Novel Piperidine and 3,4-dihydro-2H-pyrrole Alkaloids from Tilia platyphyllos and Tilia cordata Flowers.

Abstract:

:Lime flowers, traditionally used for medical purposes for the treatment of symptoms of the common cold and mental stress, consist of the dried inflorescences including the floral bracts of Tilia cordata, Tilia platyphyllos, Tilia × vulgaris, or mixtures thereof. During phytochemical investigations, 6 different alkaloids - not described until now - were detected in T. cordata and T. platyphyllos flowers. They have been isolated and characterized as alkaloids with a dihydro-pyrrole and a piperidine substructure, respectively. Compounds 1A: and 1B: (tiliines A and B) are characterized as 2 diastereomers containing a 2-methyl-3,4-dihydro-2H-pyrrol-3-ol, connected via a C-10 alkyl chain to a O-glucosylated hydroquinone moiety. Compounds 2A: and 2B: (tiliamines A and B) are diastereomers of a 2-methyl-substituted piperidin-3-ol, coupled via a C-9 alkyl chain again to an O-glucosylated hydroquinone moiety. Compounds 3A: and 3B: (tilacetines A and B) are 3-O-acetylated derivatives of tiliamines. Quantification of the 6 alkaloids by HPLC-ESI-qTOF analysis indicated the presence of all alkaloids in T. cordata flowers and T. platyphyllos flowers, bracts, and leaves, with tiliines A and B and tilacetines A and B being the major compounds. Acetone/water turned out be the best extraction solvent for the alkaloids, but ethanol and ethanol/water mixtures also can be used for effective extraction. Furthermore, the alkaloids are found in hot water extracts, which are typically used in the traditional medicine.

journal_name

Planta Med

journal_title

Planta medica

authors

Symma N,Bütergerds M,Sendker J,Petereit F,Hake A,Düfer M,Hensel A

doi

10.1055/a-1340-0099

subject

Has Abstract

pub_date

2021-01-12 00:00:00

eissn

0032-0943

issn

1439-0221

pub_type

杂志文章
  • Assessment of antimycobacterial activity of a series of mainly marine derived natural products.

    abstract::A series of mainly marine derived natural products were tested for their activities against Mycobacterium tuberculosis and M. avium. Of the thirty-nine compounds tested fifteen demonstrated minimum inhibition concentrations (MICs) of 32 micrograms/ml or less, and eleven had MICs of 16 micrograms/ml or less. The most a...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2000-8534

    authors: König GM,Wright AD,Franzblau SG

    更新日期:2000-05-01 00:00:00

  • Naturally occurring protein kinase C inhibitors; II. Isolation of oligomeric stilbenes from Caragana sinica.

    abstract::The oligomeric stilbenes (+)-alpha-viniferin (1), miyabenol C (2), and kobophenol A (3) have been isolated from Caragana sinica (Buchoz) Rehd (Leguminosae). (+)-alpha-Viniferin (1) and miyabenol C (2) exhibited protein kinase C inhibitory activity at low micromolar concentrations. (+)-alpha-Viniferin inhibited keratin...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957996

    authors: Kulanthaivel P,Janzen WP,Ballas LM,Jiang JB,Hu CQ,Darges JW,Seldin JC,Cofield DJ,Adams LM

    更新日期:1995-02-01 00:00:00

  • Diarylheptanoids from Alnus glutinosa bark and their chemoprotective effect on human lymphocytes DNA.

    abstract::A study of secondary metabolites from the bark of Alnus glutinosa led to the isolation of fourteen diarylheptanoids: oregonin (1), platyphylloside (2), rubranoside A (3), rubranoside B (4), hirsutanonol (5), hirsutenone (6), hirsutanonol-5-O-β-D-glucopyranoside (7), platyphyllonol-5-O-β-D-xylopyranoside (8), aceroside...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0032-1328301

    authors: Novaković M,Stanković M,Vučković I,Todorović N,Trifunović S,Tešević V,Vajs V,Milosavljević S

    更新日期:2013-04-01 00:00:00

  • New triterpenoids from Kadsura heteroclita and their cytotoxic activity.

    abstract::Phytochemical investigations of the stem of Kadsura heteroclita (Roxb) Craib (Schizandraceae) resulted in the isolation and structure elucidation of six new triterpenoidal compounds named heteroclitalactones A-E (1-5) as well as heteroclic acid (6) and heteroclitalactone F (7), which was isolated for the first time fr...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2005-916263

    authors: Wang W,Liu J,Han J,Xu Z,Liu R,Liu P,Wang W,Ma X,Guan S,Guo D

    更新日期:2006-04-01 00:00:00

  • Taxol biosynthesis: an update.

    abstract::The novel diterpenoid taxol (paclitaxel) is now well-established as a potent chemotherapeutic agent. Total synthesis of the drug is not commercially feasible and, in the foreseeable future, the supply of taxol and its synthetically useful progenitors must rely on biological methods of production. The first three steps...

    journal_title:Planta medica

    pub_type: 杂志文章,评审

    doi:10.1055/s-2006-957684

    authors: Hezari M,Croteau R

    更新日期:1997-08-01 00:00:00

  • Stabilization of growth factors relevant to wound healing by a plant cell wall biomaterial.

    abstract::Stabilization of growth factors in a wound environment is critical to the wound healing process. Here we report on the stabilization of key growth factors by a unique plant cell wall biomaterial. MicroSheets are clear cell wall fragments isolated from the non-living water storage cells in the pulp or inner gel of Aloe...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-990225

    authors: Ni Y,Turner D,Yates K,Tizard I

    更新日期:2007-10-01 00:00:00

  • Citral is a new inducer of caspase-3 in tumor cell lines.

    abstract::Citral, 3,7-dimethyl-2,6-octadien-1-al, a key component of the lemon-scented essential oils extracted from several herbal plants such as lemon grass (Cymbopogon citratus), melissa (Melissa officinalis), verbena (Verbena officinalis) is used as a food additive and as a fragrance in cosmetics. In this study, we investig...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2005-864146

    authors: Dudai N,Weinstein Y,Krup M,Rabinski T,Ofir R

    更新日期:2005-05-01 00:00:00

  • Tea triterpenoidal saponins from the roots of Camellia sinensis have inhibitory effects against alcohol dehydrogenase.

    abstract::Ten new polyhydroxyolean-12-ene pentacyclic triterpenoidal saponins, named rogchaponins 1-10, were isolated from the methanolic extract of the roots of Camellia sinensis by a series of chromatographic methods (silica gel flash column and C18 MPLC followed by C18 HPLC). Their structures were established by 1D and 2D-NM...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0031-1280024

    authors: Varughese T,Manir MM,Rahaman M,Kim JK,Lee BG,Moon SS

    更新日期:2011-12-01 00:00:00

  • Protein tyrosine phosphatase 1B (PTP1B)-inhibiting constituents from the leaves of Syzygium polyanthum.

    abstract::A methanol extract of the leaves of Syzygium polyanthum (Wight) Walp. afforded four new acylbenzene derivatives (1-4) together with seven known compounds (5-11). The structures of 1-11 were elucidated by extensive spectroscopic methods and comparison with the literature data. The new compounds 1-3 and a known compound...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0032-1315000

    authors: Saifudin A,Tanaka K,Kadota S,Tezuka Y

    更新日期:2012-08-01 00:00:00

  • [New cardioactive drugs II, detection and isolation of cardiotonic amines with ionpair-HPLC].

    abstract::An ionpair-HPLC-technic using a reversed-phase column was developed to screen plant extracts for cardiotonic amines and to isolate them in a preparative scale for direct MS and pharmacological investigations. By this method the positive inotropic tyramine could be isolated from Selenicereus grandiflorus (L.) Britt et ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-971397

    authors: Wagner H,Grevel J

    更新日期:1982-01-01 00:00:00

  • Targeted and untargeted phytochemistry of Ligusticum canbyi: indoleamines, phthalides, antioxidant potential, and use of metabolomics as a hypothesis-generating technique for compound discovery.

    abstract::Ligusticum canbyi (J.M. Coult & Rose) is a medicinal understory forest species used in traditional rituals and ceremonies for spiritual enlightenment and improved mental health. Very little is known about the phytochemical complexity or diversity of L. canbyi tissues or extracts. The current study was undertaken to de...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0033-1350618

    authors: Turi CE,Murch SJ

    更新日期:2013-09-01 00:00:00

  • Bioactive compounds from the buds of Platanus orientalis and isolation of a new kaempferol glycoside.

    abstract::A new compound kaempferol 3-O-alpha-L-(2"-E-p-coumaroyl)-rhamnopyranoside, as well as the known flavonoids, kaempferol 3-O-beta-D-(6"-E-p-coumaroyl)-glucopyranoside, kaempferol 3-O-alpha-L-(2",3"-di-E-p-coumaroyl)-rhamnopyranoside, and caffeic acid were obtained from the methanolic extract of Platanus orientalis L. bu...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-959751

    authors: Mitrokotsa D,Mitaku S,Demetzos C,Harvala C,Mentis A,Perez S,Kokkinopoulos D

    更新日期:1993-12-01 00:00:00

  • [A comparative study of the effects of selection and environmental factors on alkaloid accumulation in strains of Choisya ternata].

    abstract::The accumulation of two dihydrofuroquinoline alkaloids has been studied in seventeen strains of Choisya ternata (Rutaceae) initiated from the same tree. The contents of platydesminium and balfourodinium vary in heavy proportions. The effect of some factors (age of the culture, NAA or glucose concentrations of the medi...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-971221

    authors: Gras M,Crèche J,Chénieux JC,Rideau M

    更新日期:1982-12-01 00:00:00

  • Equol but not genistein improves early metaphyseal fracture healing in osteoporotic rats.

    abstract::Healing of predominantly metaphyseal fractures in postmenopausal osteoporosis is delayed and comparatively poor. Hormone replacement therapy could improve fracture healing, but, because of its potential side effects, natural alternatives are more appealing. The aim of this study was to determine if the soy metabolite ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0029-1185380

    authors: Kolios L,Sehmisch S,Daub F,Rack T,Tezval M,Stuermer KM,Stuermer EK

    更新日期:2009-04-01 00:00:00

  • Neolignan glycosides from Pedicularis longiflora.

    abstract::Four new neolignan glucosides, longiflorosides A, B, C and D, in addition to one known neolignan glucoside, dehydro-diconiferyl alcohol-4-O-beta-D-glucopyranoside were obtained from whole plants of Pedicularis longiflora. The structures of these compounds were determined mainly on spectral evidence. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957662

    authors: Wang CZ,Jia ZJ

    更新日期:1997-06-01 00:00:00

  • Prediction of the Passive Intestinal Absorption of Medicinal Plant Extract Constituents with the Parallel Artificial Membrane Permeability Assay (PAMPA).

    abstract::At the early drug discovery stage, the high-throughput parallel artificial membrane permeability assay is one of the most frequently used in vitro models to predict transcellular passive absorption. While thousands of new chemical entities have been screened with the parallel artificial membrane permeability assay, in...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0042-101247

    authors: Petit C,Bujard A,Skalicka-Woźniak K,Cretton S,Houriet J,Christen P,Carrupt PA,Wolfender JL

    更新日期:2016-03-01 00:00:00

  • Antibacterial activity of calozeyloxanthone isolated from Calophyllum species against vancomycin-resistant Enterococci (VRE) and synergism with antibiotics.

    abstract::Calozeyloxanthone ( 1) was re-isolated from the root bark of Calophyllum moonii, an endemic species of Sri Lanka, and found to be active against vancomycin-resistant Enterococci (VRE) and vancomycin-sensitive Enterococci (VSE) with MIC values of 6.25 microg/ml and 12.5 microg/ml, respectively. Further, a marked synerg...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-2002-32558

    authors: Sakagami Y,Kajimura K,Wijesinghe WM,Dharmaratne HR

    更新日期:2002-06-01 00:00:00

  • Intestinal immune system modulating polysaccharides from rhizomes of Atractylodes lancea.

    abstract::Hot water extract (ALR-0) of rhizomes of Atractylodes lanceo DC. was fractionated into MeOH-soluble fraction (ALR-1), supernatant fraction of EtOH precipitation (ALR-3 + 4), and crude polysaccharide fraction (ALR-5). Among these fractions, only ALR-5 showed potent stimulating activity for proliferation of bone marrow ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957564

    authors: Yu KW,Kiyohara H,Matsumoto T,Yang HC,Yamada H

    更新日期:1998-12-01 00:00:00

  • Anti-inflammatory Flavanones and Flavanols from the Roots of Pongamia pinnata.

    abstract::A phytochemical study of the roots of Pongamia pinnata afforded 29 flavanones and flavanols, including 7 previously undescribed compounds. The structures of the isolated compounds were determined by 1D and 2D NMR and mass spectroscopy data. The absolute configurations of the compounds were assigned via analysis of the...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/a-0626-7356

    authors: Wen R,Lv H,Jiang Y,Tu P

    更新日期:2018-11-01 00:00:00

  • Inhibition of intestinal chloride secretion by proanthocyanidins from Guazuma ulmifolia.

    abstract::The antisecretory activity of Guazuma ulmifolia bark was examined in rabbit distal colon mounted in an Ussing chamber. Chloride secretion was stimulated by cholera toxin and prostaglandin E2 (PGE2). Guazuma ulmifolia extract (GUE) completely inhibited cholera toxin-induced secretion if the extract was added to the muc...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-958057

    authors: Hör M,Rimpler H,Heinrich M

    更新日期:1995-06-01 00:00:00

  • Revised Stereochemistry of So-Called Isoselagine and Spectroscopic Analysis of 6alpha-Hydroxylycopodine from Lycopodium serratum var. longipetiolatum.

    abstract::The structure of isoselagine, isolated from the Chinese medicinal plant LYCOPODIUM SERRATUM Thunb. var. longipetiolatum Spring, was shown to be identical with huperzine A ( 1) and to have an exocyclic double bond in the E -configuration from NOE data. In the process of extraction of isoselagine, we also isolated and i...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-959735

    authors: Sun CM,Ho LK,Sun ML

    更新日期:1993-10-01 00:00:00

  • Marine natural products research: current directions and future potential.

    abstract::Natural products research is increasingly turning to marine animals, plants, and microbes as source organisms. Several marine natural products are currently in preclinical and clinical evaluation, others show promising biological activities in in vitro and in vivo assays. Investigations of biological and chemical ecol...

    journal_title:Planta medica

    pub_type: 杂志文章,评审

    doi:10.1055/s-2006-957861

    authors: König GM,Wright AD

    更新日期:1996-06-01 00:00:00

  • Inhibitory activity of soyasaponin II on virus replication in vitro.

    abstract::The antiviral activities of two saponins, soyasaponin I and II, isolated from soybean (Glycine max Merrill) were studied in vitro against herpes simplex virus type 1 (HSV-1). Soyasaponin II was more potent than soyasaponin I as shown by reduction of HSV-1 production. Soyasaponin II was also found to inhibit the replic...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957622

    authors: Hayashi K,Hayashi H,Hiraoka N,Ikeshiro Y

    更新日期:1997-04-01 00:00:00

  • Stellera chamaejasme and Its Main Compound Luteolin 7-O-Glucoside Alleviates Skin Lesions in Oxazolone- and 2,4-Dinitrochlorobenzene-Stimulated Murine Models of Atopic Dermatitis.

    abstract::Stellera chamaejasme, also known as "Langdu", has been traditionally used for the management of skin-related diseases such as psoriasis and skin ulcers. The aim of this study was to determine whether S. chamaejasme and its major component, luteolin 7-O-glucoside, have a preventive effect on the development of atopic d...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/a-0746-8698

    authors: Jo BG,Park NJ,Jegal J,Choi S,Lee SW,Yi LW,Kim SN,Yang MH

    更新日期:2019-05-01 00:00:00

  • Honokiol induces apoptosis via cytochrome c release and caspase activation in activated rat hepatic stellate cells in vitro.

    abstract::The therapeutic goal in liver fibrosis is the reversal of fibrosis and the selective clearance of activated hepatic stellate cells (HSCs) by inducing apoptosis. Over the past several years, we have screened for natural products that mediate apoptosis in activated HSCs. Among the candidate compounds, honokiol, isolated...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2005-837757

    authors: Park EJ,Zhao YZ,Kim YH,Lee BH,Sohn DH

    更新日期:2005-01-01 00:00:00

  • The effect of N-deacetylcolchiceine on serum lipoproteins in rats.

    abstract::N-Deacetylcolchiceine (DAC) administered i.p. to rats decreased the level of serum cholesterol and apoB. It was accompanied by the fall of HDL-C due to the decrease of both HDL subfractions HDLa and HDLb, and by a rather weaker decrease of LDL-C. The levels of serum and lipoprotein triacylglycerols were not significan...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:

    authors: Skottová N,Vecera R,Walterová D,Simánek V

    更新日期:1992-02-01 00:00:00

  • Naturally occurring norephedrine oxazolidine derivatives in khat (Catha edulis).

    abstract::Khat (Catha edulis Forsk.) is a perennial shrub whose young leaves are chewed for their psychostimulating and anorectic properties. The main active principles of khat are believed to be the phenylpropylamino alkaloids, primarily (-)-cathinone [(S)-α-aminopropiophenone], (+)-cathine [(1S)(2S)-norpseudoephedrine], and (...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0031-1298430

    authors: Krizevski R,Bar E,Dudai N,Levy A,Lewinsohn E,Sitrit Y,Ben-Shabat S

    更新日期:2012-05-01 00:00:00

  • Protective Effects of α-Boswellic Acids in a Pulmonary Arterial Hypertensive Rat Model.

    abstract::The purpose of this study was to observe the protective effects of α-boswellic acids on hypoxia-induced pulmonary vascular structural remodeling in pulmonary arterial smooth muscle cells in a hypertensive rat model. Pulmonary arterial smooth muscle cells were cultured and then randomly divided into four groups: normox...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0042-109069

    authors: Xiao B,Zhang G,Ali Sheikh MS,Shi R

    更新日期:2017-01-01 00:00:00

  • Shogaols from Zingiber officinale protect IMR32 human neuroblastoma and normal human umbilical vein endothelial cells from beta-amyloid(25-35) insult.

    abstract::From the rhizome of Zingiber officinale L. (Zingiberaceae), four shogaols that protect IMR32 human neuroblastoma and normal human umbilical vein endothelial cells from beta-amyloid(25 - 35) insult at EC50 = 4.5 - 81 microM were isolated. The efficacy of cell protection from beta-amyloid(25 - 35) insult by these shogao...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-2002-26757

    authors: Kim DS,Kim DS,Oppel MN

    更新日期:2002-04-01 00:00:00

  • Minor Iridoid and Phenol Glycosides of Picrorhiza kurrooa.

    abstract::From the roots of PICRORHIZA KURROOA a new iridoid glycoside, 6-feruloylcatalpol has been isolated, along with veronicoside and minecoside and two phenol glucosides, picein and androsin. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-962066

    authors: Stuppner H,Wagner H

    更新日期:1989-10-01 00:00:00