Two phenolic constituents from Alpinia galanga rhizomes

Chemical investigation of the chloroform extract of the rhizomes of Alpinia galanga yielded p-hydroxycinnamaldehyde and [di-(p-hydroxy-cis-styryl)] methane. The former is isolated for the first time in nature and the latter is a new chemical component. These compounds were characterized from spectral studies and chemical reactions.     

Bioassay-guided fractionation of a dried commercial source,Alpinia galanga (L.) Willd rhizomes extract,against Culex pipiens (Diptera: Culicidae)

The increasing risk of insecticide resistance in mosquito populations has led to the search for new larvicidal agents. Evaluation of bioassay-guided fractionation of the rhizome extract of Alpinia galanga (L.) Willd against Aedes aegypti was assessed. Bioactive fractions were isolated from the rhizome extract of A. galanga using a Soxhlet extractor and chromatography techniques, and subsequently tested against the fourth instar of Culex pipiens. The lethal concentration (LC) was calculated via log-probit analysis. The active fraction was evaluated by gas chromatography-mass spectroscopy (GC–MS) and infrared (IR) analysis. The highest larvicidal potential obtained from bioassays using the Soxhlet apparatus was observed in dichloromethane (DCM) and ethyl acetate (EtoAc) extracts, with LC₅₀ values of 124.49 and 176.30 ppm, respectively, after 24 h of exposure. Subsequently, the DCM extract was subjected to column and thin-layer chromatography. Results of the DCM extraction and the active TLC fraction (F133) of the Rf value 0.5 revealed that LC₅₀ and LC₉₀ values decreased over time. The F133 fraction of A. galanga exhibited zero hatchability (100% mortality) at LC₅₀ (63.416 ppm) and LC₂₅ (31.70 ppm) against Cx. pipiens eggs. GC–MS analysis of the active thin-layer chromatography TLC fraction (F133) revealed the presence of phenol 2 4-bis (1 1-dimethylethyl), which was identified as the major compound. Alpinia galanga extract is a promising candidate for the control of mosquito populations. Further study is required to determine the effect of the extracts on non-target organisms.     

A protocol for micropropagation of Alpinia galanga

Emerging buds of rhizome of Alpinia galanga Willd produced shoots and roots simultaneously when cultured in MS medium supplemented with kinetin 3.0 mg l^-1. Each explanted shoot bud produced 8 shoots in average and roots simultaneously within 8 weeks. Shoot proliferation could be continued even after a year by transferring each divided shoot explant to the same medium. Regenerated plantlets could be sucessfully transferred to soil where they grew well within 10–12 weeks with 80% survivality. This revised version was published online in June 2006 with corrections to the Cover Date.     

驱虫斑鸠菊的组织培养与快速繁殖

1 植物名称驱虫斑鸠菊[Vernonia anthelmintica (Linn.)Willd.],别名:印度山茴香. 2 材料类别果实. 3 培养条件以MS为基本培养基.芽诱导培养基为:(1)1/2MS;继代增殖培养基为:(2)MS+BA1.0 mg·L-1+NAA 0.2:(3)MS+BA 1.0+NAA 0.5:(4)MS+6-BA 1.0+NAA 1.0;生根培养基为:(5)MS+NAA 0.1;(6)1/2MS+NAA 0.5.     

Antioxidative compounds isolated from the rhizomes of smaller galanga (Alpinia officinarum Hance)

Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1-7) were obtained and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, (E)-p-coumaryl alcohol gamma-O-methyl ether (1) and (E)-p-coumaryl alcohol (6); and the five novel compounds, stereoisomers of (4E)-1,5-bis(4-hydroxy-phenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxy-phenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-1,5-bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (7). Compounds 1-7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bulk phase.     

Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells

The 80% aqueous acetone extract of the rhizomes of Alpinia galanga was found to inhibit release of beta-hexosaminidase, as a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells. Nine known phenylpropanoids and p-hydroxybenzaldehyde were isolated from the extract. Among them, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate exhibited potent inhibitory activity with IC(50) values of 15 and 19 microM. From the effects of various related compounds, both the 1'- and 4-acetoxyl groups of 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate were essential for their strong activity, and the 2'-3' double bond enhanced the activity. In addition, 1'S-1'-acetoxychavicol acetate and 1'S-1'-acetoxyeugenol acetate inhibited ear passive cutaneous anaphylaxis reactions in mice and the antigen-IgE-mediated TNF-alpha and IL-4 production, both of which participate in the late phase of type I allergic reactions, in RBL-2H3 cells.     

A New Monoterpene from the Rhizomes of Alpinia galanga and Its Anti-Vpr Activity

A new menthane-type monoterpene, alpigalanol ( 1 ), together with four known terpenes ( 2 – 5 ) were isolated from the ethyl acetate soluble fraction of the 70 % ethanol extract of the Alpinia galanga rhizomes. The structure of 1 was determined by spectroscopic analyses, including 1D- and 2D-NMR. The extract of the A. galanga rhizomes and all isolated compounds ( 1 – 5 ) possessed Vpr inhibitory activities against the TREx-HeLa-Vpr cells at a concentration of 1.25 μM without showing any cytotoxicity.     

Impact of Alpinia galanga rhizome extract on Bactrocera dorsalis population

The Bactrocera dorsalis (Hendel) is one of the most economically damaging pests and generally is controlled by insecticides. This research was done by evaluate the impact of rhizomes of Alpinia galanga extract on population of B. dorsalis. The rhizome of A. galanga was extracted by Soxhlet's apparatus using hexane, dichloromethane, ethyl acetate and 95% ethanol as separated solvent system. Various concentrations of all crude extracts were trailed by Topical spray application with adult B. dorsalis, completely randomized designs, 5 replicates. The results showed hexane crude extract gave the highest control efficiency to adult B. dorsalis which the 24 hours-LC50 values was 4,866.06 +/- 184.52 ppm (hexane), 24,156.66 +/- 880.33 ppm (dichloromethane), 16,744.73 +/- 641.27 ppm (ethyl acetate) and 6,337.54 +/- 145.42 ppm (95% ethanol). Thus, this extract may an alternative way for control this insect pest in the future.     

Autonomous Self pollination under Dominant Flexistylous Outcorssing Mechanism in Alpinia galanga (Zingiberaceae)

Autonomous self pollination is considered to be a reproductive assurance mechanism for plants when facing extreme environments that scarce in pollinators, and it also has disadvantages like inbreeding depression and pollen/ovule discounting. In several genera of Zingiberaceae like Alpinia and Amomum, a specialized mechanism named flexistyly exists, precedent studies consider its significance as preventing unnecessary self pollination and sexual interference. However according to our field observation, if pollen grains on cataflexistylous (CATA) flowers remain on the anther when the style curves downwardly, potential exists that the stigma contacts the pollen, thus autonomous self pollination occurs. Here, we studied the breeding system of Alpinia galanga, the results show that (1) Alpinia galanga is self compatible in which inbreeding depression occurs to some degree; (2) The anaflexistylous (ANA) morph of Alpinia galanga allocates more resource into outcrossing than the CATA morph; (3) The P/O ratio of the ANA morph is significantly lower than that of the CATA morph, as Alpinia galanga has constant six ovules in each ovary, the significant difference in P/O value reflects the contrast in pollen production. This phenomenon may be interpreted as the ANA morph provides pollen exclusively for the CATA morph. But the CATA morph, despite delivers pollen to the ANA morph, also need its own pollen for potential autonomous self pollination. In summary, autonomous self pollination exists in Alpinia galanga, and while flexistyly functions to avoid unnecessary self pollination and sexual interference, it also provides advantages for delayed autonomous self pollination as a necessary reproductive assurance and preventing conflict among these three major features by controlling the time of autonomous self pollination. This peculiar mechanism in Alpinia galanga thoroughly demonstrates its adaptation to unfavorable surrounding during the evolutionary process.     

Labdane Diterpenoids from Coleus forskohlii （Willd.） Briq.

in order to investigate the active substances of Coleus forskohlii（Wiiid.） Brlq., a new labdane dlterpenold, 12- hydroxy-8,13E-labdadlen-15.olc acid, together with two 8,13-epoxylabd-14-ene-11-one dlterpenolds, 6-acetyl-1- deoxyforskolln and 6-acetyl-1,9-dldeoxyforskolln, was Isolated on the basis of various chromatographic technlques and spectroscopic methods.     

Alpha-amylase inhibitors from roselle (Hibiscus sabdariffa Linn.) tea

A roselle (Hibiscus sabdariffa Linn.) tea extract was found to have high inhibitory activity against porcine pancreatic alpha-amylase. Hibiscus acid and its 6-methyl ester were respectively isolated as active principles from the 50% methanol and acetone extracts of roselle tea. The activity of each isolate was compared to that of structurally related citric acid, a previously known inhibitor of fungal alpha-amylase.     

Halogenated analogs of 1′-acetoxychavicol acetate,Rev-export inhibitor from Alpinia galanga,designed from mechanism of action

In the course of search for the robust analogs of 1′-acetoxychavicol acetate (ACA, 1), the Rev-export inhibitor from the medicinal plant Alpinia galanga, we clarified formation of the quinone methide intermediate ii to be essential for exerting the inhibitory activity of 1. Based on this mechanism of action, the rational design from the MO calculation of the conclusive activation energy to ii resulted in the four halogenated analogs with more potent activity than ACA (1). In particular, the difluoroanalog 20d exhibited approximately four-fold potent activity as compared with 1.     

Isolation and identification of trans-2- and trans-3-hydroxy-1,8-cineole glucosides from Alpinia galanga

Three hydroxy-1,8-cineole glucopyranosides, (1R, 2R, 4S)- and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-D-glucopyranosides, and (1R, 3S, 4S)-trans-3-hydroxy-1,8-cineole beta-D-glucopyranoside, which are possible precursors of acetoxy-1,8-cineoles as unique aroma components, were isolated from the rhizomes of greater galangal (Alpinia galanga W.). Their structures were analyzed by FAB-MS and NMR spectrometry, and the absolute configulation of each aglycone was determined by using a GC-MS analysis with a capillary column coated with a chiral stationary phase. The composition of the diastereomers of (1R, 2R, 4S)- and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-D-glucopyranosides in the rhizomes was determined as 3:7 by a GC-MS analysis after preparing the trifluoroacetate derivatives of the glucosides.     

Isolation and Identification of trans-2- and trans-3-Hydroxy-1,8-cineole Glucosides from Alpinia galanga

Three hydroxy-1,8-cineole glucopyranosides, (1R,2R,4S)- and (1S,2S,4R)-trans-2-hydroxy-1,8-cineole β-D-glucopyranosides, and (1R,3S,4S)-trans-3-hydroxy-1,8-cineole β-D-glucopyranoside, which are possible precursors of acetoxy-1,8-cineoles as unique aroma components, were isolated from the rhizomes of greater galangal (Alpinia galanga W.). Their structures were analyzed by FAB-MS and NMR spectrometry, and the absolute configulation of each aglycone was determined by using a GC-MS analysis with a capillary column coated with a chiral stationary phase. The composition of the diastereomers of (1R,2R,4S)- and (1S,2S,4R)- trans-2-hydroxy-1,8-cineole β-D-glucopyranosides in the rhizomes was determined as 3:7 by a GC-MS analysis after preparing the trifluoroacetate derivatives of the glucosides.     

Cytotoxic isoflavonoids from the roots of Desmodium velutinum (Willd.) DC

A phytochemical investigation on the roots of Desmodium velutinum (Willd.) DC. afforded five pterocarpans, desmovelutins A–E and two isoflavans, desmovelisoflavans A and B, together with seven known compounds. Their structures were established by spectroscopic methods. Several isolated compounds were evaluated for their cytotoxic activities against four human cancer cell lines (A549, HepG2, HuCCA-1, and MOLT-3). Desmovelutin D, desmovelisoflavan A, 1-methoxyerythrabyssin II, gangetin, gangetial, and desmodin showed significant cytotoxicity against MOLT-3 cells with IC₅₀ values in the range of 3.4‒27.9 μM.     

Antileishmanial activity of a guaianolide from Tanacetum parthenium (L.) Schultz Bip

Leishmaniasis is one of the major infectious diseases affecting the poorest regions of the world. The present study evaluated the antileishmanial activity of a guaianolide purified from the hydroalcoholic extract of aerial parts of Tanacetum parthenium (L.) Schultz Bip. The isolated compound showed activity against the promastigote form of Leishmania amazonensis, with 50% inhibition (IC₅₀) of cell growth at a concentration of 2.6 μg/ml. For the intracellular amastigote form, this guaianolide reduced by 10% the survival index of parasites in macrophages when it was used at 20.0 μg/ml. The selective index (SI) ratio (CC₅₀ for J774G8 cells/IC₅₀ for protozoans) was 385, showing that it is more selective against the parasite than mammalian cells. Morphological alterations of protozoans treated with IC₅₀ included changes in size, shape, and structure (more than one nucleus and flagellum) under both light and scanning electron microscopies.     

Acaricidal potential of active components derived from Alpinia galanga rhizome oils and their derivatives against Haemaphysalis longicornis (Acari: Ixodidae)

Acaricidal activities and acetylcholinesterase (AChE) inhibitory activities were evaluated of active constituents of the essential oil extracted from Alpinia galanga rhizomes cultivated from India and their derivatives against Haemaphysalis longicornis nymphs. In addition, the effect was investigated of active components of A. galanga oil on egg laying of adult females of H. longicornis and egg hatchability. Of the volatile components identified in A. galanga oil, ethyl cinnamate, ethyl methoxycinnamate, and methyl cinnamate at 0.32 mg/cm² resulted in 100% mortality, respectively, indicating that the acaricidal activity of the A. galanga oil against H. longicornis nymphs could be attributed to these compounds. To evaluate the structure–activity relationship between cinnamate derivatives and their acaricidal activities, allyl cinnamate, benzyl cinnamate, isopropyl cinnamate, isobutyl cinnamate, and isoamyl cinnamate were selected. Among cinnamate derivatives tested, allyl cinnamate exhibited the most potent toxicity (LC₅₀?=?0.055 mg/cm²) against H. longicornis nymphs. The allyl cinnamate was also tested for AChE activity in vivo in H. longicornis nymphs and was found to affect the AChE activity. Allyl cinnamate at 10–50 mg/mL inhibited egg laying of adult females of H. longicornis by 10–43%. Egg hatching was suppressed completely by treatment with allyl cinnamate at 50 mg/mL, whereas allyl cinnamate was minimally toxic against non-target earthworms, Eisenia fetida. These results suggest that allyl cinnamate can be used as an active ingredient for the development of eco-friendly tick acaricides against H. longicornis, a vector for Sever fever with thrombocytopenia syndrome (SFTS) virus.