Odorasides A and B,new sphingolipid glucosides from Klienia odora

Two new sphingolipid glucosides, odoraside A (1) and odoraside B (2), have been isolated from chloroform-soluble fraction of the total methanolic extract of Klienia odora, together with five known compounds, β-sitosterol (3), oleanolic acid (4), betulone (5), 2,3-dihydroxy-12-oleanen-28-oic acid (6), and β-sitosterol 3-O-β-d-glucopyranoside (7). Their structures were assigned from ¹H and ¹³C NMR spectra, DEPT and by 2D COSY, NOESY, HMQC, and HMBC experiments.     

Ozocardic A: a new alkylanacardic acid from Ozoroa pulcherrima

One new alkylanacardic acid, ozocardic A (1), along with the known and related metabolites 6-tridecyl anacardic acid (2) and β-sitosterol (3) was isolated from Ozoroa pulcherrima. The structure of the new compound was elucidated by detailed spectroscopic analysis such as ¹H, ¹³C NMR, COSY, HMQC, HMBC, and HREIMS. The structures of known compounds (6-tridecyl anacardic acid (2) and β-sitosterol (3)) were identified by the comparison of their spectral data with those published in the literature.     

Alliumonoate: a new cyclopentane derivative from Allium victorialis

Alliumonoate (1), a new cyclopentane derivative, has been isolated from the chloroform-soluble fraction of the ethanolic extract of Allium victorialis, along with β-amyrin acetate (2), β-sitosterol acetate (3), 22-cyclohexyl-1-docosanol (4), β-amyrin (5), β-sitosterol (6), and β-sitosterol 3-O-β-d-glucopyranoside (7), reported for the first time from this species. Their structures were elucidated on the basis of spectral data including mass spectra and 2D NMR experiments.     

C28 sterols with a cyclopentane ring at C-22 and 26 from cape gooseberry (berries of Physalis pubeacens L.)

Two new C₂₈ sterols with a cyclopentane ring at C-22 and 26, alkesterol A (1) and alkesterol B (2), along with β-sitosterol (3), were isolated from the berries of Physalis pubeacens L. (cape gooseberry). The structures of the new compounds were established by HR-EI-MS, 1D and 2D (¹H–¹H COSY, HSQC, HMBC) NMR experiments. The known compound was identified by comparison of spectral data with published references. The two new compounds showed some cytotoxic activities by MTT assay.     

A new bisabolane sesquiterpenoid from Euphorbia chrysocoma

The new sesquiterpenoid (6R)-2-chloro-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (1), together with ten known compounds, (6R)-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (2), bauerenol acetate (3), lupenone (4), α-amyrenone (5), β-sitosterol (6), stigmasterol (7), β-amyrin (8), ursolic acid (9), betulinic acid (10), scopolin (11), have been isolated from the roots of Euphorbia chrysocoma Lévl. et Vant. Their structures have been elucidated by spectroscopic data.     

Cryptoporic acid S,a new drimane-type sesquiterpene ether of isocitric acid from the fruiting bodies of Cryptoporus volvatus

A new drimane-type sesquiterpene with an isocitric acid moiety, cryptoporic acid S (1), together with six known compounds, cryptoporic acid D (2), β-sitosterol (3), β-daucosterol (4), stigmast-4-en-3-one (5), ergosterol (6), and (22E,24R)-ergosta-7,22-diene-3β,5α,6β-triol (7), was isolated from the fruiting bodies of Cryptoporus volvatus. The structures of these compounds were established on the basis of UV, IR, MS, 1D and 2D NMR analysis. In the meanwhile, compounds 1 and 2 were evaluated for antioxidant activity using the methods of 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity (DPPH-RSA) and ferric reducing antioxidant power (FRAP) assay, and they exhibited moderate antioxidant activities.     

New sterol esters from the flowers of Punica granatum Linn.

Two new β-sitosterol esters have been isolated from the flowers of Punica granatum Linn. (Punicaceae) along with the known compounds n-tricosane (3), n-heptacosanyl n-hexanoate (4), olean-5,12-dien-3β-ol-28-oic acid (5), and olean-12-en-3β-ol-28-oic acid (6). The structures of the new phytosterols have been elucidated as stigmast-5-en-3β-ol-3β-dodecanoate (β-sitosterol laurate, 1) and stigmast-5-en-3β-ol-3β-tetradecanoate (β-sitosterol myristate, 2) on the basis of spectral data and chemical analyses.     

Antibacterial sesquiterpene lactone glucoside from seed pods of Bauhinia retusa

From the seed pods of Bauhinia retusa, a new eudesmane sesquiterpene glucoside, 1-O-β-D-glucopyranosyl-9β,15-dihydroxy-5α,6βH-eudesma-3-ene-6α,12-olide (1), has been isolated together with three known compounds, 4′-hydroxy-7-methoxy flavane (2), β-sitosterol (3), and stigmasterol (4). The structures of isolated compounds were verified with the help of 1D, 2D NMR, and HR-ESI-MS spectroscopies. Compound 1 showed moderate antibacterial activity against Pseudomonas aeruginosa and Escherichia coli when a disc diffusion method is used.     

New phthalates from Phyllanthus muellerianus (Euphorbiaceae)

Species of the genus Phyllanthus are known for their medicinal values and many are explored phytochemically. Some of them produce phthalates which usually have antimicrobial properties. This paper deals with the phytochemical investigation on Phyllanthus muellerianus. As a result, five compounds, bis(2-ethyloctyl)phthalate (1), bis(2-ethylicosyl)phthalate (2), 3-friedelanone (3), β-sitosterol (4), and methyl gallate (5), have been isolated and characterized. Metabolites 1 and 2 are new compounds, while 3–5 have been isolated for the first time from this source. Structures of all the isolates were established on the basis of MS, 1D and 2D NMR spectral data and in comparison with the reported data.     

A new flavonol glucoside from the aerial parts of Sida glutinosa

Phytochemical investigation on the dried aerial parts of Sida glutinosa has led to the isolation of a new flavonol glucoside, glutinoside (1), along with seven known compounds, 24(28)-dehydromakisterone A (2), 1,2,3,9-tetrahydropyrrolo[2,1-b]-quinazolin-3-amine (3), docosanoic acid, 1-triacontanol, campesterol, stigmasterol, and β-sitosterol. The structures of these compounds were elucidated by means of extensive spectroscopic techniques as well as GC/MS analysis (for sterols) and comparison with the literature data. All these seven known compounds are reported from this plant for the first time.     

Melanogenesis inhibitory compounds from Saussureae Radix

Ten compounds were isolated from the EtOAc soluble part of the MeOH extract of Saussureae Radix, with their effects on melanin production also evaluated in B-16 mouse melanoma cell lines stimulated with 3-isobutyl-1-methylxanthine (IBMX), an elevator of cellular cAMP. The compounds were identified as aplotaxene (1), 1β-hydroxy arbusculin A (2), costunolide (3), dehydrocostuslactone (4), 11β,13-dihydrocostunolide (5), reynosin (6), heptadec-(9Z)-enoic acid (7), β-sitosterol (8), linoleic acid methyl ester (9) and betulinic acid methyl ester (10). Compounds 2, 9 and 10 were identified from Saussureae Radix for the first time. Furthermore, compounds 2, 3 and 6 showed potent inhibitory effects on the IBMX-induced melanogenesis, in dose-dependent manners, with IC₅₀ values of 11, 3 and 2.5 μg/mL, respectively. As a positive control, arbutin exhibited an IC₅₀ value of 29 μg/mL.     

A New Bicoumarin from Stellera Chamaejasme L

Abstract

Thirteen compounds were isolated from roots of Stellera chamaejasme L. (Thymelaeaceae). They are β-sitosterol (2), simplexin (3), pimelea factor P2 (4), daucosterol (5), (+)-3-hydroxy-1,5-diphenyl-1-pentanone (6), 4-ethoxy-benzoic acid (7), 2,4,6-Trimethoxy-benzoic acid (8), (+)-afzelechin (9), fumaric acid (10), N,N-dimethyl-L-aspartic acid (11), umbelliferone (12), daphniretin (13) and a novel bicoumarin named bicoumastechamin (1). Among the known compounds, 7, 8, 9, 10 and 11 were first isolated from this plant, and 6 was first isolated from the natural resources. Their structures have been elucidated on the basis of spectral data. In vitro bioassays showed that 4 inhibited cancer cell growth, 13 exhibited immunomodulatory activity, and 6 exhibited both immunomodulatory and anti-tumor activity.     

A new sesquiterpene lactone glycoside and a new quinic acid methyl ester from Patrinia villosa

A new sesquiterpene lactone glycoside (1) and a new quinic acid methyl ester (2) were isolated from Patrinia villosa, together with another two known compounds chlorogenic acid n-butyl ester (3), 3, 4-di-O-caffeoylquinic acid methyl ester (4). Their structures were established using 1D/2D-NMR spectroscopy, mass spectrometry, and comparing with spectroscopic data reported in the literature.     

A new eudesmane sesquiterpene glycosides from Liriope muscari

A new eudesmane sesquiterpene glycoside, ophiopogonoside B (1), along with five known compounds, ophiopogonoside A (2), ruscogenin-1-O-[β-d-glucopyranosyl (1 → 2)]-[β-d-xylopyranosyl (1 → 3)]-β-d-fucopyranoside (3), palmitic acid (4), palmitic acid glyceride (5), and β-sitosterol-d-glucopyranoside (6),was isolated from the tuberous roots of Liriope muscari (Decn.) Bailey (Liliaceae). Their structures were confirmed by 1D and 2D NMR spectroscopy. Among them, compounds 1, 2, 4, and 5 were the first reported from the genus Liriope. Ophiopogonoside B (1) showed moderate inhibitory activity to glycogen phosphorylase a.     

Chemical Constituents from the Leaves of Magnolia Denudata

Abstract

20 compounds were isolated from the leaves of Magnolia denudata including 16 lignans, which belong to 6 structural types. Except for (7R, 8S, 1′S) -δ^8′ - 1′, 4′ - dihydro - 5′- methoxy - 3, 4 -methylenedioxy - 4′ - oxo -7.O.2′, 8.1′ - neolignan (6), magliflonenone (9), 2,5′ - diene-2′, 8′- epoxy - 5′ - methoxy - 8 - methyl - 4′ - oxo - 3,4-methylenedioxy - spiro (5,5) - undecane (10), veraguensin (16) and β-sitosterol (20), the other 15 compounds were obtained from this species for the first time. The absolute configurations of 3 compounds (1,4,10) were determined by CD spectroscopy for the first time. The anti-inflammatory activities of compounds 1, 2 and 16 were assessed and 2 was shown to have significant inhibition effect on mice hind-paw edema induced by carrageenan.     

Constituents from <Emphasis Type="Italic">Senecio scandens</Emphasis> and their antioxidant bioactivity

Forty-one compounds including two new constituents, senecainin A (1) and 3-methoxyisonicotinic acid (2), were characterized from the methanol extracts of the whole plant of Senecio scandens. The structures of the new compounds were comprehensively established with the aid of 1D and 2D NMR spectroscopic and mass spectrometric analyses. The chemical structures of known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. In addition, the antioxidant activity of some of the isolates was examined in the DPPH free radical scavenging assay. Among the tested compounds, (−)-monoepoxylignanolide, (−)-pinoresinol and (−)-epi-pinoresinol displayed significant antioxidant bioactivity.     

A new lignan glycoside from <Emphasis Type="Italic">Juniperus rigida</Emphasis>

A new lignan glycoside, named juniperigiside (1) was isolated from the CHCl₃ soluble fraction of the MeOH extract of stems and leaves of Juniperus rigida S.et Z. Compound 1 was identified by 1D- and 2D-NMR spectroscopy as well as CD analysis as (2R,3S)-2,3-dihydro-7-methoxy-2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxymethyl-5-benzofuranpropanol 4′-O-(3-O-methyl)-α-L-rhamnopyranoside. Five known lignans, icariside E4 (2), desoxypodophyllotoxin (3), savinin (4), thujastandin (5), and (−)-nortrachelogenin (6) in addition to five known labdane diterpenes including trans-communic acid (7), 13-epi-torulosal (8), 13-epi-cupressic acid (9), imbricatoric acid (10), and isocupressic acid (11) were also isolated and their structures were characterized by comparing their spectroscopic data with those in the literature. All compounds were isolated for the first time from this plant, and 5 and 6 were first reported from the genus Juniperus. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay. Compounds 3, 4, 7, and 8 showed considerable cytotoxicity against four human cancer cell lines in vitro.     

New flavonoids and other constituents from Lespedeza cuneata

Two new flavonoids, 6,8,3′,4′-tetrahydroxy-2′-methoxy-7-methylisoflavanone (1) and 6,8,3′,4′-tetrahydroxy-2′-methoxy-6′-(1,1-dimethylallyl)-isoflavone (2), were isolated from the 95% ethanolic extract of the dried roots of Lespedeza cuneata together with betulinic acid (3), β-sitosterol (4), hexacosanoic acid 2,3-dihydroxy-propyl ester (5), which were isolated from this plant for the first time. Their structures were elucidated by spectral analysis.     

Phenolic compounds from the aqueous extract of Acacia catechu

Two new phenolic compounds, 5-hydroxy-2-[2-(4-hydroxyphenyl) acetyl]-3-methoxylbenzoic acid (1) and (2S,3S)-3,7,8,3′,4′-pentahydroxyflavane (2), were obtained from the aqueous extract of Acacia catechu, along with four known compounds identified as rhamnetin (3), 4-hydroxyphenyl ethanol (4), 3,3′,5,5′,7-pentahydroxyflavane (5), and fisetinidol (6). Their structures were determined on the basis of spectroscopic analysis. Free radical-scavenging activities of the new compounds were evaluated.     

Lipoxygenase inhibitory sphingolipids from Launaea nudicaulis

Four new sphingolipids: nudicaulin A [(2S,3S,4R,14E)-2-{[octadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 1], nudicaulin B [(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 2], nudicaulin C [(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol-1-O-β-d-glucopyranoside; 3], and nudicaulin D [(2S,3S,4R)-2-{[(2R,3S,12E)-2,3-dihydroxyeicos-12-enoyl]amino}octadecane-1,3,4-triol; 4] together with 1-hexatriacontanol, β-sitosterol, octadecyl 4-hydroxycinnamate, elaidic acid, cholesta-5,22-diene-3,7-diol, oleanolic acid, apigenin, and β-sitosterol 3-O-β-d-glucopyranoside were isolated from the methanolic extract of the whole plant of Launaea nudicaulis. Their structures were elucidated using ¹H and ¹³C NMR spectra and 2D NMR analyses (HMQC, HMBC, and COSY) in combination with mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, and HR-FAB-MS) experiments and comparison with literature data of related compounds. Compounds 1–4 displayed moderate inhibitory potential against enzyme lipoxygenase in concentration-dependent manner with IC₅₀ value ranges 103–193 μM.