1.Microbial Transformation of Two Prenylated Naringenins.
Natural Product Sciences 2017;23(4):306-309
Microbial transformation of (±)-6-(1,1-dimethylallyl)naringenin (6-DMAN, 1) and (±)-5-(O-prenyl) naringenin-4′,7-diacetate (5-O-PN, 2) was performed by using fungi. Scale-up fermentation studies with Mucor hiemalis, Cunninghamella elegans var. elegans, and Penicillium chrysogenum led to the isolation of five microbial metabolites. Chemical structures of the metabolites were determined by spectral analyses as (±)-8-prenylnaringenin (3), (2S)-5,4′-dihydroxy-7,8-[(R)-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofurano]flavanone (4), (±)-5-(O-prenyl)naringenin-4′-acetate (5), (±)-naringenin-4′-acetate (6), and (±)-naringenin (7), of which 5 was identified as a new compound.
Cunninghamella
;
Fermentation
;
Fungi
;
Mucor
;
Penicillium chrysogenum
2.Protective Effects of Cinnamic Acid Derivatives on Gastric Lesion.
Sun Yi LEE ; In Young HWANG ; Choon Sik JEONG
Natural Product Sciences 2017;23(4):299-305
P-methoxycinnamic acid and 3,4,5-trimethoxycinnamic acid are the compounds found in Polygalae Radix, the root of Polygala tenuifolia Willdenow, and have been reported to have hepatoprotective and anti-neurodegenerative effects. On the other hand, there are no reports of their effects on gastric lesions. This study examined the inhibitory effects of cinnamic acids, including p-methoxycinnamic acid, 3,4,5-trimethoxycinnamic acid, and 8 compounds (cinnamic acid, 2-(trifluoromethyl) cinnamic acid, 3-(trifluoromethyl) cinnamic acid, trans-4-(trifluoromethyl) cinnamic acid, 4-(dimethylamino) cinnamic acid, 3,4-(methylenedioxy) cinnamic acid and 3,4-dihydroxycinnamic acid), which were selected based on their presence in medicinal herbs and molecular weight, against gastric lesions. Animal models were used to confirm the protective effects on acute gastritis caused by the administration of HCl/EtOH. Gastric acid inhibition was examined by an acid-neutralizing test and the proton pump (H⁺/K⁺-ATPase) inhibiting activity. In addition, antioxidant tests were performed and the gastric emptying rate was determined. The results showed that cinnamic acid, p-methoxycinnamic acid, and 3,4,5-trimethoxycinnamic acid had an inhibitory effect on gastric lesions.
Gastric Acid
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Gastric Emptying
;
Gastritis
;
Hand
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Models, Animal
;
Molecular Weight
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Plants, Medicinal
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Polygala
;
Proton Pumps
3.Cytotoxicity and Structure Activity Relationship of Dammarane-Type Triterpenoids from the Bark of Aglaia elliptica against P-388 Murine Leukemia Cells.
Ace Tatang HIDAYAT ; Kindi FARABI ; Desi HARNETI ; Rani MAHARANI ; DARWATI ; NURLELASARI ; Tri MAYANTI ; Arlette Suzy SETIAWAN ; Unang SUPRATMAN ; Yoshihito SHIONO
Natural Product Sciences 2017;23(4):291-298
Six dammarane-type triterpenoids, dammar-24-en-3β-ol (1), 3β-epicabraleahydroxy lactone (2), (E)-25-hydroperoxydammar-23-en-3β,20-diol (3), dammar-24-en-3β,20-diol (4), 3β-acetyl-20S,24S-epoxy-25-hydroxydammarane (5), and 3β-epiocotillol (6) were isolated from the methanolic extract of the bark of Aglaia elliptica. The chemical structure were identified on the basis of spectroscopic evidence and by comparison with those spectra previously reported. Compounds 1 – 6 were isolated first time from this plant. Compounds 1 – 6, along with a known synthetic analog, cabraleone (7) were evaluated their cytotoxic activity against P-388 murine leukimia cells in vitro. Among those compounds 3β-acetyl-20S,24S-epoxy-25-hydroxydammarane (5) showed strongest cytotoxic activity with IC₅₀ value of 8.02 ± 0.06 µM.
Aglaia*
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In Vitro Techniques
;
Leukemia*
;
Meliaceae
;
Methanol
;
Plants
;
Structure-Activity Relationship*
4.Anti-inflammatory and Anti-bacterial Effects of Aloe vera MAP against Multidrug-resistant Bacteria.
Natural Product Sciences 2017;23(4):286-290
Multidrug-resistant Acinetobacter baumannii and Pseudomonas aeruginosa are highly dangerous nosocomial pathogens, cause the symptoms of skin infections, pressure sores, sepsis, blood stream and wound infections. Unfortunately, these pathogens are immune to the most common antibiotics, such as, carbapenem, aminoglycoside and fluoroquinolone. Therefore, it is imperative that new and effective antibiotics be developed. In the present study, the antimicrobial effects of Aloe vera MAP (modified Aloe polysaccharide) on Staphylococcus aureus and Bacillus subtilis, Escherichia coli and Enterobacter aerogenes, and clinical Pseudomonas aeruginosa and clinical Acinetobacter baumannii were comprehensibly investigated. Prior to the growth inhibition effect measurement and antibiotic disc diffusion assay on gram-positive and gram-negative bacteria and selected multidrug-resistant Pseudomonas aeruginosa and Acinetobacter baumannii, antimicrobial resistance screening was performed for the multidrug-resistant bacteria obtained from clinical isolates. The results for showed the Aloe vera MAP had a concentration-dependent effect on all of examined bacteria, particularly on Pseudomonas aeruginosa. Anti-inflammatory and anti-oxidant experiments were also performed dose dependently effects to confirm the beneficial physiological effects of Aloe vera MAP.
Acinetobacter baumannii
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Aloe*
;
Anti-Bacterial Agents
;
Bacillus subtilis
;
Bacteria*
;
Diffusion
;
Enterobacter aerogenes
;
Escherichia coli
;
Gram-Negative Bacteria
;
Mass Screening
;
Pressure Ulcer
;
Pseudomonas aeruginosa
;
Rivers
;
Sepsis
;
Skin
;
Staphylococcus aureus
;
Wound Infection
5.Anti-tumor Activity of Saussurea laniceps against Pancreas Adenocarcinoma.
Keyong Ho LEE ; Byeong Soo KIM ; Ki Hyeong RHEE
Natural Product Sciences 2017;23(4):281-285
The purpose of this study was to confirm the anti-tumor activity of an ethanol extract of Saussurea laniceps against pancreatic tumor and to isolate the active compound from S.laniceps extract. Treatment with S.laniceps extract and hispidulin inhibited proliferation of pancreatic cell lines, such as Capan-1, Capan-2, Panc-1 and S2-013 in a dose-dependent manner using the hollow fiber assay. Hispidulin showed typical hallmarks of apoptotic cell death a significant anti-tumor activity on Capan-2 cells at a dose of 100 mg/kg and 200 mg/kg. S.laniceps has potential cytotoxic and apoptotic effects on human pancreatic carcinoma cells. Its mechanism of action might be associated with the apoptotic cell death through DNA fragmentation.
Adenocarcinoma*
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Cell Death
;
Cell Line
;
DNA Fragmentation
;
Ethanol
;
Humans
;
Pancreas*
;
Saussurea*
6.Phenolic Compounds from the Leaves of Homonoia riparia and their Inhibitory Effects on Advanced Glycation End Product Formation.
Ik Soo LEE ; Seung Hyun JUNG ; Chan Sik KIM ; Jin Sook KIM
Natural Product Sciences 2017;23(4):274-280
In a search for novel treatments for diabetic complications from natural resources, we found that the ethyl acetate-soluble fraction from the 80% ethanol extract of the leaves of Homonoia riparia has a considerable inhibitory effect on advanced glycation end product (AGE) formation. Bioassay-guided isolation of this fraction resulted in identification of 15 phenolic compounds (1 – 15). These compounds were evaluated in vitro for inhibitory activity against the formation of AGE. The majority of tested compounds, excluding ethyl gallate (15), markedly inhibited AGE formation, with IC₅₀ values of 2.2 – 89.9 µM, compared with that of the positive control, aminoguanidine (IC₅₀ = 962.3 µM). In addition, the effects of active isolates on the dilation of hyaloid-retinal vessels induced by high glucose (HG) in larval zebrafish was investigated; (–)-epigallocatechin-3-O-gallate (6), corilagin (7), and desmanthine-2 (11) significantly decreased HG-induced dilation of hyaloid–retinal vessels compared with the HG-treated control group.
Diabetes Complications
;
Ethanol
;
Euphorbiaceae
;
Glucose
;
In Vitro Techniques
;
Natural Resources
;
Phenol*
;
Zebrafish
7.Quantitative Determination of Bakkenolide D in Petasites japonicus and Farfugium japonicum by HPLC/UV.
Norman G QUILANTANG ; Ki Ho LEE ; Dong Gu LEE ; Ju Sung LEE ; EunJu CHO ; Hyun Young KIM ; Sanghyun LEE
Natural Product Sciences 2017;23(4):270-273
A quantitative analysis of bakkenolide D in the different parts of Petasites japonicus and Farfugium japonicum was performed by HPLC. A gradient HPLC elution system with a mobile phase consisting of water:acetonitrile solution (20:80 to 0:100 for 45 min) was followed and an INNO C₁₈ column was used for the chromatographic separation. The injection volume, flow rate, and UV detection were 10 µL, 1 mL/min, and 290 nm, respectively. Results show that both species showed the highest amount of bakkenolide D in the roots being 107.203 and 166.103 mg/g for P. japonicas and F. japonicum, respectively. Content analysis on the different parts of both plants displayed remarkably lower values which ranged from 0.403 – 4.419 and 7.252 – 32.614 mg/g for P. japonicas and F. japonicum, respectively. The results show that the roots of both plants are rich in bakkenolide D showing a promising use in the development of nutraceuticals and industrial application of the compound.
Chromatography, High Pressure Liquid
;
Dietary Supplements
;
Petasites*
8.Comparative Study on the Content and Cytotoxicity of Pseudolaric Acid B in the Five Plant Parts of Pseudolarix kaempferi.
Agung NUGROHO ; Nam Tae WOO ; Kyoung Sik PARK ; Na Yun KWON ; Woo Nyung JUNG ; Sang Kook LEE ; Dong Hwa KIM ; Hee Juhn PARK
Natural Product Sciences 2017;23(4):265-269
Pseudolaric acids of Pseudolarix kaempferi (Pinaceae) have been known as diterpenoids with potent anti-fungal-, anti-microbial, and cytotoxic activities. In the present study, the five MeOH extracts were prepared from the five plant part (root bark, stem bark, leaf, the inner part of root, and cone) to find the relation between the concentration of pseudolaric acids and cytotoxicity. Pseudolaric acids B and C were isolated from the root bark of P. kaempferi to use them as standard compounds. The five extracts were tested on cytotoxicity against six cancer cell lines, A549 (lung), HCT116 (colon), MDA-MB-231 (breast), SNU638 (stomach), and SK-hep-1 (liver) by SRB assay, but against K562 (leukemia) by SRB- or MTT assay. HPLC quantification were performed on a Shisheido Capcell PAK C18 column (5 µm, 4.6 mm × 250 mm) using 254 nm wavelength. The cytotoxicity (IC₅₀, 0.36 µg/ml on K562 cell lines) of the root bark extract was potent and the content (101.1 mg/g extract) of pseudolaric acid B was very high in the root bark. These results suggest that the MeOH extract obtained from the root bark could be developed as the anti-cancer agent with a high quantity of pseudolaric acid B.
Cell Line
;
Chromatography, High Pressure Liquid
;
Diterpenes
;
Pinaceae
;
Plants*
9.Studies on the Chemical Constituents from the Seeds of Zizyphus jujuba var. inermis.
Nam Kyung LEE ; Hyun Jung SHIN ; Wan Seok KIM ; Gyo IN ; Chang Kyun HAN
Natural Product Sciences 2017;23(4):258-264
This study analyzed the seeds of Zizyphus jujuba var. inermis commonly used as a remedy in traditional Chinese medicine, in order to determine its various biologically active compounds. Through process 3-pentadecylcatechol, ρ-menth-8-ene, and γ-bisabolene were isolated and identified for the first time which are urushiol, monoterpenoidal, and sesquiterpenoidal compounds, respectively. Also, found were another sesquiterpenoidal compounds, vomifoliol, and four steroidal compounds, β-sitosterol, stigmasterol, stigmasta-5,23-dien-3β-ol, and stigmast-4-en-3-one. In addition, fourteen triterpenoidal compounds were isolated and identified. These were lupeol, betulinic acid, betulinaldehyde, alphitolic acid, 3-O-cis-ρ-coumaroyl-alphitolic acid, 3-O-trans-ρ-coumaroylalphitolic acid, 2-O-cis-ρ-coumaroyl-alphitolic acid, 2-O-trans-ρ-coumaroyl-alphitolic acid, zizyberanalic acid, ceanothic acid, oleanolic acid, maslinic acid, 3-O-cis-ρ-coumaroyl-maslinic acid, and 3-O-trans-ρ-coumaroylmaslinic acid. The structures were identified by comparing of the spectroscopic experiments, NMR and MS, and then compared that reported data, respectively. Three extracts of water, methanol, and chloroform from the seeds showed a weak anti-proliferative effect, anti-microbial activity, and anti-oxidant effect, respectively.
Antioxidants
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Chloroform
;
Medicine, Chinese Traditional
;
Methanol
;
Oleanolic Acid
;
Stigmasterol
;
Water
;
Ziziphus*
10.Chemical Constituents of Nelumbo nucifera Seeds.
Natural Product Sciences 2017;23(4):253-257
The phytochemical study for the extract of Nelumbo nucifera (Nymphaceae) seeds has led to the isolation of ten compounds including five simple phenolic compounds, two indole derivatives, a flavonoid glycoside, two abscisic acid derivatives. The interpretation of 1D and 2D NMR and ESI-Q-TOF-MS spectroscopic data revealed the chemical structures of isolates to be p-hydroxybenzoic acid (1), protocatechuic acid (2), (E)-p-coumaric acid (3), (E)-ferulic acid (4), (E)-sinapate-4-O-β-D-glucopyranoside (5), tryptophan (6), 3-indoleacetic acid (7), isoschaftoside (8), dihydrophaseic acid (9), dihydrophaseic acid 3′-O-β-D-glucopyranoside (10). To the best of our knowledge, 1 – 5 and 7 were identified for the first time from N. nucifera seeds, and the presence of dihydrophaseic acid (9) and its glucoside (10) were demonstrated secondly in this plant.
Abscisic Acid
;
Nelumbo*
;
Phenol
;
Plants
;
Tryptophan