New flavonoid glycosides and other chemical constituents from Clerodendrum phlomidis leaves: isolation and characterisation

Phytochemical investigation of the plant Clerodendrum phlomidis Linn. F. (Lamiaceae) has now led to the isolation of two new flavonoid glycosides (1, 2) together with six known compounds identified as pectolinaringenin (3), pectolinaringenin-7-O-β-d-glucopyranoside (4), 24β-ethylcholesta-5,22E,25-triene-3β-ol (5), 24β-ethylcholesta-5,22E,25-triene-3β-O-β-D-glucopyranoside (6), (2S,3S,4R,10E)-2-[(2′R)-2′-hydroxytetracosanoylamino]-10-octadecene-1,3,4-triol (7) and andrographolide (8) mainly by spectroscopic analysis. Compounds 4 and 6–8 are reported for the first time from C. phlomidis.     

A pair of unprecedented cyclohexylethanoid enantiomers containing unusual trioxabicyclo[4.2.1]nonane ring from Clerodendrum bungei

A pair of unprecedented enantiomers (1a/1b) of cyclohexylethanoid bearing an unusual trioxabicyclo[4.2.1]nonane ring, along with two known structurally related cyclohexylethanoids, (+)-rengyolone (2) and cleroindicin E (3), were isolated from the aerial parts of Clerodendrum bungei. The structures and absolute configurations of the enantiomers were determined by comprehensive spectroscopic analysis, single-crystal X-ray diffraction, and quantum mechanical calculation of the electronic circular dichroic (ECD) spectra. The postulated biogenetic pathway of 1a/1b was also discussed.     

Bioactive Abietane-Type Diterpenoid Glycosides from Leaves of Clerodendrum infortunatum (Lamiaceae)

In this study, two previously undescribed diterpenoids, (5R,10S,16R)-11,16,19-trihydroxy-12-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-17(15→16),18(4→3)-diabeo-3,8,11,13-abietatetraene-7-one (1) and (5R,10S,16R)-11,16-dihydroxy-12-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-17(15→16),18(4→3)-diabeo-4-carboxy-3,8,11,13-abietatetraene-7-one (2), and one known compound, the C₁₃-nor-isoprenoid glycoside byzantionoside B (3), were isolated from the leaves of Clerodendrum infortunatum L. (Lamiaceae). Structures were established based on spectroscopic and spectrometric data and by comparison with literature data. The three terpenoids, along with five phenylpropanoids: 6′-O-caffeoyl-12-glucopyranosyloxyjasmonic acid (4), jionoside C (5), jionoside D (6), brachynoside (7), and incanoside C (8), previously isolated from the same source, were tested for their in vitro antidiabetic (α-amylase and α-glucosidase), anticancer (Hs578T and MDA-MB-231), and anticholinesterase activities. In an in vitro test against carbohydrate digestion enzymes, compound 6 showed the most potent effect against mammalian α-amylase (IC₅₀ 3.4 ± 0.2 μM) compared to the reference standard acarbose (IC₅₀ 5.9 ± 0.1 μM). As yeast α-glucosidase inhibitors, compounds 1, 2, 5, and 6 displayed moderate inhibitory activities, ranging from 24.6 to 96.0 μM, compared to acarbose (IC₅₀ 665 ± 42 μM). All of the tested compounds demonstrated negligible anticholinesterase effects. In an anticancer test, compounds 3 and 5 exhibited moderate antiproliferative properties with IC₅₀ of 94.7 ± 1.3 and 85.3 ± 2.4 μM, respectively, against Hs578T cell, while the rest of the compounds did not show significant activity (IC₅₀ > 100 μM).     

臭牡丹黄酮类化合物提取及其抗氧化作用

研究臭牡丹中黄酮类化合物的最佳提取工艺条件及其抗氧化活性.以提取时间、料液比、提取温度、乙醇体积分数为主要影响因素,以黄酮类化合物提取率为考察指标,确定最佳提取工艺条件,并通过对亚硝酸盐、超氧阴离子自由基、羟自由基的清除效果及对猪油的抗氧化研究其抗氧化活性.结果表明,臭牡丹中黄酮类化合物的最佳提取工艺条件为提取时间2.0h、料液比1∶40（g/mL）、提取温度70℃、乙醇体积分数70％的条件下提取效果最好,臭牡丹中黄酮类化合物在各抗氧化体系中均表现出较强的抗氧化活性,且其作用具有剂量效应关系,其抗氧化活性均强于维生素C.     

Clerodendrumic Acid,a New Triterpenoid from Clerodendrum glabrum (Verbenaceae), and Antimicrobial Activities of Fractions and Constituents

One new triterpenoid, (3β,11α,19β)‐3‐(butanoyloxy)‐11‐hydroxytaraxast‐20(30)‐ene‐23,28‐dioic acid (clerodendrumic acid; 1 ) was isolated from the hexane extract of the leaves of Clerodendrum glabrum var. glabrum along with heptadecanoic acid ( 2 ). The structure of the new compound was elucidated by interpretation of its NMR (1D and 2D), MS, and IR data. Combined fractions C and D from the column chromatography of the hexane extract exhibited significant antifungal activities (average MIC of 0.10 mg/ml) against Candida albicans and Cryptococcus neoformans. C. albicans was relatively resistant to clerodendrumic acid ( 1 ; MIC 125 μg/ml) and was resistant to heptadecanoic acid ( 2 ; MIC 188 μg/ml). Both compounds had low antibacterial activities against two Gram‐positive and two Gram‐negative bacteria with average MIC values of 157 and 172 μg/ml, respectively. Compounds 1 and 2 were relatively nontoxic against monkey kidney Vero cells in vitro with IC₅₀ values of 202.6 and 108.4 μg/ml, respectively.     

Clerodendrumol,A New Triterpenoid from Clerodendrum yaundense Gürke (Lamiaceae)

A new lupane‐type triterpene named clerodendrumol ( 1 ), i.e., (16α)‐lupa‐12,20(29)‐dien‐16‐ol, together with five known compounds, octacosa‐(5Z,9Z)‐dienoic acid ( 3 ), tetracosanoic acid ( 4 ), genkwanin ( 5 ), (12S)‐hydroxyoctadeca‐(9Z,13E,15E)‐trienoic acid ( 6 ), and (9S)‐hydroxyoctadeca‐(10E,12E)‐dienoic acid ( 7 ), were isolated from the twigs of Clerodendrum yaundense. O‐Acetylclerodendrumol ( 2 ), a derivative of 1 , was prepared by a standard acetylation procedure applied to compound 1 . The structure of the new compound was elucidated using spectroscopic analysis (NMR and MS) data, and chemical conversions (acetylation and deacetylation). The human breast cancer cell line (MDA‐MB‐231) was sensitive to all test samples, and clerodendrumol ( 1 ) as well as its derivative 2 had good activity (IC₅₀ values 7.5 and 13.2 μM ). Genkwanin ( 5 ) exhibited strong activity on HeLa cell line with IC₅₀ 7.8 μM .     

A new rearranged abietane diterpene from Clerodendrum inerme with antioxidant and cytotoxic activities

Eight compounds were isolated from the leaves of Clerodendrum inerme, including one new rearranged abietane diterpene, crolerodendrum B (1). Their structures were determined by means of spectroscopic methods including one-dimensional and two-dimensional nuclear magnetic resonance (1-D and 2-DNMR), high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) and circular dichroism (CD). The DPPH radical scavenging and cytotoxic activities of isolated compounds against MCF7 (breast), HCT116 (colon) and B16F10 (melanoma) cancer cell lines were evaluated. Compounds 1, 3 and 4 exhibited strong DPPH radical-scavenging effects (ED₅₀ values of 17.6 ± 2.1, 10.1 ± 0.8 and 11.3 ± 0.3 μM, respectively) and 4 showed strong cytotoxicity against the HCT116 cell line (IC₅₀ = 3.46 ± 0.01 μM).     

A New Phenylpropanoid Glycoside: Serratumoside A from Clerodendrum serratum

In the previous papers"', we have reported some chemical constituents fromClerodendrum serratum var. amplerghlium Moldenke. A continuation of our studies onthe same plant led to the isolation of a new phenylpropanoid, serratumoside A (l), whichis reported in this paper.Serratumoside A (l) with three known phenylpropanoid glycosides identified asacteoside', mwtinoside' and myricoside', respectively, were isolated from the Cserratum. Compound I was isolated as a brown amorphous powder, laly …     

Two New Iridoid Glucosides from Clerodendrum serratum

Clerodendrumserratumcalledas"SanDuiJie"inChinese,isasmallshrubwithfragrantflowersfoundwidelyintheforestsofthesouthofChina.IthasbeenusedasafolkmedicineinYunnanfortreatmentofmanydiseasessuchashepatitisandmalaria.Inordertofindthebioactivecomponents,studiesonthechemicalconstituentsoftheleavesofClerodendrumserratum,collectedatLongLingofYunnanprovince,werecarriedout.Wehavereportedtwonewglycosidespreviously'.NoW,furtherinvestigationofglycosidesofthisplantresultedintwonewiridoidglucosides76coumar…