Structure elucidation and NMR assignments of two new triterpenoids from the stems of Paragonia pyramidata (Bignoniaceae)

Phytochemical investigation of dichloromethane (DCM) extract from the stems of Paragonia pyramidata var. pyramidata L. Rich. (Bur.) resulted in the isolation and characterization of two new triterpenoids 3β,19β-dihydroxylup-12, 20(29)-diene-28-oic acid (1) and 3β,19β-dihydroxylup-12-en-28-oic acid (2), three known triterpenoids lupeol (3), spinosic acid A (4) and oleanolic acid (5), together with four known steroids (20R)-22E-24-ethylcholesta-4,22-dien-3-one (6), (20R)-24-ethylcholest-4-en-3-one (7), stigmasterol (8) and β-sitosterol (9). HREIMS, GC-MS and NMR experiments including HSQC, HMBC, COSY and NOESY were used for the determination of the structures and NMR spectral assignments. This is the first report about the chemical constituents for this plant.     

Two new bioactive oleanane triterpene glycosides from Terminalia arjuna

Two new oleanane-type triterpene glycosides designated as Termiarjunoside I and Termiarjunoside II were isolated from stem bark of Terminalia arjuna (Combretaceae) and characterized as olean-1alpha,3beta,9alpha,22alpha-tetraol-12-en-28-oic acid-3beta-D-glucopyranoside (1) and olean-3alpha,5alpha,25-triol-12-en-23,28-dioic acid-3alpha-D-glucopyranoside (2) based on chemical and spectral data evidences. Both compounds 1 and 2 potently suppressed the release of nitric oxide and superoxide from macrophages and also inhibited aggregation of platelets.     

Putralone, a novel 10alpha-hydroxy-25-nor D:A friedo-oleanane triterpenoid from Putranjiva roxburghii

Chemical investigation of the leaves of Putranjiva roxburghii has resulted in the isolation of two new triterpenoids, putralone, a novel 10alpha-hydroxy-25-nor D:A friedo-olean-9(11)-en-3 one and 3beta-acetoxy-cycloart-24-en-23-one, along with a rare hopanoid, adian-5-en-3beta,29-diol. Other known triterpenoids isolated from this plant are 3beta-acetoxy-adian-5-ene, putrol, putrone, putranjivadione, roxburghonic acid, friedelin, friedlan-3alpha-ol, oleanolic acid and erythrodiol. Interestingly, putralone is the first example of a naturally occurring nor friedo-oleanane triterpenoid having a hydroxyl functionality at the C-10 position.     

Polyfunctional triterpenoids from the bark of Yeddo spruce

The composition of the polyfunctional triterpenoids of an extract of the Yeddo spruce has been studied. Five serratene triterpenoids have been isolated: 21β-hydroxyserrat-14-en-3-one (I), 3β-hydroxyserrat-14-en-21-one (II), serratenediol (III), episerratenediol (XII), and diepiserratenediol (V) in the form of its acetate. The structures of the compounds were confirmed by¹³C NMR spectra and XSA. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 662–667, November–December, 1992.     

The Terpenoids of Maytenus boaria MOL. (Celastraceae)

The known triterpenoids β-amyrin (= olean-12-en-3β-ol; 22 ), lupeol (= lup-20(29)-en-3β-ol; 17 ), betulin (= lup-20(29)-ene-3β,28-diol; 18 ), lup-20(29)-ene-3β,30-diol ( 20 ), oleanolic acid (= 3β-hydroxyolean-12-en-28-oic acid; 21 ), and betulonic acid (= 3-oxolup-20(29)-en-28-oic acid; 19 ), together with epicatechol (= cis-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; 23 ), 5′-O-methylgallocatechol (= trans-2-(3,4-dihydroxy-5-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; 24 ), and 4-hydroxybenzaldehyde were isolated from the aerial parts of Maytenus boaria (MOL. ). Additonally, the eight 4,C⁴-dihydro-β-agarofuran sesquiterpenoids 1–8 , one of them a diol with a (4R)-configuration, and compound 9 were present in the extract. The structures of these compounds were established by spectroscopic and chemical means.     

Constituents of the Heartwood of Diospyros Eriantha

The isolation and identification of fifteen compounds from the heartwood of Diospyros eriantha are described. Their structures were determined on the basis of spectral evidence and/or comparison with authentic samples. These compounds include three steroids (stigmast-4-en-3-one, stigmast-4-ene-3,6-dione, and 3β-hydroxystigmast-5-en-7-one), seven triterpenoids (friedelin, lupeol, betulinaldehyde, 3β-acetoxyurs-11-en-13,28-olide, 3β-acetoxyoleanolic acid, betulin, and betulinic acid), three quinones (2-ethoxy-7-methyljuglone, 3-ethoxy-7-methyljuglone, and 2,6-dimethoxy-1,4-benzoquinone), and two phenols (3,4,5-trimethoxyphenol, and syringic acid).     

舞花姜的化学成分

舞花姜（Ｇｌｏｂｂａｒａｃｅｍｏｓａｓｍｉｔｈ）为姜科舞花姜属植物,产于我国南部、西南部等地。其根和果实在民间药用,有健胃、消炎的功能,用于治疗胃炎、消化不良、急慢性肾炎等［１］。尚未见有关舞花姜属植物化学成分和药理活性的研究报道,为此我们对其地下部分的化学成分进行了研究。乙醇提取物的石油醚可溶部分经硅胶柱和萄聚糖凝胶柱层析分离得到五个化合物,经光谱鉴定为木栓酮（ｆｒｉｅｄｅｌｉｎ１）,ｃｙｃｌｏｅｕｃａｌｅｎ－ｏｌ（２）、３－羟基－豆甾－５烯－７－酮（３－ｈｙｄｒｏｘｙ－ｓｔｉｇｍａｓｔ－５－…     

A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC

A novel triterpene 1 (3-β-hydroxy-fern-7-en-6-one-acetate) together with four known compounds, urs-12-en-11-one-3-acetyl (2), 3-β-hydroxy-fern-8-en-7-one-acetate (3), olean-12-en-11-one-3-acetyl (4) and leucodin (5) were obtained from the S. latifolia roots. All compounds were isolated from the n-hexane extract of S. latifolia roots using several chromatographic techniques. The structure of the isolated compounds was elucidated on the basis of (1)H-NMR, (13)C-NMR and 2D NMR data (HMBC, HMQC, COSY, TOCSY, NOESY, DEPT) as well as GC EITOF-HRMS.     

Polyfunctional triterpenoids from the bark of Yeddo spruce

The composition of the polyfunctional triterpenoids of an extract of the Yeddo spruce has been studied. Five serratene triterpenoids have been isolated: 21-hydroxyserrat-14-en-3-one (I), 3-hydroxyserrat-14-en-21-one (II), serratenediol (III), episerratenediol (XII), and diepiserratenediol (V) in the form of its acetate. The structures of the compounds were confirmed by¹³C NMR spectra and XSA.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 662–667, November–December, 1992.     

Lupane triterpenoids from Acacia mellifera with cytotoxic activity

Three new pentacyclic triterpenoids: (20R)-3-oxolupan-30-al (1), (20S)-3-oxolupan-30-al (2) and (20R)-28-hydroxylupen-30-al-3-one (3), along with (20S)-3beta-hydroxylupan-30-al (4), the latter previously described as a constituent of an epimeric mixture, were isolated from Acacia mellifera. In addition, the known metabolites 30-hydroxylup-20-(29)-en-3-one (5), 30-hydroxylup-20-(29)-en-3beta-ol (6), atranorin, methyl 2,4-dihydroxy-3,6 dimethyl benzoate, sitosterol-3beta-O-glucoside and linoleic acid were found in the analyzed plant species for the first time. The structures of the new metabolites were elucidated by extensive spectroscopic analyses and their relative stereochemistry was determined by NOESY experiments. The new metabolite 3 exhibited significant cytotoxic activity against the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma.     

New triterpenoids from Gentiana lutea

Three new triterpenoids, 2,3-seco-3-oxours-12-en-2-oic acid, 2,3-seco-3-oxoolean-12-en-2-oic acid, and betulin 3-O-palmitate, have been isolated from the rhizomes and roots of Gentiana lutea, together with five known ones. The structures of the new compounds were determined by spectral and chemical methods.     

Triterpene glycosides from the stems of Akebia quinata

The stems of Akebia quinata have been analyzed for their triterpene glycoside constituents, resulting in the isolation of six new triterpene glycosides, along with 19 known ones. On the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence, the structures of the new compounds were deter-mined to be 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid, and 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23,29-dihydroxyolean-12-en-28-oic acid, respectively. The main triterpene glycosides contained in the stems of A. quinata were found to have two sugar units at C-3 and C-28 of the aglycone in this study, whereas those of Akebia trifoliate were reported to possess one sugar unit at C-28 of the aglycone. It may be possible to distinguish between A. quinata and A. trifoliate chemically by comparing their triterpene glycoside constituents.     

Microbial transformation of diosgenin by Syncephalastrum racemosum (Cohn) Schroeter

<正>Microbial transformation of diosgenin(1) by Syncephalastrum racemosum yielded five new polar metabolites,which wereidentified as(25R)-spirost-5-en-3β,7α,9α-triol-12-one(2),(25R)-spirost-5-en-3β,9α,12α-triol-7-one(3),(25R)-spirost-5-en-3β,9α-diol-7,12-dione(4),(25R)-spirost-4-en-9α,12β,14α-triol-3-one(5),and(25S)-spirost-4-en-9α,14α,25β-triol-3-one(6).Compounds 1-6 exhibited moderate cytotoxicity against K562 cells and among them compounds 2,3,and 6 were more potentthan the parent compound 1.     

A new pentacyclic triterpenoid glucoside from Prunus serrulata var. spontanea

A new triterpenoid, 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (4) along with four known triterpenoids, ursolic acid (1), 2alpha-hydroxyursolic acid (2), 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid (3), and 2alpha,3alpha,19alpha,24-tetrahydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (5), were isolated from the leaves of Prunus serrulata var. spontanea (Rosaceae). Compounds 3-5 showed ONOO(-) scavenging activity, whereas compounds 1 and 2 were virtually inactive.     

Cytotoxic diterpenoids from Vietnamese medicinal plant Croton tonkinensis GAGNEP

Six new ent-kaurane-type diterpenoids were isolated from the leaves of the endemic Vietnamese medicinal plant Croton tonkinensis GAGNEP. (Euphorbiaceae) together with three known ent-11alpha-acetoxy-7beta,14alpha-dihydroxykaur-16-en-15-one (1), ent-kaur-16-en-15-one 18-oic acid (5) and ent-18-hydroxykaur-16-ene (7). Their structures were determined by spectroscopic analyses to be ent-7beta-acetoxy-11alpha-hydroxykaur-16-en-15-one (2), ent-18-acetoxy-11alpha-hydroxykaur-16-en-15-one (3), ent-11alpha-acetoxykaur-16-en-18-oic acid (4), ent-15alpha,18-dihydroxykaur-16-ene (6), ent-11alpha,18-diacetoxy-7beta-hydroxykaur-16-en-15-one (8), and ent-(16S)-1alpha,14alpha-diacetoxy-7beta-hydroxy-17-methoxykauran-15-one (14). ent-Kaurane-type diterpenoids from Croton tonkinensis 2-4, 6, and 9-13, were tested for toxicity in the brine shrimp lethality assay. Compounds 9, 10, and 12 demonstrated significant activity, compounds 2, 3, 6, and 11 showed weak activity, and compounds 4 and 13 were inactive.     

Two new triterpenoids from Psidium guajava

Two new triterpenoids,named as 2 α,3 β,23-trihydroxylurs-12,20(30)-dien-28-oic acid β-D-glucopyranoside(1),and 2 α,3 β,6 β,20 β,23,30-hexahydroxyurs-12-en-28-oic acid(2),together with four known triterpenoids were isolated from the leaves of Psidium guajava L.Their structures were elucidated on the basis of mass and spectral evidence.     

Terpenoids from Chloranthus multistachys

Two new diterpenoids, ent-17-hydroxyl-16beta-methoxyl-kauran-3-one (1) and ent-17-acetoxyl-16beta-methoxyl-kauran-3-one (2), along with nine known compounds (3-12), ent-17-hydroxyl-kaur-15-en-3-one (3), ent-3beta-acetoxyl-kaur-15-en-16beta, 17-diol (4), ent-kauran-3beta, 16beta, 17-triol (5), ent-3beta-acetoxyl-kauran-16beta, 17-diol (6), ent-kauran-16beta, 17-diol (7), abbeokutone (8), ent-17alpha-acetyl-16beta-hydroxyl- kauran-3-one (9), shizukaol F (10), cycloshizukaol A (11) and curcolonol (12), were isolated from Chloranthus multistachys (Chloranthaceae). Their structures were elucidated by spectroscopic spectra.     

Triterpenoids from the roots of Sanguisorba tenuifolia var. Alba

The ethyl acetate soluble fraction from the roots of Sanguisorba tenuifolia was found to have a hypoglucemic effect in alloxan-induced diabetic rats. Two new triterpenoids, identified as 2-oxo-3β,19α-dihydroxyolean-12-en-28-oic acid β-D-gluco-pyranosyl ester (1) and 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid β-D-glucopyranosyl ester (4) were isolated from this fraction, along with thirteen known triterpenoids. Their structures were elucidated by chemical and spectroscopic methods. All these compounds demonstrated inhibitory activities against α-glucosidase with IC?? values in the 0.62-3.62 mM range.     

New antimicrobial diterpenes from the sponge spongia officinalis

The methanol extract of the sponge Spongia officinalis from Pt. Guimar, Tenerife (Canary Islands) contained new diterpenoids which inhibited the growth of microbes. The structures of the new diterpenes isolated were determined as; 11β-hydroxyspongi-12-en-16-one ($\text{2}$), 11β-acetoxyspongi-12-en-16-one ($\text{3}$), 7β,11β-dihydroxy8pongi-12-en-16-one ($\text{5}$), and 7β,11α-dihydroxy-spongi-12-en-16-one ($\text{6}$), by spectral and chemical degradation studies. The previously reported diterpenes isoagatholactone ($\text{1}$) and aplysillin ($\text{4}$) were also found in the extract.     

Two new steroidal alkaloids from Veratrum nigrum var. ussuriense

<正>Two new steroidal alkaloids,veraussines A(1) and B(2) were isolated from the roots and rhizomes of Veratrum nigrum var.ussuriense.Their structures were determined as N-(ethoxycarbonyl)- 1α,2β,3α,15α-tetrahydroxy-5β-jervanin- 12-en- 11-one(1) andN-(methoxycarbonyl)- 1α,2β,3α,15α-tetrahydroxy-5β-jervanin- 12-en- 11 -one(2) by spectroscopic analysis.