivea.
The constituents were isolated by repeated column chromatography and preparative liquid chromatography; and their structures were elucidated by chemical properties and spectroscopic analyses.
Seven compounds were isolated and their structures were identified as tormentic acid (1), hederagenin (2), maslinic acid (3), 2alpha-hydroxyursolic acid (4), trans-p-hydroxycinamic acid (5), 2,4,4'-trihydroxychalcone (6), rutin (7).
Compounds 1-6 were obtained from this genus for the first time.
To investigate the chemical constituents from Hedyotis diffusa.
The compounds were isolated and purified by various chromatographic techniques and identified by their physicochemical properties and spectral data.
Eight compounds had been reported in last paper, and this time eight more compounds were isolated and identified as 6-hydroxystigmasta-4,22-dien-3-one (1), 3-hydroxystigmasta-4,22-dien-7-one (2), 2-hydroxy-3-methylanthraquinone (3), 2,6-dihydroxy-3-methyl-4-methoxyanthraquinone (4), iso-scutellarein (5), isoetin (6), aesculetin (7), gypsogenic acid (8).
Compounds 1-3, 5-8 were obtained from the genus Hedyotis for the first time.
Three octasaccharide saponins, leonticins A, B, and C (1-3), were isolated from the tubers of Leontice kiangnanensis. Their structures were elucidated by a combination of chemical degradation and spectral methods including negative FABMS and NMR measurements as 3-O-beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosylhederagenin 28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl(1-->4)-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1), 3-O-[beta-D-xylopyranosyl(1-->3)-beta-D-galactopyranosyl(1-->4)-beta-D- glucopyranosyl (1-->3)][beta-D-glucopyranosyl(1-2)]-alpha-L-arabinopyranosyloleanoli c acid 28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside (2), and 3-O-[beta-D-xylopyranosyl (1-->3)-beta-D-galactopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->3)] [beta-D-glucopyranosyl(1-->2)]-alpha-L-arabinopyranosylechinocystic++ + acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranoside (3), respectively. The complete assignments of the proton and carbon resonances for 1-3 were achieved based on extensive 2D NMR analysis (DQF-COSY, TOCSY, ROESY, HSQC, and HMBC).
To identify herba Visci ovalifolii, Chinese medicinal materials used in Li and Miao nationalities.
Morphological, microscopical and UV spectral methods.
Dichotomous branch with a yellow surface, with leaf of 3-5 acrodromous veins originating at the base of the leaf. In transverse section, the thick outer wall of the epidermis of stem projecting like nipple; stone cells contain frequently a prismatic crystal of calcium oxalate, often occur in the cortex and phloem of the stem. Pericycle fibres and xylem fibres all with a well-developed thick wall; vessels with a bordered pits somtimes have a spiral thickened interwall; mesophyll homogeneous contain cluster crystals (not calcium oxalate); stomata present on both surfaces, mostly paracrytic, with small and narrow subsidiary cells. Hairs absent at the surface.
Above morphological and microscopical characters may be used for the identification of herba Visci ovalifolii. UV spectral method is a simple identificating method for herba Visci ovalifolii.
To investigate the chemical constituents of Ligularia xanthotricha.
Silica gel column chromatography and preparative TLC were employed for the isolation and purification. The structures were identified on the basis of spectral data (IR, EI-MS, 1H-NMR, 13C-NMR, DEPT) and chemical evidence.
Seven compounds were isolated and identified as follows: lupeol (1), lupeol palmitate (2), 3, 28-dihydroxyl-lupeol (3), betulinic acid (4), taraxasterol (5), taraxasteryl palmitat (6) and taraxasteryl acetate(7).
All the compounds were isolated from this plant for the first time.