Muricoreacin and murihexocin C, mono-tetrahydrofuran acetogenins, from the leaves of Annona muricata.

Bioactivity-directed fractionation of the leaves of Annona muricata L. (Annonaceae) resulted in the isolation of two new Annonaceous acetogenins, muricoreacin (1) and murihexocin C (2). Compounds 1 and 2 showed significant cytotoxicities among six human tumor cell lines with selectivities to the prostate adenocarcinoma (PC-3) and pancreatic carcinoma (PACA-2) cell lines.

Triterpenoid saponins from Berneuxia thebetica.

Four triterpenoid saponins were isolated from Berneuxia thibetica. On the basis of chemical and spectroscopic evidence, three new saponins, berneuxia saponins A, B and C, were elucidated as 21-tigloylbarringtogenol C-3 beta-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-galactopyranosyl(1-->3)[bet a- D-glucopyranosyl(1-->2)-beta-D-glucuronopyranoside], 28-tigloylbarringtogenol C-3 beta-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-galactopyranosyl(1-->3)[bet a- D-glucopyranosyl(1-->2)-beta-D-glucuronopyranoside] and 16 alpha-28-dihydroxyolean-12-en-21-one-3-O-alpha-L-rhamnopyranosyl(1 -->2) -beta-D-galactopyranosyl(1-->3)[beta-D-glucopyranosyl(1-->2)-beta-D- glucuronopyranoside]. The known saponin was desacyl jegosaponin.

Two new mono-tetrahydrofuran ring acetogenins, annomuricin E and muricapentocin, from the leaves of Annona muricata.

Bioactivity-directed fractionation of the leaf extract of Annona muricata L. (Annonaceae) has resulted in the isolation of two new Annonaceous acetogenins, annomuricine (1) and muricapentocin (2). Compounds 1 and 2 are monotetrahydrofuran ring acetogenins bearing two flanking hydroxyl groups; however, each has three additional hydroxyl groups. Compound 1 has an erythro 1,2-diol, and 2 has a 1,5,9-triol moiety. Both 1 and 2 showed significant cytotoxicities against six types of human tumors, with selectivities to the pancreatic carcinoma (PACA-2) and colon adenocarcinoma (HT-29) cell lines.

Triterpenoid saponins from Anemone hupehensis.

Two new triterpenoid saponins, named hupehensis saponin F and G, were isolated from the water soluble part of Anemone hupehensis Lemoine. By chemical and spectroscopic evidence, their structures were elucidated as 3-O-beta-D-ribopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1--> 2)-alpha-L-arabinopyranosyl hederagennin-28-O-alpha-rhamnopyranosyl(1--> 4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl(1--> 3)-alpha-L-rhamnopyranosyl(1-->4)-beta-glucopyranosyl(1--> 6)-beta-D-glucopyranoside and 3-O-beta-D-ribopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1--> 2)-alpha-L-arabinopyranosyl hederagenin-28-O-beta-glucopyranosyl(1-->3)-alpha-rhamnopyranosyl( 1--> 4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl(1--> 3)-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1--> 6)-beta-D-glucopyranoside, respectively.

Five new monotetrahydrofuran ring acetogenins from the leaves of Annona muricata.

Bioactivity-directed fractionation of the leaves of Annona muricata resulted in the isolation of annopentocins A (1), B (2), and C(3), and cis- and trans-annomuricin-D-ones (4, 5). Compounds 1-3 are the first acetogenins reported bearing a mono-tetrahydrofuran (THF) ring with one flanking hydroxyl, on the hydrocarbon side, and another hydroxyl, on the lactone side, that is one carbon away from the THF ring. Compounds 4 and 5 were obtained in a mixture and are new mono-THF ring acetogenins bearing two flanking hydroxyls and an erythro-diol located between the THF and the ketolactone rings. Compound 1 was selectively cytotoxic to pancreatic carcinoma cells (PACA-2), and 2 and 3 were selectively cytotoxic to lung carcinoma cells (A-549); the mixture of 4 and 5 was selectively cytotoxic for the lung (A-549), colon (HT-29), and pancreatic (PACA-2) cell lines with potencies equal to or exceeding those of Adriamycin.

Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata.

In a continuation of our research on bioactive components from the leaves of Annona muricata, three novel monotetrahydrofuran Annonaceous acetogenins, namely, annomutacin [1], (2,4-trans)-10R-annonacin-A-one [2], and (2,4-cis)-10R- annonacin-A-one [3], have been identified. Their structures were deduced by ms, nmr, ir, and uv spectral and chemical methods, and the absolute configurations were determined by Mosher ester methodology. A known bioactive amide, N-p-coumaroyl tyramine, was also found. Compound 1 and the mixture of compounds 2 and 3 showed selective cytotoxicities against the human A-549 lung tumor cell line.

Two new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annomuricins A and B, from the leaves of Annona muricata.

The leaves of Annona muricata have yielded eight monotetrahydrofuran Annonaceous acetogenins. Two of them, annomuricins A [1] and B [2], whose chemical structures were deduced by ms, nmr, ir, and uv spectral and chemical methods, are novel and unusual. Compounds 1 and 2 each possess five hydroxyl groups; two hydroxyl groups are vicinal, with the vicinal group of 1 threo and that of 2 erythro. The absolute configurations of 1 and 2 were determined by Mosher ester methodology. Six monotetrahydrofuran acetogenins, previously described in the seeds, were found in the leaves; these are gigantetrocin A, annonacin-10-one, muricatetrocins A and B, annonacin, and goniothalamicin.

Muricatocins A and B, two new bioactive monotetrahydrofuran Annonaceous acetogenins from the leaves of Annona muricata.

The leaves of Annona muricata have yielded the novel monotetrahydrofuran Annonaceous acetogenins, muricatocins A [1] and B [2]. Each compound possesses five hydroxyl groups, with two hydroxyl groups at the C-10 and C-12 positions. The absolute configurations of 1 and 2 (except for positions C-10 and C-12) were determined by Mosher ester methodology. The C-10, C-12 acetonides (1c, 2c) suggested relative stereochemistry and significantly enhanced cytotoxicity against the A-549 human lung tumor cell line. Three known monotetrahydrofuran acetogenins, annonacin A, (2,4-trans)-isoannonacin, and (2,4-cis)-isoannonacin, were also found.

New bioactive monotetrahydrofuran Annonaceous acetogenins, annomuricin C and muricatocin C, from the leaves of Annona muricata.

The leaves of Annona muricata have yielded two additional monotetrahydrofuran Annonaceous acetogenins, annomuricin C [1] and muricatocin C [2]. Compounds 1 and 2 each possess five hydroxyl groups; two hydroxyl groups are at the C-10/C-11 and C-10/C-12 positions in 1 and 2, respectively. The absolute configurations of 1 and 2, except for positions C-10 and C-11 or C-12, were determined by Mosher ester methodology. The C-10/C-11 and C-10/C-12 acetonides (1c, 2c) suggested relative stereochemistry and significantly enhanced the cytotoxicities against the A-549 human lung and the MCF-7 human beast solid tumor cell lines. One known monotetrahydrofuran acetogenin, gigantetronenin, not described previously from this plant, was also found.

Triterpenoid saponins from Anemone hupehensis.

Four triterpenoid saponins were isolated from Anemone hupehensis. On the basis of chemical and spectroscopic evidence, two new saponins, hupehensis saponins D and E, were elucidated as 3-O-beta-D-glucopyranosyl (1-->3)-beta-D-ribopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl oleanolic acid-28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside and 3-O-beta-D-glucopyransoyl (1-->3-beta-D-ribopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl hederagenin-28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside. The two known saponins were identified as huzhangosides B and D.

[Anti-hyperlipemia and anti-oxidation effects of xue zhi ling].

92 cases with complete clinical data among 125 hyperlipemia patients were randomly divided into two groups: 51 cases in the Xue Zhi Ling treatment group and 41 cases in the control group with medication of panagin. The drugs were administered to all patients for 12 weeks and the blood lipid was then examined at the 4th, 8th, 12th week after medication respectively. In treatment group, there was the effect of lowering TC, TC-HDL/HDL and raising HDL at the 4th week (P < 0.05). However, there were no significant difference in above-mentioned parameters at the 4th, 8th and 12th week respectively. The experiment also showed that Xue Zhi Ling could reduce TG at the 8th and 12th week (P < 0.05). While there was no significant difference between that of the 8th and 12th weeks. The mean reduction of TC, TG and TC-HLD/HDL were 18.7%, 19.5% and 27.6% respectively, while the elevation of HDL in average was 17.4%. All of the lipid indexes in control group had no significant changes at any stage. In addition, it was shown that Xue Zhi Ling could decrease serum LPO at 12th week (P < 0.05). The results indicated that the Xue Zhi Ling has the effect of regulating the hyperlipemia and anti-oxidation.

Two triterpenoid saponins from Pterocephalus bretschneidri.

Two new triterpenoid saponins, named bretschnosides A and B, were isolated from the roots of Pterocephalus bretschneidri. On the basis of chemical degradation and spectroscopic evidence, the structures of bretschnosides A and B were shown to be 3-O-alpha-L-rhamnopyranosyl(1-->3)- beta-D-xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-beta-D- xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside 4 and 3-O-alpha-D-glucopyranosyl(1-->3)-beta-D-xylopyranosyl(1-->3)-alpha-L- rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside 6, respectively.

Triterpenoid saponins from Pterocephalus hookeri.

Four new triterpenoid saponins, named hookerosides A-D, were isolated from Pterocephalus hookeri. Based on chemical and spectral evidence, their structures were determined as 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-xylopyranosyl(1-->3)-alpha-L- Rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside, 3-O-beta-D-xylopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->4)-beta-D- xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside, 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl(1-->4)-beta-D- glucopyranosyl(1-->4)-beta-D-xylopyranosyl(1-->3)-alpha-L-rhamnopyranosy l(1-->2 ) beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-glucopyranoside and oleanolic acid 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D- xylopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->4)-beta-D-xylopyranosyl(1 -->3)- alpha-L-rhamnopyranosyl(1-->2)-beta-D-xylopyranoside, respectively.

[Studies on the triterpenes from Bemeuxia thibetica Decne].

Four triterpenes were isolated from the alcoholic extract of Bemeuxia thibetica Decne. A new triterpene, 16 alpha, 21 beta, 22 alpha, 28-tetrahydroxyolean-12-en-3-one, named bemeuxin (I), was identified on the basis of spectral evidences. The other three triterpenes were identified as 21-tigloylbarringtogenol C(II), 2 alpha, 3 alpha-dihydroxyursolic acid (III) and 2 alpha, 3 beta-dihydroxyursolic acid (IV).

[Diterpenoid alkaloids from Aconitum gymnandrum].

Aconitum gymnandrum maxim. (ranunculaceae) is used as an herbal medicine in Tibet area. A new diterpenoid alkaloid, gymnandine (I) along with known alkaloids 14-acetyl-8-O-methyltalatisamine (II), acoforine (III), columbidine (IV), aconitine (V), ranaconitine (VI), talatizidine (VII), isotalatizidine (VIII), gymnanconitine (IX), talatisamine (X), and atisine HCI (XI) have been isolated from this unique species. The structure of I is determined on the basis of spectral evidences and comparison of the 13CNMR spectrum with that of denudatine. II has not been previously reported as a natural product and III-VII were isolated from this plant for the first time.

[A new skeleton bisditerpenoid alkaloid from Aconitum pukeense].

A novel bisditerpenoid alkaloid named pukeensine was isolated from Aconitum pukeense W. T. Wang (Ranunculaceae). Its proposed structure was suggested by spectral evidence. This bisditerpenoid alkaloid skeleton has not been found previously.

Diterpenoid Alkaloids from Aconitum vilmorrianum.

A new diterpenoid alkaloid, vilmorrianone ( 1), has been isolated from ACONITUM VILMORRIANUM Kom. The structure was elucidated by spectral methods and confirmed by X-ray diffraction analysis. Also four known diterpenoid alkaloids have been isolated and identified.

Saponins from Chinese folk medicine, "zhu jie xiang fu," Anemone raddeana REGEL.

From the Chinese folk medicine "Zhu jie xian fu" (roots of Anemone raddeana REGEL, Ranunculaceae), two new oleanane-type glycosides, named raddeanosides R8 (1) and R9 (2), were isolated. The structures of 1 and 2 were determined as 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-beta-D-glucopyranosyl- (1----2)-alpha-L-arabinopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----6)-b eta-D- glucopyranoside and 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-beta-D-glucopyranosyl-(1----2)-al pha-L- arabinopyranosyl 27-hydroxyoleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----6)-b eta-D- glucopyranoside, respectively.