Natural product isolation.

Since the 1990s, interest in natural product research has increased considerably. Following several outstanding developments in the areas of separation methods, spectroscopic techniques, and sensitive bioassays, natural product research has gained new attention for providing novel chemical entities. This updated review deals with sample preparation and purification, recent extraction techniques used for natural product separation, liquid-solid and liquid-liquid isolation techniques, as well as multi-step chromatographic operations. It covers examples of papers published since the NPR review 'Modern separation methods' by Marston and Hostettmann,1 with major emphasis on methods developed and the research undertaken since 2000.

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[10]  Jinyong Peng,et al.  Preparative isolation of four new and two known flavonoids from the leaf of Patrinia villosa Juss. by counter-current chromatography and evaluation of their anticancer activities in vitro. , 2006, Journal of chromatography. A.

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[16]  Aifeng Li,et al.  Preparative isolation and purification of coumarins from Angelica dahurica (Fisch. ex Hoffm) Benth, et Hook. f (Chinese traditional medicinal herb) by high-speed counter-current chromatography , 2004 .

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[18]  Qipeng Yuan,et al.  Preparative separation of gallic acid from Chinese traditional medicine by high-speed counter-current chromatography and followed by preparative liquid chromatography , 2007 .

[19]  Pin Chen,et al.  Preparation of Ursane Triterpenoids from Centella asiatica Using High Speed Countercurrent Chromatography with Step‐Gradient Elution , 2004 .

[20]  H. Chang,et al.  Diarylheptanoids from the Roots of Juglans mandshurica , 2004 .

[21]  Rui Liu,et al.  An effective high-speed countercurrent chromatographic method for preparative isolation and purification of mollugin directly from the ethanol extract of the Chinese medicinal plant Rubia cordifolia. , 2007, Journal of separation science.

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[29]  Jian Li,et al.  Preparative Isolation and Purification of Amygdalin from Prunus armeniaca L. with High Recovery by High‐Speed Countercurrent Chromatography , 2006 .

[30]  Feng Chen,et al.  Preparative isolation and purification of bergapten and imperatorin from the medicinal plant Cnidium monnieri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase. , 2004, Journal of chromatography. A.

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[33]  Zhaojie Cui,et al.  Supercritical fluid extraction of quinolizidine alkaloids from Sophora flavescens Ait. and purification by high-speed counter-current chromatography. , 2007, Journal of chromatography. A.

[34]  M. Grenier-loustalot,et al.  Analysis of neem oils by LC–MS and degradation kinetics of azadirachtin-A in a controlled environment , 2004, Analytical and bioanalytical chemistry.

[35]  Ren-min Liu,et al.  Separation and purification of baicalin and wogonoside from the Chinese medicinal plant Scutellaria baicalensis Georgi by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[36]  Jinyong Peng,et al.  Application of preparative high-speed counter-current chromatography for isolation and separation of schizandrin and gomisin A from Schisandra chinensis. , 2005, Journal of chromatography. A.

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[38]  Jinyong Peng,et al.  Preparative separation of isovitexin and isoorientin from Patrinia villosa Juss by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[39]  E. Ong,et al.  Determination of berberine and strychnine in medicinal plants and herbal preparations by pressurized liquid extraction with capillary zone electrophoresis , 2001, Electrophoresis.

[40]  Xiaofeng Ma,et al.  Isolation of quercetin-3-O-L-rhamnoside from Acer truncatum Bunge by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

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[44]  T. Cierpicki,et al.  Column Chromatography and Preparative TLC for Isolation and Purification of Coumarins from Peucedanum verticillare L. Koch ex DC , 2005, JPC – Journal of Planar Chromatography – Modern TLC.

[45]  Aifeng Li,et al.  Preparative isolation and purification of costunolide and dehydrocostuslactone from Aucklandia lappa Decne by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[46]  Béatrice Kaufmann,et al.  Recent extraction techniques for natural products: microwave-assisted extraction and pressurised solvent extraction. , 2002, Phytochemical analysis : PCA.

[47]  Ø. M. Andersen,et al.  Anthocyanins from fruits of Rubus pinnatus and Rubus rigidus , 2005 .

[48]  Xueli Cao,et al.  Supercritical fluid extraction of grape seed oil and subsequent separation of free fatty acids by high-speed counter-current chromatography. , 2003, Journal of chromatography. A.

[49]  G. Jham,et al.  Purification of the seven tetranortriterpenoids in neem (Azadirachta indica) seed by counter-current chromatography sequentially followed by isocratic preparative reversed-phase high-performance liquid chromatography. , 2007, Journal of chromatography. A.

[50]  P. Richomme,et al.  Multi-grams scale purification of xanthanolides from Xanthium macrocarpum. Centrifugal partition chromatography versus silica gel chromatography. , 2007, Journal of chromatography. A.

[51]  G. W. Schieffer,et al.  PRESSURIZED LIQUID EXTRACTION AND MULTIPLE, ULTRASONICALLY-ASSISTED EXTRACTIONS OF HYDRASTINE AND BERBERINE FROM GOLDENSEAL (HYDRASTIS CANADENSIS) WITH SUBSEQUENT HPLC ASSAY , 2001 .

[52]  Feng Chen,et al.  Isolation and purification of baicalein, wogonin and oroxylin A from the medicinal plant Scutellaria baicalensis by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[53]  R. Andriantsitohaina,et al.  Anti-proliferative effect of Euphorbia stenoclada in human airway smooth muscle cells in culture. , 2007, Journal of ethnopharmacology.

[54]  H. Tamura,et al.  Delphinidin 3-O-(2-O-beta-D-Glucopyranosyl-alpha-l-arabinopyranoside): a novel anthocyanin identified in Beluga black lentils. , 2005, Journal of agricultural and food chemistry.

[55]  A. Kinghorn,et al.  ISOLATION OF ALKALOIDS FROM GOLDENSEAL (HYDRASTIS CANADENSIS RHIZOMES) USING pH-ZONE REFINING COUNTERCURRENT CHROMATOGRAPHY , 2001 .

[56]  Yinmao Dong,et al.  Preparative Separation of a Minor Active Chromone from Aloe vera Leaves by CCC , 2005 .

[57]  Du,et al.  Low-speed rotary countercurrent chromatography using a convoluted multilayer helical tube for industrial separation , 2000, Analytical chemistry.

[58]  H. Bartsch,et al.  Isolation and structure elucidation of phenolic antioxidants from Tamarind (Tamarindus indica L.) seeds and pericarp. , 2005, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[59]  L. J. Mohan Rao,et al.  Triterpenoids from swallow roots--a convenient HPLC method for separation. , 2007, Journal of Chromatographic Science.

[60]  S. Divakar,et al.  Isolation and identification of a radical scavenging antioxidant – punicalagin from pith and carpellary membrane of pomegranate fruit , 2004 .

[61]  Z. Liu,et al.  Preparative Separation of Alkaloids from Green Tea by pH‐Zone‐Refining Countercurrent Chromatography , 2004 .

[62]  Jizhong Yan,et al.  Preparative isolation and purification of syringin and edgeworoside C from Edgeworthia chrysantha Lindl by high-speed counter-current chromatography. , 2004, Journal of chromatography. A.

[63]  Jian-hua Liu,et al.  Isolation and purification of four flavonoid constituents from the flowers of Paeonia suffruticosa by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[64]  Z. Su,et al.  One-step separation and purification of 3,4-dihydroxyphenyllactic acid, salvianolic acid B and protocatechualdehyde from Salvia miltiorrhiza Bunge by high-speed counter-current chromatography. , 2007, Journal of chromatography. A.

[65]  R. Fett,et al.  Characterization of anthocyanins from the fruits of baguaçu (Eugenia umbelliflora Berg). , 2003, Journal of Agricultural and Food Chemistry.

[66]  Feng Chen,et al.  Preparative purification of glycyrrhizin extracted from the root of liquorice using high-speed counter-current chromatography , 2004, Journal of Chromatography A.

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[68]  Ling Yang,et al.  Gambogic acid and epigambogic acid, C-2 epimers with novel anticancer effects from Garcinia hanburyi. , 2006, Planta medica.

[69]  R. Khan,et al.  Hypotensive activity and toxicology of constituents from root bark of Polyalthia longifolia var. pendula , 2005, Phytotherapy research : PTR.

[70]  Rui Liu,et al.  Effective two-dimensional counter-current chromatographic method for simultaneous isolation and purification of oridonin and ponicidin from the crude extract of Rabdosia rubescens. , 2007, Journal of chromatography. A.

[71]  Yu Huang,et al.  Comparison of antioxidant activity and bioavailability of tea epicatechins with their epimers. , 2004, The British journal of nutrition.

[72]  E. Yeşilada,et al.  Flavonoids with anti-Helicobacter pylori activity from Cistus laurifolius leaves. , 2006, Journal of ethnopharmacology.

[73]  Xiaofeng Ma,et al.  The isolation of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose from Acer truncatum Bunge by high-speed counter-current chromatography. , 2007, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[74]  R. Carle,et al.  Screening of mango (Mangifera indica L.) cultivars for their contents of flavonol O- and xanthone C-glycosides, anthocyanins, and pectin. , 2005, Journal of agricultural and food chemistry.

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[76]  A. Shafiee,et al.  Identification of Antifungal Compounds from Ferula persica. var. persica. , 2005, Pharmaceutical biology.

[77]  D. Wianowska,et al.  Effect of extraction method on the yield of furanocoumarins from fruits of Archangelica officinalis Hoffm. , 2004, Phytochemical analysis : PCA.

[78]  S. Apers,et al.  Antiviral activity of simalikalactone D, a quassinoid from Quassia africana. , 2002, Planta medica.

[79]  M. D. Luque de Castro,et al.  Multivariate optimisation of the microwave-assisted extraction of oleuropein and related biophenols from olive leaves , 2006, Analytical and bioanalytical chemistry.

[80]  L. Kong,et al.  Preparative isolation and purification of alkaloids from the Chinese medicinal herb Evodia rutaecarpa (Juss.) Benth by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[81]  Feng Chen,et al.  Isolation and purification of the bioactive carotenoid zeaxanthin from the microalga Microcystis aeruginosa by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

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[83]  P. Tu,et al.  Preparative isolation and purification of isoflavan and pterocarpan glycosides from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography. , 2004, Journal of chromatography. A.

[84]  Yong-Jia Shen,et al.  Preparative separation and purification of deoxyschisandrin and gamma-schisandrin from Schisandra chinensis (Turcz.) Baill by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[85]  Xueli Cao,et al.  Preparation and Purification of Epigallocatechin by High‐Speed Countercurrent Chromatography (HSCCC) , 2004 .

[86]  I. Raskin,et al.  Preparative isolation and identification of tyrosinase inhibitors from the seeds of Garcinia kola by high-speed counter-current chromatography. , 2007, Journal of chromatography. A.

[87]  Jinyong Peng,et al.  Efficient new method for extraction and isolation of three flavonoids from Patrinia villosa Juss. by supercritical fluid extraction and high-speed counter-current chromatography. , 2006, Journal of chromatography. A.

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[90]  P. Tu,et al.  Preparative isolation and purification of triterpene saponins from Clematis mandshurica by high-speed counter-current chromatography coupled with evaporative light scattering detection. , 2007, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[91]  Yong-Jia Shen,et al.  Preparative Separation and Purification of Schisandrin and Schisantherin from Schisandra Chinensis (Turcz) Baill by High Speed Countercurrent Chromatography , 2005 .

[92]  G. Fan,et al.  Isolation of six isoflavones from Semen sojae praeparatum by preparative HPLC. , 2007, Fitoterapia.

[93]  L. Kong,et al.  Isolation and purification of coumarin compounds from the root of Peucedanum decursivum (Miq.) Maxim by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[94]  Jinyong Peng,et al.  Preparative isolation and separation of a novel and two known flavonoids from Patrinia villosa Juss by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[95]  Serge Rudaz,et al.  Optimisation of accelerated solvent extraction of cocaine and benzoylecgonine from coca leaves , 2001 .

[96]  A. Delazar,et al.  Iridoid glycosides from Eremostachys glabra. , 2004, Journal of natural products.

[97]  I. Baloch,et al.  Cytotoxic macrocyclic diterpenoid esters from Euphorbia cornigera. , 2006, Planta medica.

[98]  P. Tu,et al.  Optimization of pressurized liquid extraction of five major flavanoids from Lysimachia clethroide. , 2007, Journal of pharmaceutical and biomedical analysis.

[99]  R. R. Oliveira,et al.  Gradient Elution for Triterpene Separation from Cecropia lyratiloba Miquel by HSCCC , 2005 .

[100]  Feng Chen,et al.  Application of preparative high-speed counter-current chromatography for separation of chlorogenic acid from Flos Lonicerae. , 2004, Journal of chromatography. A.

[101]  P. Tu,et al.  Preparative isolation and purification of trans-3,5,4'-trihydroxystilbene-4'-O-beta-D-glucopyranoside and (+)catechin from Rheum tanguticum Maxim. ex Balf. using high-speed counter-current chromatography by stepwise elution and stepwise increasing the flow-rate of the mobile phase. , 2005, Journal of chromatography. A.

[102]  C. Shin,et al.  Isolation and characterization of a new compound from Prunus mume fruit that inhibits cancer cells. , 2006, Journal of agricultural and food chemistry.

[103]  Wenbo Zhi,et al.  Purification of salvianolic acid B from the crude extract of Salvia miltiorrhiza with hydrophilic organic/salt-containing aqueous two-phase system by counter-current chromatography. , 2006, Journal of chromatography. A.

[104]  Aifeng Li,et al.  Preparative isolation and purification of hydroxyanthraquinones and cinnamic acid from the chinese medicinal herb Rheum officinale Baill. by high-speed counter-current chromatography. , 2004, Journal of chromatography. A.

[105]  Shiying Xu,et al.  Microwave-assisted extraction of secoisolariciresinol diglucoside from flaxseed hull , 2007 .

[106]  Y. Geng,et al.  Preparative separation of cichoric acid from Echinacea purpurea by pH-zone-refining counter-current chromatography. , 2006, Journal of chromatography. A.

[107]  K. Hostettmann,et al.  Isolation and on-line identification of antioxidant compounds from three Baccharis species by HPLC-UV-MS/MS with post-column derivatisation. , 2005, Phytochemical analysis : PCA.

[108]  M. Kelm,et al.  High-performance liquid chromatography separation and purification of cacao (Theobroma cacao L.) procyanidins according to degree of polymerization using a diol stationary phase. , 2006, Journal of agricultural and food chemistry.

[109]  R. Verpoorte,et al.  Isolation of the acetylcholinesterase inhibitor ungeremine from Nerine bowdenii by preparative HPLC coupled on-line to a flow assay system. , 2004, Biological & pharmaceutical bulletin.

[110]  Xiao-ru Wang,et al.  Isolation and purification of inflacoumarin A and licochalcone A from licorice by high-speed counter-current chromatography. , 2004, Journal of chromatography. A.

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[113]  Chaohong He,et al.  Single‐Step Preparative Separation of Barbinervic Acid and its Epimer (Rotungenic Acid), Along with Two Other Pentacyclic Triterpene Acids from the Leaves of Diospyros kaki Using HSCCC , 2006 .

[114]  Xueli Cao,et al.  Separation of Dammarane‐Saponins from Notoginseng, Root of Panax notoginseng (Burk.) F. H. Chen, by HSCCC Coupled with Evaporative Light Scattering Detector , 2003 .

[115]  Y. Yu,et al.  Development of gas chromatography-mass spectrometry with microwave distillation and simultaneous solid-phase microextraction for rapid determination of volatile constituents in ginger. , 2007, Journal of pharmaceutical and biomedical analysis.

[116]  Z. Su,et al.  Rapid purification of huperzine A and B with two polystyrene based resins by preparative low-pressure liquid chromatography , 2006 .

[117]  T. Fossen,et al.  Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug 'Crataegi folium cum flore' (hawthorn). , 2005, Phytochemical analysis : PCA.

[118]  T. Yamori,et al.  YM-216391, a Novel Cytotoxic Cyclic Peptide from Streptomyces nobilis , 2005, The Journal of Antibiotics.

[119]  Yingfeng Wang,et al.  Preparative isolation and purification of dicaffeoylquinic acids from the Ainsliaea fragrans champ by high-speed counter-current chromatography. , 2007, Phytochemical analysis : PCA.

[120]  Jinyong Peng,et al.  Isolation and purification of flavonoid glycosides from Trollius ledebouri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase. , 2005, Journal of chromatography. A.

[121]  P. C. Vieira,et al.  Isolamento do alcalóide ricinina das folhas de Ricinus communis (Euphorbiaceae) através de cromatografias em contracorrente , 2005 .

[122]  M. Hamburger,et al.  Preparative purification of the major anti-inflammatory triterpenoid esters from Marigold (Calendula officinalis). , 2003, Fitoterapia.

[123]  B. Lotina‐Hennsen,et al.  Pachypodol from Croton ciliatoglanduliferus Ort. as water-splitting enzyme inhibitor on thylakoids. , 2006, Journal of agricultural and food chemistry.

[124]  Yun Wei,et al.  Isolation of Imperatorin, Oxypeucedanin, and Isoimperatorin from Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook by Stepwise Flow Rate High‐Speed Countercurrent Chromatography , 2006 .

[125]  Yun Wei,et al.  Isolation of Hyperoside and Luteolin‐Glucoside from Agrimonia pilosa Ledeb Using Stepwise Elution by High-Speed Countercurrent Chromatography , 2007 .

[126]  Xianlong Cheng,et al.  Preparative HPLC for Purification of Four Isomeric Bioactive Saponins from the Seeds of Aesculus chinensis , 2005 .

[127]  D. Wianowska,et al.  Influence of the extraction mode on the yield of some furanocoumarins from Pastinaca sativa fruits. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

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[129]  I. Sutherland,et al.  Comparison of high-speed counter-current chromatography instruments for the separation of the extracts of the seeds of Oroxylum indicum. , 2005, Journal of chromatography. A.

[130]  Hongxi Xu,et al.  Preparative isolation of hydrolysable tannins chebulagic acid and chebulinic acid from Terminalia chebula by high-speed counter-current chromatography. , 2006, Journal of separation science.

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[133]  Feng Chen,et al.  Preparative high-speed counter-current chromatography for purification of shikonin from the Chinese medicinal plant Lithospermum erythrorhizon. , 2004, Journal of chromatography. A.

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[136]  Qinghua Sun,et al.  Preparative isolation and purification of four compounds from the Chinese medicinal herb rhizoma Anemarrhenae by high-speed counter-current chromatography. , 2006, Journal of chromatography. A.

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[139]  Dalei Zhang,et al.  Separation and Purification of Z Ligustilide and Senkyunolide A from Ligusticum chuanxiong Hort. with Supercritical Fluid Extraction and High‐Speed Counter‐Current Chromatography , 2006 .

[140]  M. Ahn,et al.  Preparative Isolation of Mangiferin from Anemarrhena asphodeloides Rhizomes by Centrifugal Partition Chromatography , 2006 .

[141]  Tian-you Zhang,et al.  Preparative isolation and purification of rupestonic acid from the Chinese medicinal plant Artemisia rupestris L. by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[142]  Chunzhao Liu,et al.  Two-step purification of scutellarin from Erigeron breviscapus (vant.) Hand. Mazz. by high-speed counter-current chromatography. , 2006, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[143]  C. Qiao,et al.  Preparative separation of gambogic acid and its C-2 epimer using recycling high-speed counter-current chromatography. , 2006, Journal of chromatography. A.

[144]  S. Rochfort,et al.  The isolation and purification of glucoraphanin from broccoli seeds by solid phase extraction and preparative high performance liquid chromatography. , 2006, Journal of chromatography. A.

[145]  T. Suganuma,et al.  Antioxidant and antimicrobial activities of the methanol extracts from pummelo (Citrus grandis Osbeck) fruit albedo tissues , 2006 .

[146]  A. Siani,et al.  Purification of betulinic acid from Eugenia florida (Myrtaceae) by high-speed counter-current chromatography. , 2005, Phytochemical analysis : PCA.

[147]  Cuirong Sun,et al.  Preparative isolation and purification of two phenylbutenoids from the rhizomes of Zingiber cassumunar by upright counter-current chromatography. , 2005, Journal of chromatography. A.

[148]  J. Lou,et al.  Preparative Isolation and Purification of Alkaloids from Corydalis yanhusuo W. T. Wang by High Speed Counter‐Current Chromatography , 2005 .

[149]  Yun Wei,et al.  Preparative separation of rhein from Chinese traditional herb by repeated high-speed counter-current chromatography. , 2003, Journal of chromatography. A.

[150]  Walédya Araújo Lopes de Melo,et al.  Separation of Free and Glycosylated Flavonoids from Siparuna guianensis by Gradient and Isocratic CCC , 2005 .

[151]  Feng Chen,et al.  Preparative isolation and purification of phillyrin from the medicinal plant Forsythia suspensa by high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[152]  Jinyong Peng,et al.  Preparative Separation and Isolation of Three Flavonoids and Three Phloroglucinol Derivatives from Hypericum japonicum Thumb. using High‐Speed Countercurrent Chromatography by Stepwise Increasing the Flow Rate of the Mobile Phase , 2006 .

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