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 new germacranolide sesquiterpene lactone, isoscabertopin, was isolated from Elephantopus scaber together with the known scabertopin. Their structures were determined by spectroscopic methods.
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
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 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 sesquite- rpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneo- linderane (6) have been isolated ...A new sesquiterpene lactone, strychnilactone (1), together with five known sesquite- rpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneo- linderane (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
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.
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.
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
Two new beta-dihydroagarofuran sesquiterpenes were isolated from Euonymus phellomana Loes. and their structures were established on the basis of spectral analysis.
One new sesquiterpene polyol eater named angulatin C was isolated from the root bark of Celastrus angulatus along with a known compound, angulatin B. Their structures were elucidated on the basis of spectral analysis.
Two new germacrane sesquiterpenes： 3,8,14-trihydroxy- 1 （10）E,4Z, 11 （13）-germacra- trien-12, 6-olide, 8-（2-methyl-4-hydroxyl-2E-butenoyl）, 3,14-diacetoxy （eupalinolide A, 1）, and 3,8,14-trihydroxy-1（10） E,...Two new germacrane sesquiterpenes： 3,8,14-trihydroxy- 1 （10）E,4Z, 11 （13）-germacra- trien-12, 6-olide, 8-（2-methyl-4-hydroxyl-2E-butenoyl）, 3,14-diacetoxy （eupalinolide A, 1）, and 3,8,14-trihydroxy-1（10） E, 4E, 11（13）-germacratrien-12,6-olide, 8-2-methyl-4-hydroxyl-2E- butenoyl）, 3,14-diacetoxy （eupalinolide B, 2） were isolated from Eupatorium lindleyanum. Their structures were elucidated by means of ^1H and ^13C NMR spectroscopic analysis, including 2D NMR technique.展开更多
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
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 new guaianolide was isolated from the roots of Scorzonera austriaca. The structure was elucidated on the basis of spectral methods including 2D NMR.
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 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
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
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 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 sesquite- rpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneo- linderane (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.
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.
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Two new beta-dihydroagarofuran sesquiterpenes were isolated from Euonymus phellomana Loes. and their structures were established on the basis of spectral analysis.
文摘One new sesquiterpene polyol eater named angulatin C was isolated from the root bark of Celastrus angulatus along with a known compound, angulatin B. Their structures were elucidated on the basis of spectral analysis.
基金This work was supported by the Natural Science Foundation of Jiangsu Science and Technology Department(No.BK2001185),which are gratefully acknowledged.
文摘Two new germacrane sesquiterpenes： 3,8,14-trihydroxy- 1 （10）E,4Z, 11 （13）-germacra- trien-12, 6-olide, 8-（2-methyl-4-hydroxyl-2E-butenoyl）, 3,14-diacetoxy （eupalinolide A, 1）, and 3,8,14-trihydroxy-1（10） E, 4E, 11（13）-germacratrien-12,6-olide, 8-2-methyl-4-hydroxyl-2E- butenoyl）, 3,14-diacetoxy （eupalinolide B, 2） were isolated from Eupatorium lindleyanum. Their structures were elucidated by means of ^1H and ^13C NMR spectroscopic analysis, including 2D NMR technique.
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.
