Advances in Chemistry and Bioactivity of the Genus Chisocheton Blume

Chisocheton is one of the genera of the family Meliaceae and consists of ca. 53 species; the distribution of most of those are confined to the Indo‐Malay region. Species of broader geographic distribution have undergone extensive phytochemical investigations. Previous phytochemical investigations of this genus resulted in the isolation of mainly limonoids, apotirucallane, tirucallane, and dammarane triterpenes. Reported bioactivities of the isolated compounds include cytotoxic, anti‐inflammatory, antifungal, antimalarial, antimycobacterial, antifeedant, and lipid droplet inhibitory activities. Aside from chemistry and biological activities, this review also deals briefly with botany, distribution, and uses of various species of this genus.     

New cytotoxic lanostanoid triterpenes from Ganoderma lingzhi

Further chemical investigation of the metabolites in the fruiting bodies of Ganoderma lingzhi resulted in isolation of eight triterpenes; two of them are new triterpene acid ethyl esters. Their structures were established based on spectroscopic studies and comparison with the known related compounds. The anticancer potential of the isolates were tested with an in vitro cytotoxic assay against five human cancer cell lines (MCF-7, HeLa, HCT-116, Caco-2 and HepG2) and two normal human cell lines (TIG-1 and HF19). Results showed that the new compounds have a strong to moderate selective cytotoxic activity against MCF-7 while they showed moderate to weak activity against HeLa cell line. Potent cytotoxic activities of some of the known isolated compounds are reported for the first time.     

Dammarane triterpenes from the resin of Boswellia freerana

The resin of Boswellia freerana afforded in addition to the known 3β,20(S)-dihydroxydammar-24-ene, its 3-acetyl derivative and (20S)-protopanaxadiol, a new triterpene that was characterized as 3β-acetoxy-16(S),20(R)-dihydroxydammar-24-ene on the basis of chemical and physico-chemical evidence.     

Insulin mimetic lanostane triterpenes from the cultivated mushroom Ganoderma orbiforme

Two new lanostane triterpenes, ganorbifoins A and B (1-2), together with the known compound (25S,3′S)-(+)-12α-hydroxy-3α-(3′-hydroxy-4′-methoxycarbonyl-3′-methylbutiryloxy)-24-methyllanosta-824-(31)-dien-26-oic acid (3) were isolated from the cultivated fruiting bodies of Ganoderma orbiforme. The structures of isolates were determined by extensive analysis of NMR and HRESIMS. All compounds induced glucose uptake in zebrafish-based system at the concentration of 10 μM. And the best performing compound is ganorbifoin A. Compounds 2 and 3 exhibited an inhibitory effect on nitric oxide production in LPS-induced BV-2 microglia cells at the concentration of 20 μM.     

Triterpenes from the leaves of Pleurostylia opposita

Friedelin, friedelan-3β-ol, sitosterol, α-amyrin, 6β,20-dihydroxylupan-3-one, lup-20(29)-en-3β,6β-diol, 6β,28-dihydroxylup-20(29)-en-3-one and dulcitol were isolated from the leaves of Pleurostylia opposita. The distribution of lupanes in the Celastraceae and their chemotaxonomic significance is discussed.     

Intracellular distribution and origin of pentacyclic triterpenes in Calendula officinalis leaves

In Calendula officinalis leaves the cyclization of squalene to β-amyrin and its further oxidation to oleanolic acid as well as the biosynthesis of all derivatives of oleanolic acid 3-glucoside and some derivatives of oleanolic acid 3-glucuronoside occur in the microsomal fraction. The final metabolites of oleanolic acid 3-glucoside series i.e. pentaglycosides, are translocated from this fraction, one to the cell wall and plasmalemma fraction and the other to the cytosol. The derivatives of oleanolic acid 3-glucoronoside are synthesized partially in other fractions and accumulate in the different membraneous structures of the cell.     

The triterpenoids

The literature on the identification and distribution of penta- and tetracyclic triterpenoids in vascular plants and fungi is reviewed for the period 1971–1977.     

New 19α-hydroxyursane-type triterpenes from the leaves of Meyna spinosa (= Vangueria spinosa), Rubiaceae

Two new 19α-hydroxyursane-type triterpenes, 2α,3α,19α,24,28-pentahydroxyurs-12-ene (1) and meyanthic acid, 3β-acetoxy-2β,19α,23-trihydroxyurs-12-en-28-oic acid (2) along with one new aliphatic ester, myricyl pentadecanoate (3) and five known compounds, 19α-hydroxyasiatic acid (4), oleanolic acid (5), myricyl alcohol (6), β-sitosterol (7) and its glycoside (8) were isolated from the methanolic leaf extract of Meyna spinosa Roxb. ex Link (= Vangueria spinosa Roxb., Rubiaceae). The structures of the new compounds were elucidated on the basis of extensive spectroscopic (including 2D NMR) analysis and comparison with literature. Except oleanolic acid, isolation of known compounds was reported for the first time from this plant.     

细锥香茶菜的化学成分研究

从云南丽江产细锥香茶菜(Rabdosia coetsa)叶中分离得到11个单体成分,根据光谱方法分别鉴定为:gesneroidin c 1、胡萝卜甙(daucosterol 2)、熊果酸(ursolic acid 3)、乌发醇(uvaol 4)、齐墩果酸(oleanolic acid 5)、2α,3β-二羟基齐墩果酸(2α,3β-dihydroxy-oleano-lic acid 6)、白桦脂酸(Betulinic acid 7)、植物醇(phytol 8)、肉豆蔻酸植物醇酯(phytyl myris-tate 9)、9Z,12Z-二烯肉豆蔻酸乙酯(ethyl 9Z,12Z-dien-palmitate 10),12Z,15Z-二烯花生酸甘油酯(glyceryl 12Z,15Z-dien-arachidate 11)。     

6-Hydroxytoxol esters and a seco-dammarane derivative from Abrotanella forsterioides

Abrotanella forsterioides afrorded euparin, 6-hydroxytremetone and three 6-hydroxytoxol esters, one of them not being isolated previously. Furthermore a seco-triterpene was isolated. The tribal position of the genus Abrotanella in the Compositae is still an unsolved problem. Morphological investigations suggest that this genus should be transferred from the tribe Anthemideae to the Senecioneae [1,2]. So far two species have been studied chemically; one atforded ent-kaurane derivatives, while both contained euparin and hydroxytremetone [3].     

Gas chromatography-mass spectrometry of oleanane- and ursane-type triterpenes—application to Chenopodium quinoa triterpenes

Nine trimethylsilylated pentacyclic triterpenes were separated by GLC on an OV-101 column employing temperature programming. Characteristic retro-Diels-Alder fragmentation was observed in their mass spectra. The fragmentation patterns allowed individual characterization except for certain isomers which, nevertheless, were resolved by GLC, thus permitting their identification. Oleanolic acid and hederagenin were confirmed to be major triterpenes of Chenopodium quinoa seed saponins.     

Chemical constituents from the roots of cultivated Ilex pubescens

Phytochemical study of butanol extract from the roots of cultivated Ilex pubescens Hook. et Arn. obtained nine ursane triterpenes (1–9), two oleanane triterpenes (10–11) and three phenylpropanoids (12–14). All of the compounds were determined on the basis of MS and NMR and comparison with literature. Among them, compounds 2 and 13 were isolated from I. pubescens for the first time, of which 13 was a new finding in the Aquifoliaceae family. Our present study exhibited the taxonomic relationships between I. pubescens and other species in genus Ilex and those between Aquifoliaceae and other families. Furthermore, the study suggested the cultivated I. pubescens may be as an alternative for those wild resource collected freshly from mountain.     

美登木属植物三萜类化学成分及生物活性研究进展

对近10年来从美登木属植物中新发现的三萜类化合物的结构类型和生物活性进行了综述;指出了研究中存在的不足并提出了今后的研究方向。     

Ganoellipsic acids A–C,lanostane triterpenoids from artificially cultivated fruiting bodies of Ganoderma ellipsoideum

Three undescribed lanostane triterpenoids, ganoellipsic acids A–C (1–3), together with seven known Ganoderma lanostanoids (4–10), were isolated from artificially cultivated fruiting bodies of Ganoderma ellipsoideum, strain BCC 16634. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The C-25 absolute configuration of 1 was determined to be 25S using the phenylglycine methyl ester (PGME) method.     

Terpenes of Dipterocarpus and Doona species

From the resins of Dipterocarpus hispidus, Dipterocarpus zeylanicus and Doona macrophylla, asiatic (2α,3β,23α-trihydroxyurs-12-en-28-oic) and 2α,3β-dihydroxyurs-12-en-28-oic acids have been isolated. The resin of Doona macrophylla contains ursolic acid and that of Doona congestiflora asiatic acid, 20β-hydroxy-3-oxo dammar-23-ene (Dipterocarpol) and a dihydroxyolean-12-en-28-oic acid. The bark of Dipterocarpus hispidus contains betulinic acid, dipterocarpol, and 3β,20β-dihydroxydammar-23-ene (dammarenediol 20S) whilst the timber contained dipterocarpol and asiatic acid.