Sesquiterpenes are the major pharmacodynamic components of agarwood,a precious traditional Chinese medicine obtained from the resinous portions of Aquilaria sinensis trees that form in response to environmental stress...Sesquiterpenes are the major pharmacodynamic components of agarwood,a precious traditional Chinese medicine obtained from the resinous portions of Aquilaria sinensis trees that form in response to environmental stressors.To characterize the sesquiterpene synthases responsible for sesquiterpene production in A.sinensis,a bioinformatics analysis of the genome of A.sinensis identifi ed six new terpene synthase genes,and 16 sesquiterpene synthase genes were identifi ed as type TPS-a in a phylogenetic analysis.The expression patterns for eight of the sesquiterpene synthase genes after treatment with various hormones or hydrogen peroxide were analyzed by real-time quantitative PCR.The results suggest that 100μM methyl jasmonate,ethephon,(±)-abscisic acid or hydrogen peroxide could be eff ective short-term eff ectors to increase the expression of sesquiterpene synthase genes,while 1 mM methyl salicylate may have long-term eff ects on increasing the expression of specifi c sesquiterpene synthase genes(e.g.,As-SesTPS,AsVS,AsTPS12 and AsTPS29).The expression changes in these genes under various conditions refl ected their specifi c roles during abiotic or biotic stresses.Heterologous expression of a novel A.sinensis sesquiterpene synthase gene,AsTPS2,in Escherichia coli produced a major humulene product,so AsTPS2 is renamed AsHS1.AsHS1 is diff erent from ASS1,AsSesTPS,and AsVS,for mainly producingα-humulene.Based on the predicted space conformation of the AsHS1 model,the small ligand molecule may bind to the free amino acid by hydrogen bonding for the catalytic function of the enzyme,while the substrate farnesyl diphosphate(FPP)probably binds to the free amino acid on one side of the RxR motif.Arg450,Asp453,Asp454,Thr457,and Glu461 from the NSE/DTE motif and D307 and D311 from the DDxxD motif were found to form a polar interaction with two Mg^(2+)clusters by docking.The Mg^(2+)-bound DDxxD and NSE/DTE motifs and the free RXR motif are jointly directed into the catalytic pocket of AsHS1.Comparison of the tertiary structural models of AsHS1 with ASS1 showed that they diff ered in structures in several positions,such as surrounding the secondary catalytic pocket,which may lead to diff erences in catalytic products.Based on the results,biosynthetic pathways for specifi c sesquiterpenes such asα-humulene in A.sinensis are proposed.This study provides novel insights into the functions of the sesquiterpene synthases of A.sinensis and enriches knowledge on agarwood formation.展开更多
Agarwood, the resinous product of Aquilaria spp.(Thymelaeaceae), is highly valued for medicinal and fragrant purposes. Unsustainable forest harvesting contributes to the declining population in the wild, threatening t...Agarwood, the resinous product of Aquilaria spp.(Thymelaeaceae), is highly valued for medicinal and fragrant purposes. Unsustainable forest harvesting contributes to the declining population in the wild, threatening their existence. As a protection effort, cultivation occurred in range countries, mainly in Asia, effectively establishing mass plantations. The success of domesticating Aquilaria relies heavily on technological advancement in agarwood induction, without which the entire thriving industry will collapse. In this paper, we describe efforts since 1929 and current progress and variation in induction as practiced in Asia. The methods include traditional practices and artificial induction via inoculum and chemical inducer, experimented and patented or otherwise. Artificial induction methods are being developed to intensify agarwood production in terms of yield and quality. While traditional methods are commonly applied by rural planters, artificial methods with the use of specific agents/chemicals are seen as more appealing for inducing agarwood, and have a higher demand from entrepreneurs and plantation owners.Several issues related to induction technology faced by stakeholders in agarwood cultivation are presented, such as safety levels, cost, yields, and quality. We conclude by highlighting remaining challenges in induction methods and their associated technologies.展开更多
Pollination and seed dispersal in angiosperms have long been investigated in order to understand the coevolution of plants and animals.However,the signals from flowers and/or seeds to attract pollinators and/or seed d...Pollination and seed dispersal in angiosperms have long been investigated in order to understand the coevolution of plants and animals.However,the signals from flowers and/or seeds to attract pollinators and/or seed dispersers have received comparatively little attention.In this study,the pollination biology and seed dispersal of the vulnerable agarwood plant Aquilaria sinensis(Lour.) Gilg,a traditional medicinal plant in China,was studied in its natural distribution range.The reproductive tactics of A.sinensis were studied in detail by employing various tests dealing with fruit set and also seed dispersal.Dynamic headspace extraction followed by GC-MS analysis was also performed in order to reveal the composition of floral scent.The results showed that noctuids and pyralids are the most effective pollinators of pollinator-dependent A.sinensis.The main compounds of the floral scent were(E,E)-α-Farnesene(61.9 ± 3.2%),trans-Ocimene(16.6 ± 1.2%),and Benzyl salicylate(4.6 ± 1.1%).The results obtained from seed dispersal experiments indicate that hornets are effective seed dispersers and they may play an important role in long-distance seed dispersal of A.sinensis.Based on our findings,we recommend several protection methods for this threatened agarwood plant in China.展开更多
Aquilaria agallocha can produce fragrant agarwood used for incense, traditional medicine and other products. An efficient plant regeneration system was established via organogenesis from shoots developed from seedling...Aquilaria agallocha can produce fragrant agarwood used for incense, traditional medicine and other products. An efficient plant regeneration system was established via organogenesis from shoots developed from seedlings of Aquilaria agallocha. Shoots generated many buds on MS medium supplemented with 1.3 μmol/L BA （6-benzylaminopurine） in the first 7 weeks, and the buds elongated on MS medium with 1.3 μmol/L BA＋0.5 μmol/L NAA （naphthaleneacetic acid） in another 7 weeks, 2.3 shoots 2 cm in length per explant were obtained within 14 weeks. Plantlets were rooted on l/2 MS medium after being immersed in 5 μmol/L NAA for 48 h, 96.7% of the roots grew up two weeks later. All plantlets that survived acclimatization grew well in the pots.展开更多
A new sesquiterpenoid,named baimuxifuranic acid,has been isolated from the volatile oil of Aquilaria sinensis(Lour.)Gilg.belonging to the family Thymelaceae by silica gel column chromatography.Based on spectral analys...A new sesquiterpenoid,named baimuxifuranic acid,has been isolated from the volatile oil of Aquilaria sinensis(Lour.)Gilg.belonging to the family Thymelaceae by silica gel column chromatography.Based on spectral analysis its structure was deduced as(1).Reduction of baimuxifuranic acid by LiAlH_4 gave a展开更多
Three cDNA clones encoding δ-guaiene synthase, a sesquiterpene cyclase, were isolated from tissue cultures of Aquilaria microcarpa, and data mining analysis of the orthologous genes suggested that 10 and 9 amino acid...Three cDNA clones encoding δ-guaiene synthase, a sesquiterpene cyclase, were isolated from tissue cultures of Aquilaria microcarpa, and data mining analysis of the orthologous genes suggested that 10 and 9 amino acid residues of N- and C-terminal ends of the translated products of these clones remained undefined. The recombinant enzyme proteins, to which the putative missing Nand C-terminal amino acid sequences (MSSAKLGSAS and ALLRHAIEI, respectively) were ligated, exhibited the catalytic activities of sesquiterpene biosynthesis. Among these three δ-guaiene synthases, two isoforms were capable of liberating α-guaiene, δ-guaiene, β-elemene plus α-humulene as a minor product, while remaining one isoenzyme generated α-, δ-guaiene and β-elemene but not α-humulene. Although the enzyme protein solely lacking in the N-terminal 10 amino acid residues was capable of synthesizing the sesquiterpenoids, the protein without 9 amino acids at Cterminal did not exhibit the catalytic activity. These results suggest that two types of δ-guaiene synthase;α-, δ-guaiene, β-elemene-producing type, and α-, δ-guaiene, β-elemene plus α-humulene-producing type;concomitantly occur in A. microcarpa cell cultures, and several amino acid residues at C-terminal of the synthase protein are essential to exhibit the catalytic activities as the sesquiterpene cyclase.展开更多
We studied seedling survival and growth ofAquilaria malaccensis in three different environmental conditions （homegardens, green house and in different canopy conditions） of northeast India. Results show that mean se...We studied seedling survival and growth ofAquilaria malaccensis in three different environmental conditions （homegardens, green house and in different canopy conditions） of northeast India. Results show that mean seasonal survival was highest in green house （95.53%±2.33）, followed by homegardens （89.3%±1.89） and different canopy conditions （77.62%±6.73）; the highest values were found during February to April for both the homegardens （96%±1.68） and green house （98% ± 0.88） and lowest during November to January （78%±2.99） in homegardens and May to July （90%：t：4.53） in green house. In case of transplanted seedlings in different canopy conditions, mean seasonal survival was highest during May to July （98%±1.92） and lowest during August to October （66%±12.81）. However, mean seasonal growth of collar diameter was highest in different canopy conditions （23.99%±1.76） compared to green house （21.52%±2.70） and homegardens （12.44%±1.33） and it was highest during rainy season （May to July） and lowest during dry winter （November to January） in all the three experi- mental sites. These variations may be due to the different microclimatic conditions as well as nutrient status of the soil in all the three experimen- tal sites. Although, seedling quality plays a great role in their survival and growth, based on the result of green house experiment, it can be concluded that maintenance of seedlings in green house conditions during their early growth period may improve both the survival and growth for large scale plantation of the species. Thus, the species can be reintroduced in its natural forest range to compensate the loss of natural population of this precious species in northeast India.展开更多
This study aimed to model the kinetic of hydro-distillation of Aquilaria malaccensis leaves oil in order to understand and optimize the extraction process. In addition, this study, for the first time, aimed to identif...This study aimed to model the kinetic of hydro-distillation of Aquilaria malaccensis leaves oil in order to understand and optimize the extraction process. In addition, this study, for the first time, aimed to identify the chemical compositions of the A. rnalaccensis leave-oil. By assessing both first-order kinetic model and the model of simultaneous washing and diffusion, the result indicated that the model of simultaneous washing and diffusion better describes the hydro-distillation mechanism of the essential oil from A. rnalaccensis leaves. The optimum time, solid to liquid ratio, and the heating power for extracting the highest amount of essential oil were found to be around 3 h, 1：10 （g. ml-1）, and 300 W respectively. Yellow essential oil with a strong smell and a yield of 0.05 v/w was extracted by hydro-distillation Clevenger apparatus. Chemical compounds of the essential oil were analyzed using gas chromatography-mass spectroscopy （GC/MS）, which resulted in identification of 42 compounds that constitute 93% of essential oil. Among the identified components, Pentadecanal （32.082%）, 9-Octadecenal, （Z） （15.894%）, and Tetradecanal （6.927%） were the major compounds. Considering the fact that all the identified major components possess pesticidal properties, A. malaccensis leaves can be regarded as a promising natural source for producing pesticides.展开更多
One novel spirolactone,aquilarisinolide(1),three new sesquiterpenoids,(2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one(2),(1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one(3),and(4R,5S,7R,8S,10S,13R)-8,13-dihydrox...One novel spirolactone,aquilarisinolide(1),three new sesquiterpenoids,(2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one(2),(1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one(3),and(4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one(4),together with 13 known compounds(5-17)were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra.The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone(CORT)and 1-methyl-4-phenylpyridine ion(MPP+),as well as inhibitory activities against BACE1.Compound 4,5,6-dihydroxy-2-(2-phenylethyl)chromone(5),daphnauranol B(7),6-methoxy-2-[2-(3-methyoxyphenyl)ethyl]chromone(10),isoagarotetrol(14),and 1-hydroxy-1,5-diphenylpentan-3-one(16)showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20μM(P<0.001).Isoagarotetrol(14)showed a significant protective effect on MPP+-induced injury in PC12 cells at a concentration of 20μM(P<0.001),while compound 4 showed a moderate activity(P<0.01).The BACE1-inhibitory activities of all tested compounds were very weak with less than 30%inhibition at a concentration of 20μM.展开更多
Aquilaria sinensis(Thymelaeaceae)is widely cultivated in southern China for its significant medicinal usage.The resinous wood,the most used part of the plant as traditional Chinese medicine(TCM),locally called“Chen X...Aquilaria sinensis(Thymelaeaceae)is widely cultivated in southern China for its significant medicinal usage.The resinous wood,the most used part of the plant as traditional Chinese medicine(TCM),locally called“Chen Xiang(沉香)”or Chinese agarwood,has been traditionally used for the treatment of circulatory disorders,abdominal pain,vomiting,and dyspnea.Till date,over 249 compounds have been isolated and identified from this plant.A range of bioactivities,including α-glucosidase inhibitory effects,anti-inflammatory,cytotoxicity,neuroprotective,anti-neuroinflammatory,antimicrobial and acetylcholinesterase inhibitory effects,along with some of the pharmacological mechanisms have been reported for the pure compounds or extracts of Aquilaria sinensis.For the purpose of quality control and clinical safety of drug usage,modern analytical instruments and chemical analysis methods have been applied for analyses of Aquilaria sinensis.In order to comprehensively understand the medicinal application and to fully utilize the plant,a literature search on the herb based on databases including SciFinder,Web of Science,Pubmed,Google Scholar and others was performed and the information regarding to the phytochemistry investigations,pharmacological studies and quality control was summarized in this paper.展开更多
Initially,Chen Xiang(沉香Lignum Aquilariae Resinatum)was exotic,but it has been playing an important role in the development of traditional Chinese culture and medicine.This article explores the reason for differences...Initially,Chen Xiang(沉香Lignum Aquilariae Resinatum)was exotic,but it has been playing an important role in the development of traditional Chinese culture and medicine.This article explores the reason for differences in the quality of ancient and modern Chen Xiang(沉香Lignum Aquilariae Resinatum)by analyzing the essential factors including the prosperity and decline of Maritime Silk Road,the relocation of the producing area,and the process of aroma forming.Based on the development and application of Chen Xiang(沉香Lignum Aquilariae Resinatum)in Chinese literature and art,traditional Chinese medicine,and folk life over the past 2000-odd years,this article puts contends that Chen Xiang(沉香Lignum Aquilariae Resinatum),which is endowed with the connotation of Chinese culture and health,should assume its new role as the traditional Chinese medical and cultural carrier on the New Silk Road.展开更多
The article "Dynamic analysis of gene expression and determination of chemicals in agarwood in Aquilaria sinensis",written by Zeqing Wu,Wanzhen Liu,Jing Li,Liangwen Yu and Li Lin was originally published ele...The article "Dynamic analysis of gene expression and determination of chemicals in agarwood in Aquilaria sinensis",written by Zeqing Wu,Wanzhen Liu,Jing Li,Liangwen Yu and Li Lin was originally published elec-tronically on the publisher’s internet portal(currently SpringerLink)on 10th May 2019 without open access.展开更多
Objective: To investigate the protective effects of Aristolochia longa (A. longa) and Aquilaria malaccensis (A. malaccensis) on acute hepatotoxicity induced by lead in female albino rats. Methods: Twenty five (25) app...Objective: To investigate the protective effects of Aristolochia longa (A. longa) and Aquilaria malaccensis (A. malaccensis) on acute hepatotoxicity induced by lead in female albino rats. Methods: Twenty five (25) apparently healthy female Wistar rats were randomly divided into five groups of five rats in each: control, Pb, Pb + A. longa (Ar), Pb+ A. malaccensis (Aq), and Pb+ A. longa (Ar) + A. malaccensis (Aq) lead (100 mg/kg b.w.) as Pb (C2H3O2)2 added in their drinking water for 75 days. A. longa (rhizome powder at a dose of 10 g/kg of diet ) and A. malaccensis (heartwood powder at a dose 10 g/kg of diet) were added to the feed during the last 15 days of lead exposed in the animals. Results: Obtained results revealed that lead treatment caused a significant increase in serum GOT, GPT and ALP activities and in liver of MDA level and CAT activity. In contrast, it led to an decrease in the liver GOT, GPT and GST activities and in GSH level in rats. Also, the results clearly showed that lead causes alterations of hepatic tissue in comparison with controls. Our results showed that treatment with A. malaccensis and A. longa a partial correction of the previous parameters. The histological observations confirmed the hepatoprotection results by the biochemical parameters. Conclusions: Results demonstrated beneficial effects of A. longa and A. malaccensis treatment in Pb-induced oxidative stress and tissue damage in liver.展开更多
Agarwood is a non-timber forest product found in tropical rain forests.It is a black and fragrant resin valued for the perfume industry and demand continues to increase.However,the Indonesian agarwood-producing specie...Agarwood is a non-timber forest product found in tropical rain forests.It is a black and fragrant resin valued for the perfume industry and demand continues to increase.However,the Indonesian agarwood-producing species,Aquilaria malaccensis and Gyrinops versteegii do not automatically produce such quality resin.Bio-induction technology or inoculation using Fusarium solani is usually applied to these species to trigger resin production.This research aims to identify agarwood compounds formed in seedlings and trees of A.malaccensis and G.versteegii after these species were inoculated with the fungus F.solani.The chemical compounds were identified by comparing the patterns of mass spectra fragmentation in the sample and in previous studies.Five groups of agarwood compounds were identified:(1)sesquiterpen group-cisjasmone and aromadendrenepoxide;(2)chromones group-8-methoxy-2-(2-phenylethyl)chromen-4-one and newly-discovered chromone derivative,7-(benzyloxy)-5-hydroxy-2-methylchromone found only in G.versteegii;(3)aromatic group-benzylacetone,guaiacol,p-ethylguaiacol,phenol,syringaldehyde,vanilin,furfuryl alcohol,and furfural;(4)fatty acid group-palmitic acid,oleic acid,and lauric acid;and,(5)triterpen group-squalene.展开更多
Objective: To investigate the effects of Aquilaria subintegra leaf aqueous extracts on the aphrodisiac properties including sexual behaviour, testosterone level, percentage of pregnancy, number of offspring and male t...Objective: To investigate the effects of Aquilaria subintegra leaf aqueous extracts on the aphrodisiac properties including sexual behaviour, testosterone level, percentage of pregnancy, number of offspring and male to female ratio of offspring in ICR mice. Methods: In this experiment, each male cohabitated with one female in a polysulfone cage. 30 ICR male mice were divided into 6 groups that received normal saline (the control group), 50 mg/kg, 100 mg/kg, 200 mg/kg, 500 mg/kg, and 1000 mg/kg body weight of Aquilaria subintegra leaf aqueous extracts orally for 21 days consecutively. Sexual behavior, percentage of pregnancy, number of offspring and male to female ratio of offspring in ICR mice were measured according to the established methods. Testosterone level was measured by using enzyme-linked immunosorbent assay. Results: Mice that received Aquilaria subintegra leaf aqueous extracts at 50 mg/kg body weight (day 0) had significantly higher mount frequency as compared to the control group;groups treated with 100, 500, 1000 mg/kg body weight extracts produced a greater number of offsprings when compared to the control group. All aphrodisiac parameters were similar between the treatment groups and the control group, indicating that Aquilaria subintegra leaf aqueous extract did not significantly alter the aphrodisiac parameters. Conclusions: Aquilaria subintegra leaf aqueous extracts have no effect on the aphrodisiac properties, but could increase the breeding rate in mice.展开更多
Bioassay-guided fractionation of the EtOH extract from the flowers of Aquilaria sinensis(Lour.)Spreng.(Thyme-laeaceae)led to the isolation of a new cucurbitane-type triterpenoid,aquilarolide A(1),along with five known...Bioassay-guided fractionation of the EtOH extract from the flowers of Aquilaria sinensis(Lour.)Spreng.(Thyme-laeaceae)led to the isolation of a new cucurbitane-type triterpenoid,aquilarolide A(1),along with five known compounds(2-6).The structure of 1 was elucidated by extensive 1D and 2D nuclear magnetic resonance(NMR)experiments and mass spectrometry(MS)data and theoretical calculations of its electronic circular dichroism(ECD)spectra.Aquilarolide A,cucurbitacin E(3),cucurbitacin B(4),and 7-hydroxy-6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one(6)showed significant cytotoxicity against human lung adenocarcinoma SPC-A-1,human lung squamous cell carcinoma NCI-H520,human lung adenocarcinoma A549,and paclitaxel-resistant A549(A549/Taxol)cell lines.All four active compounds,with IC_(50) values ranging from 0.002 to 0.91μM,had better inhibitory activities against A549/Taxol cells than paclitaxel(IC_(50)=1.80μM).Among them,cucurbitacin E(IC_(50)=0.002μM)is the most active.Further studies are needed to evaluate their in vivo antitumor activities and to clarify their mechanisms.展开更多
Five new 2-(2-phenylethyl)chromone derivatives,(5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol(1),(5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol(2),(6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(...Five new 2-(2-phenylethyl)chromone derivatives,(5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol(1),(5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol(2),(6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(3),(6S,7S,8R)-2-(2-phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(4),(5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone(5),three new sesquiterpenoids,(4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(6),(4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(7),and(4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(8),along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data,single-crystal X-ray diffraction analysis,and electronic circular dichroism(ECD)calculations.The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma(PC12)cell injury induced by corticosterone.At concentrations from 5 to 40μM,compounds 4 and 6,agarotetrol(9),and 6-hydroxy-2-(2-phenylethyl)chromone(17)showed significant protective activities against corticosterone-induced PC12 cell injury(P<0.001).展开更多
基金supported by the National Natural Science Foundation of China(81773844).
文摘Sesquiterpenes are the major pharmacodynamic components of agarwood,a precious traditional Chinese medicine obtained from the resinous portions of Aquilaria sinensis trees that form in response to environmental stressors.To characterize the sesquiterpene synthases responsible for sesquiterpene production in A.sinensis,a bioinformatics analysis of the genome of A.sinensis identifi ed six new terpene synthase genes,and 16 sesquiterpene synthase genes were identifi ed as type TPS-a in a phylogenetic analysis.The expression patterns for eight of the sesquiterpene synthase genes after treatment with various hormones or hydrogen peroxide were analyzed by real-time quantitative PCR.The results suggest that 100μM methyl jasmonate,ethephon,(±)-abscisic acid or hydrogen peroxide could be eff ective short-term eff ectors to increase the expression of sesquiterpene synthase genes,while 1 mM methyl salicylate may have long-term eff ects on increasing the expression of specifi c sesquiterpene synthase genes(e.g.,As-SesTPS,AsVS,AsTPS12 and AsTPS29).The expression changes in these genes under various conditions refl ected their specifi c roles during abiotic or biotic stresses.Heterologous expression of a novel A.sinensis sesquiterpene synthase gene,AsTPS2,in Escherichia coli produced a major humulene product,so AsTPS2 is renamed AsHS1.AsHS1 is diff erent from ASS1,AsSesTPS,and AsVS,for mainly producingα-humulene.Based on the predicted space conformation of the AsHS1 model,the small ligand molecule may bind to the free amino acid by hydrogen bonding for the catalytic function of the enzyme,while the substrate farnesyl diphosphate(FPP)probably binds to the free amino acid on one side of the RxR motif.Arg450,Asp453,Asp454,Thr457,and Glu461 from the NSE/DTE motif and D307 and D311 from the DDxxD motif were found to form a polar interaction with two Mg^(2+)clusters by docking.The Mg^(2+)-bound DDxxD and NSE/DTE motifs and the free RXR motif are jointly directed into the catalytic pocket of AsHS1.Comparison of the tertiary structural models of AsHS1 with ASS1 showed that they diff ered in structures in several positions,such as surrounding the secondary catalytic pocket,which may lead to diff erences in catalytic products.Based on the results,biosynthetic pathways for specifi c sesquiterpenes such asα-humulene in A.sinensis are proposed.This study provides novel insights into the functions of the sesquiterpene synthases of A.sinensis and enriches knowledge on agarwood formation.
基金supported by Universiti Putra Malaysia under the Putra Grant scheme(GP-IPS/2017/9554600)
文摘Agarwood, the resinous product of Aquilaria spp.(Thymelaeaceae), is highly valued for medicinal and fragrant purposes. Unsustainable forest harvesting contributes to the declining population in the wild, threatening their existence. As a protection effort, cultivation occurred in range countries, mainly in Asia, effectively establishing mass plantations. The success of domesticating Aquilaria relies heavily on technological advancement in agarwood induction, without which the entire thriving industry will collapse. In this paper, we describe efforts since 1929 and current progress and variation in induction as practiced in Asia. The methods include traditional practices and artificial induction via inoculum and chemical inducer, experimented and patented or otherwise. Artificial induction methods are being developed to intensify agarwood production in terms of yield and quality. While traditional methods are commonly applied by rural planters, artificial methods with the use of specific agents/chemicals are seen as more appealing for inducing agarwood, and have a higher demand from entrepreneurs and plantation owners.Several issues related to induction technology faced by stakeholders in agarwood cultivation are presented, such as safety levels, cost, yields, and quality. We conclude by highlighting remaining challenges in induction methods and their associated technologies.
基金provided by grants from the NSFCYunnan joint fund on key projects to W.B.Sun(No.U1302262)the National Natural Science Foundation of China to G.Chen(31670322)+1 种基金the Young Academic and Technical Leader Raising Foundation of Yunnan Province(No.2015HB091)the Science and Technology Research Program of Kunming Institute of Botany,the Chinese Academy of Sciences(No.KIB2016005)to G.Chen
文摘Pollination and seed dispersal in angiosperms have long been investigated in order to understand the coevolution of plants and animals.However,the signals from flowers and/or seeds to attract pollinators and/or seed dispersers have received comparatively little attention.In this study,the pollination biology and seed dispersal of the vulnerable agarwood plant Aquilaria sinensis(Lour.) Gilg,a traditional medicinal plant in China,was studied in its natural distribution range.The reproductive tactics of A.sinensis were studied in detail by employing various tests dealing with fruit set and also seed dispersal.Dynamic headspace extraction followed by GC-MS analysis was also performed in order to reveal the composition of floral scent.The results showed that noctuids and pyralids are the most effective pollinators of pollinator-dependent A.sinensis.The main compounds of the floral scent were(E,E)-α-Farnesene(61.9 ± 3.2%),trans-Ocimene(16.6 ± 1.2%),and Benzyl salicylate(4.6 ± 1.1%).The results obtained from seed dispersal experiments indicate that hornets are effective seed dispersers and they may play an important role in long-distance seed dispersal of A.sinensis.Based on our findings,we recommend several protection methods for this threatened agarwood plant in China.
基金Project supported by the National Natural Science Foundation of China (No. 30070066)the Science and Technology Project of Guangzhou City (No. 2003J1-C0241), China
文摘Aquilaria agallocha can produce fragrant agarwood used for incense, traditional medicine and other products. An efficient plant regeneration system was established via organogenesis from shoots developed from seedlings of Aquilaria agallocha. Shoots generated many buds on MS medium supplemented with 1.3 μmol/L BA （6-benzylaminopurine） in the first 7 weeks, and the buds elongated on MS medium with 1.3 μmol/L BA＋0.5 μmol/L NAA （naphthaleneacetic acid） in another 7 weeks, 2.3 shoots 2 cm in length per explant were obtained within 14 weeks. Plantlets were rooted on l/2 MS medium after being immersed in 5 μmol/L NAA for 48 h, 96.7% of the roots grew up two weeks later. All plantlets that survived acclimatization grew well in the pots.
文摘A new sesquiterpenoid,named baimuxifuranic acid,has been isolated from the volatile oil of Aquilaria sinensis(Lour.)Gilg.belonging to the family Thymelaceae by silica gel column chromatography.Based on spectral analysis its structure was deduced as(1).Reduction of baimuxifuranic acid by LiAlH_4 gave a
文摘Three cDNA clones encoding δ-guaiene synthase, a sesquiterpene cyclase, were isolated from tissue cultures of Aquilaria microcarpa, and data mining analysis of the orthologous genes suggested that 10 and 9 amino acid residues of N- and C-terminal ends of the translated products of these clones remained undefined. The recombinant enzyme proteins, to which the putative missing Nand C-terminal amino acid sequences (MSSAKLGSAS and ALLRHAIEI, respectively) were ligated, exhibited the catalytic activities of sesquiterpene biosynthesis. Among these three δ-guaiene synthases, two isoforms were capable of liberating α-guaiene, δ-guaiene, β-elemene plus α-humulene as a minor product, while remaining one isoenzyme generated α-, δ-guaiene and β-elemene but not α-humulene. Although the enzyme protein solely lacking in the N-terminal 10 amino acid residues was capable of synthesizing the sesquiterpenoids, the protein without 9 amino acids at Cterminal did not exhibit the catalytic activity. These results suggest that two types of δ-guaiene synthase;α-, δ-guaiene, β-elemene-producing type, and α-, δ-guaiene, β-elemene plus α-humulene-producing type;concomitantly occur in A. microcarpa cell cultures, and several amino acid residues at C-terminal of the synthase protein are essential to exhibit the catalytic activities as the sesquiterpene cyclase.
基金supported by DBT,Govt. of India through the project "Mapping and quantitative assessment of geographic distribution and population status of plant resources of Eastern Himalayan Region"
文摘We studied seedling survival and growth ofAquilaria malaccensis in three different environmental conditions （homegardens, green house and in different canopy conditions） of northeast India. Results show that mean seasonal survival was highest in green house （95.53%±2.33）, followed by homegardens （89.3%±1.89） and different canopy conditions （77.62%±6.73）; the highest values were found during February to April for both the homegardens （96%±1.68） and green house （98% ± 0.88） and lowest during November to January （78%±2.99） in homegardens and May to July （90%：t：4.53） in green house. In case of transplanted seedlings in different canopy conditions, mean seasonal survival was highest during May to July （98%±1.92） and lowest during August to October （66%±12.81）. However, mean seasonal growth of collar diameter was highest in different canopy conditions （23.99%±1.76） compared to green house （21.52%±2.70） and homegardens （12.44%±1.33） and it was highest during rainy season （May to July） and lowest during dry winter （November to January） in all the three experi- mental sites. These variations may be due to the different microclimatic conditions as well as nutrient status of the soil in all the three experimen- tal sites. Although, seedling quality plays a great role in their survival and growth, based on the result of green house experiment, it can be concluded that maintenance of seedlings in green house conditions during their early growth period may improve both the survival and growth for large scale plantation of the species. Thus, the species can be reintroduced in its natural forest range to compensate the loss of natural population of this precious species in northeast India.
文摘This study aimed to model the kinetic of hydro-distillation of Aquilaria malaccensis leaves oil in order to understand and optimize the extraction process. In addition, this study, for the first time, aimed to identify the chemical compositions of the A. rnalaccensis leave-oil. By assessing both first-order kinetic model and the model of simultaneous washing and diffusion, the result indicated that the model of simultaneous washing and diffusion better describes the hydro-distillation mechanism of the essential oil from A. rnalaccensis leaves. The optimum time, solid to liquid ratio, and the heating power for extracting the highest amount of essential oil were found to be around 3 h, 1：10 （g. ml-1）, and 300 W respectively. Yellow essential oil with a strong smell and a yield of 0.05 v/w was extracted by hydro-distillation Clevenger apparatus. Chemical compounds of the essential oil were analyzed using gas chromatography-mass spectroscopy （GC/MS）, which resulted in identification of 42 compounds that constitute 93% of essential oil. Among the identified components, Pentadecanal （32.082%）, 9-Octadecenal, （Z） （15.894%）, and Tetradecanal （6.927%） were the major compounds. Considering the fact that all the identified major components possess pesticidal properties, A. malaccensis leaves can be regarded as a promising natural source for producing pesticides.
文摘One novel spirolactone,aquilarisinolide(1),three new sesquiterpenoids,(2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one(2),(1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one(3),and(4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one(4),together with 13 known compounds(5-17)were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra.The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone(CORT)and 1-methyl-4-phenylpyridine ion(MPP+),as well as inhibitory activities against BACE1.Compound 4,5,6-dihydroxy-2-(2-phenylethyl)chromone(5),daphnauranol B(7),6-methoxy-2-[2-(3-methyoxyphenyl)ethyl]chromone(10),isoagarotetrol(14),and 1-hydroxy-1,5-diphenylpentan-3-one(16)showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20μM(P<0.001).Isoagarotetrol(14)showed a significant protective effect on MPP+-induced injury in PC12 cells at a concentration of 20μM(P<0.001),while compound 4 showed a moderate activity(P<0.01).The BACE1-inhibitory activities of all tested compounds were very weak with less than 30%inhibition at a concentration of 20μM.
基金support from the Administration of Traditional Chinese Medicine of Hunan Province(201673)Hunan Province Universities 2011 Collaborative Innovation Center of Protection and Utilization of Hu-xiang Chinese Medicine Resources(HXZY-2015-005 and HXZY-2015-012)+1 种基金the State Key Subject of TCM Diagnostics in Hunan University of Chinese Medicine(2015ZYZD06)Hunan Provincial Key Laboratory of Dong Medicine(2015TP1020-02)
文摘Aquilaria sinensis(Thymelaeaceae)is widely cultivated in southern China for its significant medicinal usage.The resinous wood,the most used part of the plant as traditional Chinese medicine(TCM),locally called“Chen Xiang(沉香)”or Chinese agarwood,has been traditionally used for the treatment of circulatory disorders,abdominal pain,vomiting,and dyspnea.Till date,over 249 compounds have been isolated and identified from this plant.A range of bioactivities,including α-glucosidase inhibitory effects,anti-inflammatory,cytotoxicity,neuroprotective,anti-neuroinflammatory,antimicrobial and acetylcholinesterase inhibitory effects,along with some of the pharmacological mechanisms have been reported for the pure compounds or extracts of Aquilaria sinensis.For the purpose of quality control and clinical safety of drug usage,modern analytical instruments and chemical analysis methods have been applied for analyses of Aquilaria sinensis.In order to comprehensively understand the medicinal application and to fully utilize the plant,a literature search on the herb based on databases including SciFinder,Web of Science,Pubmed,Google Scholar and others was performed and the information regarding to the phytochemistry investigations,pharmacological studies and quality control was summarized in this paper.
文摘Initially,Chen Xiang(沉香Lignum Aquilariae Resinatum)was exotic,but it has been playing an important role in the development of traditional Chinese culture and medicine.This article explores the reason for differences in the quality of ancient and modern Chen Xiang(沉香Lignum Aquilariae Resinatum)by analyzing the essential factors including the prosperity and decline of Maritime Silk Road,the relocation of the producing area,and the process of aroma forming.Based on the development and application of Chen Xiang(沉香Lignum Aquilariae Resinatum)in Chinese literature and art,traditional Chinese medicine,and folk life over the past 2000-odd years,this article puts contends that Chen Xiang(沉香Lignum Aquilariae Resinatum),which is endowed with the connotation of Chinese culture and health,should assume its new role as the traditional Chinese medical and cultural carrier on the New Silk Road.
文摘The article "Dynamic analysis of gene expression and determination of chemicals in agarwood in Aquilaria sinensis",written by Zeqing Wu,Wanzhen Liu,Jing Li,Liangwen Yu and Li Lin was originally published elec-tronically on the publisher’s internet portal(currently SpringerLink)on 10th May 2019 without open access.
文摘Objective: To investigate the protective effects of Aristolochia longa (A. longa) and Aquilaria malaccensis (A. malaccensis) on acute hepatotoxicity induced by lead in female albino rats. Methods: Twenty five (25) apparently healthy female Wistar rats were randomly divided into five groups of five rats in each: control, Pb, Pb + A. longa (Ar), Pb+ A. malaccensis (Aq), and Pb+ A. longa (Ar) + A. malaccensis (Aq) lead (100 mg/kg b.w.) as Pb (C2H3O2)2 added in their drinking water for 75 days. A. longa (rhizome powder at a dose of 10 g/kg of diet ) and A. malaccensis (heartwood powder at a dose 10 g/kg of diet) were added to the feed during the last 15 days of lead exposed in the animals. Results: Obtained results revealed that lead treatment caused a significant increase in serum GOT, GPT and ALP activities and in liver of MDA level and CAT activity. In contrast, it led to an decrease in the liver GOT, GPT and GST activities and in GSH level in rats. Also, the results clearly showed that lead causes alterations of hepatic tissue in comparison with controls. Our results showed that treatment with A. malaccensis and A. longa a partial correction of the previous parameters. The histological observations confirmed the hepatoprotection results by the biochemical parameters. Conclusions: Results demonstrated beneficial effects of A. longa and A. malaccensis treatment in Pb-induced oxidative stress and tissue damage in liver.
基金The work was supported by SEAMEO-BIOTROP Indonesia with a special Grant to Dr.Ulfah J.Siregar.
文摘Agarwood is a non-timber forest product found in tropical rain forests.It is a black and fragrant resin valued for the perfume industry and demand continues to increase.However,the Indonesian agarwood-producing species,Aquilaria malaccensis and Gyrinops versteegii do not automatically produce such quality resin.Bio-induction technology or inoculation using Fusarium solani is usually applied to these species to trigger resin production.This research aims to identify agarwood compounds formed in seedlings and trees of A.malaccensis and G.versteegii after these species were inoculated with the fungus F.solani.The chemical compounds were identified by comparing the patterns of mass spectra fragmentation in the sample and in previous studies.Five groups of agarwood compounds were identified:(1)sesquiterpen group-cisjasmone and aromadendrenepoxide;(2)chromones group-8-methoxy-2-(2-phenylethyl)chromen-4-one and newly-discovered chromone derivative,7-(benzyloxy)-5-hydroxy-2-methylchromone found only in G.versteegii;(3)aromatic group-benzylacetone,guaiacol,p-ethylguaiacol,phenol,syringaldehyde,vanilin,furfuryl alcohol,and furfural;(4)fatty acid group-palmitic acid,oleic acid,and lauric acid;and,(5)triterpen group-squalene.
文摘Objective: To investigate the effects of Aquilaria subintegra leaf aqueous extracts on the aphrodisiac properties including sexual behaviour, testosterone level, percentage of pregnancy, number of offspring and male to female ratio of offspring in ICR mice. Methods: In this experiment, each male cohabitated with one female in a polysulfone cage. 30 ICR male mice were divided into 6 groups that received normal saline (the control group), 50 mg/kg, 100 mg/kg, 200 mg/kg, 500 mg/kg, and 1000 mg/kg body weight of Aquilaria subintegra leaf aqueous extracts orally for 21 days consecutively. Sexual behavior, percentage of pregnancy, number of offspring and male to female ratio of offspring in ICR mice were measured according to the established methods. Testosterone level was measured by using enzyme-linked immunosorbent assay. Results: Mice that received Aquilaria subintegra leaf aqueous extracts at 50 mg/kg body weight (day 0) had significantly higher mount frequency as compared to the control group;groups treated with 100, 500, 1000 mg/kg body weight extracts produced a greater number of offsprings when compared to the control group. All aphrodisiac parameters were similar between the treatment groups and the control group, indicating that Aquilaria subintegra leaf aqueous extract did not significantly alter the aphrodisiac parameters. Conclusions: Aquilaria subintegra leaf aqueous extracts have no effect on the aphrodisiac properties, but could increase the breeding rate in mice.
基金Funding was provided by Beijing Sino-Science Aquilaria Technology Co.,Ltd.,Beijing,China (Grant No.KET202101).
文摘Bioassay-guided fractionation of the EtOH extract from the flowers of Aquilaria sinensis(Lour.)Spreng.(Thyme-laeaceae)led to the isolation of a new cucurbitane-type triterpenoid,aquilarolide A(1),along with five known compounds(2-6).The structure of 1 was elucidated by extensive 1D and 2D nuclear magnetic resonance(NMR)experiments and mass spectrometry(MS)data and theoretical calculations of its electronic circular dichroism(ECD)spectra.Aquilarolide A,cucurbitacin E(3),cucurbitacin B(4),and 7-hydroxy-6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one(6)showed significant cytotoxicity against human lung adenocarcinoma SPC-A-1,human lung squamous cell carcinoma NCI-H520,human lung adenocarcinoma A549,and paclitaxel-resistant A549(A549/Taxol)cell lines.All four active compounds,with IC_(50) values ranging from 0.002 to 0.91μM,had better inhibitory activities against A549/Taxol cells than paclitaxel(IC_(50)=1.80μM).Among them,cucurbitacin E(IC_(50)=0.002μM)is the most active.Further studies are needed to evaluate their in vivo antitumor activities and to clarify their mechanisms.
基金supported by Beijing Sino-Science Aquilaria Technology Co.,Ltd.,Beijing,China (no.KET202101).
文摘Five new 2-(2-phenylethyl)chromone derivatives,(5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol(1),(5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol(2),(6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(3),(6S,7S,8R)-2-(2-phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone(4),(5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone(5),three new sesquiterpenoids,(4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(6),(4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(7),and(4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one(8),along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis(Thymelaeaceae).The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data,single-crystal X-ray diffraction analysis,and electronic circular dichroism(ECD)calculations.The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma(PC12)cell injury induced by corticosterone.At concentrations from 5 to 40μM,compounds 4 and 6,agarotetrol(9),and 6-hydroxy-2-(2-phenylethyl)chromone(17)showed significant protective activities against corticosterone-induced PC12 cell injury(P<0.001).
