Four new steroid constituents from the waste residue of fibre separation from Agave americana leaves

Three new steroidal saponins, named agamenosides H-J (1-3), and a new cholestane steroid agavegenin D (4) were isolated from the waste residue of fibre separation from Agave americana leaves, together with six known steroids. Structures of the new compounds 1-4 were deduced to be (22S,23S,24R,25S)-24-[(beta-D-glucopyranosyl)oxy]-5alpha-spirostane-3beta,6alpha,23-triol 6-O-beta-D-glucopyranoside (1), (22S,23S,24R,25S)-5alpha-spirostane-3beta,23,24-triol 24-O-beta-D-glucopyranoside (2), (22S,23S,25R,26S)-23,26-epoxy-5alpha-furostane-3beta,22,26-triol 26-O-beta-D-glucopyranoside (3), and (22S,25S)-5alpha-cholestane-3beta,16beta,22,26-tetrol (4), respectively, by means of spectroscopic analysis, including extensive 1D and 2D NMR data, and the results of hydrolytic cleavage.     

Further bisabolenes and dammarane triterpenes of Commiphora kua resin

From the resins of Commiphora kua a novel bisabolene; 6-hydroxy-2-methyl-5-(5'-hydroxy-1'(R),5'-dimethylhex-3'-enyl)-phenol together with two new dammarane triterpenes, 3beta,16beta,20(S),25-tetrahydroxydammar-23-ene and 3beta-acetoxy-16beta,20(S),25-trihydroxydammar-23-ene, have been isolated. In addition, being reported are known compounds identified as 2-methyl-5-(4'(S)-hydroxy-1'(R),5'-dimethylhex-5'-enyl)-phenol, 2-acetoxyfuranodienone, 2-methoxyfuranodienone, 3beta,16beta,20(R)-trihydroxydammar-24-ene and its acetate derivative, 3beta-acetoxy-16beta,20(R)-dihydroxydammar-24-ene, and beta-amyrin and its acetate derivative. 2-Methyl-5-(4'(S)-hydroxy-1'(R),5'-dimethylhex-5'-enyl)-phenol displayed fungicidal activity against Cladosporium cucumernum on TLC assay.     

Macrophyllosaponin E: a novel compound from the roots of Astragalus. oleifolius

Macrophyllosaponin E, a novel cycloartane-type triterpene, has been isolated from the roots of Astragalus oleifolius. The structure elucidation of the compound was achieved by a combination of one- and two-dimensional NMR techniques [1H-1H-correlation spectroscopy (COSY), 1H-13C-heteronuclear multiple guantum correlation spectroscopy (HMQC), and 1H-13C-heteronuclear multiple-bond correlation spectroscopy (HMBC)l and high resolution electrospray ionization Fourier transformation mass spectrometry (HR-ESI-FT-MS).     

Eurycomaoside: a new quassinoid-type glycoside from the roots of Eurycoma longifolia

A new C(19)-quassinoid-type glycoside has been isolated from the roots of Eurycoma longifolia. The structure elucidation of the compound was achieved by a combination of one- and two-dimensional NMR techniques, including (1)H-(1)H-correlation spectroscopy (COSY), (1)H-(13)C-heteronuclear correlation spectroscopy (HMQC), and (1)H-(13)C-heteronuclear multiple-bond correlation spectroscopy (HMBC), as well as high resolution electrospray ionization Fourier transformation mass spectrometry (HR-ESI-FT-MS) data. The C(1)-glycosidation site in the quassinoid framework is encountered for the first time.     

Six new dammarane-type triterpene saponins from the leaves of Panax ginseng

Six new minor saponins, together with known ginsenosides, were isolated from the leaves of Panax ginseng. The new saponins were named as ginsenoside-Rh5, -Rh6, -Rh7 -Rh8, -Rh9 and -Rg7, and their structures were elucidated on the basis of chemical and physicochemical evidence to be as follows: ginsenoside-Rh5: 3beta,6alpha,12beta,24zeta-tetrahydroxy-dammar-20(22),25-diene 6-O-beta-D-glucopyranoside (1), -Rh6: 3beta,6alpha12beta,20(S)-tetrahydroxy-25-hydroperoxy-dammar-23-ene 20-O-beta-D-glucopyranoside (2), -Rh7: 3beta,7beta,12beta,20(S)-tetrahydroxy-dammar-5,24-diene 20-O-beta-D-glucopyranoside (3), -Rh8: 3beta,6alpha,20(S)-trihydroxy-dammar-24-ene-12-one 20-O-beta-D-glucopyranoside (4), -Rh9: 3beta,6alpha,20(S)-trihydroxy-12beta,23-epoxy-dammar-24-ene 20-O-beta-D-glucopyranoside (5) and -Rg7: 3-O-beta-D-glucopyranosyl 3beta,12beta,20(S),24(R)-tetrahydroxy-dammar-25-ene 20-O-beta-D-glucopyranoside (6).     

Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities

Five new withanolide derivatives (1, 9-12) were isolated from the roots of Withania somnifera together with fourteen known compounds (2-8, 13-19). On the basis of spectroscopic and physiochemical evidence, compounds 1 and 9-12 were determined to be (20S,22R)-3 alpha,6 alpha-epoxy-4 beta,5 beta,27-trihydroxy-1-oxowitha-24-enolide (1), 27-O-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside (withanoside VIII, 9), 27-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside (withanoside IX, 10), 27-O-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranoside (withanoside X, 11), and (20R,22R)-1 alpha,3 beta,20,27-tetrahydroxywitha-5,24-dienolide 3-O-beta-D-glucopyranoside (withanoside XI, 12). Of the isolated compounds, 1, withanolide A (2), (20S,22R)-4 beta,5 beta,6 alpha,27-tetrahydroxy-1-oxowitha-2,24-dienolide (6), withanoside IV (14), withanoside VI (15) and coagulin Q (16) showed significant neurite outgrowth activity at a concentration of 1 microM on a human neuroblastoma SH-SY5Y cell line.     

Five new triterpenoid saponins from the roots of Platycodon grandiflorum

Five new triterpenoid saponins, platycoside H [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside I [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside J [3-O-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside K [3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28-oic acid], and platycoside L [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28 oic acid], and three known triterpenoid saponins, platycoside F, platycoside B, and platycoside C, were isolated from the roots of Platycodon grandiflorum A. DC. Their chemical structures were elucidated on the basis of their spectral data and chemical evidence.     

New triterpene diglycosides from the rhizome of Cimifuga foetida

Five new 9,19-cycloartane triterpene diglycosides, which have been named cimiaceroside C (1), and cimifosides A-D (2-5) together with the known compounds cimiracemoside D (6), cimidahurine (7) and alpha-D-glucopyranosyl-l-beta-D-fructofuranoside (8) were isolated from the rhizome of Cimicifuga foetida. The new triterpene diglycosides 1-5 were identified as cimiacerol-3-O-beta-D-xylopyranosyl-(1'-->3')-beta-D-xylopyranoside, 12beta-hydroxycimigenol-3-O-beta-D-xylopyranosyl-(1'-->3')-beta-D-xylopyranoside, 25-Oacetylcimig-enol-3-O-beta-D-xylopyranosyl-(1'-->3')-beta-D-xylopyranoside, 24- acetylhydroshengmanol-3-O-beta-D-xylopyranosyl-(1'-->3')-beta-D-xylopyranoside and 26-deoxyacetylacteol-3-O-beta-D-xylo- pyranosyl-(1'-->3')-beta-D-xylopyranoside, respectively, based on analysis of their spectral data and chemical reactions.     

Triterpene glycosides of Astragalus quisqualis. I. The structure of quisquagenin

The hydrolysis of the glycoside quisqualoside B, isolated from the herbAstragalus quisqualis Bunge, has given the new cycloartane triterpenoid quisquagenin, which has the structure of 20(R),24(S)-epoxycycloartane-3β,16β,25-triol.     

Two new polyporusterones isolated from the sclerotia of Polyporus umbellatus

In the course of searching for marker components, two new polyporusterones were isolated from the sclerotia of Polyporus umbellatus, together with another three known analogs. The structures of the new ones were elucidated as (20S,22R,24R)-16,22-epoxy-3beta,14alpha,23beta,25-tetrahydroxyergost-7-en-6-one (1) and (23R,24R,25R)-23,26-epoxy-3beta,14alpha,21alpha,22alpha-tetrahydroxyergost-7-en-6-one (2) by chemical and spectroscopic means, including HR-FAB-MS, 1D- and 2D-NMR.     

Cucurbitacins from Cayaponia racemosa: isolation and total assignment of 1H and 13C NMR spectra

Two new cucurbitane-type triterpenoids, 2beta,3beta,16alpha,20(R),25-pentahydroxy-9-methyl-19-norlanost-5-en-7,22-dione and 2beta,3beta,16alpha,20(R),25-pentahydroxy-9-methyl-19-norlanost-5-en-7,11,22-trione, were isolated from fruits of Cayaponia racemosa. The total (1)H and (13)C chemical shift assignment of these two closely related compounds is described, making use of one- and two-dimensional NMR techniques.     

Steroidal oligoglycosides from Solanum nigrum

Two new steroidal saponins, named nigrumnins I and II, together with two known saponins were obtained from the whole plant of Solanum nigrum L. On the basis of spectroscopic analysis (1H-NMR, 13C-NMR, 1H-1H COSY, TOCSY, HMQC, HMBC and FAB-MS), nigrumnin I was established as (25R)-5alpha-spirostan-3beta-ol 3-O-betaD-xylopyranosyl-(1-->3)-[alpha-L-arabinopyranosyl-(1 -->2)]-beta-D- glucopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl(1-->2)]-beta-D- galactopyranoside (1), and nigrumnin II was elucidated as (25R)-3beta,17alpha-dihydroxy-5alpha-spirostan-1 2-one 3-O-beta-D-xylopyranosyl-(1-->3)-[alpha-L-arabinopyranosyl-(1--> 2)]-beta-D-glucopyranosyl-(1-->4)-[alpha-L-rhamnopyra- nosyl-(1-->2)l-beta-D-galactopyranoside (2).     

Synthesis of α-aryloxy-2,4-dihydroxyacetophenone 4-O-β-D-glucopyranosides and their conversion into 3-aryloxy-7-glucosyloxychromones

The hydrolysis of the glycoside quisqualoside B, isolated from the herbAstragalus quisqualis Bunge, has given the new cycloartane triterpenoid quisquagenin, which has the structure of 20(R),24(S)-epoxycycloartane-3,16,25-triol.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 527–532, July–August, 1987.     

Complete 1H and 13C NMR assignments of three new polyhydroxylated sterols from the South China Sea gorgonian Subergorgia suberosa

Three new polyhydroxylated sterols, 3beta,6alpha,11,20beta,24-pentahydroxy- 9,11-seco-5alpha-24-ethylcholest-7,28-diene-9-one (1), 3-(1',2'-ethandiol)-24- methylcholest-8(9),22E-diene-3beta,5alpha,6alpha,7alpha,11alpha-pentaol (2), 24-methylcholest-7,22 E-diene-3beta,5alpha,6beta,25-tetraol (3) together with five known sterols, were isolated from the EtOH/CH2Cl2 extract of the South China Sea gorgonian Subergorgia suberosa. The complete assignments of the 1H and 13C NMR chemical shifts for these new compounds were achieved by means of 1D and 2D NMR techniques, including HSQC, HMBC, 1H--1H COSY, and NOESY spectra.     

Triterpene glycosides ofAstragalus and their genins. II. The structure of cyclosieversigenin

The bitter plantAstragalus sieversianus has yielded a new isoprenoid cyclosieversigenin the structure of which has been established on the basis of spectral characteristics and chemical transformations as 20(S),24(R)-epoxycycloartane-3,6,16, 25-tetraol.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 67–76, January–February, 1981.     

New triterpenoids from Corchorus trilocularis

Two new tetracyclic triterpenoid trilocularol A and trilocularol A 3-glucoside and one pentacyclic triterpenoid tirlocularoside A were isolated from Corchorus trilocularis L., their structure were elucidated as 3beta,6alpha,16alpha,20(S),27-pentahydroxydammar-24(Z)-ene (1), 3beta-D-glucopyranosyloxy-6alpha,16alpha,20(S),27-tetrahydroxydammar-24(Z)-ene (2) and 2alpha,3beta,19alpha,30-tetrahydroxyurs-12-en-24,28-dioic acid 28-O-beta-D-glucopyranosyl ester (3). respectively, on the basis of detailed spectroscopic studies.     

Novel steroids from the seeds of Centratherum anthelminticum

Two novel and two known steroids were isolated respectively from benzene: acetone and ethanolic extracts of the seeds of C. anthelminticum and, identified as (24alpha/R)-Stigmasta-7-en-3-one (1), (24alpha/R)-Stigmasta-7, 9(11)-dien-3-one (2), (24alpha/S)-Stigmasta-5, 22-dien-3beta-ol (3) and (24alpha/S)-Stigmasta-7, 22-dien-3beta-ol (4). The structures were assigned on the basis of their IR, 1H NMR, 13C NMR (DEPT), 2D NMR (1H-1H COSY and 1H-13C COSY), mass spectra, chemical analyses and on comparison with literature values. The novel steroids (1) and (2) were also tested against several human pathogenic bacteria and fungi.     

Six new withanolide-type steroids from the leaves of Solanum cilistum

Six new withanolide-type steroids, designated cilistols v, t, i, j, y and w (1-6, respectively), were obtained from the leaves of Solanum cilistum. Their respective structures were characterized by spectroscopic means as follows: Cilistol v (1) was (22R,24Z)-1alpha,3beta,22,26-tetrahydroxyergost-5,24-diene 26-O-beta-D-glucopyranoside, which is regarded as the precursor of other withanolide-type steroids included in this title plant. Cilistol t (2) was (22R,24S,25R,26S)-24,25;22,26-diepoxy-1alpha,3beta,26-trihydroxyergost-5-ene 26-O-beta-D-glucopyranoside, and cilistols j (3) and i (4) corresponded to the substances probably formed by the cleavage of the epoxy ring at C-24 and 25 of 2. Cilistol y (5) was 3-O-sulphonyl (22R,24S,25R,26R)-1-oxo-24,25; 22,26-diepoxy-3beta,17alpha,26-trihydroxyergost-5-ene 26-O-beta-D-glucopyranoside, and cilistol w (6) corresponded to the substance obtained by the fission of the epoxy ring at C-24 and 25 of 5. The occurrence of these withanolide type steroids from Solanum genera is rare and worthy of note.     

Pregnane- and furostane-type oligoglycosides from the seeds of Allium tuberosum

Two furostane-type steroidal oligoglycosides (1, 2), together with a new pregnane-type oligoglycoside (3), were obtained from the seeds of Allium tuberosum ROTTLER. On the basis of spectroscopic analysis, the structures of three new oligoglycosides (1-3) were elucidated as 26-O-beta-D-glucopyranosyl-(25R)-3beta,22xi,26-trihydroxyl-5alpha-furostane 3-O-beta-chacotrioside, 26-O-beta-D-glucopyranosyl-(25S)-3beta,5beta,6alpha,22xi,26-pentahydroxyl-5beta-furostane 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside, and 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl 3beta,5beta,6alpha,16beta-tetrahydroxypregnane 16-(5-O-beta-D-glucopyranoyl-4(S)-methyl-5-hydroxypentanoic acid) ester, respectively.     

Dammarane triterpenes of Commiphora confusa resin

Fractionation of a steam distilled residue of Commiphora confusa resin has yielded four novel dammarane triterpenes characterised as (20S)-3beta-acetoxy-12beta,16beta-trihydroxydammar-24-ene, (20S)-12beta,16beta-trihydroxydammar-24-ene-3beta-O-beta-glucopyranoside, (20S)-3beta-acetoxy-12beta,16beta,25-tetrahydroxydammar-23-ene, and (20S)-3beta,12beta,16beta,25-pentahydroxydammar-23-ene. The known compounds beta-amyrin, 3beta-amyrinacetate, 2-methoxyfuranodienone, 2-acetoxyfuranodienone, (20R)-3beta-acetoxy-16beta-dihydroxydammar-24-ene, (20R)-3beta,16beta-trihydroxydammar-24-ene, 3beta-acetoxy-16beta-hydroxydammar-24-ene, 3beta-hydroxydammar-24-ene, 3beta-acetoxydammar-24-ene, and beta-sistosterol were also isolated from the same extract. The structures of the compounds were determined using spectroscopic, physical, and chemical methods.