Cytotoxic 7,20-epoxy ent-kauranoids from Isodon xerophilus.

Four 7,20-epoxy ent-kaurane diterpenoids, xerophilusins G (1) and I-K (2-4), were isolated from the leaves of Isodon xerophilus, along with four known ones, enanderianin C (5), rosthorin A (6), longikaurin B (7), and rabdoternin D (8). Their structures were determined primarily using NMR spectroscopic techniques. The structure and stereochemistry of 3 were confirmed by X-ray crystallography. Compounds 4 and 7 exhibited broad cytotoxicity against four kinds of human tumor cells (K562, HL-60, HCT, and MKN-28 cells) in the range of 2.23-15.35 and 0.30-8.61 microg/ml, respectively.

[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.

[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.

[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.

[Crystal and molecular structure of the antimalarial agent alpha-(dibutylaminomethyl)-2, 7-dichloro-9-(p-chlorobenzylidene)-4- fluorenemethanol(benflumetol)].

The three-dimensional crystal and molecular structure of benflumetol(I), alpha-(dibutylaminomethyl)-2, 7-dichloro-9-(p-chlorobenzylidene)-4-fluorenemethanol, was determined by X-ray crystallography and compared with the crystal structures of the cinchona alkaloids. The aromatic rings of fluorene-phenyl system of benflumetol are twisted from each other by 52.8 degrees. The torsion angle of N-C-C-O of benflumetol is 47.6 degrees. The intramolecular aliphatic N-O distance in benflumetol is 2.709A, which is close to the N-O distance found in antimalarial cinchona alkaloids. Benflumetol contains an intramolecular hydrogen bond between the aliphatic nitrogen and oxygen atoms, no intermolecular hydrogen bond was found, which is different from the known amino alcohol antimalarials.

[Studies on the chemical constituents of the root of Desmos cochinchinensis Lour].

Desmos cochinchinensis as a folk medicine is used for treatment of malaria in China. Pharmacological studies showed that the petroleum ether extract of the root of the plant exhibited anti-malarial activity. Three flavonoids were isolated from this extract, of which two were identified as lawinal and isounonal. Compound III is a new flavanol. On the basis of spectroscopic analyses (UV, IR, MS, 1HNMR, 13CNMR and X-RD) the structure was established as 4,7-dihydroxyl-5-methoxyl-6-methyl-8-formyl-flavan. I and II were found from this plant for the first time.

[The isolation and structure identification of triptotriterpenic acid C].

A new ursolic-type acid named triptotriterpenic acid C was obtained from the total glycosides extracted from the root of Tripterygium wilfordii Hook.f. Its structure was inferred from chemical reaction, IR, 1HNMR, 13CNMR and MS spectral data. The structure and stereochemistry of this compound was confirmed to be 3 beta,22 alpha-dihydroxy-delta 12-ursene-30-oic acid by X-ray crystallo-diffraction analysis of its methyl ester.

[The structure of versicolactone D].

The extracts of Aristolochia versicolar S.M. Huang root afforded a new dimeric sesquiterpene lactone, versicolactone D, with a novel skeleton. Its structure was established by spectroscopic methods, mainly X-ray and 2D-NMR.

[Selective isolation of isopsoralen from crude extract of Psoralea corylifolia. L by using inclusion method of host-guest molecules].

AIM: To isolate the chemical components from extracted crude of Psoralea corylifolia L. METHODS: Applicate the function of molecular recognition in supramolecular chemistry, use 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol as the host molecule and chemical components in extracted crude of Psoralea corylifolia L. as guest molecules, which represent different from either in sort, quantity and sites of function groups or in structural topological character, 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol could selectively form inclusion compound with component endowed with interactional complementarity and isolate as crystalline from the extracted crude of Psoralea corylifolia L. RESULTS: The isopsoralen as guest molecule is selectively included by 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol in inclusion crystal and removed by acetone from the inclusion compound and total yield is 0.18%. Isopsoralen is determined by UV, IR, 1HNMR and MS and its inclusion compound is determined by means of IR, powder XRD and single crystal XRD. The isolation effect is analyzed by GC/MS. CONCLUSION: The method is simple and selective for isolation isopsoralen from extracted crude of Psoralea corylifolia L.

[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.

[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.

[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.

[Studies on the chemical constituents of Aquilaria sinensis (Lour) Gilg. III. Elucidation of the structure of isobaimuxinol and isolation and identification of the constituents of lower boiling fraction of the volatile oil].

A new sesquiterpenoid, named isobaimuxinol, C15H26O2, mp 73-75 degrees C, [a]D12-68(0) (c 0.10, CHCl3), was isolated from the volatile oil of Aquilaria sinensis (Lour), Gilg. (Thymeleaceae). Based on spectral (IR, 1H-NMR, 13C-NMR and 2D-NMR as well as MS) analysis its structure was identified as isobaimuxinol. The relative stereochemistry of isobaimuxinol was determined by X-ray crystallograhy. In addition, four known compounds, benzylacetone, p-methoxybenzylacetone, anisic acid and beta-agarofuran were isolated and identified from the lower boiling fraction of the volatile oil of this plant. These compounds were obtained for the first time from this plant.

[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.

[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.