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不同微生物誘導沉香木產生的二次代謝產物差異

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IntroductionA. sinensis is an evergreen tree species native to South China and a common species to produce agarwood. Agarwood is an aromatic resin produced by the immunological responses of the host tree against biotic and abiotic stress. The microbial infection could be the potential agents to sti

mulate the agarwood formation through activation of the phytoalexin to secrete secondary metabolite. The formation of agarwood formed on the trunk and branches of the entire tree through the microbial mobility, the plant transpiration, and new cell formation from the cambium to the xylem. There are

several factors to affect agarwood formation and their essential oil quality. The different species of microbial injection might give the different secondary metabolites of the agarwood.PurposeThe objectives of this study were to identify microbial species to inject Aquilaria sinensis from mixed cul

ture media through morphology and molecular method. The chemical constituents were analyzed by HPLC and GC-MS analysis to investigate the compounds of agarwood of Aquilaria sinensis induced by different identified microbial species. The horizontal (color formation) and vertical (cutting layers) comp

ounds changed and analyzed to reveal differences of chemical profiles. Four different extraction solvents were used to obtain the agarwood essential oil and distinguish the difference profile of agarwood essential oil compounds by different extraction methods using GC-MS.Materials and MethodsThe unk

nown species from mixed culture media obtained from the farmer were cultivated into single colonies with Luria Agar (LA) and Potato Dextrose Agar (PDA). There were two batches for microbial identification confirmation. Each strain was identified by morphology, staining via gram staining, and lactoph

enol cotton blue stain and molecular identification using Polymerase Chain Reaction (PCR) amplification and DNA sequencing.. The second batch was analyzed after the first batch were sequenced. The strains were injected into the different A. sinensis trees with two replications for five months. The a

garwood was harvested and extracted by 100% MeOH (1:10) to determine the phytochemicals using reversed-phase high-performance liquid chromatography (HPLC) on LiChrospher 100 RP-18e column(4 mm i.d x 250 mm, 5μm). The mobile phase 95:5 composed of 0.05% Trifluoroacetic aicd and CH3CN linear gradient.

GC-MS analysis was carried out using GC-2010 with GC-MS-QP 2010 Shimadzu with EquityTM-5 column (Supelco) (30m x 0.25mm x 0.25µm film thickness) and helium as the carrier gas. The chemical compounds were identified by matching them to the mass spectral library (NIST). Agarwood of A. sinensis was u

sed to distinguish the phytochemicals based on the different cutting layers and color formation with the same procedures. Normal wood was used as negative control and two different agarwoods obtained from the different places were used as positive controls. The essential oils were extracted by four

different methods using water by distillation method, maceration method by hexane (in water extraction), methanol (hexane removed), and hexane solvent.Results and DiscussionSequence comparison was performed using the software of DNA Baser v4 and BLAST of NCBI. There were six fungus were identified,

the first batch identified, such as SIN1 and SIN5 for Pichia kudriavzevii (500 bp), SIN2 for Taiwanofungus camphoratus (700 bp), SIN3 and SIN4 for Geotrichum candidum (400 bp), SIN7 for Aspergillus costaricensis (600 bp), and one bacteria SIN6 for Salmonella enterica subsp. enterica serovar Agona (9

96 bp). In the second batch identified four fungal species such as PDBB and LBB for Hanseniaspora uvarum, PDBK for Talaromyces chloroloma, T1 and T4 for Fusarium oxysporum, and T8 for Pichia kudriavzevii. The remaining six strains (T2, T3, T5, T6, and T7) is still unknown. Pichia sp. G. candidum, A

spergillus sp., and Fusarium sp. were found in agarwood which Aspergillus sp. and Fusarium sp. were known as agarwood inducers. The differences in species of microbes in the first and second batch indicate that might have contamination in preparation due to the different conditions, which can affect

the agarwood quality. The contamination can be prevented by tracking and following the sterilized conditions in every step of procedures.The different compounds were associated with strains injected. Fungal injection (SIN1, SIN2, SIN3, and SIN7) stimulated abundant of fatty acids compared to the ba

cterial injection (SIN6) that triggers oxidative burst and fatty acid oxidation cascades leading to the production jasmonates. Among the fungal injections, SIN1 was the highest compound producer, followed by SIN3, SIN7, and SIN2. SIN1 associated in the AAA pathway to produce the alkaloid (2-[bis(phe

nylmethyl)amino]-4-methyl-pentanal and 5-Benzyloxy-6-methoxy-8-nitroquinoline) and shikimate pathway to produce the aromatic or phenolic compounds and continue via chalcone synthase to produces the chromones such as 6-benzyloxy-3,4-dihydro-4,4-dimethyl-coumarin. SIN3 was strongly correlated in speci

fic volatile compounds in maltose production from sugar transporters (STPs) by the accumulation of sugars in the cell wall space by secondary active retrieval. SIN7 were correlated with aromatic compounds of 2-[bis(phenylmethyl)amino]-4-methyl-pentanal. SIN2 was the lowest production of the compoun

ds due to the low pathogenicity. Fungal injection of SIN1 (P. kudriavzevii) might be the potential agarwood inducers due to the higher compound similarity with commercial agarwood (Out and In), while SIN6 has the same aromatic compounds (1,5-diphenyl-3-pentanone; 1,5-diphenyl-1-Penten-3-one; 1-(benz

yloxy)-8-Naphthol) with commercial agarwood. SIN2 (T. champoratus) was not suitable for agarwood formation. The absence in sesquiterpenes production were determined in all agarwood samples except in commercial agarwood (Out and In), because of the wide variety of sesquiterpene skeletons to make them

difficult to be identified, or the amount was too low to detect because the sesquiterpene formation needs a longer time than others.The horizontal compound formation were formed from the injection site to the outer layer of the tree due to the change of concentration based on different colors (hori

zontal change). The color formation caused by the difference in the pathway for each compound. The white-part of agarwood contained abundant content of low molecular weight compounds (others), aromatic compounds, fatty acids, and alkaloids via LOX pathway, shikimate pathway, and AAA pathway. In the

brown part, MVA pathway was active to produce terpenoids (1a,2,5,5a6,9,10,10a-octahydro-5,5a,6-trihydroxy-1,4-methanocyclopenta [a] cyclopropa [e] cyclodecen-11-one) and sesquiterpenes (β-Eudesmol), then activated AsCHS1 proteins synthesis via chalcone synthase to produce chromones (6-benzyloxy-3,4-

dihydro-4,4-dimethyl-coumarin) from the shikimate pathway that already activated in the early stage of infection. The black-part considered as decayed wood and accumulated alkaloids from AAA pathways. The brown-part revealed similar results to the commercial agarwood able to serve in the global mark

et.The vertical compounds change was highest in the lower part (L6 and L5) due to the location near the injection part near the lower trunk of the tree, and was attacked from the microbes first before other layers. The compound distribution was correlated with the water transpiration from the root t

hat leads to the new invasion of the healthy tissue plant. The water absorbed by plant tissue carried the microbes to the larger intercellular spaces. The presence of pathogen microbes leads A. sinesis to synthesizes the secondary metabolite to suppress the microbial attack. Fatty acids found in hig

h concentrations at L6 and L5 are correlated with high detection of terpenoid and sesquiterpenes as the first stage compound synthesized in agarwood formation.The different extraction methods and solvents for agarwood compounds were usually dependent on the purpose of the extract. This study showed

that different colors of wood with different oil quality based on the compounds. The black-part agarwood mostly contained alkaloids, while brown-part of agarwood mostly contained sesquiterpenes. The alkaloids in the agarwood suggested have wide polarities. Essential oil extracted by methanol (hexane

removed), resulted higher in alkaloids (-hydroxy-4-benzyloxy-benzaldehyde and 5-Benzyloxy-6-methoxy-8-nitroquinoline) in the black agarwood, while sesquiterpenes were high caryophyllene oxide and cubenol in the brown agarwood. Aromatic compounds were low detected in methanol solvent because there m

ight be less polarity (semi-polar) in the hexane extract. In the hexane extraction, fatty acids (hexadecanoic acid and octadecanoic acid) and sesquiterpenes were higher in brown part than in the black part. Other compounds and alkaloids were higher in the black part. The fatty acids in brown agarwoo

d might due to the severity of the pathogen invasion to activate the sesquiterpenes via LOX pathway. Agarwood extract from hexane (in water extraction) was carried, chromones in the black agarwood was higher than in brown agarwood. The water extracts (distillation method) was higher in sesquiterpen

es and alkaloids in black agarwood, while brown agarwood was high only in sesquiterpenes. These results showed that mostly the sesquiterpenes in the agarwood occur a high polarity. The combinations of the heat might extract the sesquiterpenes from the agarwood.ConclusionIn this study, different mic

robes injection induced the different result compounds in agarwood. P. kudriavzevi injection might be the potential inducer because of similar compounds as the commercial agarwood, compared to the other microbial species. The color formation caused by the difference in the pathway for each compound.

The white part mainly activates the LOX pathway, shikimate pathway, and AAA pathway. In the brown part, the MVA pathway was active to produce terpenoids and sesquiterpenes, activated AsCHS1 proteins synthesis via chalcone synthase at the last. The black-part considered as decayed wood and accumulat

ed alkaloids from AAA pathways. The brown part demonstrated similar results to the commercial agarwood able to serve in the global market. The different extraction methods and solvents for agarwood compounds were usually dependent on the purpose of the extract use. Different colors of wood revealed

different essential oil quality based on the compounds. The black part agarwood mostly contained alkaloids, while brown part agarwood mostly contained sesquiterpenes. The black part mostly contained conjugated compounds related to the polar polymer, while in brown part were major in non-polar and se

mi-polar compounds.