Two New Acridone Alkaloids from Glycosmis Species

Ono, Takeya; Ito, Chihiro; Furukawa, Hiroshi; Wu, Tian Shung; Kuoh, Chang Sheng; Hsu, Kuo Shih

doi:10.1021/np50124a028

Cited by 18 publications

(16 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…al., 2018). Juoichi et al, 1985;Yamamoto et al, 1989;Ono et al, 1995) 28 Juoichi et al, 1985;Yamamoto et al, 1989;Ono et al, 1995) values of the compound on PNT2 cells to those in the cancer cell lines.…”

Section: Cytotoxicity Assaymentioning

confidence: 97%

“…Spectroscopic analysis, mainly, 1 H NMR, 13 C NMR, 13 C DEPTQ, 1 H-13 C HSQC, 1 H-13 C HMBC and 1 H-1 H NOESY and mass spectrometry (MS) were used to unambiguously elucidate the structures of the isolated compounds. All spectral data were compared with the published literature data and the compounds were identified as citrusinine-I (1) ), citracridone-I (2) , 5-hydroxynoracronycine (3) Yamamoto et al, 1989), natsucitrine-I (4) (Juoichi et al, 1985), glycofolinine (5) (Ono et al, 1995) and citracridone-III (6) (Yamamoto et al, 1989). This is the first report of the isolation of these compounds from C. aurantium, though they have been reported from other…”

Section: Structure Determinationmentioning

confidence: 97%

See 1 more Smart Citation

Acridone alkaloids from the stem bark of Citrus aurantium display selective cytotoxicity against breast, liver, lung and prostate human carcinoma cells

Segun

Ismail

Ogbole

et al. 2018

Journal of Ethnopharmacology

View full text Add to dashboard Cite

show abstract

Section: Cytotoxicity Assaymentioning

confidence: 97%

Section: Structure Determinationmentioning

confidence: 97%

Acridone alkaloids from the stem bark of Citrus aurantium display selective cytotoxicity against breast, liver, lung and prostate human carcinoma cells

Segun

Ismail

Ogbole

et al. 2018

Journal of Ethnopharmacology

View full text Add to dashboard Cite

show abstract

“…A part (79 mg) of LE5-3 (260 mg) was washed with Et 2 O, followed by recrystallization from CH 2 Cl 2 -Et 2 O, to afford 12 (15 mg) as colorless needles, mp 136-138°C (lit. 15) mp 134-137°C). The evaporated supernatant (44 mg) was purified by repeated CC using different solvent systems (4% MeOH/CHCl 3 , 60-70% EtOAc/hexane, and 45% EtOAc/CHCl 3 ) to afford 13 (8 mg).…”

Section: Extraction and Isolationmentioning

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

View full text Add to dashboard Cite

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.

show abstract

“…(e.g., 61, 62) [40]. Extractions were conducted using acetone under long reflux conditions (30-40 h), while authors working with ethanol as an extraction solvent seem to obtain monomers only (e.g., 63, 64) [41]. A Norrish type I reaction of the solvent could be hypothesized as a source of free radicals, 9) but, notably, more ''classical'' artifacts were not obtained (see Section 24.9).…”

Section: Oxidative Couplingmentioning

confidence: 99%

Artifacts and Natural Substances Formed Spontaneously

Champy

2011

Biomimetic Organic Synthesis

View full text Add to dashboard Cite

Two New Acridone Alkaloids from Glycosmis Species

Abstract: TWO new acridone alkaloids, named glycofolinine 111 and acrifoline 121, were isolated from the root bark and stem bark of Glycosmis citrifolia collected in Taiwan. Their structures were elucidated by spectroscopic methods.Receiwd I8 April 1995

Cited by 18 publications

References 4 publications

Acridone alkaloids from the stem bark of Citrus aurantium display selective cytotoxicity against breast, liver, lung and prostate human carcinoma cells

Acridone alkaloids from the stem bark of Citrus aurantium display selective cytotoxicity against breast, liver, lung and prostate human carcinoma cells

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

Artifacts and Natural Substances Formed Spontaneously

Contact Info

Product

Resources

About