New (9βH)‐Lanostanes and Lanostanes from Mikania aff. jeffreyi (Asteraceae)

Four new (9βH)‐lanostanes, i.e., (9βH)‐3β‐acetoxylanosta‐7,24‐diene, (9βH)‐3‐oxolanosta‐7,24‐diene, (9βH,24R)‐3β‐acetoxy‐24‐hydroxylanosta‐7,25‐diene, and (9βH,24S)‐3β‐acetoxy‐24‐hydroxylanosta‐7,25‐diene, two new lanostanes, i.e., (24R)‐3β‐acetoxy‐24‐hydroxylanosta‐8,25‐diene and (24S)‐3β‐acetoxy‐24‐hydroxylanosta‐8,25‐diene, and two known lanostanes, i.e., 3β‐acetoxylanosta‐8,24‐diene and 3‐oxolanosta‐8,24‐diene, were obtained from a new Mikania species (Asteraceae) besides pentacyclic triterpenes, steroids, and diterpenes. The structures of the compounds were determined by spectroscopic methods. This is the second study about acetyl‐lanosterols from higher plants. Moreover, (9βH)‐lanostanes are very rare metabolites from dicotyledone angiosperms. The occurrence of these terpenes together in the same plant makes the species a good source for lanostane‐ and (9βH)‐lanostane‐biosynthesis studies.     

Protective devices of early developmental stages in Pyrrhalta viburni (Coleoptera,Chrysomelidae)

Summary Larvae and eggs of the leaf beetle Pyrrhalta viburni were investigated for protective devices against predators. The eggs are covered with faeces, which appeared to have no feeding deterrent activity against the ant Myrmica sabuleti. Chemical analyses of the material covering the eggs by gas chromatography-mass spectrometry (GC-MS) showed the triterpenes -amyrin and -amyrin as main components. Both compounds are also present in the hostplant Viburnum lantana. GC-MS analyses of eggs and larvae showed that 1,8-dihydroxy-3-methylanthraquinone (=chrysophanol) was present in both developmental stages. In the larvae, 1,8-dihydroxyanthraquinone (=chrysazin) and 1,8,9-trihydroxyanthracene (dithranol) were also detected. Neither hydroxylated anthraquinones nor dithranol were found in bark and leaf extracts of the hostplant. After assessing the total amounts of these compounds in a single larva, their ecological significance was studied in feeding bioassays with M. sabuleti. Both P. viburni larvae and equivalent amounts of anthraquinones and dithranol deterred feeding by the ants. The role of anthraquinones and triterpenes in P. viburni is discussed.     

黄棉木中两个新的三萜类化合物

从黄棉木（Metadina trichotoma（Zoll．et．Mor．）Bakn．）树皮中分离得到2个新的三萜类化合物：3-oxo-29-hydroxy-urs-12-en-27,28-dioicacid（黄棉木素A,1）和3-oxo-21β-hydroxy-urs-12-en-27,28-dioicacid（黄棉木素B,2）。其结构主要通过MS,1D以及2DNMR等波谱方法鉴定。     

Anxiolytic and antidepressant-like activity of a standardized extract from Galphimia glauca

An infusion prepared with aerial parts from Galphimia glauca has been widely used in Mexican traditional medicine as a remedy for nervous excitement. The sedative activity of a methanolic extract from this plant has been demonstrated by neuropharmacological tests. This effect was attributed to the nor-secotriterpene named galphimine B (GB). In the present work, the anxiolytic and antidepressant-like effects of G. glauca methanolic extract (standardized on GB content, 8.3mg/g) were assayed by using the elevated plus-maze, light-dark test and the forced swimming paradigm, on ICR albino mice. This extract, administered orally, three times (24, 18 and 1h before the test), and in different doses (125, 250, 500, 1,000 and 2,000 mg/kg) was able to increase significantly (p<0.05) the number of entries, as well as the time spent in the open arms of the elevated plus-maze, indicating an anxiolytic-like effect. A similar effect was observed in the light-dark paradigm test, the time spent in the light box was increased in treated mice. Nevertheless, this treatment was unable to change any parameter in the forced swimming test. Altogether, these results suggest an anxiolytic-like effect to the methanolic standardized extract of G. glauca on ICR inbred mice.     

New pentacyclic triterpenes from Gypsophila oldhamiana and their biological evaluation as glycogen phosphorylase inhibitors

The three new pentacyclic triterpenes 1-3 were isolated and elucidated from the roots of Gypsophila oldhamiana, together with seven known triterpenes (4-10). These triterpenes were evaluated for their glycogen phosphorylase inhibitory activity and preliminary structure-activity trends are suggested.     

Synthesis and biological evaluation of novel pyrazolo[4,3-b]oleanane derivatives as inhibitors of glycogen phosphorylase

Eighteen pyrazolo[4,3-b]oleanane derivatives have been synthesized and biologically evaluated as inhibitors of rabbit muscle GPa. Key compound 5 was readily obtained in four steps starting from oleanolic acid (OA; 1). Further modification based on pyrazolo triterpene 5 resulted in 17 novel pyrazolo pentacyclic triterpenes. All of the synthesized pyrazolo[4,3-b]oleanane derivatives were biologically assayed against rabbit muscle GPa. Within this series of compounds, pyrazole triterpene 19 (IC(50)=9.9 microM) exhibited more potent activity than the parent compound 1. Preliminary structure-activity relationship analysis of the pyrazolo[4,3-b]oleanane derivatives as GPa inhibitors is discussed.     

Anti-inflammatory and anti-tumor-promoting effects of triterpene acids and sterols from the fungus Ganoderma lucidum

A series of lanostane-type triterpene acids, including eleven lucidenic acids (3, 4, 9, 10, 13-19) and six ganoderic acids (20-22, 24, 26, 27), as well as six sterols (28-33), all isolated from the fruiting bodies of the fungus Ganoderma lucidum, were examined for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, a known primary screening test for anti-tumor promoters. All of the compounds tested, except for ganolactone (27) and three sterols (29-31), showed potent inhibitory effects on EBV-EA induction, with IC(50) values of 235-370 mol ratio/32 pmol TPA. In addition, nine lucidenic acids (1, 2, 5-8, 11, 12, 18) and four ganoderic acids (20, 23-25) were found to inhibit TPA-induced inflammation (1 microg/ear) in mice, with ID(50) values of 0.07-0.39 mg per ear. Further, 20-hydroxylucidenic acid N (18) exhibited inhibitory effects on skin-tumor promotion in an in vivo two-stage mouse-skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as promoter.     

黄桐树皮的化学成分研究

从黄桐(Endospermum chinense Benth.)树皮中分离获得了10个化合物。通过光谱分析,分别鉴定为3-羰基齐墩果酸(1)、齐墩果酸(2)、7-羰基谷甾醇(3)、β-谷甾醇(4)、β-胡萝卜甙(5)、7-羰基-β-胡萝卜甙(6)、4-羟基-3-甲氧基苯甲醛(7)、7-羟基-6-甲氧基香豆素(8)、3-羟基-4-甲氧基苯甲酸(9)和壬二酸(10)。10个化合物均为首次从黄桐树皮中分离得到。