Qi-Shi Song

Volatiles from Ficus hispida and Their Attractiveness to Fig Wasps

Volatile compositions of receptive (ready to be pollinated), postpollinated, and postparasitized figs, and leaves of Ficus hispida were analyzed. Differences among them were examined, and the specificity of fig wasp attractiveness was investigated. Linalool was the major constituent of steam-distilled oil of either male or female receptive figs, while dibutyl phthalate was the major compound of the oils of postparasitized and postpollinated figs. In petroleum ether extracts, palmitic oil, and 9,12-octadecadienoic acid were the main constituents of male and female receptive figs, while hexadecanoic acid ethyl ester was the major compound of postparasitized and postpollinated figs. In dichloromethane extracts, linalool was the major constituent of male and female receptive figs, 1-hydroxylinalool was the major component of male postparasitized figs, and 1-hydroxylinalool and benzyl alcohol were the major constituents of female postpollinated figs. Bioassays with sticky traps showed that Ceratosolen solmsimarchal was attracted to dichloromethane extracts of male and female receptive figs and to petroleum ether extracts of female receptive figs, but was not attracted to dichloromethane and petroleum ether extracts of male postparasitized and female postpollinated figs. Figs were attractive to pollinating wasps only at the receptive stage. The volatile constituents of receptive figs were different from those of postpollinated or postparasitized figs. From a receptive to a postpollinated state, figs changed in their volatile composition. Some compounds disappeared or decreased in amount. These include linalool, linalool oxide, α-terpeneol, and 2,6-dimethyl-1,7-octadiene-3,6-diol, which may act as the attractants of the wasps. Others increased in amount, or several additional chemicals appeared. These include dibutyl phthalate, 1-hydroxylinalool, and benzyl alcohol, which may be repellents of the wasps. That dichloromethane extracts of male and female receptive figs showed similar activities in attracting fig wasps indicates that receptive figs of both sexes are similarly attractive to fig wasps, which is further supported by their similar volatile composition. Leaf extract was not attractive to the wasps.

Responses of the pollinating wasp Ceratosolen solmsi marchali to odor variation between two floral stages of Ficus hispida.

During development of figs on Ficus hispida, only the female floral stage is receptive to its pollinator Ceratosolen solmsi marchali. After this stage, the quantity of fig odor decreases. The effects of F. hispida volatiles from receptive figs (figs at the female floral stage, when they are pollinated) and interfloral figs (between the female floral and male floral stages) on their pollinator were studied, together with responses to compounds present in the odor. Odors emitted by both receptive and interfloral figs were attractive to the pollinator. However, wasps preferred the odor of receptive figs to that of interfloral figs even though the quantity of interfloral volatiles increased. Three monoterpenes that included linalool (major constitutent) and two minor compounds limonene and β-pinene from the receptive fig volatiles were used to test the pollinator responses. The levoisomer and racemic mixtures of linalool were attractive to the pollinator at high doses, but the dextroisomer was neutral. (±)-Limonene and (−)-β-pinene at high doses were even less attractive to the pollinator than clean air and were neutral at low doses, while (R)-(+)-, (S)-(−)-limonene were neutral at all doses. In blend tests, all four mixtures of (±)-linalool or (S)-(−)-linalool combined with (±)-limonene or (−)-β-pinene attracted C. solmsi marchali when administered at high doses. (R)-(+)-linalool and (−)-β-pinene enhanced the attractiveness of (S)-(−)-linalool to the pollinator, while enantiomers of limonene did not. These results suggest that both quality and quantity of fig volatiles regulate C. solmsi marchali response and that quality is the main host-finding and floral stage-distinguishing cue for the pollinator. Synergistic effects of some compounds may play a role in enhancing attractiveness of the active compounds.

Antimicrobial anthraquinones from Morinda angustifolia

Investigation on Morinda angustifolia resulted in the isolation of a new anthraquinone, 1,8-dihydroxy-2-methyl-3,7-dimethoxyanthraquinone (1), along with five known analogues, lucidin 3-O-beta-primeveroside (2), 1,3-dihydroxy-2-methylanthraquinone (3), lucidin- omega -ethyl ether (4), lucidin-omega-butyl ether (5) and damnacanthol (6). The new compound demonstrated significant antimicrobial activity against Bacillus subtilis, Escherichia coli, Micrococcus luteus, Sarcina lutea, Candida albicans and Saccharomyces sake.

Chemical constituents and anti-inflammatory activities of Maqian ( Zanthoxylum myriacanthum var. pubescens ) bark extracts

In this study, 44 compounds in the petroleum ether extract of Maqian (Zanthoxylum myriacanthum var. pubescens) bark, a traditional Dai herbal medicine, were identified by GC-MS. Major components included 3(2H)-benzofuranone, asarinin and (dimethoxymethyl)-3-methoxy-benzene. A total of 18 compounds were isolated from the ethyl acetate extracts of Maqian bark by column chromatography and identified by chemical and spectral analyses. Rhoifoline B, zanthoxyline dimethoxy derivative, N-nortidine, nitidine, decarine are the major alkaloids. Both the petroleum ether and ethyl acetate extracts showed significant inhibition on NO production, which imply anti-inflammatory activity, in lipopolysaccharide-induced RAW 264.7 cells without cell toxicity. Decarine is the major anti-inflammatory constituent with NO IC50 values of 48.43 μM on RAW264.7 cells. The petroleum ether extract, the ethyl acetate extract and decarine showed anti-inflammatory activities through inhibiting TNF-α and IL-1β production in lipopolysaccharide-stimulated THP-1 cells without cell toxicity too. Decarine showed anti-inflammatory activity on human colon cells by reducing IL-6 and IL-8 production in TNF-α+IL-1β-induced Caco-2 cells. These results support the use of Maqian bark as a remedy for enteritis and colitis recorded by Dai medicine in China, and elucidate the major pharmacological compounds in Maqian bark.

Two new triterpenoid glycosides from the leaves of Anthocephalus chinensis

Nine compounds were isolated from the leaves of Anthocephalus chinensis by column chromatography on silica gel and Sephadex LH-20, and their structures were elucidated by spectroscopic techniques as clethric acid-28-O-β-d-glucopyranosyl ester (1), mussaendoside T (2), β-stigmasterol (3), hederagenin (4), ursolic acid (5), clethric acid (6), 3β,6β,19α,24-tetrahydroxyurs-12-en-28-oic acid (7), mussaendoside I (8), and cadambine (9). Compounds 1 and 2, and 7 and 8 were isolated from the plants of this genus for the first time, and compounds 1 and 2 were new triterpenoid glycosides.

Anticancer Activity of Tirucallane Triterpenoids from Amoora dasyclada

A new tetranortriterpene 3α-acetoxy-24,25,26,27-tetranortirucalla-7-ene-23(21)-lactone (3), and eleven other compounds were isolated from the twigs of Amoora dasyclada. The structure of compound 3 was identified on the basis of spectroscopic data, and the bioactive experiments of 1 and 3-5 against AGZY 83-a (human lung cancer cells) and SMMC-7721 (human liver cancer cells) are documented. Among them, compound 5 exhibited a strong activity against SMMC-7721.

A new isoflavone glycoside from Pueraria alopecuroides

A new isoflavone glycoside, (−)-tuberosin-3-O-β-D-glucopyranoside (1), along with 10 known compounds 1a-10, was isolated from Pueraria alopecuroides. Their structures were determined on the basis of spectral data including 1D and 2D NMR and HREIMS. These compounds were isolated from this plant for the first time.

One new flavonoid from Oroxylum indicum

One new flavonoid, 5,6,7-trimethoxyflavone-8-O-β-d-glucopyranoside (1), along with six known compounds 2–7, was isolated from Oroxylum indicum. Their structures were determined on the basis of spectral data. The antibacterial activities of compounds 1–4 were studied. Compounds 1 and 3 showed medium antibacterial activity against Staphylococcus aureus with MIC/MBC at 32–128 μg/ml.

Chemical Constituents of Afzelia xylocarpa

Afzelia belongs to the family Leguminosae, which has about 14 species and is distributed in the tropical regions of Africa and Asia [1, 2]. Afzelia xylocarpa (Kurz) Craib has been widely used as an important folk medicine by the Dai people to treat toothache and eye diseases [3]. According to the literatures, plants of this genus exhibited antioxidant [4], antidiabetic [5], antimicrobial [6], and anti-inflammatory [6] activities. The chemical investigations on Afzelia plants have revealed the presence of six flavonoids from Afzelia bella Harms var. glacicolor [7] and Afzelia doussie [8], and a novel xyloglucan from Afzelia africana Se. Pers [9]. However, no phytochemical investigation has been reported on A. xylocarpa. In order to reveal the chemical basis, we carried out an extensive chemical investigation on A. xylocarpa. The air-dried powder of the branches and leaves of A. xylocarpa (5.0 kg) was extracted with 90% MeOH at room temperature to give the crude extract, which was fractionated on silica gel, MCI gel, Sephadex LH-20, and RP-C18 columns to yield 12 compounds. All compounds (1–12) were identified by means of spectroscopic methods as well as comparison with literature data, including NMR. NMR spectra were acquired on a Bruker DRX-600 spectrometer, operating at 600 (1H) and 150 (13C and DEPT) MHz. Compound 1, C13H22O4, white amorphous powder. 1H NMR (600 MHz, CD3OD, , ppm, J/Hz): 1.48 (1H, ddd, J = 12.1, 4.4, 2.0, Heq-2), 1.66 (1H, t, J = 12.1, Hax-2), 4.09 (1H, m, H-3), 1.80 (1H, ddd, J = 12.9, 4.8, 2.0, H-4), 1.74 (1H, t, J = 12.9, H-4), 7.40 (1H, d, J = 16.3, H-7), 6.35 (1H, d, J = 16.3, H-8), 2.31 (3H, s, H-10), 1.27 (3H, s, H-11), 0.85 (3H, s, H-12), 1.11 (3H, s, H-13). 13C NMR (150 MHz, CD3OD, , ppm): 41.4 (C-1), 46.4 (C-2), 65.2 (C-3), 45.6 (C-4), 77.7 (C-5), 80.0 (C-6), 132.4 (C-7), 153.0 (C-8), 201.3 (C-9), 26.4 (C-10), 27.6 (C-11), 27.1 (C-12), 27.4 (C-13). Based on the NMR spectral data and their comparison with those reported in the literature, 1 was identified as (3S,5R,6R,7E)-3,5,6-trihydroxy-7megastigmen-9-one [10]. Compound 3, C21H20O11, yellow needle crystals. Based on the NMR spectral data and their comparison with those reported in the literature, 3 was identified as kaempferol-7-O-D-glucopyranoside [11]. Compound 5, C30H50O, white needle crystals. Based on the NMR spectral data and their comparison with those reported in the literature, 5 was identified as friedelin [12]. Compound 7, C29H48O, white needle crystals. Based on the NMR spectral data and their comparison with those reported in the literature, 7 was identified as -sitosterol [13].

Two new lignans from Saururus chinensis

Abstract Two new lignans, (Z)-14-bis(3′,4′-dimethoxyphenyl)-2,3-dimethylbut-2-ene-1,4-dione (1), threo-2-methyl-3-oxo-1-(3′,4′,5′-trimethoxyphenyl)butyl-3″,4″-dimethoxybenzoate (2), together with 15 known derivatives (3–17) were isolated from Saururus chinensis. Their structures were determined on the basis of spectral data, including 1D and 2D NMR experiments and HREIMS spectra. The antitumour activity was screened by MTT assay, compounds 1, 2, 3, 5, 9–11 and 13–15 showed no cytotoxic activity against HL-60, SMMC-7721, A549, MCF-7 and SW480 cell lines.