Phenethylamides With an Unusual 4-Oxo-2-oxolenyl Terpenoid Side Chain from Glycosmis Species

Hofer, Otmar; Vajrodaya, Srunya; Greger, Harald

doi:10.1007/pl00010157

Cited by 3 publications

(3 citation statements)

References 7 publications

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“…In the lower field, the spectrum were observed seven protons, six of which were assignable (Table 2) supported the above assignments and showed the presence of one additional quaternary carbon (d C 88.6). These spectral data were similar to those of a known dihydroglyparvin, 22) which was formally composed of monoterpene, p-hydroxyphenethylamine, and trans-b-methylsulfonylacrylic acid subunits, except the surrounding of sulfur atom. The presence of 5-(1-methylpropyl)-3(2H)-furanone system as a monoterpene unit was suggested by HMBC correlations of d Vol.…”

Section: Resultssupporting

confidence: 66%

“…S-Deoxydihydroglyparvin (10) and S-deoxytetrahydroglyparvin ( Co-isolation of a known (ϩ)-dihydroglyparvin (13), lacking the sulfur chiral center, 22) suggested that the carbon chiral center of the monoterpene units in these three might be the same absolute stereochemistry, even remaining unknown. (ϩ)-Entadamide C had been isolated from Entada phaseoloides as a related and simple b-methylsufinylcarboxyamide derivative, and the absolute configuration of the sulfur atom had been reported to be an R configuration.…”

Section: Resultsmentioning

confidence: 99%

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Isolation of Acridone Alkaloids and N-[(4-Monoterpenyloxy)phenylethyl]-Substituted Sulfur-Containing Propanamide Derivatives from Glycosmis parva and Their Anti-herpes Simplex Virus Activity

Chansriniyom

Ruangrungsi

Lipipun

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Glycosmis parva CRAIB (Rutaceae) is a wild small shrub distributed in Thailand.1) Some plants in the genus Glycosmis have been used as Thai traditional medicines for treatments of abscess, scabies, and snakebite. The genus Glycosmis is a rich source of acridone alkaloids and sulfur-containing propanamides especially in branches and leaves, respectively. 2)Biological activities of acridone alkaloids were reported such as antimalarial activity, 3) anti-herpes simplex virus (HSV) activity, 4) tumor cell growth inhibition, 5) suppression of human immunodeficiency virus type 1 (HIV-1) replication, 6) induction of human promyelocytic leukemia (HL-60) cellular differentiation, 7) antiproliferative activity, 8) cancer chemopreventive activity, 9) and modulation of P-glycoprotein activity.10) For sulfur-containing propanamides, antifungal activities were mainly reported. 11) We examined the crude extracts of the branches and leaves of G. parva focused on anti-HSV activities against HSV-1 and HSV-2 and observed positive activities. In this paper, we report the structure elucidation of a new acridone alkaloid, glycosparvarine (1), two new N- [(4-monoterpenyloxy)phenylethyl]-substituted sulfur-containing propanamide derivatives, S-deoxydihydroglyparvin (10) and S-deoxytetrahydroglyparvin (11), which were isolated together with nine known compounds, and the anti-HSV activity of the isolates. Results and DiscussionThe MeOH extracts of the branches and the leaves of G. parva were partitioned with hexane. The remaining layers were further partitioned with EtOAc and n-BuOH after addition of water. Organic extracts were subjected to antiviral activity tests in plaque reduction assays against HSV-1 and HSV-2. The hexane and EtOAc extracts from branches, and the hexane extract from leaves displayed the anti-herpes virus activities in the inactivation inhibition, while the EtOAc extract from leaves exhibited the anti-herpes virus activities in both inactivation treatment and post-inhibition (Table 1).Repeated chromatographies of the EtOAc extract of branches using the solvent systems of MeOH-CHCl 3 , acetone-hexane, and acetone-CHCl 3 led to the isolation of a new acridone alkaloid, glycosparvarine (1) Six acridone alkaloids including a new glycosparvarine (1), three limonoids, and four N-[(4-monoterpenyloxy)phenylethyl]-substituted sulfur-containing propanamide derivatives including two new species, (؉ ؉)-S-deoxydihydroglyparvin (10) and (؉ ؉)-S-deoxytetrahydroglyparvin (11), were isolated from the branches and the leaves of Glycosmis parva CRAIB collected in the east of Thailand. Antiviral activity evaluation of isolates against herpes simplex virus (HSV) type 1 and 2 disclosed that two acridone alkaloids, glycosparvarine (1) and glycofolinine (4), showed moderate inhibitory activities with 50% effective concentration (EC 50 ) of 348 m mM and 151 m mM, respectively; as well, (؉ ؉)-S-deoxydihydroglyparvin (10) exhibited anti-HSV activity at the lower concentration.

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Section: Resultssupporting

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Isolation of Acridone Alkaloids and N-[(4-Monoterpenyloxy)phenylethyl]-Substituted Sulfur-Containing Propanamide Derivatives from Glycosmis parva and Their Anti-herpes Simplex Virus Activity

Chansriniyom

Ruangrungsi

Lipipun

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Species in the genus Glycosmis (Stone, 1985) contain a wide variety of compounds with potential biological activity. These include terpenoids (Chakra-varty et al, 1996), amides (Greger et al, 1992(Greger et al, , 1993a(Greger et al, ,b, 1994(Greger et al, , 1996Hofer et al, 1995aHofer et al, , 1998, imides (Hofer et al, 1995b), alkaloids (Wu et al, 1983;Wurz et al, 1993;Ono et al, 1995), coumarins (Rahmani et al, 1998), and flavonoids (Tian-Shung et al, 1995). Compounds exhibiting antifungal and insecticidal activities (Greger et al, 1996) have already been isolated from several Glycosmis species.…”

Section: Introductionmentioning

confidence: 99%

Dehydrothalebanin: A Source of Resistance from Glycosmis pentaphylla against the Citrus Root Weevil Diaprepes abbreviatus

Shapiro¹,

Bowman²,

Lapointe³

2000

J. Agric. Food Chem.

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Roots of a citrus relative, Glycosmis pentaphylla (orangeberry), were shown to inhibit the growth and survival of larvae of the citrus root weevil Diaprepes abbreviatus. Roots of G. pentaphyllaincorporated into the diet of D. abbreviatus increasingly inhibited the growth of neonate larvae with increased concentration of roots, while roots from citrus rootstocks produced little inhibition. The diet-incorporation assay was used to guide fractionation of an active acetone extract of G.pentaphylla roots. Three major fractions from silica open-column liquid chromatography were active, and these were purified using semipreparative normal-phase HPLC. A single active HPLC subfraction was isolated from each of the three liquid chromatography fractions, and two active compounds were isolated and identified by GC-MSD. GC-MSD and NMR identified one compound as the amide dehydrothalebanin B, and the other was identified by GC-MSD as dieldrin, a chlorinated hydrocarbon insecticide whose origin in our samples is uncertain.

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Screening of Glycosmis pentaphylla for Cytotoxic and Repellent Potentials agains Artemia salina Nauplii and Tribolium castaneum (Herbst) Adults

et al. 1970

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Chloroform extracts of the leaf, stem bark, stem wood and roots of Glycosmis pentaphylla (Retz.) were tested against the brine shrimp, Artemia salina nauplii for cytotoxic activity in which the dose-mortality assay revealed LC50 values of 28.579, 28.659, 57.213 and 84.111 ppm respectively, for the plant parts efficacy of which could be arranged in the order of leaf > stem bark > stem wood > root. The same extracts were tested for repellency against Tribolium castaneum (Herbst) adults where the root bark and root wood were separately extracted and used. The F values of the arcsin transformed data were 60.983, 14.177, 19.437, 15.429 and 1.082 respectively for the leaf, stem bark, stem wood, root bark and root wood extracts. Except for the root wood extract, strong repellent activity was observed for the rest of the extracts (P<0.001). Key words: Artemia salina; Tribolium castaneum; Glycosmis pentaphylla; cytotoxic activity; repellent activity. DOI: 10.3329/jles.v3i0.7443 J. Life Earth Sci., Vols. 3-4: 33-36, 2009

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Phenethylamides With an Unusual 4-Oxo-2-oxolenyl Terpenoid Side Chain from Glycosmis Species

Cited by 3 publications

References 7 publications

Isolation of Acridone Alkaloids and N-[(4-Monoterpenyloxy)phenylethyl]-Substituted Sulfur-Containing Propanamide Derivatives from Glycosmis parva and Their Anti-herpes Simplex Virus Activity

Isolation of Acridone Alkaloids and N-[(4-Monoterpenyloxy)phenylethyl]-Substituted Sulfur-Containing Propanamide Derivatives from Glycosmis parva and Their Anti-herpes Simplex Virus Activity

Dehydrothalebanin: A Source of Resistance from Glycosmis pentaphylla against the Citrus Root Weevil Diaprepes abbreviatus

Screening of <i>Glycosmis pentaphylla</i> for Cytotoxic and Repellent Potentials agains <i>Artemia salina</i> Nauplii and <i>Tribolium castaneum</i> (Herbst) Adults

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