New withanolides from Mandragora officinarum: First report of withanolides from the Genus Mandragora

Two new withanolides named mandragorolide A (1) and mandragorolide B (2) were isolated from the MeOH extract of the whole plant of Mandragora officinarum of Jordanian origin, along with five known withanolides namely larnaxolide A (3), withanolide B (4), datura lactone 2 (5), withanicandrin (6) and salpichrolide C (7). Compound 3 has been reported only once before, from the leaves of Larnax glabra. This is the first report of withanolides of different biogenetic types from the genus Mandragora. Isolation of known fatty compounds, coumarins, sterols and tropane alkaloids was also achieved in this study.     

Diarylheptanoids from the rhizomes of Alpinia officinarum and their anticancer activity

Two new diarylheptanoids (1, 2), together with two known analogs (3, 4), were isolated from the rhizomes of Alpinia officinarum. The new compounds were elucidated to be (5S)-5-hydroxy-7-(3, 4-dihydroxyphenyl)-1-phenyl-3-heptanone (1) and (5R)-5-hydroxy-7-(3-methoxy-4, 5-dihydroxyphenyl)-1-phenyl-3-heptanone (2) based on their spectral analysis. Compound 4 showed moderate cytotoxicity against human tumor cell lines, HepG2, MCF-7 and SF-268, while no significant effect were found for compounds 1-3.     

A new 9-nor-atractylodin from Atractylodes lancea and the antibacterial activity of the atractylodin derivatives

A new compound, namely, 9-nor-atractylodin (1) and one known atractylodin (2) were isolated from the rhizomes of Atractylodes lancea. The structural modifications of atractylodin were carried out and a series of atractylodin derivatives (3-10) were obtained. The antibacterial activities of 1-10 were examined against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Candida albicans. Compounds 4 and 8, which contained the α, β-unsaturated carbonyl fragment, were found to be active against E. coli and S. aureus.     

New antibacterial triterpenoid saponin from Lactuca scariola

A new antibacterial triterpenoid saponin, 3beta-O-[alpha-L-rhamnopyranosyl]-30-norolean-12,19-diene-28-oic acid 28-O-[beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl]-ester (1); has been isolated from the stems of Lactuca scariola. Its structure was determined by chemical degradations and spectral analysis.     

A new coumarin from Sarcandra glabra

Sarcandracoumarin (1), the first coumarin having a 1-phenylethyl substituent at the C-3 position, was isolated along with eleven known phenolic compounds from the water extract of Sarcandra glabra. Its structure was elucidated on the basis of spectroscopic data. Compound 1 exhibited moderate or weak cytotoxicity against several tumor cell lines.     

Three new triterpenoid saponins from root of Gardenia jasminoides Ellis

Three new compounds (Gardeniside A–C), 11α,12α-epoxy-3β-[(O-β-D-glucuronopyranoside-6′-O-methly ester)oxy]olean-28,13-olide (1), siaresinolic acid 3-O-β-D-glucuronopyranoside-6′-O-methly ester (2), and 3-O-β-D- glucuronopyranoside-6′-O-methly ester-siaresinolic acid-28-O-β-D- glucopyranoside (3), with seven known compounds oleanolic acid 3-O-β-D- glucuronopyranoside-6′-O-methly ester (4), oleanolic acid 3-O-β-D- glucuropyranoside (5), hederagenin 3-O-β-D- glucuronopyranoside-6′-O- methly ester (6), chikusetsusaponin IVa methyl ester (7), chikusetsusaponin (8), chikusetsusaponin IVa butyl ester (9), siaresinolic acid 28-o-β-d-glucopyranosyl ester (10) were isolated from the root of Gardenia jasminoides Ellis. Six compounds (1, 4–7, and 9) showed cytotoxic activities against HeLa, A549, MCF-7 and A354-S2 cell lines.     

Four new phenanthrenes from Monomeria barbata Lindl

Three biphenanthrene compounds (1–3) and a triphenanthrene compound (4), together with six known biphenanthrene compounds (5–10), were isolated from the tubers of Monomeria barbata Lindl. Their structures were elucidated on the basis of extensive spectroscopic analysis (1D-, 2D-NMR, and HR-ESI-MS). These four new compounds were tested in vitro for the cytotoxic activity against liver carcinoma (HepG-2), promyelocytic leukaemia (HL60), ovarian carcinoma (Skov-3) and epidermoid carcinoma (A431) cancer cell lines and the antioxidant activity in DPPH radical scavenging. Compounds 1–4 exhibited significant cytotoxic activity against HepG-2 and HL60 cell lines, and potent antioxidant activity in DPPH radical scavenging.     

One new sesquiterpene from Saussurea laniceps

One new guaiane-type sesquiterpene (1) was isolated from Saussurea laniceps. The structure of the new compound was elucidated by spectroscopic data analysis. The immunomodulatory activity of compound 1 was evaluated. It was found that compound 1 showed significant inhibition for proliferation of murine T cells in vitro.     

Antibacterial triterpenes from the threatened wood-decay fungus Fomitopsis rosea

From a biologically active extract from the fungus Fomitopsis rosea, two new lanostane triterpenes were isolated, 3α-(3′-butylcarboxyacetoxy)oxepanoquercinic acid C 1 and 3α-hydroxy-24-methylene-23-oxolanost-8-en-26-carboxylic acid 2, along with three known triterpenes, 3–5, and the epidioxy sterol derivative 6. The structures of the compounds were elucidated based on their spectral properties. All triterpenes demonstrated antibacterial activity against S. aureus but possessed no antiradical activity against DPPH radicals.     

Three new oleanane triterpenoid saponins acetylated with monoterpenoid acid from Albizia julibrissin

Three new minor oleanane triterpenoid saponins acetylated with monoterpenoid acid, julibroside J₃₂, julibroside J₃₅ and julibroside J₃₆, along with one new natural product, prosapogenin 9, were isolated from the stem bark of Albizia julibrissin. Their structures were elucidated on the basis of the chemical and spectroscopic evidences.     

Phytogrowth-inhibitory and antibacterial activity of Verbascum sinuatum

The methanolic extract of Verbascum sinuatum inflorescences and isolated compounds were tested for their antibacterial activity against 13 Gram(+) and Gram(-) bacteria and for their allelopathic activity against radish.     

Three new sesquiterpenes from Tithonia diversifolia and their anti-hyperglycemic activity

Three new germacrane sesquiterpenes (1), (2), (3), along with eleven known sesquiterpenes, namely, tirotundin-3-O-methyl ether (4), deacetylvguiestin (5), 1β-hydroxydiversifolin-3-O-methyl ether (6), tagitinin C (7), 1β-hydroxytirotundin-3-O-methyl ether (8), 1β-hydroxytirotundin-1,3-O-dimethyl ether (9), tagitinin F-3-O-methyl ether (10), tagitinin F (11), tagitinin A (12), 3β-acetoxy-4α-hydroxyeduesm-11(13)-en-12-oic acid (13) and ilicic acid (14) were isolated from the aerial parts of Tithonia diversifolia. Their structures were established by spectroscopic analysis, while the relative configuration of compound 1 was confirmed by X-ray diffraction analysis. In addition, compounds 1–14 were evaluated in vitro for their anti-hyperglycemic activity by glucose uptake in 3T3-L1 adipocytes. It was found that 10 μg/mL 1, 3, 6 and 8 could significantly increase glucose uptake without significant toxic effects.     

A new dicoumarin and anticoagulant activity from Viola yedoensis Makino

A new dicoumarin, named as dimeresculetin (1), together with another dicoumarin, euphorbetin (2) and esculetin (3) were isolated from the ethyl acetate extract of the dried whole plants of Viola yedoensis Makino. The structure of 1 was elucidated as 7-hydroxy-6-[(6,7-dihydroxy-2-oxo-2H-1-benzopyran-5-yl)oxy]-2H-1-benzopyran-2-one on the basis of extensive NMR, as well as the other spectral analysis. Compounds 1–3 exhibited anticoagulant activities with respect to activated partial thromboplastin time (APTT), prothrombin time (PT) and thrombin time (TT).     

Antibacterial dihydrobenzopyran and xanthone derivatives from Garcinia cowa stem barks

Two new compounds, garciniacowol (1) and garciniacowone (2) along with 15 known compounds were isolated from the stem barks of Garcinia cowa. Their structures were determined by intensive spectroscopic methods. The structure of 1 was a symmetrical dimeric dihydrobenzopyran derivative, whereas the framework of 2 was a triprenyl caged-xanthone precursor. The antibacterial activities against Escherichia coli TISTR 780, Salmonella typhimurium TISTR 292, Staphylococcus aureus TISTR 1466, and methicillin-resistant S. aureus (MRSA) SK1 of the isolated compounds were also evaluated. Compounds 2 and 9 exhibited good antibacterial activity against MRSA SK1 with the same minimum inhibitory concentration (MIC) value of 2 μg/mL. Moreover, compound 2 also showed good antibacterial activity against S. aureus with an MIC value of 2 μg/mL.     

Three new germacrane-type sesquiterpene stereoisomers from the flowers of Chrysanthemum indicum

From the flowers of Chrysanthemum indicum, three new germacrane-type sesquiterpene stereoisomers (1β,3α,5β-trihydroxyl-7-isopropenyl-germacren-4(15), 10(14)-diene (1), 1β,3β,5α-trihydroxyl-7-isopropenyl-germacren-4(15), 10(14)-diene (2), 1β,3β,5β-trihydroxyl-7-isopropenyl-germacren-4(15), 10(14)-diene (3)) were isolated, whose structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configuration of compound 1 was determined by a single crystal X-ray diffraction study using a mirror Cu Kα radiation.     

Malaysianol B,an oligostilbenoid derivative from Dryobalanops lanceolata

A new oligostilbenoid tetramer, malaysianol B (1), was isolated from the acetone extract of the stem bark of Dryobalanops lanceolata along with seven oligostilbenoids tetramers; hopeaphenol (2), stenophyllol A (3), nepalensinol B (4), vaticanol B (5) and C (6), upunaphenol D (7), and flexuosol A (8). The structures of the isolated compounds were established on the basis of their spectroscopic data evidence. The antibacterial activity of the isolated compounds was evaluated using resazurin microtitre-plate assay.     

Two new benzofuran derivatives with anti-inflammatory activity from Liriope spicata var. prolifera

Two new benzofuran derivatives, 2-(4′-hydroxybenzyl)-5,6-methylenedioxy-benzofuran () and 2-(4′-hydroxybenzoyl)-5,6-methylenedioxy-benzofuran (), along with 8 known compounds were isolated from 60% EtOH extract of the fibrous roots of Liriope spicata var. prolifera. Their structures were elucidated on the basis of extensive spectroscopic analysis. In an in vitro bioactive assay, the two new benzofuran derivatives showed anti-inflammatory activity. Compounds 1 and 2 exhibited significant inhibitory activity against neutrophil respiratory burst stimulated by phorbol 12-myristate 13-acetate (PMA) with IC₅₀ value of 4.15 ± 0.07 and 5.96 ± 0.37 μM, respectively.     

A new proaporphine alkaloid from Meconopsishorridula

A new proaporphine alkaloid, 8, 9-dihydroprooxocryptochine (1), together with three known alkaloids, was isolated from the aerial parts of Meconopsishorridula Hook. f. & Thomson (Papaveraceae), a traditional Tibetan medicine. The structure of 1 was determined by spectroscopic methods.     

A new dilactone from the seeds of Gaultheria yunnanensis

Gaultheriadiolide (1), a new compound, together with the known dauosterol (2), ginkgetin (3), myricetin (4), 6-ethyl-5-hydroxy-2,7-dimethoxy-1,4-naphthoquinone (5), ursolic acid (6), methyl salicylate 2-O-β-d-xylosyl(1→6)β-d-glucopyranoside (7), and methyl salicylate 2-O-β-d-glucopyranoside (8) were isolated from Gaultheria yunnanensis. The structure was elucidated on the basic of spectral analysis, especially 1D and 2D NMR. Primary bioassays showed that compound 1 had medium cytotoxic activity against HEp-2 and HepG2 Cells, with IC₅₀ of 23.337 μM and 29.4497 μM, respectively.