• Archives of Pharmacal Research
• /
• v.20 no.3
• /
• pp.201-205
• /
• 1997

A very high content (at least 0.23%) of ergosterol peroxide was isolated from Naematoloma fasciculare Karst. Not only ergosterol peroxide but also ergosterol showed very strong anticomplementary activity on the classical pathway, the $IC_{50}$ values being $5.0 {\mu}M$ and $1.0 {\mu}M$, respectively. The $ ^{1}H $and $^{13}C$ NMR data of ergosterol peroxide were revised and completely assigned by DEPT, $^{1}H-^{1}H$ COSY, HMQC and HMBC correlations.

• Journal of the Korean Society of Food Science and Nutrition
• /
• v.24 no.5
• /
• pp.702-706
• /
• 1995

A major component(compound A) in the ethylacetate fraction exhibited a strong antimicrobial activity was identified by UV, IR, FABMS and NMR. The compound A showed strong absorbance at 209, 259 and 359nm, indicating a flavonoid ring structure. IR spectrum possessed absorbance of OH at 3400∼3300cm-1, ketone at around 1650cm-1, and aromatic C=C at around 1660cm-1. Molecular weight of the compound A calculated as 478 from the information of m/z 479(M＋H)+ and m/z 477(M-H)+ in the FABMS spectrum. Molecular formula of this compound was found to be C22H22O12 from m/z 479.1220(＋3.1mmu for C22H23O12) of HRFABMS spectrum and from 13C-NMR spectrum. 1H-NMR and 13C-NMR spectra of the compound A revealed aromatic proton and benzene rings. Distortionless enhancement by polarization transfer(DEPT) exhibited that the compound A possessed 10 quaternary carbons and 3 substituted benzene rings including a methoxy group substitution. The compound A was identified as isorhamnetin 3-O-β-glucopyranoside by spectrophotometric methods in conjunction with 1H-1H COSY, 1H-13C COSY and HMBC, which revealed a flavone with OH group at 3, 5, 7, and 4' and methoxy group at 3' positions esterified to glucose.

• Natural Product Sciences
• /
• v.27 no.2
• /
• pp.122-127
• /
• 2021

A new steroidal saponin, (23S,24S)-spirosta-5,25(27)-diene-1𝛽,3𝛽,23,24-tetrol 1-O-((2,3-diacetyl-α-L-rhamnopyranosyl)-(1→2)-[𝛽-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside)-24-O-𝛽-D-glucopyranoside (humilisoside) together with the known 𝛽-sitosterol 3-O-glucopyranoside, adenosine, dioscin, and methylprotodioscin were isolated from the leaves of Dracaena humilis. Their structures were elucidated by spectral techniques including mass spectrometry (ESIMS, HRESIMS, tandem MS-MS), 1D NMR (¹H, ¹³C NMR), 2D NMR (HSQC, ¹H-¹H COSY, HMBC, NOESY), chemical method as well as by comparison with spectroscopic data reported in the literature. The chemotaxonomic significance of the isolation of these compounds is discussed. This is the first report on the phytochemical investigation of D. humilis.

• Archives of Pharmacal Research
• /
• v.20 no.3
• /
• pp.291-296
• /
• 1997

The studies were carried out to evaluate the constituents in the aerial part of Isodon excisus var. coreanus (Labiatae). From the aqueous fraction of methanol extract, compound I (${\alpha}$-[[3-(3, 4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-benzenepropanoic acid), compound II (9-methyl-dihydroferulic acid-4-O-.betha.-D-glucopyranosyl $(1{\rightarrow}2)$-${\alpha}$-L- rhamnopyranosyl (1.rarw.4)-.betha.-D-glucopyranoside), compound III (ent-7.alpha., 11${\alpha}$,15.betha.-trihydroxy-kaur-16-en-1-O-.betha.-D-glucopyranoside) and compound IV ($2{\alpha}$,3${\beta}$,$7{\alpha}$,23-tetrahydroxy-olean-12 -en-28-oic acid 28-O-${\beta}$-D-glucopyranoside) were isolated and identified on the basis of their physicochemical and spectroscopic evidences[IR, FAB(-)MS,$^{1}H-NMR,$$^{13}C-NMR,$$ HMQC$$^{1}H-^{1}H $COSY and HMBC (Heteronuclear Multiple Bond Connectivity)]. Especially, New compounds II and III were named Isodonin A and Isodonin B respectively.

• Korean Journal of Pharmacognosy
• /
• v.26 no.1
• /
• pp.23-26
• /
• 1995

6-Hydroxykynurenic acid and ginkgolide B together with flavonol glycosides and biflavonoids were isolated from the yellow leaves of Ginkgo biloba and identified by means of spectroscopic methods. The correctness of $H{\"{o}}lzl's$ ${13}^C-NMR$ assignments for 6-hydroxykynurenic acid was confirmed by HMQC and HMBC techniques. Based on our present findings, it may be considered that the yellow Ginkgo leaves may contribute to be a source of high medicinal values.

• Journal of the Korean Magnetic Resonance Society
• /
• v.23 no.4
• /
• pp.87-92
• /
• 2019

Allium hookeri (Liliaceae) has been received the increasing attention as a bioactive resource due to its potent biological activities including anti-oxidant, anti-obesity, anti-microbial and lipid-regulating activities. The beneficial effects of A. hookeri are known contributed from the high content of organosulfur compounds in A. hookeri. Though a variety of articles demonstrated that A. hookeri contains 'saponin' as a bioactive constituent, the scientific evidence to prove it was limited. In the present study, we have attempted to identify saponin contained in A. hookeri through chromatographic isolation and NMR spectroscopic methods. As a result, a spirostane-type steroidal saponin (1) has been successfully isolated from the methanolic extract of A. hookeri roots. The structure of 1 was elucidated by extensive 1D and 2D spectroscopic methods including ¹H-NMR, ¹³C-NMR, ¹H-¹H COSY, HSQC, HMBC and NOESY; identified as (3β, 22R, 25S)-spirost-5-en-3yl O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-[6-deoxy-α-L-mannopyranosyl-(1→2)]-β-D-gluco pyranoside. 1 showed the significant inhibitory activity on mushroom tyrosinase with IC₅₀ values of 248.7 μM while the inhibition on alpha-glucosidase was not significant.

• Microbiology and Biotechnology Letters
• /
• v.23 no.6
• /
• pp.641-646
• /
• 1995

During the screening of inhibitors of melanin biosynthesis from microbial secondary metabolites, a fungal strain MR304 which was capable of producing high level of an inhibitor was selected. Based on taxonomic studies, this fungus could be classified as Trichoderma harzianum. The active compound (MR304-1) was purified from culture broth by Diaion HP-20 column chromatography, ethylacetate extraction, Sephadex LH-20 column chromatographv and HPLC. The inhibitor was identified as 3-(1,5-dihvdroxy-3-isocyanocyclopent-(E)-3-envl)prop-2-enoate by spectroscopic methods of UV, ESIMS, $^{1}$H-NMR, $^{13}$C-NMR, NOE, HMQC and HMBC. MR304-1 showed strong mushroom tyrosinase inhibitory activity with IC$_{50}$ value of 0.25 $\mu $g/ml. It inhibited melanin biosynthesis with 15 mm inhibition zone at 30 $\mu $g/paper disc in Streptomyces bikiniensis, a bacterium used as an indicator organism in this work. It also inhibited melanin biosynthesis in B16 melanoma cells with a niinimum inhibitory concentration of 0.05 $\mu $g/ml.

• Natural Product Sciences
• /
• v.23 no.2
• /
• pp.113-118
• /
• 2017

A new tetracyclic triterpenoid [4,4,24-trimethylcholesta-${\Delta}^{8,9;14,5;24,28}$-trien-$3{\beta},11{\beta},12{\alpha}$-triol-12-acetate, 3-sulfate] sodium salt (1), together with eight known compounds including ergosterol $5{\alpha},8{\alpha}$-endoperoxide (2), 1,9-dihydroxy-3-methoxy-2-methylpterocarpan (3), 3-O-${\beta}$-D-2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (4), hydnocarpin (5), derrone (6), isovitexin (7), erythrinin C (8), and 5,4'-dihydroxy-2"-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone (9), were isolated from the EtOAc soluble fraction of the methanol extract of aerial part of Desmodium uncinatum collected in the western highland of Cameroon. The structures of these compounds were established by comprehensive interpretation of their spectral data mainly including 1D- ($^1H$ and $^{13}C$), 2D-NMR($^1H$-$^1H$ COSY, HMQC, HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis. The isolation of an integracide-like compound from plant origin is a very unusual finding.