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
A 1 886 bp full-length sesquiterpene synthase (AaSES) cDNA was cloned front a high-yield Artemisia annua L. strain 001 by a rapid amplification of cDNA end (RACE) strategy. AaSES is 59% identical to Artemisia cyclase ...A 1 886 bp full-length sesquiterpene synthase (AaSES) cDNA was cloned front a high-yield Artemisia annua L. strain 001 by a rapid amplification of cDNA end (RACE) strategy. AaSES is 59% identical to Artemisia cyclase cDNA clone cASC125, 50% identical to epi-cedrol synthase from A. annua , 48% identical to amorpha-4, 11-diene synthase from A. annua, 39% identical to the 5-epi-aristolechene synthase from tabacco, 38 % identical to vetispiradiene synthase front H. muticus, 41 % identical to the, delta-cadinene synthase from cotton. The coding region of the cDNA was inserted into a procaryotic expression vector pET-30a and overexpressed in E. coli BL21 ( DE3). The cyclase proteins extracted front bacterial culture were found largely in an insoluble protein fraction. AaSES expresses in leaves, stems a-rid flowers, not in roots as indicated by Northern blotting analysis.展开更多
A protoilludane sesquiterpene (named xanthocerapene) was isolated from the wood of Xanthoceras sorbifolia Bunge. Its structure, including the relative configuration was established by spectroscopic and chemical methods.
From Senecio tsoongianus, two pairs of enantiomeric isomers, tsoongianolides A (1) and B (2), tsoongianolides C (3) and D (4) were isolated. Their structures were elucidated by 1D and 2D-NMR techniques and X-ray diffr...From Senecio tsoongianus, two pairs of enantiomeric isomers, tsoongianolides A (1) and B (2), tsoongianolides C (3) and D (4) were isolated. Their structures were elucidated by 1D and 2D-NMR techniques and X-ray diffractions. The cytotoxicity to KB cell of 1 and 2 is also reported.展开更多
A new sesquiterpene, named vladimenal （1）, was isolated from the roots of Vladimiria souliei. The structure was elucidated on the basis of spectroscopic analysis.
A new germacranolide sesquiterpene lactone, isoscabertopin, was isolated from Elephantopus scaber together with the known scabertopin. Their structures were determined by spectroscopic methods.
A new acyclic sesquiterpene oligoglycoside, named mukurozioside A, was isolated from pericarps of Sapindus mukurossi. On the basis of chemical and spectral evidence, the structure of mukurozioside A has been establis...A new acyclic sesquiterpene oligoglycoside, named mukurozioside A, was isolated from pericarps of Sapindus mukurossi. On the basis of chemical and spectral evidence, the structure of mukurozioside A has been established as: 11(S)-2, 6(E, E)-dodecadiene-3, 7, 11-trimethyl-1, 12-diol-1, 12-bis-O--L-rhamnopyranosyl-(12)-[-L-rhamnopyranosyl-(13)]-6-O-acetyl--D- Glucopyranoside (1).展开更多
A new sesquiterpene lactone, strychnilactone (1), together with five known sesquiterpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneolinderane (6) have been isolated from...A new sesquiterpene lactone, strychnilactone (1), together with five known sesquiterpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneolinderane (6) have been isolated from the extracts of Supercritical Fluid Extraction of Lindera strychnifolia. The structure of the new compound was elucidated by means of spectroscopic analysis. And the relative configuration of 1 was assigned on the basis of NOE analysis.展开更多
Three new sesquiterpene alkaloids,1-desacetylwilforgine（1）,1-desacetylwilforine（2）,and 9′-hydroxy-2-nicotinoylwilforine （3） were isolated from the roots of Tripterygium wilfordii Hook f.,along with six known al...Three new sesquiterpene alkaloids,1-desacetylwilforgine（1）,1-desacetylwilforine（2）,and 9′-hydroxy-2-nicotinoylwilforine （3） were isolated from the roots of Tripterygium wilfordii Hook f.,along with six known alkaloids.Their structures were established on the basis of spectral analysis.展开更多
A new picrotoxane type sesquiterpene named dendrodensiflorol has been isolated from the stems of Dendrobium densiflorum. Its structure was identified on the basis of spectroscopic method.
A new sesquiterpene lactone eupatoranolide was isolated from the flowers of Eupatorium adenophorum, its structure was elucidated as 2 beta-acetoxy-(7 alpha, 9 beta H)-3.6(11)-cadinadien-12(7)-olide by spectral analysis.
Two new beta-dihydroagarofuran sesquiterpenes were isolated from Euonymus phellomana Loes. and their structures were established on the basis of spectral analysis.
Two new eudesmane sesquiterpene lactones were isolated from the stalk of Lactuca sativa vat anagustata L and their structures were elucidated by means of spectroscopic methods, including 2D NMR （1H-1H COSY, HMBC and ...Two new eudesmane sesquiterpene lactones were isolated from the stalk of Lactuca sativa vat anagustata L and their structures were elucidated by means of spectroscopic methods, including 2D NMR （1H-1H COSY, HMBC and NOESY） as 1β-O-β-D- glucopyranosyl-4α-hydroxyl-5α, 6β, 11βH-eudesma-12, 6α-olide （1） and 1β-hydroxyl-15-O-（p-methoxyphenylacetyl）-5α, 6β, 11 βH-eudesma-3-en- 12, 6a-olide （2）.展开更多
A new sesquiterpene polyol ester, angulatin D, has been isolated from the root bark of Celastrus angulatus. The chemical structure is elucidated on the basis of spectral analysis.
Two new bisabolane sesquiterpenes were isolated from the roots of Leontoptdium longifolium. Their structures were elucidated as 4α, 5α-diacetoxy-lα-angeloyloxybisabol-2, 9, ll-triene and 4α, 5α-diacetoxy-lα-ange...Two new bisabolane sesquiterpenes were isolated from the roots of Leontoptdium longifolium. Their structures were elucidated as 4α, 5α-diacetoxy-lα-angeloyloxybisabol-2, 9, ll-triene and 4α, 5α-diacetoxy-lα-angeloyloxy-ll-hydroxybisabol-2, 9-diene by spectroscopic methods including the 2D NMR techniques.展开更多
A new sesquiterpene trilactone, named bilobanol （1）, along with four known terpene trilactones （ginkgolide A, B, C and bilobalide） were isolated from the roots of Ginkgo biloba collected in Jiangsu Province, China...A new sesquiterpene trilactone, named bilobanol （1）, along with four known terpene trilactones （ginkgolide A, B, C and bilobalide） were isolated from the roots of Ginkgo biloba collected in Jiangsu Province, China. The structure elucidation was accomplished by 1D and 2D NMR methods, HR-ESI-MS, and CD spectrum.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.
文摘A 1 886 bp full-length sesquiterpene synthase (AaSES) cDNA was cloned front a high-yield Artemisia annua L. strain 001 by a rapid amplification of cDNA end (RACE) strategy. AaSES is 59% identical to Artemisia cyclase cDNA clone cASC125, 50% identical to epi-cedrol synthase from A. annua , 48% identical to amorpha-4, 11-diene synthase from A. annua, 39% identical to the 5-epi-aristolechene synthase from tabacco, 38 % identical to vetispiradiene synthase front H. muticus, 41 % identical to the, delta-cadinene synthase from cotton. The coding region of the cDNA was inserted into a procaryotic expression vector pET-30a and overexpressed in E. coli BL21 ( DE3). The cyclase proteins extracted front bacterial culture were found largely in an insoluble protein fraction. AaSES expresses in leaves, stems a-rid flowers, not in roots as indicated by Northern blotting analysis.
文摘A protoilludane sesquiterpene (named xanthocerapene) was isolated from the wood of Xanthoceras sorbifolia Bunge. Its structure, including the relative configuration was established by spectroscopic and chemical methods.
文摘A new guaianolide was isolated from the roots of Scorzonera austriaca. The structure was elucidated on the basis of spectral methods including 2D NMR.
基金This work is financially supported in part by the Life Sciences Special Fund of Chinese Academy of Sciences Supported by the Ministry of Finance (STZ-00-24) the Yunnan Province Foundation of Applied Basic Research (2000C0072M) the Chine-France PRA (g
文摘From Senecio tsoongianus, two pairs of enantiomeric isomers, tsoongianolides A (1) and B (2), tsoongianolides C (3) and D (4) were isolated. Their structures were elucidated by 1D and 2D-NMR techniques and X-ray diffractions. The cytotoxicity to KB cell of 1 and 2 is also reported.
基金supported in part by the Natural Science Foundation of Tianjin(No.06YFJMJC15800),China.
文摘A new sesquiterpene, named vladimenal （1）, was isolated from the roots of Vladimiria souliei. The structure was elucidated on the basis of spectroscopic analysis.
文摘A new germacranolide sesquiterpene lactone, isoscabertopin, was isolated from Elephantopus scaber together with the known scabertopin. Their structures were determined by spectroscopic methods.
文摘A new acyclic sesquiterpene oligoglycoside, named mukurozioside A, was isolated from pericarps of Sapindus mukurossi. On the basis of chemical and spectral evidence, the structure of mukurozioside A has been established as: 11(S)-2, 6(E, E)-dodecadiene-3, 7, 11-trimethyl-1, 12-diol-1, 12-bis-O--L-rhamnopyranosyl-(12)-[-L-rhamnopyranosyl-(13)]-6-O-acetyl--D- Glucopyranoside (1).
文摘A new sesquiterpene lactone, strychnilactone (1), together with five known sesquiterpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneolinderane (6) have been isolated from the extracts of Supercritical Fluid Extraction of Lindera strychnifolia. The structure of the new compound was elucidated by means of spectroscopic analysis. And the relative configuration of 1 was assigned on the basis of NOE analysis.
基金supported by the Natural Science Foundation of Fujian Province,China(No. 2009J01103).
文摘Three new sesquiterpene alkaloids,1-desacetylwilforgine（1）,1-desacetylwilforine（2）,and 9′-hydroxy-2-nicotinoylwilforine （3） were isolated from the roots of Tripterygium wilfordii Hook f.,along with six known alkaloids.Their structures were established on the basis of spectral analysis.
文摘A new picrotoxane type sesquiterpene named dendrodensiflorol has been isolated from the stems of Dendrobium densiflorum. Its structure was identified on the basis of spectroscopic method.
文摘A new sesquiterpene lactone eupatoranolide was isolated from the flowers of Eupatorium adenophorum, its structure was elucidated as 2 beta-acetoxy-(7 alpha, 9 beta H)-3.6(11)-cadinadien-12(7)-olide by spectral analysis.
文摘Two new beta-dihydroagarofuran sesquiterpenes were isolated from Euonymus phellomana Loes. and their structures were established on the basis of spectral analysis.
基金financed by the Science Foundation of Zhejiang Sci-Tech University(No.0613266-Y)the Talents Training Foundation of Key Laboratory of Advanced Textile Materials and Manufacturing Technology (Zhejiang Sci-Tech University),Ministry of Education(No.2006QN04)
文摘Two new eudesmane sesquiterpene lactones were isolated from the stalk of Lactuca sativa vat anagustata L and their structures were elucidated by means of spectroscopic methods, including 2D NMR （1H-1H COSY, HMBC and NOESY） as 1β-O-β-D- glucopyranosyl-4α-hydroxyl-5α, 6β, 11βH-eudesma-12, 6α-olide （1） and 1β-hydroxyl-15-O-（p-methoxyphenylacetyl）-5α, 6β, 11 βH-eudesma-3-en- 12, 6a-olide （2）.
文摘A new sesquiterpene polyol ester, angulatin D, has been isolated from the root bark of Celastrus angulatus. The chemical structure is elucidated on the basis of spectral analysis.
文摘Two new bisabolane sesquiterpenes were isolated from the roots of Leontoptdium longifolium. Their structures were elucidated as 4α, 5α-diacetoxy-lα-angeloyloxybisabol-2, 9, ll-triene and 4α, 5α-diacetoxy-lα-angeloyloxy-ll-hydroxybisabol-2, 9-diene by spectroscopic methods including the 2D NMR techniques.
文摘A new sesquiterpene trilactone, named bilobanol （1）, along with four known terpene trilactones （ginkgolide A, B, C and bilobalide） were isolated from the roots of Ginkgo biloba collected in Jiangsu Province, China. The structure elucidation was accomplished by 1D and 2D NMR methods, HR-ESI-MS, and CD spectrum.
