Supporting Information Chemistry, Biological Activities .
Electronic Supplementary Material (ESI) for Natural Product Reports.This journal is The Royal Society of Chemistry 2020Supporting informationNatural Products in Agarwood and Aquilaria Plants:Chemistry, Biological Activities and BiosynthesisWei Li#abc, Hui-Qin Chen#abc, Hao Wang#abc, Wen-Li Mei*abc and Hao-Fu Dai*abcaHainanEngineering Research Center of Agarwood, Institute of Tropical Bioscience andBiotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, PR China.E-mail: meiwenli@itbb.org.cn; daihaofu@itbb.org.cnbHainan Key Laboratory for Research and Development of Natural Products from Li FolkMedicine, Haikou 571101, PR China.cHainan Institute for Tropical Agricultural Resources, CATAS, Haikou 571101, PR China.#Theseauthors contributed equally to this yofsesquiterpenesfromagarwood 1Table S1 Eudesmane-type sesquiterpenes identified in agarwood 2Table S2 Eremophilane-type sesquiterpenes identified in agarwood 5Table S3 Guaiane-type sesquiterpenes identified in agarwood 7Table S4 Agarospirane-type sesquiterpenes identified in agarwood 9Table S5 Acorane-type sesquiterpenes identified in agarwood 10Table S6 Cadinane-type sesquiterpenes identified in agarwood 10Table S7 Prezizaane-type sesquiterpenes identified in agarwood 10Table S8 Zizaane-type sesquiterpenes identified in agarwood 11Table S9 Humulane-type sesquiterpenes identified in agarwood 11Table S10 Other sesquiterpenes identified in agarwood 12Table S11 Distribution of sesquiterpenoids in agarwood from different origins 13Table S12 Flindersia 2-(2-phenylethyl)chromones identified in agarwood 14Table S13 5,6,7,8-Tetrahydro-2-(2-phenylethyl)chromones identified in agarwood 19Table S14 Mono- and nes identified inagarwood 21Table S15 2-(2-Phenylethenyl)chromones identified in agarwood 23Table S16 Bi-2-(2-phenylethyl)chromones with C–C bond identified in agarwood 24Table S17 Bi-2-(2-phenylethyl)chromones with C–O–C bond identified in agarwood 24Table S18 Bi-2-(2-phenylethyl)chromones with double C–O–C bonds identified in agarwood 26Table S19 Bi-2-(2-phenylethyl)chromones with C–O–C and C–C bond identified in agarwood.27I
Table S20 Sesquiterpenoid-4H-chromone derivatives identified in agarwood 28Table S21 Benzylacetone-4H-chromone derivatives identified in agarwood 28Table S22 Tri-2-(2-phenylethyl)chromones identified in agarwood 29Table S23 Simple phenolic compounds identified in agarwood 29Table S24 Inhibition of LPS induced NO production activity of compounds from agarwood 31Table S25 Cytotoxicity of compounds from agarwood 32Table S26 AChE inhibitory activity of compounds from agarwood at 50 μg/mL 34Table S27 Diameters of the inhibition zone (mm) of isolated compounds from agarwood against S.aureus and R. solanacearum 35Fig. S1 Flavonoids identified from Aquilaria plants 36Table S28 Flavonoids identified from Aquilaria plants 37Fig. S2 Benzophenones identified from Aquilaria plants 40Table S29 Benzophenones identified from Aquilaria plants 41Fig. S3 Xanthones identified from Aquilaria plants 42Table S30 Xanthones identified from Aquilaria plants 42Fig. S4 Lignans identified from Aquilaria plants 43Table S31 Lignans identified from Aquilaria plants 44Fig. S5 2-(2-Phenylethyl)chromones identified from Aquilaria plants 45Table S32 2-(2-Phenylethyl)chromones identified from Aquilaria plants 46Fig. S6 Simple phenolic compounds identified from Aquilaria plants 47Table S33 Simple phenolic compounds identified from Aquilaria plants 48Fig. S7 Sesquiterpenes and degraded sesquiterpenes identified from Aquilaria plants 49Table S34 Sesquiterpenes and degraded sesquiterpenes identified from Aquilaria plants 50Fig. S8 Diterpenoids and diterpenoid derivatives identified from Aquilaria plants 51Table S35 Diterpenoids and diterpenoid derivatives identified from Aquilaria plants 52Fig. S9 Triterpenes identified from Aquilaria plants 53Table S36 Triterpenes identified from Aquilaria plants 54Fig. S10 Steroids identified from Aquilaria plants 55Table S37 Steroids identified from Aquilaria plants 56Fig. S11 Alkaloids identified from Aquilaria plants 56Table S38 Alkaloids identified from Aquilaria plants 57Fig. S12 Other compounds identified from Aquilaria plants nts 58Table S40 Genes related to the biosynthesis of sesquiterpenes in Aquilaria species 59II
Table S41 Enzymes of the biosynthetic pathways of terpenes, steriols and aromatic polyketides 61III
caryophyllene ,10closurecaryophyllenylcationgermacrene A72, ureslcohumulyl cation11,1closure HS147eudesmare110, uresclosure(E,E)-germacradienyl cation1GS2,6OPPFPPisomerization14110, uresocl731511sucloreguaiane guaieneGS1,6closure(Z,E)-germacradienyl cationcadinane irane3128,26,1closure13NPP bisabolenebisabolyl cationOH10,6closure3,11closurenerolidol 2acorane1,2-CH3shiftprezizaanezizaaneScheme 1 A simplified proposed biosynthetic pathway of sesquiterpenes from agarwood.1
Table S1 Eudesmane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or 2A. 8A. agallocha23E3Selina-3,11-dien-14-oic acidC15H22O2234A. na-3,11-diene-12,15-dial]C15H22O2234C15H20O2232A. malaccensisA. sinensisA. sinensisG. 4-olC15H20O220A. 236A. sinensis29E8(5S,7S,9S,10S)-( )-9-Hydroxy-selina-3,11-dien-12-alC15H22O2234A. sinensis28,29E9(5S,7S,9S,10S)-( )-9-Hydroxy-eudesma-3,11(13)-dien-12-methyl esterC16H24O3264A. ina-3,11-dien-14-alC15H22O2234A. sinensis29E11(5S,7S,9S,10S)-( )-Selina-3,11-dien-9-olC15H24O220A. agallocha22E12( 4A. sinensis28E13Petafolia AC15H24O2236A. A. sinensis33E15( )-Eudesma-3,11(13)-dien-8α,9β-diolC15H24O2236A. oneC15H22O218A. agallocha22E17Selina-4,11-dien-14-alC15H22O218A. agallocha23E18Selina-4,11-dien-14-oic acidC15H22O2234A. agallocha232
No.NameFormulaMWSource or ,11-diene-12,15-dial]C15H20O2232A. malaccensisA. -dien-12-oateC16H22O3262A. crassna34E21(‒)-10-Epi-γ-eudesmolC15H26O222A. . crassna34E23Eudesma-4-en-11,15-diolC15H26O2238A. malaccensisA. sinensisA. -15-alC15H22O2234A. sinensis28,30E25(7S,8R,10S)-( A. sinensis29E26(7S,9S,10S)-( )-9-Hydroxy-selina-4,11-dien-14-alC15H22O2234A. sinensis28-30E279-Hydroxy-selina-4,11-dien-14-oic acidC15H22O3250A. agallocha23E28( 4A. sinensis28E29( )-Eudesma-4,11(13)-dien-8α,9β-diolC15H24O2236A. sinensis28E30( 6A. sinensis28E315-DesoxylongilobolC15H26O2238A. diolC15H26O2238A. A. 28O2240A. )-en-4,9-diolC15H26O2238A. sinensis28,30E36Selin-11-en-4α-olC15H26O222A. ,6,7-octahydro-2-naphthyl)-propan-2-olC14H22O208A. agallocha263
No.NameFormulaMWSource or a,5,6,7-hexahydronapthaleneC14H22190A. -1,2,3,4,4a,5,6,7-octahydronaphthaleneC14H22190A. . agallocha26E41β-AgarofuranC15H24O220A. agallochaA. sinensis22,3638,42,43E42BaimuxinolC15H26O2238A. sinensis39,43E434-Hydroxyl-baimuxinolC15H26O3254A. sinensis41E44DehydrobaimuxinolC15H24O2236A. sinensis39,43E45IsobaimuxinolC15H26O2238A. sinensis38E46Baimuxifuranic acidC15H24O3252A. 24O2236A. agallocha44E48Dihydro-β-agarofuranC15H26O222A. agallocha36E49α-AgarofuranC15H24O220A. agallochaA. malaccensis3624E50Epoxy-β-agarofuranC15H24O2236A. 238A. 26O3254A. ricyclo[7.2.1.01.6]dodecaneC14H24O208A. xatricyclo[7.2.1.01.6]dodecan-2-olC14H24O2224A. agallocha26E55Nor-ketoagarofuranC14H22O2222A. agallocha374
Table S2 Eremophilane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or -olC15H26O2238A. malaccensisA. sinensisA. malaccensisA. 2-enalC15H24O2236M3( )-9β,10β-Epoxyeremophila-11(13)-enC15H24O220A. ]oxiren-2-olC15H24O2236A. -diolC15H26O2238A. 0A. agallocha46M7Valenc- or eremophil-9-en-12-al (tentative)C15H24O220A. agallocha46M8Jinkoh-eremolC15H26O222A. 6O3254Aquilaria 15H26O2238G. 2,13-triolC15H26O3254G. 26O2238G. 8α-olideC15H22O2234G. neC15H22O218A. xyemophilaneC15H24O3252A. crassnaAquilaria epoxy-11α,13-diolC15H24O3252G. salicifolia20M17CyclodebneyolC15H24O2236A. 26O2238A. sinensisA. crassna2834M19Ligudicin CC15H24O2236A. remophilaneC15H22O2234A. sinensis415
No.NameFormulaMWSource or ophilaneC15H22O2234A. sinensisA. crassna41,45,5135M22Petafolia BC15H22O2234A. e]C15H22O218M24( C15H22O218A. agallochaA. malaccensisA. sinensisA. sinensisA. agallocha235230,32,41,45,5130,32,42,43,5122,53M25( )-(4S,5R)-KaranoneC15H20O216A. agallocha22M26Dehydro-jinkoh-eremolC15H24O220A. 11,12,13-triolC15H24O220G. l-1(10)-ene-11-methyl esterC16H26O4282G. salicifolia20M29( )-trans-NootkatolC15H24O220G. salicifolia20M30Methyl crassicidC16H26O4282A. thoxypropanoic acidC16H26O4282A. crassna34M32Kusunol[Valerianol]C15H26O222A. malaccensisA. agallochaA. e-1,2diolC15H26O2238A. 1(10)-ene-2-oxo-11-methylesterC16H24O5296A. O2236A. sinensis28,30,45M36( )-11-Hydroxyvalenc-1(10),8-dien-2-oneC15H22O2234A. . methyl-2-butenyl)-1-cyclohexanone]C13H22O194A. agallocha446
Table S3 Guaiane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or originRef.G1α-GuaieneC15H24204A. agallocha22G2α-BulneseneC15H24204A. O218A. H24O220A. lic acidC15H22O2234A. agallocha55G6Methyl guaia-1(10),11-diene-15-carboxylateC16H24O2248A. A. agallocha55G8( )-Guaia-1(10),11-dien-9-oneC15H22O218A. 15H20O2232A. -15-oic acidC15H22O3250A. agallocha56G11(‒)-RotundoneC15H22O218A. agallocha55G12( )-1,5-Epoxy-nor-ketoguaieneC14H20O2220A. agallocha23G13Chamaejasmone EC16H20O5292A. malaccensis57G14Chamaejasmone DC15H22O3250A. malaccensis57G15Auranticanol AC15H20O3248A. malaccensis57G16( )-12,13-DihydroxyguaiolC15H26O3254Aquilaria spp.48G17Epi-guaidiol AC15H26O2238A. sinensis50G18α-Kessyl alcoholC15H26O2238A. sinensis58G19Qinan-guaiane-oneC15H20O3248A. sinensis587
No.NameFormulaMWSource or originRef.G20Qinanol AC15H26O2238A. sinensis59G21Qinanol BC15H26O2238A. sinensis59G22Qinanol CC15H26O3254A. sinensis59G23Qinanol DC15H26O3254A. sinensis59G24Qinanol EC15H26O3254A. sinensis59G25SinenofuranolC15H26O2238A. sinensis42,59G26SinenofuranalC15H24O2236A. sinensis42G273-Oxo-7-hydroxylholosericin AC15H20O5280A. 50A. tahydro-azulen-8-oneC12H20O2196A. secoguaia-9(10)-en-8,12-olideC15H24O4268A. secoguaia-2(3)-en-12,8β-olideC15H20O4264A. 0O3248A. sinensis31G33QinanlactoneC15H22O4266A. H20O3248A. O3248A. e-8,12-epoxy-guaia-12-oneC15H22O3250G. salicifolia20G37GuaianolideC15H22O2234G. salicifoliaA. filaria2060G38( )-GweicurculactoneC15H16O2228G. ulactoneC15H16O3244A. filaria608
No.NameFormulaMWSource or 2A. 2,8-olideC15H12O3240G. salicifoliaA. filaria2060Table S4 Agarospirane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or originRef.44,634743,64S1AgarospirolC15H26O222A. agallochaA. malaccensisA. sinensisS2BaimuxinolC15H26O2238A. sinensis30S3Baimuxinic acidC15H24O3252A. 36A. sinensisA. malaccensisA. pirovetiven-11-ol-2-oneC15H24O2236Kyara 1st (Vietnam)65S62-Oxo-12-hydroxy-hinesolC15H24O3252A. 11),6(14)-dien-7-olC15H24O220A. 8A. . 5H22O218A. ,12,13-triolC15H26O3254Aquilaria spp.4891
Table S5 Acorane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or originRef.R14-Epi-10-hydroxyacoroneneC15H24O2236A. sinensis58R24-Epi-15-hydroxyacorenoneC15H24O2236A. sinensis45,58R315-HydroxyacorenoneC15H24O2236A. snensis28Table S6 Cadinane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or originRef.C1cis-7-HydroxycalamenenC15H22O218A. eC14H16O2216A. crassna35Table S7 Prezizaane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or originRef.P1Agarozizanol BC15H26O2238Aquilaria spp.68P2Jinkohol ⅡC15H26O222A. malaccensisAquilaria spp.4768P3Aquilarene DC15H26O2238Aquilaria spp.69P4Aquilarene EC15H26O2238Aquilaria spp.69P5Jinkoholic acidC15H24O2236Aquilaria spp.68P6Agarozizanol DC15H26O2238Aquilaria spp.68P7JinkoholC15H26O222A. malaccensisAquilaria spp.6768P8Agarozizanol CC15H26O2238Aquilaria spp.68P9Aquilarene AC15H26O2238Aquilaria spp.6910
No.NameFormulaMWSource or originRef.P10Aquilarene CC15H26O3254Aquilaria spp.69P11Aquilarene BC15H24O3252Aquilaria spp.69P12Agarozizanol AC15H24O2236Aquilaria spp.68P13Aquilarene HC15H24O220Aquilaria spp.69P14Aquilarene IC15H24O2236Aquilaria spp.69P15Aquilarene GC15H24O220Aquilaria spp.69P16Aquilarene JC15H22O2234Aquilaria spp.69P17Aquilarene FC14H20O2220Aquilaria spp.69Table S8 Zizaane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or originRef.Z1Agarozizanol EC15H24O220Aquilaria spp.68Z2Agarozizanol FC15H24O2236Aquilaria spp.68Z3IsokhusenolC15H24O220Aquilaria spp.68Table S9 Humulane-type sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or originRef.H1Aquilanol AC15H24O2236A. malaccensis57H2Aquilanol BC15H24O3252A. H24O220A. malaccensis57H414-Hydroxy-α-humuleneC15H24O220A. sinensis2811
Table S10 Other sesquiterpenes identified in agarwoodNo.NameFormulaMWSource or originRef.O1Daphnauranol DC16H22O4278A. malaccensis57O2Daphnauranol BC15H20O3248A. malaccensis57O3Daphnauranol CC15H20O2232A. 3254G. salicifolia49O5Malacinone AC17H24O5308A. malaccensis70O6Malacinone BC17H24O5308A. ieneC15H24204A. sinensis4512
Table S11 Distribution of sesquiterpenoids in agarwood from different originsNo.12Sesquiterpenoid skeletoneudesmaneeremophilaneA. sinensisA. agallochaA. malaccensisA. crassnaA. filariaA. spp.G. 968--8nor-sesquiterpenes-1-----(1) bearing 7-isopropenyl moiety110-----(2) patchoulanes--3----7------3---3-22----------3-2(5) nor-sesquiterpenes11-----(6) others–(3) possessing a 5,11-epoxy ring3guaiane(4) bearing a fivememberedlactone ring 1– 2 with cleft ring 3 conjugated double bonds within theseven-membered ring and fivememberedα,β-unsaturatedlactone 9humulane1-3----with a rare 5/6/7 ring skeleton--3----with a rearranged eudesmane skeleton-----1-with a 6/6/5 ring skeleton--2----with a large ring1------725026136231310otherstotal13
Table S12 Flindersia 2-(2-phenylethyl)chromones identified in hyl) chromone36-Hydroxy-2-(2-phenylethyl)chromone ethyl]chromone [Qinanone F]782-[2-(3-Hydroxyphenyl)ethyl]chromone [Qinanone E]2-[2-(4-Hydroxyphenyl)ethyl]chromone [Qinanone phenylethyl)chromone H14O2OHOCH3FormulaSource or originRef.VietnamA. agallochaA. sinensisA. malaccensisA. crassnaA. filariaG. salicifoliaAquilaria spp.(Indonesia)A. sinensisA. m
I Supporting information Natural Products in Agarwood and Aquilaria Plants: Chemistry, Biological Activities and Biosynthesis Wei Li#abc, Hui-Qin Chen#abc, Hao Wang#abc, Wen-Li Mei*abc and Hao-Fu Dai*abc aHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of
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PASSOVER BLUEBERRY MUFFINS (Alexa & Riley Newbold) Ingredients: -1/3 cup butter -1 scant cup of sugar -3 eggs -1/2 teaspoon vanilla -1/2 cup matzo cake meal -1/4 cup potato starch -1/4 teaspoon salt -1 cup blueberries (frozen, drained)— don’t defrost -Cinnamon sugar . Directions: Cream sugar and butter. Add three eggs one at a time, beating after each. Add vanilla and mix. Add matzo cake .
