Paeonilide, a novel anti-PAF-active monoterpenoid-derived metabolite from Paeonia delavayi.

A novel monoterpenoid-derived metabolite, paeonilide, was isolated from the roots of Paeonia delavayi. Its structure was established by a combination of spectroscopic and X-ray crystallographic analyses. It showed an anti-PAF effect with an IC50 value of ca. 8 microg/ml.

[X-ray diffraction Fourier pattern analysis of natural caculus bovis].

OBJECTIVE: To set up a method for analyzing and distinguishing all the chemical components in natural Caoulus Bovis. METHOD: Powder X-ray diffraction analyses was used to analyze four samples of natural Caculus Bovis, and the X-ray diffraction Fourier pattern was obtained for distinguishing natural Caculus Bovis. RESULT AND CONCLUSION: The method can be used for distinguishing animal medicinal materials.

[Studies on X-ray diffraction pattern of traditional Chinese medicinal materials].

Traditional Chinese medicine(TCM) as prescribed by Chinese traditional physicians is usually available as "decoction slices" which calls for a ready method for assessment of quantity or even genuineness. Three groups of TCM drugs (radix Rubiae, bulbus Fritillariae and rhizoma Dioscoreae) were selected by using powder X-ray diffraction analysis with complete absorption profile. Topological regularity and characteristic peaks of the absorption profile were obtained as fingerprint in X-ray diffraction diagrams of the pertinent medicinal materials. We have discovered the similarities of 3 radix Rubiae samples gathered from different localities and their differences with Rubia tinctorum, the similarities and differences between 7 species belonging to Fritillaria Genus, the similarities of 2 rhizoma Dioscoreae samples from different localities and their differences with 2 counterfeits. The result points to a promising prospect in achieving an objective assessment of genuineness at TCM drugs.

[The structure correction of villosolside].

The crystal structure of villosolside was determined by X-ray diffraction, which led to some stereochemical amendment of the structure proposed in the article by Xu CJ et al. in Acta Pharm Sin 1985, 20:652.

[The structure identification of zhepiresionol].

A new 3,7-dioxabicyclo[3, 3, O] octan-6-one named zhepeiresinol was isolated from Fritillaria thumbergii Miq. The spectroscopic and X-ray diffraction analysis established the structure as 2-(3',5'-dimethoxy-4'-hjydroxyphenyl)-3,7-dioxabicyclo[3, 3, O]octan-6-one.

[The crystal structure atlas data base system for chemical constituents of Chinese traditional and folk medicine].

The atlas data base system for chemical constituents of Chinese traditional and folk medicine is the first one for single crystal structure in China. It includes about 250 crystal structures of chemical ingredients of Chinese traditional and folk medicine. It has searching, plotting and computing functions. It is a useful reference base. All softwares are written in dbaseIII, FORTRAN and Assembler Languages. They can be run on PC-286,386,486 and their compatible microcomputers.

[Study on the chemical constituents of Tripterygium hypoglaucum (Lévl.) Hutch].

Two new diterpenes, named triptoditerpenic acid B(2) and hypodiolide A(3), respectively, were isolated from Tripterygium hypoglaucum (Lévl.) Hutch. Their structures were elucidated on the basis of spectra and X-ray analysis.

[Studies on the chemical constituents of Ventilago leiocarpa Benth].

Three anthraquinones (1-3) and two naphthoquinones(4,5) were isolated from the root of Ventilago leiocarpa Benth (Rhamnaceae). On the basis of spectroscopic data and X-ray diffraction analysis compound 5, ventilagolin, was shown to be a new naphthoquinone occurring as a racemate.

[Studies on diterpenoids from leaves of Tripterygium wilfordii].

Tripterygium wilfordii Hook f. has been used as a medicinal herb in traditional Chinese medicine and as an insecticide by the Chinese for hundreds of years. Recently, this plant has been used to treat cancer, rheumatic arthritis and various skin diseases in some Chinese clinics. It is of interest to note that Tripterygium also showed significant antifertility activities. The active principles of the anti-inflammatory, immunosuppressive and antifertile actions in Tripterygium are diterpenoid containing triepoxides, but information on its chemistry is limited to the woody part of the root and the root bark. Recently, we have studies the leaves of Tripterygium (collected at Zhejiang province, China), and isolated two novel diterpenoids by chromatography named tripdioltonide (8) and 13,14-epoxide 9,11,12-trihydroxytriptolide (9), besides triptonide (1), triptolide (2), tripdiolide (3), triptolidenol (4), 16-hydroxyl-triptolide (5), tripchlorolide (6) and triptriolide (7). Their structures were established by chemical reactions, TLC, UV, MS, IR, 1H-1H COSY, 1H-13C COSY, DEPT spectrometric investigation. The structure of tripdioltonide was further confirmed by X-ray analysis.

Studies on the Constituents of Adelostemma gracillimum.

The glycone portion of the glycoside of ADELOSTEMMA GRACILLIMUM Hook. f. (Asclepiadaceae) was investigated. Three known polyoxypregnane ester-type aglycones, penupogenin ( 1) (1, 2), kidjoranine ( 2) (1, 3), and gagamine ( 3) (4, 5), and one new compound named gracigenin ( 4) were isolated and their structures were characterized on the basis of spectroscopic evidence, and that of ( 4) was determined by X-ray crystallography. It was found to possess an unprecedented 8,14- SECO-polyoxypregnane ester-type skeleton, and 4 is the first compound with this C (21)-steroid type skeleton to be found in nature.

[Gloeosteretriol, a new sesquiterpene from the fermentation products of Gloeostereum incarnatum S. Ito et Imai].

A new sesquiterpenoid, named gloesteretriol, C15H26O3, mp 205-206 degrees C, [alpha]22D + 5.6 degrees (c 0.115, EtOH), was isolated from the fermentation products of Gloeostereum incarnatum S. Ito et Imai.. On the basis of spectral analysis its structure was deduced as I and confirmed by single-crystal X-ray analysis.

New Indole Alkaloids from Amsonia sinensis.

Fourteen indole alkaloids, Delta (14)-isoeburnamine ( 1), amsosinine ( 2), tabersonine, vincadifformine, lochnericine, tetrahydroalstonine, beta-yohimbine, isoeburnamine, minovicinine, picrinine, strictamine, rhazimine, vincanidine, and decarbomethoxytetrahydrosecamine, were isolated from AMSONIA SINENSIS. Delta (14)-isoeburnamine ( 1) and amsosinine ( 2) are new compounds, their structures have been established by spectral and chemical methods. A known sterol glycoside, daucosterol, has also been obtained. The structures of compounds 1 and 2 were finally confirmed by X-ray diffraction of single crystals.

[16-Hydroxytriptolide, a new active diterpene isolated from Tripterygium wilford II].

A new diterpene triepoxide, 16-hydroxytriptolide was isolated from the root and leaves of Tripterygium wilfordii Hook.f. 16-Hydroxytriptolide was obtained as white cluster crystal, mp 232-233.5 degrees C. Its molecular formula is C20H24O7. The structure and stereochemistry of 16-hydroxytriptolide was established as L2 on the basis of spectral data (IR, MS, UV, 1H-NMR, 13C-NMR, 2d-NMR, NOE) and X-ray crystallographic analysis. In the pharmacologic screening, 16-hydroxytriptolide showed definite antiinflammatory actions and strong immunosuppressive and antifertile activities. In antiinflammatory action, its half effective dose (ED50) was 0.12 mg/kg with the model of croton oil induced ear swelling of mice. In immunosuppressive action, its ED50 was 0.05 mg/kg with the model of the formation of haemolysinantibody of mice. Its lowest effective dose (po) was 0.027mg/kg x 33d in antifertile action.

[Studies on the chemical constituents of Taxus yunnanensis].

The ethanolic extract of the bark of Taxus yunnanensis Cheng et L. K. Fu. showed significant antineoplastic effect on the transplantable tumors in mice. The life survival of P388 leukemic bearing mice was increased (84%) and the growth of B16 melanoma in mice was inhibited (53%). From this extract eight taxane diterpenoids and taxane alkaloids have been isolated. Seven of them have been identified as taxinine E(1), taxinine J(2), 1-acetoxy-5-deacetyl baccatin I(4), baccatin III(5), taxol (6), cephalomannine (7), 7-xylosyl-10-deacetyl taxol (8) from their physical and spectroscopic properties. A new taxane diterpenoid, named yunnanxane (3) was elucidated as taxa-4 (20), 11-diene-2 alpha, 5 alpha, 10 beta, 14 beta-tetraoln2 alpha,5 alpha,10 beta-triacetaten-14 beta-alpha-methyl-beta- hydroxylbutyratebyhighfield 1H NMR, 13C NMR, 1H-1HCOSY, 13C-1HCOSY, 13C-1HCOLOC and X-ray analysis. It showed the inhibitory effect on A2780 DDP, KB and HCT-8 cell line in vitro. All of the eight compounds were isolated from this species for the first time.

Isolation and structure elucidation of armillaricin1.

From the petroleum ether extracts of the artificially cultured mycelium of ARMILLARIA MELLEA, a novel sesquiterpenoid aromatic ester named armillaricin has been isolated by silica gel column chromatography. Its structure was deduced from spectral data and confirmed by single-crystal X-ray analysis.

[Studies on the chemical constituents of Curcuma kwangsiensis].

A new sesquiterpene lactone named gweicurculactone, along with beta-sitosterol, germacrone, daucosterin and palmitic acid, was isolated from Curcuma kwangsiensis. Its structure has been confirmed by means of spectral and X-ray diffraction analysis.

[The isolation and identification of PAF inhibitors from Piper wallichii (Miq.) Hand-Mazz and P. hancei Maxim].

Platelet activating factor (PAF) is a highly potent endogenous phospholipid mediator, involved in various inflammatory and cardiovascular disorders. As part of a research program dealing with PAF inhibitors isolated from Piper plant species, we have isolated kadsurenone (I), denudatin B (II), and N-isobutyl-deca-trans-2-trans-4-dienamide (III) from Piped wallichii (Miq.) Hand-Mazz. and P. hancei Maxim. In a continuing search for potential PAF inhibitor from plants, using PAF induced platelet aggregation as a guide, a new neolignan named hancinone D (IV) was isolated from P. hancei maxim. By X-ray analysis it was identified as a racemate. The X-ray analysis led to a revision of the previously made structure assignment of hancinone C. Another new neolignan named wallichinine (V), which was identified as an analogue of (IV), along with the known compounds hancinone C (VI), galgravin (VII), dihydropiperlonguminine (VIII) and crotepoxide (IX) were isolated from P. wallichii (Miq.) Hand-Mazz. The structure determination was based upon spectroscopic analysis. All of the compounds were for the first time obtained from both plants. In the test of platelet aggregation caused by PAF, I, II, V, VI, VII showed inhibitory activity, whereas III, IV, VII, IX showed no activity.

[Coetsoidin A, a new diterpenoid from Rabdosia coetsoides C. Y. Wu].

From the leaves of Rabdosia coetsoides C. Y. Wu, a new diterpenoid, coetsoidin A (I) was isolated and its structure was established by spectroscopic and X-ray diffraction analysis. It is the first instance of a kaurene type diterpenoid possessing alpha,beta-unsaturated ketone functionality in ring B.

[Chemical studies of flower buds of Tussilago farfara L].

We have studied the flower buds of Tussilago farfara L. collected from Yulin county Shaanxi Province and have isolated a new terpenoid compound I with the composition C23H34O5, M+ 390.2416, mp 100-101 degrees C. On basis of physical and chemical properties and spectroscopic analysis (UV, IR, 1HNMR, 13CNMR, 1H-1H-COSY, 13C-1H-COSY DEPT, EI-MS, FAB-MS, HR-MS) and X-ray, the structure of I has been elucidated as a novel sesquiterpenoid compound, which is named farfaratin.