Search

Species misidentification in the field of natural products is an acknowledged problem. These errors are especially widespread in sponge studies, albeit rarely assessed and documented. As a case study, we aim to revisit reports of isomalabaricane triterpenes, isolated from four demosponge genera: Jaspis , Geodia , Stelletta and Rhabdastrella . From a total of 44 articles (1981-2022), 27 unique vouchers were listed, 21 of which were accessed and re-examined here: 11 (52.4%) of these were misidentified. Overall, 65.9% of the studies published an incorrect species name: previously identified Jaspis and Stelletta species were all in fact Rhabdastrella globostellata . We conclude that isomalabaricane triterpenes were isolated from only two Rhabdastrella species and possibly one Geodia species. In addition to shedding a new light on the distribution of isomalabaricane triterpenes, this study is an opportunity to highlight the crucial importance of vouchers in natural product studies. Doing so, we discuss the impact of species misidentification and poor accessibility of vouchers in the field of sponge natural products. We advocate for stricter voucher guidelines in natural product journals and propose a common protocol of good practice, in the hope of reducing misidentifications in sponge studies, ensure reproducibility of studies, and facilitate follow-up work on the original material.

Objectives: To explore the effective and safe medicines for treating diabetes., Methods: Hydroalcoholic extracts of 130 medicinal plants belonging to 66 families were evaluated using porcine pancreatic lipase (PPL) inhibition and glucose uptake methods together with a literature review., Results: The extracts of 22 species showed the PPL inhibition activity; 18 extracts of 15 species stimulated glucose uptake in 3T3-L1 adipocytes. Among them, Mansonia gagei J.R. Drumm., Mesua ferrea L., and Centella asiatica (L.) Urb. exhibited both activities. The extracts of Caladium lindenii (André) Madison rhizomes and Azadirachta indica A. Juss. leaves presented the utmost lipase inhibitory activity with IC 50 of 6.86 ± 0.25 and 11.46 ± 0.06  μ g/mL, respectively. The extracts of Coptis teeta Wall. rhizomes and Croton tiglium L. seeds stimulated the maximum glucose uptake. Ten species are reported to have antidiabetic activity for the first time. Flavonoids and triterpenoids are the dominant antidiabetic compounds in selected medicinal plants from Myanmar., Conclusions: P. zeylanica , L. cubeba, H. crenulate , M. gagei , C. teeta , and M. ferrea are worthy to advance further study according to their strong antidiabetic activities and limited research on effects in in vivo animal studies, unclear chemical constitutes, and safety., Competing Interests: The authors declare that they have no conflicts of interest regarding the publication of this paper., (Copyright © 2021 Dongdong Zhang et al.)

The genus Maytenus is a member of the Celastraceae family, of which several species have long been used in traditional medicine. Between 1976 and 2021, nearly 270 new compounds have been isolated and elucidated from the genus Maytenus . Among these, maytansine and its homologues are extremely rare in nature. Owing to its unique skeleton and remarkable bioactivities, maytansine has attracted many synthetic endeavors in order to construct its core structure. In this paper, the current status of the past 45 years of research on Maytenus , with respect to its chemical and biological activities are discussed. The chemical research includes its structural classification into triterpenoids, sesquiterpenes and alkaloids, along with several chemical synthesis methods of maytansine or maytansine fragments. The biological activity research includes activities, such as anti-tumor, anti-bacterial and anti-inflammatory activities, as well as HIV inhibition, which can provide a theoretical basis for the better development and utilization of the Maytenus .

Ethnopharmacological Relevance: In the quilombola communities of the municipality of Oriximiná (Pará State, Brazil), Protium spp. (Burseraceae) oleoresins are distinguished in black and white pitch. White pitch oleoresins may be superior to black pitch in terms of quality, but the criteria used for their differentiation are fairly subjective., Aim of the Study: This study was designed to provide a scientific rationale for the traditional differentiation of black and white pitch oleoresins based on their non-volatile fraction., Materials and Methods: Black and white pitch oleoresin samples collected in quilombola territories in Oriximiná were analysed by GC-EI-MS and UPLC-APCI-MS. The feasibility of EI and APCI mass spectrometry-based pattern recognition methods PLS-DA and Random Forest Analysis (RFA) for black and white pitch oleoresins differentiation was demonstrated., Results: The UPLC-APCI-MS method allowed the separation of 43 triterpenoids. Assessment of the triterpenoid fingerprints by GC-EI-MS led to the tentative identification of ursa-9(11),12-dien-3-ol as a potential marker for black pitch oleoresins. PLS-DA and RFA applied to the APCI-MS and EI-MS data gave good models for black and white pitch oleoresins classification. The most important ions for the classifications of black pitch oleoresins by APCI-MS/PLS-DA and APCI-MS/RFA likely represented triterpenoid acids., Conclusions: The triterpenoid pattern differs between black and white pitch oleoresins. The characteristic presence of ursa-9(11),12-dien-3-ol and triterpenoids acids in black pitch oleoresins, along with other field observations, suggest that black pitch oleoresins are actually aged white pitch oleoresins., Competing Interests: Declaration of competing interest The authors declare that they have no conflicts of interest., (Copyright © 2020 Elsevier B.V. All rights reserved.)

Poria cocos , an important medicinal and edible fungus, is well known in East Asia. The main active components are water-soluble polysaccharides (WPS) and triterpenoids. Due to the growing market demand, long cultivation period, and consumption of pine trunk during cultivation, alternative methods for producing P. cocos or its active components should be investigated. In this study, WPS, triterpenoids, monosaccharide composition, and essential oil in fermented mycelia and cultivated sclerotium were analyzed using UV spectrophotometry, HPLC, pre-column derivatization, and HS-GC/MS, respectively. Our results showed that the WPS and triterpenoids in mycelia are several times higher than those in sclerotium. Among the 62 compounds identified by HS-GC/MS analysis from the essential oil obtained from the fermentation media and a fresh external layer, the two main fragrances in common were linalool and methyl phenylacetate. Our results suggested that it is applicable to produce polysaccharides and triterpenoids by the fermentation of P. cocos , and a strategy to improve triterpenoid production in the fermentation process was proposed.

Four new constituents, as c is -6-oxogeran-4-enyl-10-oxy- O -β-arabinopyranosyl-4'- O -β-arabinopyranosyl-2''-octadec-9''',12''',15'''-trienoate ( 1 ), geran-3(10)-enyl-1-oxy- O -β-arabinopyranosyl-4'- O -β-arabinopyranosyl-2''-octadec-9''',12''',15'''-trienoate ( 2 ), geranilan-8-oxy- O - α -d-xylopyranosyl-2'- n -octadec-9'',12'',15''-trienoate ( 3 ), 1-cyclohex-2', 5'-dienyl 1-cyclohexylethanol- O -β-d-xylopyranoside ( 4 ), along with six known constituents, guaiacol- O -β-d-arabinopyaranoside ( 5 ), n -tetradecanyl oleate ( 6 ), oleyl- O- β-d-xyloside ( 7 ), n -octadec-9,12-dienoyl- O -β-d-arabinopyranoside ( 8 ), linolenyl- O -β-d-arabinofuranoside ( 9 ) andglyceryl-1,3-dipalmito-2-olein ( 10 ), were isolated and identified from the Dendropanax morbifera bark. The new structures were established by one-and two-dimensional NMR (and in combination with IR, FAB-MSand HR-ESI-FTMS. The comparative evaluation of antioxidant potential by phosphomolybdenum, DPPH, FRAP and the NO assay of four different compounds ( 1 - 4 ), we have found that the compounds 1 and 2 have power as a natural antioxidant, whereas the compound 3 and 4 exhibited mild activity in comparison to compounds 1 and 2 ., Competing Interests: The authors declare that they have no conflicts of interest.

The phytochemistry of the genera Androsace , Cortusa , Soldanella, and Vitaliana , belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from Vitaliana primuliflora subsp. praetutiana . These two nor -triterpenoid saponins were characterized as (23 S )-17α,23-epoxy-29-hydroxy-3β-[( O -β-d-glucopyranosyl-(1→2)- O -α-l-rhamnopyranosyl-(1→2)- O -β-d-glucopyranosyl-(1→2)- O -α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27- nor -lanost-8-en-25-one and (23 S )-17α,23-epoxy-29-hydroxy-3β-[( O -α-l-rhamnopyranosyl-(1→2)- O -β-d-glucopyranosyl-(1→2)- O -α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27- nor -lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27- nor -lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in Vitaliana and also in Androsace species belonging to the Aretia section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae., Competing Interests: The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

The important role of histone deacetylases (HDACs) in the development of cancer has been demonstrated by various studies. Thus targeting HDACs with inhibitors is a major focus in anticancer drug research. Although few synthetic HDAC inhibitors (HDIs) have been approved for cancer treatment, they have significant undesirable side effects. Therefore emphases have been placed on natural HDIs as substitutes for the synthetic ones. In a bid to identify more HDIs, this study evaluated the binding tendency of compounds derived from Morinda lucida Benth. towards selected HDACs for the discovery of potent HDIs as potential candidates for anticancer therapeutics, based on the report of anticancer potentials of Morinda lucida-derived extracts and compounds. Givinostat and 49 Morinda-lucida derived compounds were docked against selected HDAC isoforms using AutodockVina, while binding interactions were viewed with Discovery Studio Visualizer, BIOVIA, 2016. Druglikeness and Absorption-Distribution-Metabolism-Excretion (ADME) parameters of the top 7 compounds were evaluated using the Swiss online ADME web tool. The results revealed that out of the 49 compounds, 3 phytosterols (campesterol, cycloartenol, and stigmasterol) and 2 triterpenes (oleanolic acid and ursolic acid) exhibited high HDAC inhibitory activity compared to givinostat. These 5 compounds also fulfill oral drugability of Lipinski rule of five. Morinda lucida-derived phytosterols and triterpenes show high binding tendency towards the selected HDACs and exhibited good drugability characteristics and are therefore good candidates for further studies in the search for therapies against abnormalities linked with over-activity of HDACs.

Three ceanothane-type and three lupane-type triterpenoids, as well as three known compounds, were isolated from the roots of Hovenia dulcis (Rhamnaceae), based on LC-MS dereplication. The previously undescribed compounds were determined to be 27-O-protocatechuoyl-3-dehydroxyisoceanothanolic acid, 27-O-protocatechuoyl-3-dehydroxycolubrinic acid, 27-O-protocatechuoyl-3-dehydroxyepicolubrinic acid, 27-O-protocatechuoylbetulinic acid, 27-O-p-hydroxybenzoylbetulinic acid, and 27-O-syringoylbetulinic acid by 1D and 2D NMR spectroscopic and HR mass spectrometric data analysis. The isolates were examined for their antiproliferative activity in HSC-T6 hepatic stellate cells; compounds 1, 2, 3, and 6 showed IC 50 values in the range of 15-50 μM., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Herbgenomics provides a global platform to explore the genetics and biology of herbs on the genome level. Panax ginseng C.A. Meyer is an important medicinal plant with numerous pharmaceutical effects. Previous reports mainly discussed the transcriptome of ginseng at the organ level. However, based on mass spectrometry imaging analyses, the ginsenosides varied among different tissues. In this work, ginseng root was separated into three tissues-periderm, cortex and stele-each for five duplicates. The chemical analysis and transcriptome analysis were conducted simultaneously. Gene-encoding enzymes involved in ginsenosides biosynthesis and modification were studied based on gene and molecule data. Eight widely-used ginsenosides were distributed unevenly in ginseng roots. A total of 182,881 unigenes were assembled with an N50 contig size of 1374 bp. About 21,000 of these unigenes were positively correlated with the content of ginsenosides. Additionally, we identified 192 transcripts encoding enzymes involved in two triterpenoid biosynthesis pathways and 290 transcripts encoding UDP-glycosyltransferases (UGTs). Of these UGTs, 195 UGTs (67.2%) were more highly expressed in the periderm, and that seven UGTs and one UGT were specifically expressed in the periderm and stele, respectively. This genetic resource will help to improve the interpretation on complex mechanisms of ginsenosides biosynthesis, accumulation, and transportation., Competing Interests: The authors declare no conflict of interest.

The basic chemical composition, bioactive compounds, and antioxidant capacity of fruits of three new Polish breeding clones (No. 5/6, type S, and type N) and four Canadian cultivars (cvs.) ("Martin", "Smoky", "Pembina", and "Honeywood") grown in Poland in 2016 were investigated. Fruits were analyzed for their contents of triterpenoids, carotenoids, chlorophylls, and polyphenolics with the ultra-performance liquid chromatography photodiode detector-quadrupole/time-of-flight mass spectrometry (UPLC-PDA-Q/TOF-MS) method, sugar with the high-performance liquid chromatography-evaporative light scattering detector (HPLC-ELSD) method, and antioxidant capacity with the ability to reduce free radical (ABTS) and ferric reducing ability of plasma (FRAP) method. Thirty-eight bioactive compounds, including twenty-eight polyphenolic compounds (four anthocyanins, nine phenolic acids, nine flavonols, and seven flavan-3-ols), four carotenoids, two chlorophylls, and three triterpenoids were identified in the fruits. The fruits of the tested Saskatoon berry genotypes were found to be rich in phenolic compounds (3773.94-6390.36 mg/100 g·dm), triterpenoids (66.55-91.31 mg/kg·dm), and carotenoids (478.62-561.57 mg/kg·dm), with high ABTS and FRAP capacity (10.38-34.49 and 9.66-25.34 mmol·Trolox/100 g·dm, respectively). Additionally, the berries of these genotypes seemed to be a good source of sugar (9.02-19.69 g/100 g), pectins (0.67%-1.33%), and ash (0.59%-0.67%). Some genotypes of Saskatoon berry, especially the clones type S, type N, and cvs. "Honeywood" and "Smoky", may be selected for their potential applications in commercial cultivation to produce fruits with valuable health-promoting nutritional effects on human health. Additionally, three new genotypes that may offer new functional materials can be recommended for fruit growers., Competing Interests: The authors declare no conflict of interest.

Phytochemical investigation on the stems of Picrasma quassioides led to the isolation of a novel compound, picraquassin A (1), with an unprecedented 21,24-cycloapotirucallane skeleton, and four new apotirucallane-type triterpenoids (2-5), together with 15 new tirucallane-type triterpenoids (6-20) and 10 known tirucallane-type triterpenoids (21-30). To our knowledge, this is the first report demonstrating the presence of apotirucallane-type triterpenoids in the genus Picrasma. The structures of the new compounds were determined based on spectroscopic data interpretation. Cytotoxicities of the isolated compounds were evaluated using three human cancer cell lines, MKN-28, A-549, and MCF-7. Compound 2 exhibited the most potent activity against MKN-28 cells with an IC50 value of 2.5 μM. Flow cytometry and Western blot analysis revealed that 2 induces the apoptosis of MKN-28 cells via activating caspase-3/-9, while increasing Bax and Bad and decreasing Bcl-2 expression levels.

During the search for secondary metabolites with antiproliferative activity, six new lanostane triterpenoids, tyrosamic acids A-F (1-6) together with ten known compounds (7-16), were isolated from the fruiting body of Tyromyces sambuceus. Their structures were elucidated using MS analyses, extensive 2D-heteronuclear NMR data interpretation and the structure of 3 was further confirmed by single-crystal X-ray data analyses. All lanostane triterpenoids (1-16) possesses a carboxy group at C-20 position and their strength of antiproliferative activity was affected by the presence or absence of a hydroxy group at C-15 position and at the side chain. Four of the compounds (1, 6, 10, 14) showed antiproliferative activities against human cancer cell lines with IC₅₀ values of 16.8-48.3 µM (HL-60).

The objective of this study was to compare the mycochemical profiles, antioxidant activities, and antidiabetic effects of 2 species of genus Ganoderma, the red lingzhi (G. lucidum) and purple lingzhi (G. sinense) mushrooms. In Chinese medicinal practice, hot water and ethanol are used as solvents to extract samples. In this study, a total of 4 extracts (ethanol and hot water extracts from G. lucidum and G. sinense) were prepared for further assays. Hot water extracts presented much higher values for total phenolic content and ferric-reducing antioxidant power than the ethanol extracts. Ethanol (70%) extract of G. lucidum had the strongest α-glycosidase inhibitory capacity, but the lingzhi polysaccharides showed no inhibitory effect. It also had the largest amount of total ganoderic acids. The results indicated that ethanol extracts from both G. lucidum and G. sinense showed better antidiabetic effects than the hot water extracts. Ganoderic acids, rather than polysaccharides, may contribute the antidiabetic effects of both the Ganoderma species.

Ganoderic acids (GAs) produced by Ganoderma lucidum possess anticancer activities with the generation of reactive oxygen species (ROS). However, the role of oxidative stress in apoptotic process induced by GAs is still undefined. In this study, the effects of four structurally related GAs, i.e. GA-T, GA-Mk, and two deacetylated derivatives of GA-T (GA-T1 and GA-T2) on the antioxidant defense system and induced apoptosis in cervical cancer cells HeLa were investigated in vitro. Our results indicated that the tested GAs (5-40 μM) induced apoptotic cell death through mitochondrial membrane potential decrease and activation of caspase-9 and caspase-3. Furthermore, GAs increased the generation of intracellular ROS and attenuated antioxidant defense system by decreasing glutathione (GSH) level, superoxide dismutase (SOD) and glutathione peroxidase (GPX) activities. The above effects were remarkably blocked by the exogenous antioxidants, i.e. N-acetylcysteine, catalase and diphenyleneiodonium chloride. The potency of the four GAs toward induced apoptosis, generation of ROS and suppression of antioxidant defense system was in the order of: GA-T > GA-Mk ≈ GA-T1 > GA-T2 in HeLa cells. These findings suggest that GAs induced mitochondria-dependent cell apoptosis in HeLa cells are mediated via enhancing oxidative stress and depressing antioxidant defense. Additionally, the acetylation of hydroxyl groups in GAs may contribute to their pro-oxidant activities and cytotoxicity, which is helpful to the development of novel chemotherapy agents., (Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.)

Since the discovery of saponins in sea cucumbers, more than 150 triterpene glycosides have been described for the class Holothuroidea. The family Holothuriidae has been increasingly studied in search for these compounds. With many species awaiting recognition and formal description this family currently consists of five genera and the systematics at the species-level taxonomy is, however, not yet fully understood. We provide a bibliographic review of the triterpene glycosides that has been reported within the Holothuriidae and analyzed the relationship of certain compounds with the presence of Cuvierian tubules. We found 40 species belonging to four genera and 121 compounds. Holothurin A and B are the most common saponins for Actinopyga, Holothuria, and Pearsonothuria. The genus Bohadschia presents mainly bivittoside C and D. Actinopyga has only sulfated saponins mainly oxidized, Bohadschia non-sulfated ones mainly non-oxidized, Holothuria and Pearsonothuria contain both types of compounds, mainly oxidized. Within the genus Holothuria, the subgenus Panningothuria only has non-sulfated saponins. The presence of sulfated and non-sulfated compounds seemingly relates to the expellability or the absence of Cuvierian tubules and the temporal or permanent concealing habits of the species. Our study concludes that better insights into the systematic distribution of saponins in Holothuriidae will only be possible if the identifications of the investigated species are confirmed by a taxonomist, especially in this group wherein cryptic species and variation between life-history stages are common and yet poorly understood. Understanding of saponin distribution within the Holothuriidae would also benefit from a stabilization of triterpene glycoside nomenclature., (Copyright © 2014 Elsevier Inc. All rights reserved.)

Triterpenes are compounds of natural origin, which have numerously biological activities: anti-cancer properties, anti-inflammatory, anti-oxidative, anti-viral, anti-bacterial and anti-fungal. These substances can be isolated from plants, animals or fungi. Nowadays, when neoplasms are main cause of death, triterpenes can become an alternative method for treating cancer because of their cytotoxic properties and chemopreventive activities.

The aerial parts of Spergula fallax afforded four glycosides (1-4) based on two new triterpene aglycones (1a and 2a), along with the known hopane glycoside succulentoside A. Compound 1 was identified as belonging to the fernane class, unusual migrated hopane triterpenoids, mainly isolated from ferns and only rarely from higher plants. Compounds 2-4 were assigned as gammacerane glycosides, having as aglycone a hydroxylated derivative of tetrahymanol. The structures of the isolated compounds 1-4 and their aglycones 1a and 2a obtained by acid hydrolysis were elucidated by spectroscopic data interpretation. The growth inhibitory activity of the isolated compounds and their aglycones was evaluated against the HeLa and DLD-1 cancer cell lines.

Aim of the Study: To investigate the chemical differences between Ganoderma lucidum (G. lucidum, Chizhi) and Ganoderma sinense (G. sinense, Zizhi)., Materials and Methods: Thirty two batches of commercial Ganoderma samples were collected, including 20 batches of G. lucidum and 12 batches of G. sinense cultivated in different geographical regions. Chemical substances in aqueous extract and alcoholic extract, mainly polysaccharides and triterpenes respectively, were investigated. Determination of polysaccharides was carried out with a high performance liquid chromatography with an variable wavelength detector. Meanwhile, analysis of triterpenes were performed on an ultraviolet spectrophotometer, an ultra performance liquid chromatography and a rapid resolution liquid chromatograph combined with an electrospray ionization mass spectrometer. Chromatograms and spectra for all batches and reference standards of main components were obtained and used for direct comparison. Further discussion was made on the basis of the result of principal component analysis (PCA)., Results: Significant difference of triterpenes was shown between G. lucidum and G. sinense. In 20 batches of G. lucidum, 12 main components, including eight ganoderic acids and four ganoderenic acids were identified and ten of them were quantitatively determined, with the total content from 0.249% to 0.690%. However, none of those triterpenes was found in either batch of G. sinense. As for constituents of polysaccharides, seven monosaccharides were identified and four main components among them were quantitatively determined. Difference of polysaccharides was not directly observed, but latent information was revealed by PCA and the discrimination became feasible., Conclusions: G. lucidum and G. sinense were chemically different, which might result in pharmacological distinction. Preparations of traditional Chinese medicine (TCM) from Ganoderma should make accurate specification on the origin of species., (Copyright © 2011 Elsevier B.V. All rights reserved.)

A new allose-containing triterpenoid saponin (1), along with a known saponin (2), were isolated from the aerial parts of Cephalaria ambrosioides. Their structures were determined by spectroscopic (2D-NMR and ESI-MS) methods. The preferred conformation of 1 was determined by the NOESY spectrum.

This review covers the isolation and structure determination of triterpenoids including squalene derivatives, protostanes, lanostanes, holostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, lupanes, oleananes, friedelanes, ursanes, hopanes, isomalabaricanes and saponins; 574 references are cited.

Maytenus ilicifolia and Maytenus aquifolia species are widely used as a cicatrisation agent, an anti-spasmodic, contraceptive, antiulcerogenic, diuretic and analgesic. Considering the importance of these species in popular medicine, this work is focused on the determination of the chemical content of tannins and the triterpenes friedelan-3-one, friedelan-3-ol and friedelin in 15 native populations of Maytenus ilicifolia distributed in the south and mind-west regions of Brazil. Correlation of the concentration of these compounds with the environmental parameters such as average annual temperature, climate, vegetation, geomorphology, latitude and altitude was determined using Pearson's coefficient. Results showed that average annual temperature and climate have significant effect on tannin content at a 95% confidence level. The highest tannin concentration was found in Ponta Porã population, and for the triterpenes investigated, a significant correlation between their concentrations with the environmental variables studied was not verified.

This review covers the isolation and structure determination of triterpenoids including squalene derivatives, protostanes, lanostanes, holostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, isomalabaricanes and saponins. The literature from January 2005 to December 2006 is reviewed and 478 references are cited.

Two new nortriterpenoids, designated as schintrilactones A (1) and B (2), with modified five-membered D ring and delta-lactone E ring, were isolated from Schisandra chinensis. Their structures were determined to have a unique carbon skeleton by elucidation of spectroscopic evidence and density functional theory calculations of circular dichroism. Schintrilactones A and B occur as a pair of configurationally unstable and thus slowly interconverting diastereomers.

Thirteen cucurbitane-type triterpene glycosides, including eight new compounds named charantosides I (6), II (7), III (10), IV (11), V (12), VI (13), VII (16), and VIII (17), and five known compounds, 8, 9, 14, 15, and 18, were isolated from a methanol extract of the fruits of Japanese Momordica charantia. The structures of the new compounds were determined on the basis of spectroscopic methods. On evaluation of these triterpene glycosides and five other cucurbitane-type triterpenes, 1-5, also isolated from the extract of M. charantia fruits, 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, these compounds showed inhibitory effects on EBV-EA induction with IC(50) values of 200-409 mol ratio/32 pmol TPA. In addition, upon evaluation of compounds 1-5 for inhibitory effects against activation of (+/-)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, compounds 1-3 showed moderate inhibitory effects. Compounds 1 and 2 exhibited marked inhibitory effects in both 7,12-dimethylbenz[a]anthracene (DMBA)- and peroxynitrite (ONOO-; PN)-induced mouse skin carcinogenesis tests.

Six new triterpenoids named spirocarcolitones (G-L), which belong to a novel class of CD-spiro triterpenoids, were isolated from the dichloromethane-soluble fraction of the bark of Ruptiliocarpon caracolito. The structures of these natural products were established using mainly 1D and 2D NMR spectroscopy. One known CD-spiro triterpenoid and canophyllol were also isolated from the same source.

From the hexane extracts of Senecio sinuatus roots, the new 3beta-angeloyloxy-6beta-hydroxyeremophil-1(10)-en-8beta,12-olide (3), along with the known compounds 3beta-angeloyloxy-6beta-hydroxyeremophil-1(10)-ene (1), 3beta-senecioyloxy-6beta-hydroxyeremophil-1(10)-ene (2), and 3beta-angeloyloxy-6beta,8alpha-dihydroxyeremophil-1(10)-en-8beta,12-olide (4), were isolated. Complete 1H and 13C NMR chemical shift assignments of 1-4 were achieved using one- and two-dimensional NMR techniques, including gHMQC and gHMBC experiments. A Monte Carlo search, followed by B3LYP/6-31G*DFT calculation, provided the theoretical conformations of the eremophilane rings, which were in agreement with results derived from 1H-1H NMR coupling constant analysis, and confirmed by NOESY experiments., (Copyright 2007 John Wiley & Sons, Ltd.)

This review covers the isolation and structure determination of triterpenoids including squalene derivatives, lanostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, uranes, hopanes, isomalabaricanes and saponins. The literature from January to December 2004 is reviewed and 243 references are cited.

Five new cucurbitane-type triterpenes, (23E)-25-methoxycucurbit-23-ene-3beta,7beta-diol (1), (23E)-cucurbita-5,23,25-triene-3beta,7beta-diol (2), (23E)-25-hydroxycucurbita-5,23-diene-3,7-dione (3), (23E)-cucurbita-5,23,25-triene-3,7-dione (4), and (23E)-5beta,19-epoxycucurbita-6,23-diene-3beta,25-diol (5), together with one known triterpene, (23E)-5beta,19-epoxy-25-methoxycucurbita-6,23-dien-3beta-ol (6), have been isolated from the methanol extract of the stems of Momordica charantia. The structures of the new compounds were elucidated by spectroscopic methods.

Two new taraxasterane-type triterpenes, 20beta,28-epoxy-28alpha-methoxytaraxasteran-3beta-ol (1) and 20beta,28-epoxytaraxaster-21-en-3beta-ol (2), were isolated from an ethyl acetate extract of the leaves of Nerium oleander, together with ursane-type triterpenes, 28-nor-urs-12-ene-3beta,17beta-diol (3) and 3beta-hydroxyurs-12-en-28-aldehyde (4). The structures of 1 and 2 were established on the basis of their spectroscopic data. Anti-inflammatory activity of 1-4 was examined on the basis of inhibitory activity against the induction of intercellular adhesion molecule-1 (ICAM-1). Cytotoxic activity of 1-4 was evaluated against four human cell lines, A-549, WI-38, VA-13, and HepG2 cells.

Three new hexaprenoid hydroquinones, adociaquinol (1), adociasulfate 11 (2), and adociasulfate 12 (3), together with the known adociasulfates 2, 4, and 6, were isolated from the marine sponge Haliclona (aka Adocia) sp. The structures of these compounds were elucidated by interpretation of spectroscopic data.

In the present report, the use of the atom-based linear indices for finding functions that discriminate between the tyrosinase inhibitor compounds and inactive ones is presented. In this sense, discriminant models were applied and globally good classifications of 93.51% and 92.46% were observed for non-stochastic and stochastic linear indices best models, respectively, in the training set. The external prediction sets had accuracies of 91.67% and 89.44%. In addition, these fitted models were used in the screening of new cycloartane compounds isolated from herbal plants. A good behavior is shown between the theoretical and experimental results. These results provide a tool that can be used in the identification of new tyrosinase inhibitor compounds.

[structure: see text] A novel triterpenoid, 21,25-cyclodammar-20(22)-ene-3beta,24alpha-diol, has been isolated from Aglaia odorata. Its structure was elucidated on the basis of 1D- and 2D-NMR and MS spectra and then confirmed by X-ray diffraction. It represents a new type of natural five-membered-ring triterpenoid, named cyclodammarane. Its possible biopathway was that squalene-2,3;22,23-diepioxide was directly cyclized to form 24,25-epoxydammar-20(21)-en-3-ol, followed by protonation of the remaining 24,25-epoxide and the cation attacking 21(20) methylene to generate the E ring.

Although HIV infection is now primarily treated with reverse transcriptase and protease inhibitors, HIV therapy must look toward new drugs with novel mechanism(s) of action to both improve efficacy and address the growing problem of drug resistance. Using natural products as a source of biologically active compounds, our drug discovery program has successfully optimised the natural product betulinic acid to the first-in-class maturation inhibitor 3-O-(3',3'-dimethylsuccinyl)-betulinic acid (DSB). DSB's unique viral target has been identified as a late step in Gag processing. Specifically, it inhibits the cleavage of the capsid precursor, CA-SP1, resulting in a block to the processing of mature capsid protein leading to a defect in viral core condensation. DSB represents a unique class of anti-HIV compounds that inhibit virus maturation and provide additional opportunities for anti-HIV therapy. In this review, the discovery of DSB and its mode of action are summarised. Anti-AIDS Agents part 64. For part 63 in the series, see YU D, LEE KH: Recent progress and prospects on plant-derived anti-HIV agents and analogs. In: Medicinal Chemistry of Bioactive Natural Products. XT Liang, WS Fang (Eds), Wiley, New York, USA (2005) (In Press).

Four new, highly oxygenated nortriterpenoids with unique schisanartane skeletons, micrandilactones D-G (1-4), have been isolated from the leaves and stems of Schisandra micrantha, and their structures have been elucidated on the basis of extensive spectral studies. The postulated biogenetic sequences of sixteen highly oxygenated nortriterpenoids and bisnortriterpenoids with new skeletons from three Schisandra species are discussed and have been compared from a chemotaxonomic standpoint.

This review covers the isolation and structure determination of triterpenoids including squalene derivatives, lanostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleannes, friedelanes, ursanes, hopanes, isomalabaricanes and saponins. The literature from January to December 2002 is reviewed and 221 references are used.

This review covers the isolation and structure determination of triterpenoids including squalene derivatives, lanostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, fernanes, sipholanes, isomalabaricanes, serratanes and saponins The literature from January to December 2001 is reviewed and 242 references are cited.

An investigation on the constituents of the callus tissues of Ternstroemia gymnanthera has led to the isolation of five phytosterols, 15 known triterpenoids, and four new triterpenoids (1-4). The new compounds were characterized by spectroscopic study as 3-epi-corosolic acid lactone (2 alpha,3 alpha-dihydroxyurs-11-en-13 beta,28-olide) (1), 3-epi-ternstroemic acid (2 alpha,3 alpha-dihydroxyurs-12-en-11-on-28-oic acid) (2), ternstroemic acid (2 alpha,3 beta-dihydroxyurs-12-en-11-on-28-oic acid) (3), and gymnantheraic acid (2 alpha,3 alpha-dihydroxy-11 alpha-methoxyurs-12-en-28-oic acid) (4). The isolated triterpenes were compared with those from actinidiaceous plant callus tissues from a chemotaxonomic point of view.

Objective: To establish a method for HPLC fingerprint determination of the triterpene acids in Poria cocos., Method: RP-HPLC, linear gradient elution and LC/MS, etc. were used to optimize the fingerprint determination method, and identify the main peaks in the HPLC fingerprint., Result: A preferable method for HPLC fingerprint determination of the triterpene acids in P. cocos was established, and 9 peaks in the HPLC fingerprint were identified., Conclusion: A general acquaintance of the triterpene acids in P. cocos can be obtained by using the preferable HPLC fingerprint determination method, which is useful for quality evaluation of the crud drug of P. cocos.