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A new neolignan glucoside has been isolated from Chrysanthemum morifolium ‘Baekma’ cultivar through repeated silica gel and octadecyl silica gel (ODS) column chromatographies. On the basis of spectroscopic data including NMR, MS, and IR, the chemical structure of the new neolignan glucoside was determined to be (7S,8S)-7-O-[1′-(4′,5′-dihydroxy-3′-methoxyphenyl)propanol]guaiacylglycerol 4-O-β-D-glucopyranoside (1), named baekmaoside A.

꼬리겨우살이(Loranthus tanakae) 전초를 80% MeOH 수용액으로 4회 반복 추출한 뒤, 감압 농축한 추출물을 ethyl acetate(EtOAc), n-butyl alcohol (n-BuOH)과 H2O층으로 계통 분획을 실시하였다. n-BuOH 분획에 대하여 silica gel (SiO2), octadecyl silica gel (ODS), Sephadex LH-20 column chromatographies를 반복실시하여 1종의 cyclofarnesane sesquiterpene glucoside 화합물을 분리 및 정제하였다. 스펙트럼 데이터를 분석하여 입체 구조를 포함한 화합물의 구조를 (1''R,3''S,5''R, 8''S,2E,4E)-dihydrophaseic acid 3''-O-β-D-glucopyranoside로 구조동정 하였다. 이 화합물은 이번 실험을 통하여 꼬리겨우살이로부터는 최초로 분리되었다. 분리한 단일 물질은 AGS (Caucasian gastric adenocarcinoma cells)와 Hepatocyte carcinoma cells에 대하여 50 μg/mL 이상에서 농도 의존적으로 유의한 정도의 세포독성을 보이는 것이 확인되었다.

Cough and phlegm frequently occur in respiratory diseases like upper respiratory tract infections, acute bronchitis, and chronic obstructive pulmonary diseases. To relieve these symptoms and diseases, various ingredients are being used despite the debates on their clinical efficacy. We aimed to investigate the effects of the extract CKD-497, composed of Atractylodis Rhizoma Alba and Fructus Schisandrae, in relieving cough and facilitating expectoration of phlegm. CKD-497 was found to inhibit inflammatory mediators such as interleukin-8 (IL-8) and tumor necrosis factor &alpha, (TNF-&alpha, ) in lipopolysaccharide (LPS)-treated mouse macrophages and transient receptor potential cation channel 1 (TRPV-1)-overexpressed human bronchial epithelial cells stimulated by capsaicin. CKD-497 decreased the viscosity of the mucin solution. During in vivo experiments, CKD-497 reduced coughing numbers and increased expectoration of phlegm via mucociliary clearance enhancement. Collectively, these data suggest that CKD-497 possesses potential for cough and phlegm expectoration treatment.

A preliminary study revealed that a 10 µg/mL n-BuOH fraction of Malva verticillata aerial parts significantly enhanced splenocyte proliferation and induced significant enhancement of natural-killer (NK) cell activity against tumor cells (YAC-1). This study was initiated to identify the principal components that exhibited these activities, and four glycerides were isolated through repeated SiO2 and ODS column chromatography. Structures of compounds 1–4 were determined to be (2S)-1-O-palmitoyl glyceride, (2S)-1-O-stearoyl glyceride, (2S)-1-O-linolenoyl glyceride, and (2S)-1,2-di-O-linoleoyl glyceride, respectively. Compounds 1–3 showed potential immune-enhancing activity in murine splenocyte and natural-killer (NK) cells at 10 µM. In contrast, compound 4 showed weak activity, indicating the monoacyl glycerides (1–3) are more effective than diacyl glyceride (4). Also, the longer the carbon number of the fatty acid in monoacyl glyceride, the better the activity, and the monoacyl glyceride including an unsaturated fatty acid (3) is more effective than the glycerides including the saturated fatty acids (1–2).

Malva verticillata (Chinese mallow) has long been used in traditional medicines and herbal teas in Asia. The n-BuOH fraction (Fr) from M. verticillata promoted significant recovery of alloxan-damaged (AXD) pancreatic islets (PIs) in zebrafish (ZF). Two major components were isolated from M. verticillata through repeated-column chromatography. Based on several spectroscopic methods, including nuclear magnetic resonance (NMR), infrared spectroscopy (IR), and fast atom bombardment-mass spectrometry (FAB-MS), the chemical structures of compounds 1 and 2 were determined. In addition, the quantity of both compounds in the n-BuOH Fr was investigated through high-performance liquid chromatography (HPLC) and the quantities of compounds 1 and 2 in the n-BuOH Fr were determined to be 5.58% ± 0.16% and 2.85% ± 0.13%, respectively. The n-BuOH Fr, compounds 1 and 2, and the mixture of compounds 1 and 2 (MX, 1 and 2, the ratio of both compounds in n-BuOH Fr, 1.96:1) were evaluated for their ability to recover AXD PIs and for their KATP channel-blocking mechanism using diazoxide in ZF. The n-BuOH Fr (10 μg/mL) and compounds 1 and MX (1 μg/mL) exhibited a recovery effect on AXD PIs. The n-BuOH Fr (10 μg/mL) and MX (1 μg/mL) were also confirmed to be useful KATP channel activators. A synergistic effect of MX in the recovery of AXD PIs was first confirmed in ZF, and it was discovered that 2 acted as an insulin sensitivity activator that increased the activity of compound 1.

The EtOAc, n-BuOH, and aqueous fractions from the aerial parts of Malva verticillata have been shown to promote significant recovery from alloxan-induced pancreatic islet (PI) damage in zebrafish larvae at 10 μg/mL. Therefore, this study aimed to identify the principal active components of these plant parts and their pharmacological properties. Repeated SiO2 and octadecyl SiO2 column chromatography with the aerial parts of M. verticillata led to isolation of four phenolic compounds; these compounds were identified as benzyl-α-D-galactopyranoside (1), (-)-secoisolariciresinol-9'-O-β-D-glucopyranoside (2), transferulic acid (3), and trans-ferulic acid methyl ester (4) on the basis of physicochemical and spectroscopic analyses including infrared, nuclear magnetic resonance, and fast atom bombardment-mass spectroscopy. Compounds 14 were first isolated from M. verticillata in this study. Furthermore, compounds 1–4 recovered alloxan-induced PI damage in zebrafish. Especially, compound 3 recovered the size of the injured PIs by 83.8% ( p=0.0007) compared to the alloxan-induced group, while compound 4 by 33.4% ( p=0.0072). It is the first report that trans-ferulic acid (3) exhibited the protective effect on zebrafish larvae PIs damaged by alloxan.

Malva verticillata (Cluster mallow), a leafy vegetable that has been popular in East Asia for a long time, has also been used in herbal teas and medicines. The aqueous fraction of the aerial parts of Malva verticillata, exhibiting a very high quantity of flavonoids compared to the EtOAc and n-BuOH fractions, exhibited significant recovery effects on pancreatic islets damaged by alloxan in zebrafish larvae. Thus, the bioactive components responsible for this anti-diabetic activity were investigated. A new flavonoid glucuronide (1) and five known flavonoids were isolated from the aqueous fraction. Based on several spectroscopic methods, compound 1 was identified to be nortangeretin-8-O-β-d-glucuronide, and was named malvaflavone A. The A-ring of compound 1 had a 5,6,7,8-tetrahydroxy moiety, which rarely occurs in plant systems. Also 8-O-glucuronide attached to the flavonoid moiety was rarely occurred in plant system. Compounds 1, 3, 4, and 6 significantly improved the pancreatic islet size in zebrafish at 0.1 μM, and compounds 1 and 6 were found to block β-cell K+ channels in experiments with diazoxide. In ABTS, ORAC, and SOD assays, compounds 1–5 exhibited high anti-oxidant activities compared with quercetin and BHA (positive controls), indicating that the 8-O-glucuronide attached to the flavonoid moiety is a key structure for the expression of anti-oxidant activity. This is the first report of the isolation of compounds 1–6 from M. verticillata as well evaluated for anti-diabetic and anti-oxidant ativities.