Biomedical subjects
Publications and source records attributed to D Q Yu.
Structure and stereochemistry of ganosporelactone A and B isolated from the spores of Ganoderma lucidum have been elucidated by the use of 1H-1H COSY, 1H-13C COSY, 1H-13C COLOC and NOESY 2D NMR spectroscopy. Ganosporelactone A and B are two novel pentacyclic triterpenoids which may be biogenetically derived from lanostane skeleton through the construction of C16 and C23 bond.
A new sesquiterpene compound named isorupestonic acid was isolated from Artemisia rupestris and its absolute stereostructure was elucidated as 3B by spectral and X-ray crystallographic methods. Interestingly, the isorupestonic acid is based upon an unusual 6, 7 membered ring skeleton differing from the 5, 7 membered ring rupestonic acid although both have the same absolute configuration at C-1. The biogenesis of isorupestonic acid most likely involves breaking the C4-C5 bond of rupestonic skeleton and forming the C5-C14 bond. The absolute configuration of rupestonic acid was also determined as 4C by X-ray analysis and CD data.
Eight compounds were isolated from the acetone extract of artificially cultured mycelium of Armillaria mellea (Vahl. ex Fr.)Quel.(Tricholomataceae). Three of them are protoilludane sesquiterpenoid aromatic esters. Their structures were elucidated by spectral data analysis as the known 4'-methylmelledonal (I)and two new compounds named armillaritin (II) and armillarivin (III). In addition, five known compounds were identified as D-erythritol, D-mannitol, azelaic acid, orsellinic acid and glycerin-alpha-monooleate.
A novel alkaloid, named hypodematine, was isolated from Hypodematium sinense Iwatsuki (belonging to the lypterdaceae). Its structure has been elucidated to have a novel skeleton of benzo-aza-cyclooctatetraene with a phenyl substitution by means of the 1H-1H COSY, 1H-13C COSY and long-range 1H-13C COSY spectroscopy.
A new flavonoid glycoside, named linariifolioside, C29H32O17 with mp at 232-234 degrees C (dec.), was isolated from the alcohol extract of the dried whole herb of Veronica linariifolia Pall. ex Link sub. dilatata (Nakai et Kitagawa) Hong. Based on spactral (IR, UV, 1HNMR, 13CNMR and FAB-MS) analysis and hydrolysis products its structure was identified as luteolin-7-O-6"'-O-acetyl-beta-D-glucosyl-(1----2)-beta-D-glucoside (I). In addition, four known compounds, luteolin-7-O-beta-D-glucosyl-(1----2)-beta-D-glucoside (II), apigenin-7-O-alpha-L-rhamnoside (III), luteolin (IV), and apigenin (V) were isolated from the same fraction and identified. These compounds were obtained for the first time from this plant.
Five compounds were isolated from the ether soluble fraction of the spores of Ganoderma lucidum. On the basis of their chemical properties and spectral data (MS, UV, IR, 1H and 13CNMR), they were identified as 3,7,11,12,15,23-hexaoxo-5 alpha-lanosta-8-en-26-oic acid (I), 3 beta,7 beta-dihydroxy-11,15,23-trioxo-5 alpha-lanosta-8-en-26-oic acid (II), 7 beta-hydroxy-3,11,15,23-tetraoxo-5 alpha-lanosta-8-en-26-oic acid (III), 3,7,11,15,23-pentaoxo-5 alpha-lanosta-8-en-26-oic acid (IV), 24,25,26-trihydroxy-5 alpha-lanosta-7,9 (11)-dien-3-one (V), Compound I is a new natural product, named ganosporeric acid A. Compounds II, III, IV and V were obtained for the first time from the spores of Ganoderma lucidum.
Three triterpene compounds have been isolated from the roots of Tripterygium wilfordii Hook F. The structure of the new compound, 3-hydroxy-25-norfriedel-3, 1 (10)-dien-2-one-30 oic acid named tripterygone (III), and the identity of others, 3 beta, 22 beta-dihydroxy-delta 12-oleanen-29-oic acid (I) and 2 alpha, 3 alpha, 24-trihydroxy-delta 12-ursene-28-oic acid (II) have been established by spectral data and physical properties. Compound II was isolated for the first time from the title plant.
Successive purification of a crude extract of cultured Mi Huan Jun mycelia, followed by an assay of the effect on complete ischemia in mice, led to the isolation of a new compound with cerebral protecting activity, hereafter designated as AMG-1. The structure of AMG-1 was proposed as being 6-(5-hydroxy-2-pyridyl-methylamino)-9-beta-ribofuranosylpurine (1) on the basis of its UV, mass, 1H-NMR, and 13C-NMR spectra.
From roots of TRIPTERYGIUM WILFORDII used in Chinese folk medicine, a new ursane-triterpene named tripterygic acid A was isolated along with a known triterpene and their structures were elucidated by means of spectral analysis and chemical transformation.
Ganoderma alkaloid A (IA, 1-isopentyl-2-formyl-5-hydroxymethylpyrrole) and B (IB, 1-phenylethyl-2-formyl-5-hydroxymethylpyrrole) were discovered in the hypha of deep fermented Ganoderma capense. Both are new pyrrole alkaloids. In order to provide samples for bioassay, we completed the synthesis of these new alkaloids and their acetyl derivatives. The route of synthesis included six steps. The whole yields were 20.7% for IA and 24.7% for IB. Synthetic IA and IB were found to be identical with the natural compounds by comparison of spectral data. IA and IB showed some antiinflammatory activity in animal experiments.
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A new protoilludane sesquiterpenoid aromatic ester, named armillaripin, C24H30O6, mp 202-204 degrees C, [alpha]D15 + 130 degrees (c 0.055, CHCl3), was isolated from the petroleum ether extract of the artificially cultured mycelium of Armillaria mellea (Vahl. ex Fr.) Quel. (Tricolometaceae) by silica gel chromatography. On the basis of spectral (UV, IR, 1HNMR 13CNMR and MS) analysis its structure was deduced as I and confirmed by single-crystal X-ray analysis.
Two new protoilludane sesquiterpenoid aromatic esters, armillarilin C24H30O7, mp 179-180 degrees C, [alpha]D14 + 162 (c 0.97 CHC1(3] and armillarinin C24H29O7 C1, mp 152-155 degrees C, [alpha]D17 + 153.6, (c 0.09, CHC1(3], have been isolated from the artifically cultured mycelium of Armillaria mellea (Vahl. ex Fr.) Quel (Tricholometaceae). On the basis of spectral (UV, IR, 1HNMR, 13CNMR and MS) analysis their structures were identified as I and II, respectively.
The ether extract of musk, artificially bred musk and original musk reacted with 2,4-dinitrophenylhydrazine to form corresponding phenylhydrazones. The products were determined by HPLC. The conditions of quantitative analysis of muscone hydrazone and qualitative analysis of delta 5-androstene-3 beta-hydroxy-17-one hydrazone and 3 alpha-hydroxy-5 alpha-androstan-17-one hydrazone, such as the choice of chromatographic columns and mobile phase were studied. The results of standard curve and recovery experiment are satisfactory. Dual detection and MS were used to identify and analyse the purity of the chromatographic peak of muscone hydrazone. Experiments of addition of standards were used to confirm the peaks of delta 5-androstene-3 beta-hydroxy-17-one hydrazone and 3 alpha-hydroxy-5 alpha-androstan-17-one hydrazone.
Two new nortriterpenoid saponins, named yemuoside YM10 (I) and YM12 (II), were isolated from Stauntonia chinensis Decne. A new prosaponin (VI) was isolated from the cleavage of ester-glycoside linkage. Their chemical structures were elucidated by means of chemical and spectrometric analysis. Yemuoside YM10 (I): C58H92O25, a white powder, mp 215-219 degrees C (dec), [alpha]D20-4.41 degrees (c 0.272, CH3OH). Its structure was found to be 28-O-alpha-L-rhamnopyranosyl- (1----4) -beta-D-glucopyranosyl- (1----6) -beta-D-glucopyranosyl ester of 3-O-alpha-L-rhamnopyranosyl-(1----2)-alpha-L-arabinopyranosyl-30-+ ++norolean-12, 20 (29) -dien-28-oic acid. Yemuoside YM12 (II): C52H82O21, a white powder, mp 200-204 degrees C (dec.), [alpha]D20 + 10.12 degrees (c 0.346, CH3OH). Its structure was found to be 28-O-beta-D-glucopyranosyl- (1----6) -beta-D-glucopyranosyl ester of 3-O-alpha-L-rhamnopyranosyl- (1----2) -alpha-L-arabinopyranosyl-30-norolean-12, 20 (29)-dien-28-oic acid. Prosaponin (VI): C40H62O11, a white powder, mp 243-246 degrees C (dec.), [alpha]D22 + 12.13 degrees (c 0.128, CH3OH). Its structure was found to be 3-O-alpha-L-rhamnopyranosyl- (1----2)-alpha-L-arabinopyranosyl-30-norolean-12, 20 (29)-dien-28-oic acid.
Three indolic alkaloidal glucosides were isolated from the polar fraction of the stems of Nauclea officinalis. Two are new, named naucleoside (Ia) and nauclecosidine (IIa) and the other is a well known alkaloid, vincoside lactam. The structures of Ia and IIa were elucidated on the basis of spectroscopic data (IR, MS, HNMR and CNMR) and chemical evidence.
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