A new prenylated naphthoquinoid, named (3R,4aR,10bR)-3,10-dihydroxy-2,2-dimethyl-3,4,4a,10b-tetrahydro-2H-naphtho[1,2-b]-pyran-5H-6-one (1), was isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze, together with six known compounds: apigenin (2), luteolin (3), neoeriocitrin (4), naringenin (5), narirutin (6), and didymin (7). Neoeriocitrin was isolated for the first time from the species C. chinense. Their structures were elucidated by spectroscopic methods, including 1D, 2D (¹H-¹H-COSY, HSQC, HMBC and NOESY) NMR, HR-ESI-MS. The absolute configuration of 1 was determinated using the CD method. We highlight that the structure of 1 is characterized by a rarely seen prenylated naphthoquinoid framework. Full article

Phenolic acid derivatives are typical constituents of Clerodendranthus spicatus which were considered to the active principles of this medicinal plant. These chemical constituents with their interesting frameworks and biological significance attracted our attention. As part of our ongoing chemical investigation of C. spicatus using various column chromatography techniques, a new phenolic compound, named clerodendranoic acid (1), was isolated from the aerial parts of C. spicatus together with five known ones, including rosmarinic acid (2), methyl rosmarinate (3), caffeic acid (4), methyl caffeate (5), ethyl caffeate (6). Their structures, including stereochemical configurations, were completely established by extensive spectroscopic methods, mainly inclvolving 1D, 2D NMR, as well as HRESIMS. Full article

Daphniphyllum calycinum (DC), a main component of Chinese patent drug Fengliao-Changweikang, is effectively used to cure bowel disease in the clinic. It was recorded that DC possessed slight toxicity, which was caused by the alkaloids existing in its extract. Unfortunately, to date the toxicity level and toxic constituents are still unclear. The present study is designed to illustrate the acute toxicity and induced organ damages of the total alkaloids as well as to determine the toxic constituents. Based on the above studies, not only was the acute toxicity determined but also hepatic toxicity was characterized by increased plasma biomarkers of ALT and AST and liver cell inflammatory infiltrate as well necrosis that was firstly observed. Significantly, deoxycalyciphylline B exhibited exactly the same hepatic toxicity so it was identified as the main toxic constituent in DC. An obvious dose-effect relationship between the toxic compound and induced hepatic injuries was also observed. Moreover, the Chinese patent drug Fengliao-Changweikang contained low levels of the toxic compound, compared with the total alkaloids. Therefore, this Chinese patent drug could be regarded to be safe in this point of view. Full article

From the whole plant of Sarcandra glabra, a new phenolic acid glycoside, benzyl 2-β-glucopyranosyloxybenzoate (1), together with seven known compounds including eleutheroside B₁ (2), 5-O-caffeoylshikimic acid (3), (–)-(7S, 8R)-dihydrodehydro-diconiferyl alcohol (4), (–)-(7S, 8R)-dihydrodehydrodiconiferyl alcohol 9-, 9′- and 4-O-â-D-glucopyranoside (5–7), and (–)-(7S, 8R)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (8) was isolated. Their structures were elucidated by spectral analysis including 1D-, 2D-NMR and HR-ESI-MS. Compound 2 was found to exhibit potent cytotoxic activity against BGC-823 and A2780 cancer cell lines using MTT method with IC₅₀ value of 2.53 and 1.85 µM, respectively. Full article

On our ongoing investigation, a new oleanolic triterpene, 3β,6β,19α-trihydroxy-12-oleanen-28-oic acid (1) was obtained from the chloroform-soluble portion of the 90% alcohol-water extract of the stem bark of Uncaria macrophylla. Its structure was elucidated by extensive spectroscopic methods, including 1D and 2D (¹H-¹H COSY, HSQC and HMBC) NMR and HR-ESI-MS. The cytotoxicities of the compound was evaluated against two cancer cell lines of MCF-7 and HepG2 by the MTT method, and the compound exhibited weak activities with the IC₅₀ values of 78.2 µg/mL and 73.9 µg/mL. Full article

Our ongoing investigations on the stem bark of Uncaria macrophylla afforded a new ursolic triterpene, 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid-24-carboxylic acid methyl ester (1), named uncariursanic acid, and three known ursolic triterpenes including 3β,6β,19α-trihydroxy-23-oxo-urs-12-en-28-oic acid (2), 3β,6β,19α-trihydroxy-urs-12-en-28-oic acid (3) and ursolic acid (4). Their structures were elucidated by extensive spectral methods, including 1D and 2D NMR and HR-ESI-MS. The cytotoxicities of the four compounds were evaluated against two cancer cell lines (MCF-7 and HepG2) by the MTT method, and only compound 4 exhibited potent activity. Full article