Triterpenes from Astilbe chinensis

Six new triterpenes, 3β,6β-dihydroxyurs-12-en-27-oic acid (1), 3β,6β,24-trihydroxyurs-12-en-27-oic acid (2), 3β,6β,7α-trihydroxyurs-12-en-27-oic acid (3), 3β-acetoxy-6β-hydroxyurs-12-en-27-oic acid (4), 3β,6β,24-trihydroxyolean-12-en-27-oic acid (5), and 3β,6β,7α-trihydroxyolean-12-en-27-oic acid (6), were isolated from the rhizomes of Astilbe chinensis. Their structures were elucidated on the basis of 1D- and 2D-NMR analyses and HR-MS experiments. The isolated compounds exhibited significant cytotoxic activities against the SK-N-SH and HL-60 cell lines.     

Microbial transformation of the anti-diabetic agent corosolic acid by Cunninghamella echinulata

The pentacyclic triterpenoid corosolic acid was metabolized by Cunninghamella echinulata CGMCC 3.2000 to its C-24 aldehyde group metabolite and five other hydroxylated metabolites: madasiatic acid (2), 2α, 3β, 7β-trihydroxyurs-12-en-28-oic acid (3), 2α, 3β, 15α-trihydroxyurs-12-en-28-oic acid (4), 2α, 3β, 6β, 7β-tetrahydroxyurs-12-en-28-oic acid (5), 2α, 3β, 7β, 15α-tetrahydroxyurs-12-en-28-oic acid (6), and 2α, 3β,7β-trihydroxy-24-al-urs-12-en-28-oic acid (7); compounds 3, 5, and 7 were new compounds. The α-glucosidase inhibitory effects of the metabolites were also evaluated.     

Two new triterpenoids from Callicarpa kwangtungensis

Two new triterpenoids, 2α,3β,16α,19α,23-pentahydroxyolean-12-en-28-oic acid (1) and 2α,3α,11α,21α,23-pentahydroxyurs-12-en-28-oic acid (2), were isolated from the aerial parts of Callicarpa kwangtungensis. Their structures were elucidated by 1D and 2D analyses, as well as MS and IR spectra.     

New compounds with antimicrobial activities from Elaeodendron buchananii stem bark

The plant species Elaeodendron buchananii Loes is widely used in folklore medicine to manage microbial infections in Kenya. Previous studies on the plant fruits and root bark revealed the presence of steroids and terpenoids. The present phytochemical analysis of the plant stem bark has led to the isolation of four new triterpenes characterized as methyl 3β-acetoxy-11α, 19α, 28-trihydroxyurs-12-en-23-oic acid (1), 3β, 11α, 19α-trihydroxyurs-12-en-23, 28-dioic acid (2), 3β-acetoxy-19α, 23, 28-trihydroxyurs-12-ene (3) and 3-oxo-19α, 28-dihydroxyurs-12-en-24-oic acid (4), together with ten known ones (5–14), whose structures were elucidated using spectroscopic techniques. The isolate canophyllol (8) showed promising antibacterial activity against N. meningitides with MIC value of 31.25 μg/ml.     

Inhaltsstoffe von Boraginaceae, 6. Mitt. Anchusosid-4, ein neues Triterpensaponin aus Anchusa officinalis L.

Constituents of Boraginaceae, VI: Anchusoside-4, a new Triterpene Saponin from Anchusa officinalis L From Anchusa officinalis L. the new pentacyclic triterpene anchusoside-4 ( 1 ) has been isolated. Its structure was elucidated by IR, ¹H-NMR, ¹³C-NMR and mass spectroscopy and by chemical degradation. The compound 1 is 21-O-β-D -glucopyranosyl-3β,21β,23-trihydroxyolean-12-en-28-oic acid.     

Inhaltsstoffe von Boraginaceen, 9. Mitt. Anchusosid-11, ein neues Nebensaponin aus Anchusa officinalis L

Constituents of Boraginaceae, IX: Anchusoside-11, a New Minor Saponin from Anchusa officinalis L. From Anchusa officinalis L. the new pentacyclic triterpene Anchusoside 11 (1) has been isolated. Its structure was elucidated by IR-, ¹H-NMR-, ¹³C-NMR- and FAB-MS-data and by chemical degradation as 3-O-(β-D-Xylopyranosyl)-21-O-(β-sophorosyl)-3β,21β,23-trihydroxyolean-12-en-28-oic acid (1) .     

Inhaltsstoffe von Boraginaceae, 8. Mitt.1). Anchusosid-5, ein neues Nebensaponin aus Anchusa officinalis L.

Constituents of Boraginaceae, VIII: Anchusoside-5, a New Minor Saponin from Anchusa, officinalis L. From Anchusa officinalis L. the new pentacyclic triterpene Anchusoside-5 ;( 1 ) has been isolated. Its structure was elucidated by IR, ¹³C-NMR and mass spectrometry and by chemical degradation. The compound is 21-O-β-sophorosyl-3β,21β,23-trihydroxyolean-12-en-28-oic acid.     

Triterpene Glycoside from Terminalia Arjuna

Abstract

A new triterpene glycoside, arjunetoside, together with oleanolic and arjunic acids has been isolated from the root bark of Terminalia arjuna. The structure of arjunetoside has been established as 3-O-β-D-glucopyranosyl-2α,3β, 19α-trihydroxyolean-12-en-28-oic acid, 28-O-β-D-glucopyranoside by chemical and spectral data.     

New sterol esters from the flowers of Punica granatum Linn.

Two new β-sitosterol esters have been isolated from the flowers of Punica granatum Linn. (Punicaceae) along with the known compounds n-tricosane (3), n-heptacosanyl n-hexanoate (4), olean-5,12-dien-3β-ol-28-oic acid (5), and olean-12-en-3β-ol-28-oic acid (6). The structures of the new phytosterols have been elucidated as stigmast-5-en-3β-ol-3β-dodecanoate (β-sitosterol laurate, 1) and stigmast-5-en-3β-ol-3β-tetradecanoate (β-sitosterol myristate, 2) on the basis of spectral data and chemical analyses.     

Inhibitory effects of oleanane-type triterpenes and saponins from the stem bark of Kalopanax pictus on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells

Kalopanax pictus (Araliaceae) is a deciduous tree distributed in Korea, Japan, and China. The stem bark of K. pictus has been functionally used as a traditional crude drug for the treatment of various inflammatory diseases. In the present study, we describe the inhibitory effects of oleanane-type triterpenes and saponins isolated from the stem bark of K. pictus on production of pro-inflammatory cytokines in LPS-stimulated bone marrow-derived dendritic cells. Of the compounds tested, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (3), nipponogenin E (6), 3β,6β,23-trihydroxyolean-12-en-28-oic acid (7), and caulophyllogenin (19) significantly inhibited the production of IL-12 p40 and IL-6 with IC₅₀ values ranging from 3.3 to 9.1 μM. Compounds 2, 3, 7, and 19 significantly suppressed the secretion of TNF-α with IC₅₀ ranging from 8.8 to 20.0 μM. These data provide scientific support for the use of K. pictus stem bark and its triterpene and saponin components in the inhibition of pro-inflammatory cytokine secretion, including IL-12 p40, IL-6, and TNF-α, and for prevention and treatment of inflammatory diseases.     

白木通中一个新的三萜皂苷类化合物

目的研究木通科植物白木通藤茎的化学成分。方法通过反复硅胶柱色谱、ODS柱色谱和重结晶等方法进行分离纯化，根据化合物的理化性质和波谱数据鉴定结构。结果从白木通藤茎70%乙醇提取物中分离得到6个化合物。分别鉴定为2α,3β,23-trihydroxyolean-12-en-28-oic acid =O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (I), 2α,3β,23-trihydroxyurs-12-en-28-oic acid O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (II), 2α,3β,23-trihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (III), 2α,3β,23-trihydroxyurs-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (IV), 2α,3β,23-trihydroxyolean-12-en-28-oic acid O-β-D-glucopyranosyl ester (V), 2α,3β,23-trihydroxyurs-12-en-28-oic acid O-β-D-glucopyranosyl ester (VI)。结论化合物II为新化合物，命名为mutongsaponin C，其他均为首次从该植物藤茎中分离得到。     

New terpenes from Salvia palaestina Benth. and Salvia syriaca L. growing wild in Jordan

The novel seco-ursane-type triterpenoid 3β,11α-dihydroxy-17,22-seco-17(28), 12-ursadien-22-oic acid (1) was isolated for the first time from a natural source from two Salvia species growing wild in Jordan, Salvia palaestina Benth. and Salvia syrica L. In addition to compound 1, S. syriaca afforded a new sesquiterpene named syriacine (2). S. palaestina also afforded 15 other known compounds, 6 of which are isolated for the first time from the plant, and these include velutin, hyptadienic acid, cirsilineol, 2α,3β-dihydroxyurs-12-en-28-oic acid, 2α,3α-dihydroxy-24-nor-4(23),12-oleanan-28-oic acid, and 2α,3β,24-trihydroxyurs-12-en-28-oic acid. S. syriaca also afforded 16 other known compounds, 7 of which are isolated for the first time from the plant. These are 1α,3α-dihydroxyolean-9(11),12-diene, maslinic acid, 2α,3β,24-trihydroxyolean-12-en-28-oic acid, 11-oxo-oleanolic acid, 11-oxo-ursolic acid, poriferast-5-en-3,7-diol, and pectolinangenin.     

Two new triterpenoid glycosides from the leaves of Anthocephalus chinensis

Nine compounds were isolated from the leaves of Anthocephalus chinensis by column chromatography on silica gel and Sephadex LH-20, and their structures were elucidated by spectroscopic techniques as clethric acid-28-O-β-d-glucopyranosyl ester (1), mussaendoside T (2), β-stigmasterol (3), hederagenin (4), ursolic acid (5), clethric acid (6), 3β,6β,19α,24-tetrahydroxyurs-12-en-28-oic acid (7), mussaendoside I (8), and cadambine (9). Compounds 1 and 2, and 7 and 8 were isolated from the plants of this genus for the first time, and compounds 1 and 2 were new triterpenoid glycosides.     

Microbial transformation of asiatic acid by Alternaria longipes

Asiatic acid is a major pentacyclic triterpene isolated from Centella asiatica. It shows a variety of bioactivities. In order to obtain its derivatives, potentially useful for detailed pharmacological studies, the substrate was subjected to incubations with selected micro-organisms. In this work, asiatic acid was converted into three new compounds: 2α,3β,23,30-tetrahydroxyurs-12-ene-28-oic acid (1), 2α,3β,22β,23-tetrahydroxyurs-12-ene-28-oic acid (2), and 2α,3β,22β,23,30-pentahydroxyurs-12-ene-28-oic acid (3) by the fungus Alternaria longipes AS 3.2875. The structures of the three metabolites were determined by 1D and 2D NMR spectral data.     

Microbial transformation of oleanolic acid by Trichothecium roseum

Microbial transformation of the oleanolic acid (1) using Trichothecium roseum (pers.) Link (M 95.56) has resulted in the isolation of two new hydroxylated type metabolites, characterized as 15α-hydroxy-3-oxo-olean-12-en-28-oic acid (2) and 7β,15α-dihydroxy-3-oxo-olean-12-en-28-oic acid (3). The structure elucidation of these metabolites was based primarily on HR-EIMS, 1D NMR, and 2D NMR analyses.     

Triterpenoids from the Flower of Campsis grandiflora K. Schum. as Human Acyl-CoA: Cholesterol Acyltransferase Inhibitors

The flower of Campsis grandiflora K. Schum. was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and H2O. From the EtOAc fraction, seven triterpenoids were isolated through the repeated silica gel, ODS column chromatographies and preparative HPLC. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as 3beta-hydroxyolean-12-en-28-oic acid (oleanolic acid, 1), 3beta-hydroxyurs-12-en-28-oic acid (ursolic acid, 2), 3beta-hydroxyurs-12-en-28-al (ursolic aldehyde, 3), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (maslinic acid, 4), 2alpha,3beta-dihydroxyurs-12-en-28-oic acid (corosolic acid, 5), 3beta,23-dihydroxyurs-12-en-28-oic acid (23-hydroxyursolic acid, 6) and 2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid (arjunolic acid, 7). These teriterpenoids were isolated for the first time from this plant. Also, compounds 4, 5, 6, and 7 revealed relatively high hACAT-1 inhibitory activity with the value of 46.2+/-1.1, 46.7+/-0.9, 41.5+/-1.3 and 60.8+/-1.1% at the concentration of 100 microg/mL, respectively.     

An efficient semi-synthesis of 1-hydroxyl oleanolic acid analogs

An efficient route for the semi-synthesis of either 1α- or 1β-OH epimers of 1-hydroxy-3-deoxyolean-12-en-28-oic acid (1), 6–8 steps from oleanolic acid is reported. The synthesis involves stereoselective formation of α,β-unsaturated epoxy ketone and subsequent Wharton reaction as key steps, offering a new access to the 1-O-substituted oleanolic acid-type pentacyclic triterpenoids.     

Chemical constituents from the roots of Biondia chinensis

Two new triterpenoid saponins, biondianosides F and G, together with 13 known compounds, were isolated from the ethanolic extract of the roots of Biondia chinensis Schltr. (Asclepiadaceae). Their structures were characterized as 3-O-β-d-glucopyranosyl-2α,3β-dihydroxyurs-12-en-28-oic acid-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranosyl ester (biondianoside F) (14) and 3-O-β-d-glucopyranosyl-2α,3β,23-trihydroxyolean-12-en-28-oic acid-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (biondianoside G) (15) by spectral and chemical evidence.     

Constituents of the root of <Emphasis Type="Italic">Anemone tomentosa</Emphasis>

A new diterpene glycoside, tomentoside I (1), along with eleven known compounds, including the four coumarins, 4,5-dimethoxyl-7-methylcoumarin (2), 4,7-dimethoxyl-5-methylcoumarin (3), isofraxidin (4) and fraxidin (5) as well as the seven triterpenoids, oleanolic acid (6), oleanolic acid 3-O-α-L-arabinopyranoside (7), oleanolic acid 3-O-β-D-galactopyranosyl-(1→3)-β-D-glucopyranoside (8), hederagenin 3-O-α-L-arabinopyranoside (9), betulinic acid (10), 18-hydroxyursolic acid (11) and 2α,3β,23-trihydroxyurs-12-en-28-oic acid (12) were isolated from the ethanolic extract of the root of Anemone tomentosa and their chemical structures were elucidated by spectroscopic methods. The antimicrobial activities of compounds 1–12 were measured using the agar disc-diffusion method. Also, their antioxidant activities against 1,1-diphenyl-2-picrylhydrazyl (DPPH) were evaluated.     

Microbial transformation of diosgenin by filamentous fungus Cunninghamella echinulata

Microbial transformation of diosgenin (1) by suspended-cell cultures of the filamentous fungus Cunninghamella echinulata CGMCC 3.2000 was investigated. Incubation of the substrate diosgenin (1) with this fungus led to the isolation of three products: two known compounds, (25R)-spirost-5-en-3β,7β,12β-triol (2) and (25R)-spirost-5-en-3β,7β,11α-triol (3), and a new compound (25R)-spirost-5-en-3β,7α,11α-triol (4). The structural elucidations of the three compounds were achieved mainly by the MS, 1D and 2D NMR spectroscopic methods and comparison with known compounds. C. echinulata CGMCC 3.2000 has not been used before in the biotransformation of diosgenin (1).