Microbial transformation of resibufogenin by Curvularia lunata AS 3.4381

In this paper, the microbial transformation of resibufogenin (1) by Curvularia lunata AS 3.4381 was investigated, and four transformed products were isolated and characterized as 3-epi-resibufogenin (2), 12α-hydroxy-3-epi-resibufogenin (3), 12-oxo-16β-hydroxy-3-epi-resibufogenin (4), and 12β,15-epoxy-3-epi-bufalin-14,15-ene (5). Among them, 4 and 5 are new compounds, and isomerization, hydroxylation, and oxidation reactions in microbial transformation process were observed. Additionally, the cytotoxicities of transformed products (2–5) were also investigated.     

Novel microbial transformation of resibufogenin by Fusarium solani

In this paper, microbial transformation of resibufogenin by Fusarium solani AS 3.1829 was investigated, and five transformed products were isolated and identified as 3-ketone-resibufogenin (2), 3-one-cyclic 3-(1,2-dimethyl-1,2-ethanediylacetal)-resibufogenin (3), 3-dimethoxyl-resibufogenin (4), 3-epi-resibufogenin (5), and 3-epi-15α-hydroxy-7βH-bufalin (6), respectively. Among them, 3, 4, and 6 are new compounds, and the rare double oxidization of C-3 was reported. In addition, the cytotoxicities of transformed products were also investigated.     

Two new isoflavanones from Erythrina costaricensis

Two new isoflavanones, 5,3′-dihydroxy-4′-methoxy-5′-(3-methyl-1,3-butadienyl)-2″,2″-dimethylpyrano[5,6:6,7]isoflavanone (1) and 5,3′-dihydroxy-5′-(3-hydroxy-3-methyl-1-butenyl)-4′-methoxy-2″,2″-dimethylpyrano[5,6:6,7]isoflavanone (2), together with two known isoflavonoids, cristacarpin, and euchrenone b₁₀, were isolated from the stems of Erythrina costaricensis. Their structures were established on the basis of spectroscopic evidence. These new compounds are rare isoflavanones, possessing both a 2,2-dimethylpyran substituent and a prenyl analog. The antibacterial activities of 1 and 2 against the methicillin-resistant Staphylococcus aureus were examined.     

Antioxidant and α-amylase inhibitory activities of extract and isolates from Zygogynum pancheri subsp. arrhantum

One new sesquiterpenoid (5R^*,8R^*,9R^*,10R^*)-cinnamolide (8), and seven known compounds, 5-hydroxy-7-methoxyflavonone (1), 8-hydroxy-3-(4′-hydroxyphenyl)-6,7-(2″,2″-dimethylchromene)-tetralone (2), 8-hydroxy-3-(3′,4′-dihydroxyphenyl)-6,7-(2″,2″-dimethylchromene)-tetralone (3), 1β-E-O-p-methoxycinnamoyl-bemadienolide (4), 1β-O-(E-cinnamoyl)-6α-hydroxy-9-epi-polygodial (5), 1β-O-(E-cinnamoyl)-6α-hydroxypolygodial (6), and 1β-O-E-cinnamoylpolygodial (7) were isolated from the ethyl acetate extract of barks of Zygogynum pancheri subsp. arrhantum (Winteraceae). The structures of these molecules were assigned predominantly based on spectral data. The structure of compound 8 was confirmed by X-ray crystallographic analysis. Compounds 2 and 3 exhibited significant antioxidant activity, whereas compounds 1 and 4–7 showed significant α-amylase inhibitory activity.     

Four new lignans from Schisandra sphenanthera

Three new 7,8-secolignans, schisandlignans A–C (1, 2, and 4), one new dibenzocyclooctadiene lignan, schisandlignan D (5), together with nine known lignans 3′,4′-dimethoxybenzoic acid (3″,4″-dimethoxyphenyl)-2-methyl-3-oxobutyl ester (3), gomisin J (6), rubrisandrin A(1b) (7), interiotherin B (8), schisantherin D (9), ( ? )-machilusin (10), ganschisandrine (11), henricine A (12), and (+)-1-hydroxy pinoresinol (13), were isolated from the rattan of Schisandra sphenanthera. Their structures were determined by analysis of 1D and 2D NMR spectroscopic data.     

Two novel flavanes from the leaves of Morus alba L.

Two new flavanes, (2R,4S)-2′,4′-dihydroxy-2H-furan-(3″,4″:8,7)-flavan-4-ol (1) and (2S)-2′,4′-dihydroxy-7-methoxyl-8-butyricflavane (2), together with four known flavonoids, were isolated from the leaves of Morus alba L. Their structures were determined on the basis of spectroscopic analysis.     

东风桔化学成分研究

东风桔是芸香科酒饼簕属植物,学名为Atalantia buxifolia (Poir)Oliv,民间用于去瘀去痛,顺气化痰,治跌打肿痛,风湿痛,疟疾。药理试验证明,东风桔叶有明显的抗疟作用。有效成分不明。东风桔化学成分前人有过报道,但国内对东风桔叶化学成分尚末进行过研究。为阐明其有效成分,我们对其化学成分进行了研究,从叶子的石油醚提取部位     

Isolation and identification of phase I metabolites of butyrolactone I in rats

1.?Butyrolactone I (BL-I), one of the major secondary metabolites of fungus Aspergillus terreus, is a selective cdc2 kinase inhibitor. In the present study, the metabolism of BL-I in male Wistar rats was investigated by characterizing metabolites excreted into feces.

2.?Following an oral dose of 40?mg/kg BL-I, 10 phase I metabolites were isolated from the feces of rats, and their structures were identified on the basis of a range of spectroscopic data and ICD analysis. These metabolites were fully characterized as butyrolactone VI (M1), aspernolide E (M2), 7′′S-hydroxy-9′′-ene-butyrolactone I (M3), 7′′R-hydroxy-9′′-ene-butyrolactone I (M4), 7″S, 8″R-dihydroxy-aspernolide E (M5), 7″R, 8″S-dihydroxy-aspernolide E (M6), 7″R-acetyl-8″S-hydroxy-aspernolide E (M7), 7″S-acetyl-8″R-hydroxy-aspernolide E (M8), 7″R-methoxy-8″S-hydroxy-aspernolide E (M9), butyrolactone V (M10), respectively. It is the first time to describe the metabolites of BL-I in vivo, and metabolites M3 to M9 are new compounds.

3.?BL-I and metabolites M2 to M10 were evaluated for their antimicrobial activity and in vitro antiproliferative activities. Only M-3 and M-4 showed inhibitory effect against staphylococcus aureus both with MIC of 125?μg/ml. BL-I and metabolites M-4 and M-5 exhibited potent cancer cell growth inhibitory activities against HL-60 (human leukemia) cell lines with the IC₅₀ values of 13.2, 28.8 and 35.7?μM, respectively.

4.?On the basis of metabolites profile, a possible metabolism pathway for BL-I in rats has been proposed. This is the first systematic study on the phase I metabolites of BL-I.     

Three new acylated flavone C-glycosides from the flowers of Trollius chinensis

Three new flavone C-glycosides with the substitution of the unusual acyl, 2″-O-veratroylisoswertisin (1), 3″-O-2-methylbutyrylisoswertiajaponin (2), and 3″-O-2-methylbutyrylvitexin (3), together with the known compounds of 2″-O-2-methylbutyrylisoswertisin (4), 3″-O-2-methylbutyrylisoswertisin (5), and trollisin I (6) were isolated from the antibacterial fraction of the aqueous extract of the flowers of Trollius chinensis. The structural elucidations of these compounds were carried out by a detailed analysis of the NMR and MS spectra.     

Microbial transformation of deoxyandrographolide by Fusarium graminearum AS 3.4598

Biotransformation of deoxyandrographolide (1) by Fusarium graminearum AS 3.4598 was investigated in this paper. And five transformed products of 1 by F. graminearum AS 3.4598 were obtained. Their chemical structures were characterized as 3-oxo-8α,17β-epoxy-14-deoxyandrographolide (2), 3-oxo-14-deoxyandrographolide (3), 3-oxo-17,19-dihydroxyl-8,13-ent-labdadien-15,16-olide (4), 1β-hydroxyl-14-deoxyandrographolide (5), and 7β-hydroxyl-14-deoxyandrographolide (6) by spectral methods including 2D NMR. Among them, products 2, 4, and 5 are new.     

A new cerebroside from Uvaria tonkinensis var. subglabra

A new cerebroside, subglain A (1), together with five known compounds (2–6) have been isolated from the stems of Uvaria tonkinensis var. subglabra. The structure of 1 has been determined to be 1-O-β-D-glucopyranosyl-(2S,3S,4R,8Z,2′R)-2-[N-(2′-hydroxytetracosanyl)-N-(1″,2″-dihydroxyethyl)-amide]-8-tetradecene-1,3,4-triol by spectroscopic evidence. The known compounds were identified as schisandriside (2), erythritol (3), β-D-glucopyranose (4), kaempferol-3,7-O-α-L-dirhamnoside (5), and (+)-lyoniresinol (6).     

Two new furaldehyde compounds from the rhizomes of Gastrodia elata

Two new compounds 5-[4′-(4″-hydroxybenzyl)-3′-hydroxybenzyloxymethyl]-furan-2-carbaldehyde (1) and 5-[4′-(4″-hydroxybenzyl)-3′-hydroxybenzyl]-furan-2-carbal-dehyde (2), together with two known 5-(4-hydroxbenzyloxymethyl)-furan-2-carbaldehyde] (3) and 5-(hydroxymethyl)-2-furaldehyde (4), were isolated from the rhizome of Gastrodia elata. Their structures were elucidated by spectroscopic analysis and comparison of their spectral data with those reported previously. All compounds exhibited weak or no cytotoxicity against human colon carcinoma cell line (HT-29) and human chronic myelogenous leukemia cell line (K-562).     

Novel 19F‐MRS β‐galactosidase reporter molecules incorporated nitrogen mustard analogues

In this study, we propose a novel molecular platform‐integrated fluorinated antitumor nitrogen mustards for ¹⁹F‐MRS assay of β‐galactosidase (β‐gal) activity. Following this idea, we have designed, synthesized, and characterized 2‐fluoro‐4‐[bis(2′‐chloroethyl)amino]phenyl β‐D‐galactopyranoside 5 , 2‐fluoro‐4‐{bis[2′‐O‐(β‐D‐galactopyranosyl)ethyl]amino}phenyl β‐D‐galactopyranoside 8 , 2‐fluoro‐4‐{bis[[1″‐(β‐D‐galactopyranosyl)‐1″, 2″, 3″‐triazol‐4″‐yl]methyl] amino}phenyl β‐D‐galactopyranoside 14 and 2‐fluoro‐4‐{bis[[1″‐(β‐D‐glucopyranosyl)‐1″, 2″, 3″‐triazol‐4″‐yl]methyl]amino}phenyl β‐D‐galactopyranoside 15 through glycosylation and click reaction strategies, and their structures were confirmed by NMR and HRMS or elemental analysis data. Among them, 2‐fluoro‐4‐[bis(2′‐chloroethyl)amino]phenyl β‐D‐galacto‐pyranoside 5 was found very sensitive to β‐gal (E801A) in PBS at 37°C with big Δδ_F response. Here, we demonstrated the feasibility of this platform for assessing β‐gal activity in solution, and in vitro with lacZ‐transfected human MCF7 breast and PC3 prostate tumor cells, by the characterization of β‐gal‐responsive ¹⁹F‐chemical shift changes Δδ_F and hydrolytic kinetics.     

4-〔4'-(2',2',6',6'-四甲基哌啶氮氧自由基)氨基〕-4'-去甲表鬼臼毒及其自由基还原物抗肿瘤作用比较

目的：比较鬼臼毒氮氧自由基衍生物４－〔４″－（２″，２″，６″，６″－四甲基哌啶氮氧自由基）氨基〕－４′－去甲表鬼臼毒（ＧＰ－７）及其自由基还原物ＧＰ－７－Ｈ和ＧＰ－７－ＯＨ的抗肿瘤活性和急性毒性。方法：采用小鼠移植性肿瘤Ｓ１８０、ＨｅＰＳ和腹腔注射ＬＤ５０值。结果：ＧＰ－７、ＧＰ－７－Ｈ、ＧＰ－７－ＯＨ５～１０ｍｇ·ｋｇ－１给药１０ｄ，对Ｓ１８０肉瘤的抑制率分别为３９．７％～４６．８％、１７．３％～２９．５％和１９．９％～２２．４％，对ＨｅＰＳ的抑制率分别为３８．７％～４８．８％、１５．５％～３５．１％和１８．４％～３３．３％。昆明种小鼠腹腔注射一次给药，ＬＤ５０分别为２３１．２、８９．７和１２９．５ｍｇ·ｋｇ－１。结论：ＧＰ－７对Ｓ１８０、ＨｅＰＳ生长抑制作用均较其还原物ＧＰ－７－Ｈ、ＧＰ－７－ＯＨ强，急性毒性较其还原物ＧＰ－７－Ｈ和ＧＰ－７－ＯＨ小；提示ＧＰ－７中的自由基在加强抗肿瘤作用和降低毒性方面起着重要的作用。     

Two new isoarylbenzofuran diglucosides from the root bark of Morus alba

Two new arylbenzofuran diglucopyranosides, (2″R)-(–)-moracin-O-5′,3″-β-d-diglucopyranoside (1) and (2″R)-(–)-moracin-P-5′,2″-β-d-diglucopyranoside (2), along with known arylbenzofurans, moracin M 6-β-d-glucopyranoside (3), and an isomeric mixture of R-(–)-moracin O (4) and R-(–)-moracin P (5), were isolated from the root bark of Morus alba L. The structure of the compounds was elucidated based on mass spectrometry, infrared, 1D and 2D nuclear magnetic resonance spectroscopic data.     

Antioxidant and urease inhibitory C-glycosylflavonoids from Celtis africana

Two new C-glycosylflavonoids celtisides A (1) and B (2) have been isolated from n-butanol-soluble fraction of Celtis africana, along with five known C-glycosylflavonoids vitexin (3), orientin (4), isoswertiajaponin (5), isoswertisin (6), and 2″-O-rhamnosyl vitexin (7) reported for the first time from this species. Their structures were assigned from 1D and 2D NMR spectra. These compounds were investigated for biological activities and showed significant antioxidant and urease inhibitory activities.     

Biotransformation of oleanolic acid by Alternaria longipes and Penicillium adametzi

Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2–7) from 1 by Alternaria longipes and three transformed products (8–10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2α,3α,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (2), 2α,3β,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (3), oleanolic acid 28-O-β-d-glucopyranosyl ester (4), oleanolic acid-3-O-β-d-glucopyranoside (5), 3-O-(β-d-glucopyranosyl)-oleanolic acid-28-O-β-d-glucopyranoside (6), 2α,3β,19a-trihydroxy-oleanolic acid-28-O-β-d-glucopyranoside (7), 21β-hydroxyl oleanolic acid-28-O-β-d-glucopyranoside (8), 21β-hydroxyl oleanolic acid (9), and 7α,21β-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8–10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.     

Phenolic constituents from stem bark of Erythrina poeppigiana and their inhibitory activity on human glyoxalase I

A novel isoflavone, erythgianin A (1), along with nine known compounds 2–10, was isolated from the stem bark of Erythrina poeppigiana (Leguminosae). The unusual isoflavone structure of 1, possessing a highly oxidized 3″,4″-dihydroxy-2″-hydroxymethyl-2″-methyl-2″,3″-dihydropyrano substituent, was determined on the basis of spectroscopic analyses. All of the isolated compounds were evaluated for their in vitro inhibitory activity toward human glyoxalase I. Among the isolates, isolupalbigenin (10) with two prenyl groups showed the highest inhibitory activity.     

Three new lignans from the seeds of Saussurea involucrata

Three new lignans, arctigenin-4-O-(6″-O-acetyl-β-d-glucoside) (1), arctigenin-4-O-(2″-O-acetyl-β-d-glucoside) (2), and arctigenin-4-O-(3″-O-acetyl-β-d-glucoside) (3), together with two known lignans, were isolated from the seeds of Saussurea involucrata. Their structures were established by spectroscopic methods, mainly 1D and 2D NMR, and mass spectral analysis.     

Two new flavonoid alkaloids from Senecio argunensis

Two new flavonoid alkaloids, 8-(2″-pyrrolidinone-5″-yl)-quercetin (1) and 8-(2″-pyrrolidinone-5″-yl)-isorhamnetin (2), were isolated from the herb of Senecio argunensis. Their structures were elucidated by spectral analysis.