Yong-Sheng Jin

Two new triterpenoids from the roots of Actinidia chinensis

Two new triterpenoids (1, 2), together with one flavonoid glycoside and thirteen known triterpenoids were isolated from the roots of Actinidia chinensis Planch (Actinidiaceae). The structures of the new constituents were elucidated as 12α-chloro-2α, 3β, 13β, 23-tetrahydroxyolean-28-oic acid-13-lactone (1), 2α, 3α, 19α, 23, 24-pentahydroxyurs-12-en-28-oic acid (2). Structure elucidation was accomplished by 1D, 2D NMR spectra (HMQC, HMBC, (1)H-(1)H COSY, TOCSY, and NOESY) and mass spectrometry (ESIMS). Moreover, two known triterpenoids showed positive cytotoxic activity against LOVO and HepG2 cell lines.

Chemical constituents from Belamcanda chinensis.

One new flavone and one new isoflavone glycoside were isolated along with 15 known compounds from the rhizome of Belamcanda chinensis (Iridaceae), and their structures were characterised as 5,4′-dihydroxy-6,7-methylenedioxy-3′-methoxyflavone (1) and 3′,5′-dimethoxy irisolone-4′-O-β-d-glucoside (2) on the basis of spectroscopic methods.

A new indole alkaloid from Ervatamia yunnanensis

The stems of Ervatamia yunnanensis have afforded a new indole alkaloid, ervataine (1), whose structure was determined by spectroscopic analysis. Five known compounds, ibogaine (2) coronaridine (3), heyneanine (4), voacangine hydroxyindolenine (5) and coronaridine hydroxyindolenine (6), were also isolated.

Phenolic constituents of Canarium album

Canarium album (Lour.) Raeusch (Burseraceae) is widely distributed in southern China. Its fruits have been used as food in China. Also, the dried fruits of Canarium album (Lour.) Raeusch have been used in Chinese folk medicine for the treatment of angina, dysentery, snake bites, cough-hematemesis, falling sickness, enteritis, diarrhea, toxicosis from swellfish, and alcoholism [1]. Recently, phytochemical investigations found that this drug contained a number of phenolic compounds, such as gallic acid, brevifolin, scoparone, and hyperoside [2–4]. In the course of further studies, three monocyclic phenolic compounds: 3,4-dihydroxybenzoic acid ethyl ether (1) [5], 2-hydroxybenzoic acid (2) [5], ethyl gallate (3) [6]; two flavones: luteolin (4) [5], luteolin-7-O-D-glucoside (5) [7]; three flavonols: quercetin (6) [8], quercetin-3-O-D-glucoside (7) [9], kaempferol (8) [5], one flavanone: 7,8,3 ,4 -tetrahydroxyflavanone (9) [10], and one flavanonol: 3,5,7,3 -tetrahydroxy-4 -methoxyflavanonol (10) [11] have been isolated from the fruits. All the above compounds have not been reported before from this plant source. The EtOH extract was separated by repeated column chromatography using silica gel. The dried fruits (6 kg) were chopped and extracted with 80% EtOH three times under reflux and concentrated under vacuum to yield an EtOH extract (300 g). The concentrated solution was diluted with H2O and extracted successively with petroleum ether, EtOAc, and n-butanol. The EtOAc extract was separated by repeated column chromatography using silica gel and Sephadex LH-20 to afford compounds 1–10. All the phenolic compounds were identified by comparison of their 1H and 13C, DEPT NMR data. The 13C NMR data of the isolated phenolic compounds are shown in Tables 1 and 2.

Three new compounds from Arnebia euchroma.

A new naphthoquinone dimer, arnebiabinone (1), a new phenolic compound, ethyl 9-(2′,5′-dihydroxyphenyl) nonanoate (2), and a new natural product, octyl ferulate (3), were isolated from the EtOH extract of dried roots of Arnebia euchroma (Royle) Johnst. Their structures were elucidated on the basis of chemical reaction and spectral analysis.A new naphthoquinone dimer, arnebiabinone (1), a new phenolic compound, ethyl 9-(2′,5′-dihydroxyphenyl) nonanoate (2), and a new natural product, octyl ferulate (3), were isolated from the EtOH extract of dried roots of Arnebia euchroma (Royle) Johnst. Their structures were elucidated on the basis of chemical reaction and spectral analysis.

Chemical and biologically active constituents of Salsola collina

A new natural product (N-acetyltryptophan), together with 22 known constituents, including seven alkaloids, six flavonoids, six organic acids, and other compounds, were isolated from Salsola collina Pall. Their structures were elucidated on the basis of chemical reaction and spectral evidence. Among the isolated compounds, N-acetyltryptophan (8) showed moderate inhibition of a-amylase activity, and terrestric acid (9) showed positive antifungal activity.

Amides from Uvaria microcarpa

The dried stems of Uvaria microcarpa Champ. ex Benth. have significant antiplasmodia activity [1]. Previous studies showed that this plant contained a number of phenanthrene-carboxylic acid lactams [2]. Nine phenanthrene-carboxylic acid lactams and one amide were isolated from the EtOAc fraction of extracts of the stems of Uvaria microcarpa Champ. ex Benth., of which velutinam (1), enterocarpam II (2), goniopedaline (3), uvariadiamide (9), aristololactam B (10) were obtained from this plant for the first time. The stems of Uvaria microcarpa Champ. ex Benth. were collected from Hainan Province in June 2007 and identified by Mr. Zhu Ping, Hainan Tropical Botanic Garden of the Chinese Academy of Sciences. A voucher specimen has been deposited at the Department of Natural Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai. The dried and chopped stems of Uvaria microcarpa Champ. ex Benth. (10 kg) were extracted with 95% EtOH (5 L 4) under reflux, then evaporated in vacuum. The residue (530 g) was further suspended in water and extracted successively with petroleum ether, EtOAc, and BuOH. The EtOAc extract was separated by repeated column chromatography using silica gel and Sephadex LH-20 to afford compounds 1–10. All compounds were identified by comparison of their 1H and 13C NMR data. The spectroscopic data of all compounds were in good agreement with the literature data [3–8]. The 1H NMR data are shown in Tables 1 and 2. The 13C NMR data are shown in Table 3. Uvariadiamide (9). Colorless needles (CH3OH). C18H20N2O2, 296. 1H NMR (DMSO-d6, , ppm, J/Hz): 1.57 (4H, br.t, J = 5.4, 2, 3-H), 3.27 (4H, br.t, J = 5.4, 1, 4-H), 7.42–7.83 (10H, m, Ar-H); 13C NMR (DMSO-d6): 168.1 (C=O), 26.7 (2, 3-C), 39.9 (1, 4-C), 127.1, 128.2, 131.0, 134.7 (Ar-C), 1H NMR and 13C NMR spectra have been published [8].

Constituents from the roots of Actinidia chinensis and their inhibitory activities toward cytochrome P450.

A newly discovered triterpenoid, (2α,3β)‐2,3,23‐trihydroxyurs‐13(18)‐en‐28‐oic acid (1), along with twelve known compounds (2 – 13), were isolated from the roots of Actinidia chinensis Planch (Actinidiaceae). Their chemical structures were determined by 1D‐ and 2D‐NMR spectra and mass spectrometry (MS). The crude extracts and six main constituents (8 – 13) were tested for cytochrome P450 (CYPs) enzyme inhibitory activity. The results showed that, except for compound 8, compounds 9 – 13 had different inhibitory effects on the cytochrome P450 (CYPs) enzyme, and compound 9 significantly inhibited the catalytic activities of CYP3A4 to < 10% of its control activities.

Synthesis and cdc25B inhibitory activity evaluation of chalcones

A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of more potent antiproliferative agents.

Two new triterpenoid acids from Kadsura coccinea

An investigation of EtOAc extracts of Kadsura coccinea (Lem.) A. C. Smith, has led to the isolation of two new compounds characterized as 3-hydroxy-12-hydroxyl coccinic acid (1) and 3-hydroxy-neokadsuranic acid A (2). Their structures were established by 1D and 2D NMR techniques and mass spectroscopy. Antiproliferative effects of the isolated compounds were evaluated against four human tumor cell lines (A549, HCT116, HL-60 and HepG2), and it was found that compound 1 exhibited antiproliferative effects with IC50 values ranging from 3.01 to 18.08 μg/mL.