Studies on inhibitors of rat mast cell degranulation produced by microorganisms. I. Screening of microorganisms, and isolation and physico-chemical properties of eurocidins C, D and E

Microorganisms producing anti-inflammatory substances were screened by the inhibitory effect on mast cell degranulation. Three new compounds related to pentaene macrolide eurocidins, eurocidins C, D and E, have been isolated from the culture broth of Streptoverticillium eurocidicum IFO 13491 as the inhibitors. Their molecular weights and molecular formulae were estimated as 781.89 and C39H59NO15 for eurocidin C, 795.92 and C40H61NO15 for eurocidin D, and 779.92 and C40H61NO14 for eurocidin E, respectively.     

Highly oxidized humulane sesquiterpenes from the basidiomycete Lactarius mitissimus

Two new highly oxidized humulane sesquiterpenes, mitissimols D (1) and E (2) were isolated from the fruiting bodies of Lactarius mitissimus. Their structures were elucidated using extensive spectroscopic techniques including 1D and 2D NMR spectra.     

Three new secolignan glycosides from Urtica fissa E. Pritz

Three new secolignan glycosides {3,4-trans-4-[bis(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-β-glucopyranoside (1), {3,4-trans-4-[(3-methoxy-4-hydroxyphenyl)(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-β-glucopyranoside (2) and {3,4-cis-4-[(3-methoxy-4-hydroxyphenyl)(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-β-glucopyranoside (3) were isolated from the roots of Urtica fissa E. Pritz. Their structures were identified by spectral methods including 1D NMR, 2D NMR and HR-EI-MS.     

Three novel bicyclic taxane diterpenoids with verticillene skeleton from the needles of Chinese yew, Taxus chinensis var. mairei.

Three novel bicyclic taxane diterpenoids with the verticillene skeleton were isolated from the needles of Chinese yew, Taxus chinensis var. mairei. Their structures were established as (3E,7E)-2 alpha, 10 beta, 13 alpha, 20-tetraacetoxy-5 alpha-hydroxy-3,8-secotaxa-3,7,11-trien-9-one (1), (3E,7E)-2 alpha, 5 alpha, 10 beta, 13 alpha-tetraacetoxy-20-hydroxy-3,8-secotaxa-3,7,11-trien-9-one (2), and (3E,7E)-10 beta, 13 alpha-diacetoxy-2 alpha, 5 alpha, 20-trihydroxy-3,8-secotaxa-3,7,11-trien-9-one (3) on the basis of 1D, 2D NMR and HR-MS spectroscopic analysis. Verticillene skeleton was considered as the biogenetic intermediate of taxane diterpenoids, isolation of bicyclic taxane diterpenoids with verticillene skeleton from this plant provides direct proof for this hypothesis.     

Two new meroterpenes from endophytic fungus A1 of Scyphiphora hydrophyllacea

Two new meroterpenes, guignardone D (1) and guignardone E (2), were isolated from endophytic fungus A1 of Scyphiphora hydrophyllacea Gaertn. F. Their structures were established based on spectroscopic methods including 1D and 2D NMR (HMQC, (1)H-(1)H COSY, HMBC, and ROESY).     

Two new sesquiterpene lactones from Montanoa tomentosa ssp. microcephala.

Two new sesquiterpene lactones: 8alpha-(4'-acetoxymethacryloyloxy)-3alpha,9beta-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6alpha-olide (1) and 8alpha-(2'E)-(2'-acetoxymethyl-2'-butenoyloxy)-3alpha,9beta-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6alphaolide (2), together with the known zoapatanolide A were isolated from the aerial parts of Montanoa tomentosa Cerv. in La Llave et Lex ssp. microcephala (Sch. Bip. In K. Koch) V.A. Funk (Asteraceae). The structures of all compounds were established on the basis of 1D, 2D NMR, and EIMS analysis.     

Kigamicins, novel antitumor antibiotics. II. Structure determination

Kigamicin A (1), B (2), C (3), D (4) and E (5) are novel antitumor antibiotics. Their structures were determined by spectroscopic analyses including various NMR measurements. Kigamicins have a unique aglycone of fused octacyclic ring system containing seven of six-membered rings and one oxazolidine. The aglycone links a sugar chain composed of one to four deoxysugars. These sugars were found to be amicetose and oleandrose.     

New beauvericins, potentiators of antifungal miconazole activity, Produced by Beauveria sp. FKI-1366. II. Structure elucidation

The structures of beauvericins D, E and F, novel potentiators of miconazole activity against Candida albicans produced by Beauveria sp. FKI 1366, were elucidated by various spectroscopic analyses including UV, NMR, and MS and degradation experiments. They have the common skeleton of the 18-membered cyclodepsipeptides.     

Two new tocopherol polymers from the seeds of Euryale ferox

Two new tocopherol polymers, chroman-type dimer named ferotocodimer A (1) and spiro-type trimer named ferotocotrimer E (2), were isolated from the seeds of Euryale ferox. Their structures were elucidated on the basis of spectroscopic methods including HR-ESI-MS and 1D and 2D NMR. The absolute configurations of 1 and 2 were determined by CD and ROESY experiments.     

Three new dammarane-type triterpene saponins from the leaves of Panax ginseng C.A. Meyer

Three new dammarane-type triterpene ginsenosides, together with six known ginsenosides, were isolated from the leaves of Panax ginseng C.A. Meyer. The new saponins were named as ginsenoside Rh??, ginsenoside Rh??, and ginsenoside Rh??. Their structures were elucidated as (20S)-3β,6α,12β,20-tetrahydroxydammara-25-ene-24-one 20-O-β-d-glucopyranoside (1), (20S)-3β,12β,20,24,25-pentahydroxydammarane 20-O-β-d-glucopyranoside (2), and (20S,23E)-3β,12β,20,25-tetrahydroxydammara-23-ene 20-O-β-d-glucopyranoside (3) on the basis of 1D and 2D NMR experiments and mass spectra. The known ginsenosides were identified as ginsenoside M(?cd), ginsenoside Rg?, ginsenoside Rb?, gypenoside XVII, gypenoside IX, and 20-(E)-ginsenoside F?.     

Two new C19-diterpenoid alkaloids from Aconitum transsectum

Two new C(19)-diterpenoid alkaloids, named aconitramines D (1) and E (2), were isolated from the roots of Aconitum transsectum. Based on comprehensive spectroscopic analyses including IR, ESI-MS, HR-ESI-MS, and 1D and 2D NMR, their structures were elucidated as 18-demethoxyltransconitine A (1) and 8-O-anisoyl-14-hydroxylacoforesticine (2).     

Chloropolysporins A, B and C, novel glycopeptide antibiotics from Faenia interjecta sp. nov. III. Structure elucidation of chloropolysporins

Structure elucidations of chloropolysporins A, B and C were achieved mainly by chemical degradation studies. These components possessed the same pseudoaglycone in common and their structures were closely related to that of beta-avoparcin. The structures of chloropolysporins differ from that of beta-avoparcin in the presence of vancomycinic acid moiety instead of monodechlorovancomycinic acid moiety and glucose, not ristosaminylglucose, in its side chain. Chloropolysporin C was identified as derhamnosylchloropolysporin B based on its 1H NMR and mass spectral analysis and degradation studies. Two minor components, chloropolysporins D and E, were identified as the epimers of each of chloropolysporins B and C, respectively, based on their Cotton effects and retention times on reverse phase HPLC.     

Lignans from Schisandra lancifolia

Two new neolignans, schilancifolignans D and E (1 and 2), together with eight known ones, were isolated from the leaves and stems of Schisandra lancifolia. The structures of 1 and 2 were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 were tested for their anti-HIV-1 activities and cytotoxicity. Both showed significant potential cytotoxic ability and weak anti-HIV-1 activities.     

New cytotoxic bis-labdanic diterpenoids from Alpinia calcarata

Two novel bis-labdanic diterpenoids named calcaratarin D and calcaratarin E were isolated from the rhizomes of Alpinia calcarata. Their structures were elucidated as a pair of stereoisomers on the basis of the spectral evidence. 2D NMR techniques including (1)H- (1)H COSY, HMQC, HMBC, NOESY spectra and HRFABMS were extensively applied to establish the structures. The two bis-labdanic diterpenoids showed cytotoxic activity against human KB cells in vitro.     

Novel cholecystokinin antagonists from Aspergillus alliaceus. II. Structure determination of asperlicins B, C, D, and E

Asperlicins B (1, C31H29N5O5), C (2, C25H18N4O2), D (3, C25H18N4O2), and E (4, C25H18N4O3) are novel cholecystokinin antagonists produced by Aspergillus alliaceus. The structures of these compounds have been determined by 1H NMR and MS analysis.     

Four new C19-diterpenoid alkaloids from Aconitum hemsleyanum var. circinatum

Four new C19-diterpenoid alkaloids, hemaconitines A–D (1–4), were isolated from the roots of Aconitum hemsleyanum var. circinatum. Their structures were elucidated as 19R-hydroxyl-secoyunnaconitine (1), (3R)-hydroxyl-liwaconitine (2), 14-anisoyl-leucanthumsine E (3), and 19R -acetonyl-8-O-methyltalatisamine (4) by extensive spectroscopic analysis (IR, UV, HR-ESI-MS, 1D, and 2D NMR).     

羊踯躅的化学成分研究

对羊踯躅植物花蕾的化学成分进行研究,应用多种色谱技术进行分离纯化、波谱技术鉴定其结构。从羊踯躅花蕾中分离并鉴定了15个化合物,分别为2E,4Z-脱落酸（1）,2α-羟基齐墩果酸（2）,齐墩果酸（3）,积雪草酸（4）,苯甲基糖苷（5）,邻苯二甲酸二丁酯（6）,β-谷甾醇（7）,牡荆素（8）,槲皮素（9）,硬脂酸（10）,rhodomollein Ⅰ（11）,rhodojaponin Ⅵ（12）,rhodomollein Ⅺ（13）,rhodojaponin Ⅱ（14）,kalmanol（15）。其中,化合物1 10为首次从羊踯躅植物中得到。     

Clavamycins, new clavam antibiotics from two variants of Streptomyces hygroscopicus. II. Isolation and structures of clavamycins A, B and C from Streptomyces hygroscopicus NRRL 15846, and of clavamycins D, E and F from Streptomyces hygroscopicus NRRL 15879

Clavamycins A, B, C, D, E and F represent new members of the clavam antibiotics group. Their purification was achieved by a variety of preparative chromatographic methods, essentially on reversed phase carrier. The structures were deduced from spectroscopic properties, especially from extensive NMR studies.     

Two new trans-clerodane diterpenoids from Otostegia limbata

Two new tricyclic clerodane-type diterpenoids, limbatolide D (1) and limbatolide E (2), have been isolated from the roots of Otostegia limbata. Their structures and the relative configuration were established on the basis of spectral methods, especially two-dimensional (2D) NMR techniques.     

New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Kaempferia?parviflora

Two new flav-3-en-3-ol glycosides, kaempferiaosides C (3) and D(4), and two new acetophenone glycosides, kaempferiaosides E (5) and F (6), were isolated from the Thai natural medicine Krachai Dum, the rhizomes of Kaempferia parviflora Wall. ex Baker. Their structures were established mainly on the basis of 1D and 2D NMR spectral data.