Haihui Xie

A-Type Proanthocyanidins from Lychee Seeds and Their Antioxidant and Antiviral Activities

Two new A-type trimeric proanthocyanidins with two doubly bonded interflavanoid linkages, litchitannin A1 [epicatechin-(2β→O→7,4β→6)-epicatechin-(2β→O→7,4β→8)-catechin] (1) and litchitannin A2 [epicatechin-(2β→O→7,4β→6)-epicatechin-(2β→O→7,4β→6)-epicatechin] (2), were isolated from lychee (Litchi chinensis Sonn. cv. Heiye) seeds together with aesculitannin A (3), epicatechin-(2β→O→7,4β→8)-epiafzelechin-(4α→8)-epicatechin (4), proanthocyanidin A1 (5), proanthocyanidin A2 (6), proanthocyanidin A6 (7), epicatechin-(7,8-bc)-4β-(4-hydroxyphenyl)-dihydro-2(3H)-pyranone (8), and epicatechin (9). Their structures were elucidated on the basis of spectroscopic and chemical evidence. It is the first time that compounds 1-4, 7, and 8 have been reported in this species. Compounds 1-9 showed more potent antioxidant activity than L-ascorbic acid with ferric reducing antioxidant power (FRAP) values of 3.71-24.18 mmol/g and IC50 values of 5.25-20.07 μM toward DPPH radicals. Moreover, litchitannin A2 (2) was found to exhibit in vitro antiviral activity against coxsackie virus B3 (CVB3) and compounds 3 and 6 displayed antiherpes simplex virus 1 (HSV-1) activity.

Abietane diterpenoids from Isodon lophanthoides var. graciliflorus and their cytotoxicity

Seven new (1-7) and three known (8-10) abietane diterpenoids were isolated from the methanolic extract of the aerial parts of Isodon lophanthoides var. graciliflorus (Lamiaceae), a folk Chinese medicine and an herb for functional beverages. They were identified as 16-acetoxylsugiol (1), graciliflorin E (2), graciliflorin F (3), 15-O-methylgraciliflorin F (4), 15-hydroxy-20-deoxocarnosol (5), 3β-hydroxysempervirol (6), 15-hydroxy-1-oxosalvibretol (7), abieta-8,11,13-triene-14,19-diol (8), 6,12,15-trihydroxy-5,8,11,13-abietatetraen-7-one (9), and 3α-hinokiol (10) based on the spectroscopic data including COSY (correlated spectroscopy), HMBC (heteronuclear multiple bond correlation), and HR-ESI-MS (high-resolution electrospray ionization mass spectrometry). All the compounds except 10 were obtained from I. lophanthoides for the first time. Compounds 1, 2, 5, 6, 8, and 9 exhibited in vitro cytotoxicity against A549 (human lung adenocarcinoma), MCF-7 (human breast adenocarcinoma), and HeLa (human cervical carcinoma) cell lines with the IC(50) values of 1.79-52.67 μM.

Polyoxygenated methyl cyclohexanoids from a terrestrial ampelomyces fungus.

Seven structurally related new polyoxygenated methyl cyclohexanoids, ampelomins A-G (1-7), were isolated from the mycelial solid culture of a soil-derived Ampelomyces fungus. Their structures were determined by spectroscopic and chemical means. Ampelomins A (1), C (3), E (5), and G (7) exhibited weak activity against alpha-glucosidase with IC(50) values of 1.74-5.93 mM, and ampelomin A (1) showed moderate antibacterial activity with MIC(90) values ranging from 202.4 to 1015.9 microM. A plausible polyketide biogenetic pathway is postulated for these compounds.

Two New Antifungal Alkaloids Produced by Streptoverticillium morookaense

A new carbazole alkaloid, streptoverticillin, and a new 2-azetidinone, streptoverticillinone, along with three known cyclodipeptides were isolated from the mycelial solid culture of Streptoverticillium morookaense. Their structures were elucidated by analysis of 1D and 2D NMR, mass spectra and optical rotation data. Two new compounds exhibited antifungal activity against Peronophythora litchii.

A novel cyclopropyl-containing fatty acid glucoside from the seeds of Litchi chinensis

3,12-Dihydroxy-cis-3,4-methylenedodecanoic acid 3-O-β-d-glucopyranoside, trivially named litchioside C (1), the first cyclopropyl-containing fatty acid glycoside, was isolated along with three previously uncharacterized galactosylacylglycerols from the seeds of Litchi chinensis. Its structure was established on the basis of spectroscopic analysis including HRESIMS and 2D NMR spectra. Its antioxidant and antibacterial activities were evaluated and its biogenetic pathway was discussed.

BIOACTIVE CONSTITUENTS FROM CHINESE NATURAL MEDICINES. XXXI.1 HEPATOPROTECTIVE PRINCIPLES FROM SINOCRASSULA INDICA : STRUCTURES OF SINOCRASSOSIDES A8, A9, A10, A11, AND A12

-The methanolic extract from the whole plant of Sinocrassula indica (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, five new acylated flavonol glycosides, sinocrassosides A 8 (1), A 9 (2), A 10 (3), An (4), and A 12 (5), were isolated together with 25 compounds. The structures of 1-5 were elucidated on the basis of chemical and physicochemical evidence. Among the isolated compounds, sinocrassosides A 1 (6), A 2 (7), and B 2 (14) were found to show potent hepatoprotective effect.

Podocarpane, isopimarane, and abietane diterpenoids from Isodon lophanthoides var. graciliflorus.

Four new diterpenoids including two podocarpanes, graciliflorins A (1) and B (2), an isopimarane acetal, graciliflorin C (3), and a rearranged abietane, graciliflorin D (4) were isolated from the aerial parts of Isodon lophanthoides var. graciliflorus (Lamiaceae) along with podocarpa-8,11,13-triene-3α,13-diol (5) and micranthin B (6). Their structures were elucidated based on the spectroscopic data. The in vitro cytotoxicity of compounds 1-4 and 6 against human carcinoma A549, MCF-7, and HeLa cell lines were evaluated using the MTT colourimetric assay. Micranthin B (6) showed moderate activity against all the cells with IC(50) values of 16.29, 18.20, and 22.25 μM, while compounds 1-4 were inactive (IC(50)>50 μg/ml).

Phytoecdysteroids from the rhizomes of Brainea insignis

Phytoecdysteroid glucosides, brainesterosides A-E, were isolated from the rhizomes of Brainea insignis along with three known phytoecdysteroids, ponasteroside A, ponasterone A, and 20-hydroxyecdysone. Their structures were elucidated by spectroscopic and chemical means. A possible biogenetic pathway is postulated for these compounds. The chemosystematic significance of ponasterone A is discussed.

Anti-inflammatory cyclopeptides from exocarps of sugar-apples

Two new cyclic peptides, fanlizhicyclopeptide A, cyclo(Pro(1)-Pro(2)-Tyr(3)-Leu(4)-Pro(5)-Gly(6)-Val(7)) (1), and fanlizhicyclopeptide B, cyclo(Pro(1)-Ile(2)-Tyr(3)-Ala(4)-Gly(5)) (2), were isolated along with six known kaurane diterpenoids and a known clovane sesquiterpene from the exocarps of sugar-apples, the fruit of Annona squamosa. Their structures were elucidated by ESI MS/MS experiments, 1D and 2D NMR data and chemical degradation. In the anti-inflammatory assay, both 1 and 2 showed in vitro inhibitory effects on the production of pro-inflammatory cytokines, TNF-α and IL-6, in LPS-stimulated RAW 264.7 macrophages.

Monoterpenoid indole alkaloids mediating DNA strand scission from Turpinia arguta.

Two new monoterpenoid indole alkaloid derivatives, turpiniside (1) and 11-methoxyjavaniside (2), along with the known alkaloids, vincosamide (3), (3 R)-pumiloside (4), and paratunamide C (5), were isolated from the leaves of Turpinia arguta (Lindl.) Seem. Their structures were determined on the basis of spectroscopic data. Compounds 1 and 3-5 were found to effect relaxation of the supercoiled pBR322 plasmid DNA in the presence of Cu²+.