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1.
Four new des-A-ergostane derivatives including blazeispirols B, C, E and F were isolated from the cultured mycelia of fungus Agaricus blazei Murill and were established to be (20S, 22R, 23R, 24S)-14beta,22: 22,25-diepoxy-5-methoxy-des-A-ergosta-5,7,9,11-tetraen-23-ol; (20S, 22S, 23R, 24S)-14beta,22: 22,25-diepoxy-5-methoxy-des-A-ergosta-5,7,9-trien-23-ol; (20S, 22S, 23R, 24S)-14beta, 22: 22, 25-diepoxy-5-methoxy-des-A-ergosta-5,7,9,11-tetraene-19,23-diol and (20S, 22S, 23R, 24S)-14beta,22: 22,25-diepoxy-des-A-ergosta-5,7,9-triene-5,23-diol by comparison of extensive 1D and 2D NMR spectral data with that of blazeispirol A.  相似文献   

2.
Lago JH  Roque NF 《Phytochemistry》2002,60(4):329-332
Nine cycloartane triterpenoids, including two new derivatives 22,25-dihydroxy-cycloart-23E-en-3-one and 24-methylenecycloartane-3 beta,22-diol have been isolated from leaves of Guarea macrophylla. The structures were elucidated by interpretation of spectral data, mainly 1H and 13C NMR, including bidimensional analysis (HOMOCOSY, HMQC and HMBC).  相似文献   

3.
New tyrosinase inhibitory cycloartane triterpenoids have been discovered from the methanol extract of the whole plant of Amberboa ramosa (Roxb.) Jafri, which is a member from the Compositae family. Utilizing the conventional spectroscopic techniques, including 1D and 2D NMR analysis, and also by comparing the experimental with literature data, the isolated compounds proved to be cycloartane type triterpenoids. These cycloartanes are: (22R)-cycloart-20, 25-dien-2alpha3beta22alpha triol (1), (22R)-cycloart-23-ene-3beta, 22alpha, 25-triol (2), cycloartenol (3), cycloart-23-ene-3beta, 25-diol (4), cycloart-20-ene-3beta, 25-diol (5), cycloart-25-ene-3beta, (22R) 22-diol (6), 3beta, 21, 22, 23-tetrahydroxy-cycloart-24 (31), 25 (26)-diene (7), and (23R)-5alpha-cycloart-24-ene-3beta, 21, 23-triol (8). Out of these eight compounds, compound 3 did not show any activity against the enzyme tyrosinase. Among them compound 7 was found to be the most potent (1.32 microM) when compared with the standard tyrosinase inhibitors kojic acid (16.67 microM) and L-mimosine (3.68 microM). Finally in this paper, we have discussed the structure-activity relationships of these molecules.  相似文献   

4.
Six new ergosterols from the marine-derived fungus Rhizopus sp   总被引:1,自引:0,他引:1  
Wang F  Fang Y  Zhang M  Lin A  Zhu T  Gu Q  Zhu W 《Steroids》2008,73(1):19-26
Six new ergosterols, including 3beta-hydroxyl-(22E, 24R)-ergosta-5,8,22-trien-7,15-dione (1), 3beta-hydroxyl-(22E, 24R)-ergosta-5,8,14,22-tetraen-7-one (2), 3beta,15beta-dihydroxyl-(22E, 24R)-ergosta-5,8(14),22-trien-7-one (3), 3beta,15alpha-dihydroxyl-(22E, 24R)-ergosta-5,8(14),22-trien-7-one (4), 3beta-hydroxyl-(22E, 24R)-ergosta-5,8(14),22-trien-7,15-dione (5), and 5alpha,8alpha-epidioxy-23,24(R)-dimethylcholesta-6,9(11),22-trien-3beta-ol (6), have been isolated from the marine-derived fungus Rhizopus sp., along with four known ones (7-10). The structures of the new compounds were determined on the basis of extensive spectroscopic data. All compounds were evaluated for their cytotoxic activities on P388, A549, HL-60, and BEL-7420 cell lines by the MTT and SRB methods.  相似文献   

5.
Zhang Y  Li XM  Proksch P  Wang BG 《Steroids》2007,72(9-10):723-727
Ergosterimide (1), a natural Diels-Alder adduct of ergosteroid and maleimide, was characterized from the culture extract of Aspergillus niger EN-13, an endophytic fungus isolated from the marine brown alga Colpomenia sinuosa. In addition, four known steroids including (22E,24R)-ergosta-5,7,22-trien-3beta-ol (2), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (3), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol (4), and (22E,24R)-ergosta-7,22-dien-3beta,5alpha,6beta-triol (5) were also isolated and identified. The structures of these compounds were elucidated by extensive analysis of 1D and 2D NMR and IR spectra and MS data. The plausible biosynthetic pathway of 1 was also discussed. To the best of our knowledge, 1 is the first natural Diels-Alder adduct of steroid and maleimide reported so far.  相似文献   

6.
Na Z  Xiang W  Niu XM  Mei SX  Lin ZW  Li CM  Sun HD 《Phytochemistry》2002,60(1):55-60
Four ent-kauranoids, 6-epiangustifolin and enanderinanins F-H, as well as 11 known ent-kaurane diterpenoids, macrocalin B, xerophilusin A, trichorabdal A, trichorabdal B, effusin, angustifolin, longikaurin D, longikaurin F, enanderinanin B, xerophilusin G and shikokianin were isolated from the aerial parts of Isodon enanderianus. The new diterpenoids were identified as 6-epiangustifolin (11alpha-hydroxy-6alpha-methoxy-6,19-epoxy-6,7-seco-ent-kaur-16-en-15-one-7,20-olide), enanderinanin F (19-acetoxy-6,20:6,11beta-diepoxy-6,7-seco-ent-kaur-16-en-15-one-1beta,7-olide), enanderinanin G (1beta,6beta,7beta-trihydroxy-19-acetoxy-16beta-methoxymethyl-7alpha,20-epoxy-ent-kaur-15-one) and enanderinanin H (6beta,7beta,14beta-trihydroxy-1alpha,11beta-acetonide-7alpha,20-epoxy-ent-kaur-16-en-15-one), respectively, on the basis of spectral data, especially by 2D NMR techniques. 6-Epiangustifolin showed significant cytotoxic activity against K562 cell.  相似文献   

7.
Three labdane diterpenes 15,16-epoxy-6-hydroxylabda-5,8,13(16),14-tretraen-7-one (leojaponin), (9alpha,13S);15,16-diepoxy-7beta-hydroxylabd-14-en-6-one (13-epi-preleoheterin), and (9alpha,13R);15,16-diepoxy-6beta-hydroxylabd-14-en-7-one (iso-preleoheterin) were isolated from the leaves of Leonurus japonicus, in addition to the previously reported preleoheterin. The structure elucidations were made based on analysis of their spectroscopic data.  相似文献   

8.
Shang XY  Li JJ  Liu MT  Li S  Liu Y  Wang YF  Huang X  Jin ZL 《Steroids》2011,76(10-11):1185-1189
Bioassay-guided fractionation of an EtOH extract of Monascus purpureus-fermented rice led to the isolation of two new steroids (22S, 23R, 24S)-20β,23α,25α-trihydroxy-16,22-epoxy-4,6,8(14)-trienergosta-3-one (1), the first example of a steroid possessing both a conjugated triene ketone system and a fused 4H-furan ring side chain within one molecule, and (22E, 24R)-3β,5α-dihydroxyergosta-23-methyl-7,22-dien-6-one (2), as well as two known compounds (22E, 24R)-3β,5α-dihydroxyergosta-7,22-dien-6-one (3) and (22E, 24R)-6β-methoxy-ergosta-7,22-diene-3β,5α-diol (4). Their structures were assigned by detailed interpretation of HRESIMS, 1D and 2D NMR spectroscopic data. The absolute stereochemistry of 1 was determined by single-crystal X-ray crystallography while the absolute stereochemistry of 2 was established by CD. Compounds 1-4 showed cytotoxic activity against the lung adenocarcinoma (A549) with IC(50) values of 0.08, 0.94, 12.6 and 13.5 μM, respectively. In addition, compounds 1 and 2 exhibited moderate activities against human ovarian cancer (A2780), with IC(50) values of 2.8 and 5.1 μM.  相似文献   

9.
Bläs B  Zapp J  Becker H 《Phytochemistry》2004,65(1):127-137
Eleven ent-clerodanes, 13-hydroxy-cis-ent-cleroda-3,14-diene, 15-hydroxy-cis-ent-cleroda-3,13(E)-diene, 1beta,12:15,16-diepoxy-cis-ent-cleroda-13(16),14-dien-18alpha,6alpha-olide, 8beta,12:15, 16-diepoxy-cis-ent-cleroda-13(16),14-dien-18alpha,6alpha-olide, 1beta,16:15,16-diepoxy-cis-ent-cleroda-12,14-dien-18alpha,6alpha-olide, 7beta,12:8beta,12-diepoxy-15-hydroxy-cis-ent-cleroda-13-en-16,15:18alpha,6alpha-diolide, 7beta,12:8beta,12-diepoxy-16-hydroxy-cis-ent-cleroda-13-en-15,16:18alpha,6alpha-diolide, 1alpha-acetoxy-8beta,12-epoxy-15-hydroxy-cis-ent-cleroda-13-en-16,15:18alpha,6alpha-diolide, 1beta,12-epoxy-16-hydroxy-cis-ent-cleroda-13-en-15,16:18alpha,6alpha-diolide, 8beta,12-epoxy-15-hydroxy-trans-cleroda-13-en-16,15:18alpha,6alpha-diolide, 8beta,12-epoxy-16-hydroxy-trans-cleroda-13-en-15,16:18alpha,6alpha-diolide along with the known clerodane diterpenes anastreptin and orcadensin have been isolated from the liverwort Adelanthus lindenbergianus (Lehm.) Mitt. Furthermore, three eudesmane sesquiterpenes together with the known (-)-1beta,10-epoxyaristolan, 3,4-seco-4(23),20(29)-lupadien-3,28-dicarboxylic acid dimethyl ester and two acetophenone derivatives were identified by spectroscopic methods, essentially MS and NMR experiments.  相似文献   

10.
Four new analogs of 28-homocastasterone have been synthesized and completely characterized for the first time from stigmasterol. (22R, 23R,24S)-3beta-acetoxy-22,23-dihydroxy-5alpha-stigmastan+ ++-6-one (17), (22R,23R,24S)-3beta-bromo-22,23-dihydroxy-5alpha-stigmast an-6-one (18), (22R,23R,24S)-3beta-acetoxy-5,22, 23-trihydroxy-5alpha-stigmastan-6-one (20), and (22R,23R, 24S)-3beta-bromo-5,22,23-trihydroxy-5alpha-stigmastan-6-one (21), were obtained through a synthetic route based on regioselective Delta(5) epoxidation. Compounds 17 and 18, bearing a 5alphaH moiety, were prepared through a reductive opening of the 5beta,6beta epoxy precursor, and compounds 20 and 21, analogs with a 5alphaOH moiety were obtained by hydrolytic opening of a mixture of 5alpha,6alpha and 5beta,6beta epoxy precursors. Known compounds 19 and 22 were also obtained following the described synthetic routes, respectively. The new compounds were tested with the traditional auxin-like bioassay for brassinosteroids with 19 and 22 as standards. All compounds were comparatively evaluated for their inhibitory effect on the replication of DNA (HSV-1) virus.  相似文献   

11.
The CHCl(3) extract of the bark of Garcinia speciosa contained four 17,14-friedolanostanes and five lanostanes as well as friedelin and common plant constituents. The friedolanostanes were the previously known methyl ester of (24E)-3 alpha,23 alpha-dihydroxy-17,14-friedolanostan-8,14,24-trien-26-oic acid and the methyl esters of three hitherto unknown acids, 3 alpha-hydroxy-16 alpha,23 alpha-epoxy-17,14-friedolanostan-8,14,24-trien-26-oic acid, 3 alpha,23 alpha-dihydroxy-8 alpha,9 alpha-epoxy-17,14-friedolanostan-15-oxo-24-en-26-oic acid and 3 alpha,23 alpha-dihydroxy-17,14-friedolanostan-15-oxo-8(14),24-dien-26-oic acid. New lanostanes were 3 beta,9 alpha-dihydroxylanost-24-en-26-al and the methyl ester of 3 beta-hydroxy-23-oxo-9,16-lanostadien-26-oic acid. Structures were established by analysis of spectroscopic data. In the case of the lanostanes the previously unassigned C-25 stereochemistry was shown to be 25R by X-ray analysis of 3 beta-hydroxy-23-oxo-9,16-lanostadien-26-oic acid. In the case of the friedolanostanes the configuration at C-23 was established as 23R, identical with the absolute configuration at C-23 of mariesiic acids A and B.  相似文献   

12.
Siddiqui BS  Afshan F  Gulzar T  Hanif M 《Phytochemistry》2004,65(16):2363-2367
Two new tetracyclic triterpenoids zafaral [24,25,26,27-tetranorapotirucalla-(apoeupha)-6alpha-methoxy-7alpha-acetoxy-1,14-dien-3,16-dione-21-al] (1) and meliacinanhydride [24,25,26,27-tetranorapotirucalla-(apoeupha)-6alpha-hydroxy,11alpha-methoxy-7alpha,12alpha-diacetoxy,1,14,20(22)-trien-3-one] (2) have been isolated from the methanolic extract of neem leaves along with two known constituents nimocinol and isomeldenin. Their structures and the relative configurations were determined by spectroscopic methods ((1)H and (13)C NMR, IR, and MS) and 2D NMR experiments.  相似文献   

13.
Chemical examination of the hexane extract of the roots of Excoecaria agallocha Linn collected from the Godavari estuary resulted in the isolation of altogether eleven diterpenoids of which five (1-5) are new. The structures of the new diterpenoids have been elucidated by a study of their physical and spectral (UV, IR, 1H, 13C, DEPT, 1H-1H COSY, NOESY, HMQC, HMBC and MASS) data as 3-oxo-ent-13epi-8(13)-epoxy-15-chloro-14-hydroxylabdane (1), ent-15-chloro-13,14-dihydroxylabd-8(9)-en-3-one (2), ent-15-chloro-labd-8(9)ene-3alpha,13,14-triol (3), ent-11beta-hydroxy-8(14),15-isopimaradien-3-one (4), 8,13-epoxy-3-nor-2,3-seco-14-epilabden-2,4-olide (5). The six known diterpenoids have been characterised respectively as ent-3-oxo-13-epi-manoyl oxide (6), ent-3beta-hydroxy-13-epi-manoyl oxide (7), (13R,14S)-ent-8alpha,13;14,15-diepoxy-13-epi-labdan-3-one (8), ent-16-hydroxy-3-oxo-13-epimanoyl oxide (9), ent-15-hydroxylabda-8(17),13E-dien-3-one (10), labda-8(17),13E-diene-3beta,15-diol (11) by a comparative study of their spectral data with the literature values.  相似文献   

14.
Siddiqui BS  Ilyas F  Rasheed M  Begum S 《Phytochemistry》2004,65(14):2077-2084
The continued studies on the constituents of the fresh leaves and stem bark of Plumeria obtusa Linn. have led to the isolation and characterization of four new triterpenoids, dammara-12,20(22)Z-dien-3-one (1), dammara-12,20(22)Z-dien-3beta-ol (2), olean-12-en-3beta,27-diol (3), and 27-hydroxyolean-12-en-3-one (4) and 12 known compounds, which included eight triterpenoids; dammara-3beta,20(S),25-triol (5), urs-12-en-3beta-hydroxy-27-Z-feruloyloxy-28-oic acid (6), 3beta-hydroxyolean-12-en-28-oic acid (7), 3beta,27-dihydroxylupan-29-ene (8), 3beta-hydroxylupan-29-en-28-oic acid (9), 3beta-hydroxyursan-12-en-28-oic acid (11), 3beta-hydroxy-27-p-coumaroyloxy-olea-12-en-28-oic acid (12) and urs-12-en-3-one (15); an iridoid 1alpha-plumieride (10); a cardenolide 3alpha,14beta-dihydroxy-17beta-card-20(22)-enolide (13); a fatty acid ester methyl n-octadecanoate (14) and a steroid 3beta-hydroxy-delta5-stigmastane (16). The new constituents were characterized through spectroscopic studies including 1D (1H and 31C NMR) and 2D (COSY-45, NOESY, J-resolved, HMQC and HMBC) NMR and chemical transformations. This is the first report on the isolation of dammarane triterpenoids from P. obtusa. Compounds 5 and 6 are hitherto unreported from P. obtusa. The known compounds were identified by comparison of their spectral data with those reported in the literature.  相似文献   

15.
The methanol extract of the seeds of Turraea parvifolia has yielded seven novel triterpenoid derivatives: 12alpha-acetoxyazadironolide, turraparvin A (12alpha-acetoxy-7alpha,23-dihydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,14,20(22)-trien-21,23-olide), turraparvin B (12alpha-acetoxy-7alpha,21-dihydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,14,20(22)-trien-23,21-olide), turraparvin C (7alpha,12alpha-diacetoxy-21-hydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,14,20(22)-trien-23,21-olide), 11-epi-21-hydroxytoonacilide, 11-epi-23-hydroxytoonacilide and turraparvin D (12alpha-acetoxy-7alpha-hydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,14,20(22)-trien-21,23-lactam).  相似文献   

16.
Two triterpenes 21R,23R-epoxy-21alpha-ethoxy-24S,25-dihydroxyapotirucall-7-en-3-one and 24R-acetoxy-3beta,25-dihydroxycycloartane were isolated from the leaves of Dysoxylum malabaricum together with eight known compounds lupeone, lupeol. sitosterol, dipterocarpol, cycloart-25-ene-3beta,24-diol, 24R,25-dihydroxycycloartan-3-one, 3beta,24R,25-trihydroxycycloartane and ergosta-5,24(24(1))-diene-3beta,4beta,20S-triol. The complete 1H and 13C NMR spectral assignment of the new apotirucallene triterpenoid has been achieved by 1H-1H COSY, HMQC and HMBC experiments.  相似文献   

17.
Two new brassinosteroids, (22R,23R,24S)-22,23-dihydroxy-24-methyl-5alpha-cholest-2-en-6-one (secasterol) and (22R,23R,24S)-22,23-dihydroxy-2alpha,3alpha-epoxy-24-methyl-5alpha-cholest-6-one (2,3-diepisecasterone) have been identified together with a known 2,3-epoxybrassinosteroid, secasterone, in seedlings of Secale cereale. Deuterated secasterol, teasterone, and typhasterol, upon administration to rye seedlings, were incorporated into secasterone and 2,3-diepisecasterone, indicating a biosynthetic route via teasterone/typhasterol to secasterol to 2,3-epoxybrassinosteroids.  相似文献   

18.
Recently, 25-hydroxyvitamin D3-24-hydroxylase (CYP24A1) has been shown to catalyze not only hydroxylation at C-24 but also hydroxylations at C-23 and C-26 of the secosteroid hormone 1alpha, 25-dihydroxyvitamin D3 (1alpha,25(OH)2D3). It remains to be determined whether CYP24A1 has the ability to hydroxylate vitamin D3 compounds at C-25. 1alpha,24(R)-dihydroxyvitamin D3 (1alpha,24(R)(OH)2D3) is a non-25-hydroxylated synthetic vitamin D3 analog that is presently being used as an antipsoriatic drug. In the present study, we investigated the metabolism of 1alpha,24(R)(OH)2D3 in human keratinocytes in order to examine the ability of CYP24A1 to hydroxylate 1alpha,24(R)(OH)2D3 at C-25. The results indicated that keratinocytes metabolize 1alpha,24(R)(OH)2D3 into several previously known both 25-hydroxylated and non-25-hydroxylated metabolites along with two new metabolites, namely 1alpha,23,24(OH)3D3 and 1alpha,24(OH)2-23-oxo-D3. Production of the metabolites including the 25-hydroxylated ones was detectable only when CYP24A1 activity was induced in keratinocytes 1alpha,25(OH)2D3. This finding provided indirect evidence to indicate that CYP24A1 catalyzes C-25 hydroxylation of 1alpha,24(R)(OH)2D3. The final proof for this finding was obtained through our metabolism studies using highly purified recombinant rat CYP24A1 in a reconstituted system. Incubation of this system with 1alpha,24(R)(OH)2D3 resulted in the production of both 25-hydroxylated and non-25-hydroxylated metabolites. Thus, in our present study, we identified CYP24A1 as the main enzyme responsible for the metabolism of 1alpha,24(R)(OH)2D3 in human keratinocytes, and provided unequivocal evidence to indicate that the multicatalytic enzyme CYP24A1 has the ability to hydroxylate 1alpha,24(R)(OH)2D3 at C-25.  相似文献   

19.
Two bis-tetrahydrofuran acetogenins, squamocin-O(1) (1) and squamocin-O(2) (2), were isolated from a MeOH extract of seeds of Annona squamosa L. Their structures were determined by spectral means including precursor-ion scanning mass spectral analysis for their aminal derivatives. The configurations at the oxymethine chiral centers were assigned as 12R,15R,16R,19R,20R,23R,24S,28S,36S for 1 and 12S,15R,16R,19R,20R,23R,24S, 28S,36S for 2, based on 1H NMR analysis of their Mosher's ester derivatives and CD data.  相似文献   

20.
New analogues of 3beta-hydroxy-5alpha-cholest-8(14)-en-15-one (15-ketosterol) with modified 17-chains [(22S,23S,24S)- and (22R,23R,24S)-3beta-hydroxy-24-methyl-22,23-oxido-5alpha-cholest-8(14)-en-15-ones and (22RS,23xi,24S)-24-methyl-5alpha-cholesta-3beta,22,23-triol-15-one] were synthesized from (22E,24S)-3beta-acetoxy-24-methyl-5alpha-cholesta-8(14),22-dien-15-one. The chiralities of their 22 and 23 centers were determined by NMR spectroscopy. The isomeric 22,23-epoxides effectively inhibited cholesterol biosynthesis in hepatoma Hep G2 cells (IC50 0.9 +/- 0.2 and 0.7 +/- 0.2 microM, respectively), and their activities significantly exceeded those of 15-ketosterol (IC50 4.0 +/- 0.5 microM), (22E,24S)-3beta-hydroxy-24-methyl-5alpha-cholesta-8(14),22-dien-15-one (IC50 3.1 +/- 0.4 microM), and the 3beta,22,23-triol synthesized (IC50 6.0 +/- 1.0 microM). The English version of the paper: Russian Journal of Bioorganic Chemistry, 2005, vol. 31, no. 3; see also http://www.maik.ru.  相似文献   

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