三种没药中次生代谢产物的分离鉴定、活性评价及微生物转化
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摘要
本文对三种没药属(Commiphora)植物爱伦堡没药(C.opobalsamum)、正品没药(C.myrrha)和穆库尔没药(C.mukul)胶状分泌物进行了系统的化学成分研究和细胞毒活性测试。从三种没药中分离鉴定了25个新化合物,包括9个环阿尔廷烷型三萜,1个重排达玛烷型三萜,1个长链脂肪醇苷,2个甾体化合物,12个倍半萜类化合物。采用水蒸气蒸馏法提取爱伦堡没药和正品没药挥发油,运用GC-MS法对挥发油化学成分进行分析,并测定其抗真菌活性。对分离获得的环阿尔廷烷型三萜进行微生物转化研究,获得了2个新化合物。
本文首次对爱伦堡没药石油醚提取物进行系统的化学成分研究,共分离鉴定27个化合物,包括9个环阿尔廷烷型三萜(1-9),1个长链脂肪醇苷(10),15个倍半萜(11-25),1个长链脂肪酸(26),1个甾体化合物(27)。其中新化合物15个,包括:环阿尔廷-24-烯-1α,2α,3β-三醇(1),环阿尔廷-24-烯-1α,2α,3α-三醇(2),3β-乙酰氧基-环阿尔廷-24-烯-1α,2α-二醇(3),1α-乙酰氧基-环阿尔廷-24-烯-2α,3β-二醇(4),3β-异戊酰氧基-环阿尔廷-24-烯-1α,2α-二醇(5),环阿尔廷-24-烯-1α,3β-二醇(6),环阿尔廷-23E-烯-1α,2α,3β,25-四醇(7),24,25-环氧-环阿尔廷-1α,2α,3β-三醇(8-9),十八烷-1,2S,3S,4R-四醇1-O-α-L-鼠李糖苷(10),桉烷-1β,5α,11-三醇(11),愈创木烷-6α,7α-环氧-4α,10α-二醇(12),吉玛烷-2α-甲氧基-1(10),7(11)-二烯-6-羰基-8,12-内酯(13),愈创木烷-2α-甲氧基-7(11),8(9)-二烯-10α-羟基-6-羰基-8,12-内酯(14)和呋喃杜松烷-1(10),6,8-三烯-4-醇(15)。化合物1-10对前列腺癌细胞株PC3和DU145表现出中等的生长抑制作用,其半数抑制浓度(IC_(50)值)为7.1至34.7μM。此外,化合物1和10能够明显抑制前列腺癌LNCaP细胞中雄激素受体的表达。
本文对正品没药的石油醚提取物进行系统的化学成分研究,共分离鉴定17个化合物,包括1个重排达玛烷型三萜(28),4个环阿尔廷烷型三萜(1,7-9),12个倍半萜类化合物(16-20,22,32-34)。Myrrhasin(28)和myrrhanolides A-C(29-31)4个为新化合物。Myrrhasin(28)为新30(14→13)-重排-达玛烷型三萜;myrrhanolideA为新14(10→1)-重排-桉烷型倍半萜。化合物29和30/31的混合物对人前列腺癌PC3细胞株显示较弱的细胞毒活性,其IC_(50)值分别为38.3和46.0μM。
本文对来源于穆库尔没药胶状分泌物的乙酸乙酯提取物进行系统的化学成分研究,共分离获得14个化合物,采用波谱法对其进行结构鉴定,包括3个甾体(35-37),10个倍半萜(24,33-34,38-44),1个三萜类化合物(1)。其中化合物豆甾烷-5,22E-二烯-3β,11α-二醇(35),豆甾烷-5,22E-二烯-3β,7α,11α-三醇(36),穆库尔内酯A-B(38-39)和穆库尔素A-B(40-41)等6个为新化合物。穆库尔内酯A-B(38-39)为新的倍半萜骨架。
采用GC-MS方法分别从爱伦堡没药和正品没药挥发油中鉴定出25和20种化学成分,主要成分分别为莪术烯(38.91%)和呋喃桉烷-1,3-二烯(30.24%)。两种没药挥发油对植物致病性真菌尖镰孢表现出很好的生长抑制作用,IC_(50)值分别为11.7和9.16μg/mL。
本文评价了刺囊毛霉等14种微生物菌种对环阿尔廷烷型三萜的转化能力,并选定微紫青霉(Penicillium janthinellum)进行环阿尔廷-24-烯-1α,2α,3β-三醇生物转化制备型实验,并获得2个转化产物,分别为环阿尔廷-1α,2α,3β,24α,25-五醇(45)和环阿尔廷-1α,2α,3β,24β,25-五醇(46)。
The resinous exudates of three Commiphora species,C.opobalsamum,C.myrrha, and C.mukul,have been phytochemically investigated,and their cytotoxicities against human prostate cancer cells have also been evaluated.A total of twenty-five new secondary metabolites,including nine cycloartane-type triterpenoids,one rearranged dammarane-type triterpenoid,one aliphatic alcohol glycoside,two steroids,and twelve sesquiterpenoids,were isolated from above three Commiphora species.The essential oil of C.opobalsamum and C.myrrha was extracted hydrodistillation using a Clevenger-type apparatus,separated by gas chromatography(GC),and identified by GC-MS.The antifungal activity was also tested.In addition,microbial transformation of cycloartane-type triterpenoid was carded out,and two new compounds were obtained.
Twenty-seven compounds,including cycloartane-type nine tfiterpenoids(1-9),an aliphatic alcohol glycoside(10),fifteen sesquiterpenoids(11-25),one long chain aliphatic alcohol(26),and one steroid(27) were isolated from the PE extract of C. opobalsamum,of which fifteen were new compounds.The new isolates were identified to be cycloartan-24-ene-1α,2α,3β-triol(1),cycloartan-24-ene-1α,2α,3α-triol(2),3β-acetoxy cycloartan-24-ene-1α,2α-diol(3),1α-acetoxycycloartan-24-ene-2α,3β-diol(4), 3β-isovaleroyloxycycloartan-24-ene-1α,2α-diol(5),cycloartan-24-ene-1α,3β-diol(6), cycloartan-23E-ene-1α,2α,3β,25-tetrol(7),24,25-epoxy cycloartane-1α,2α,3β-triol(8 and 9),octadeeane-1,2S,3S,4R-tetrol 1-O-α-L-rhamnopyranoside(10),eudesmane-1β, 5α,11-triol(11),guaia-6α,7α-epoxy-4α,10α-diol(12),germacr-2α-methoxy-1(10), 7(11)-dien-6-oxo-8,12-olide(13),guaia-2α-methoxy-7(11),8(9)-dien-10α-hydroxy-6-oxo-8,12-olide(14),and furanocadina-1(10),6,8-triene-4-ol(15).The new cycloartane- type triterpenoids 1-9 and aliphatic alcohol glycoside 10 exhibited moderate inhibitory effect against human prostate cancer cells PC3 and DU145 with IC_(50) values ranging from 7.1 to 34.7μM.Furthermore,1 and 10 were able to inhibit the expression of androgen receptor(AR) in LNCaP cells.
Seventeen compounds were obtained from the PE extract of C.myrrha,including five triterpenoids(28,1,7-9),and twelve sesquiterpenoids(16-20,22,32-34). Myrrhasin(28),a 30(14→13)abeo-dammarane triterpenoid,myrrhanolide A(29),a 14(10→1)abeo-eudesmane sesquiterpenoid,and myrrhanolides B-C(30-31),were four new compounds.Compound 29 and the mixture of 30 and 31 exhibited weak cytoxicity against the PC3 cell line with IC_(50) values of 38.3 to 46.0μM,respectively.
Fourteen compounds,including three steroids(35-37),ten sesquiterpenoids(24, 33-34,38-44),and one triterpenoids(1),were isolated from the EtOAc extract of C. mukul.The two steroids,stigmasta-5,22E-diene-3β,11α-diol(35),stigmasta-5,22Ediene -3β,7α,11α-triol(36),and four sesquiterpenoids,mukulolides A-B(38-39) and mukulsins A-B(40-41),were new compounds.Mukulolides A-B(38-39) were novel sesquterpenoid skeleton.
Twenty-five and twenty components were identified from the essential oil of C. opobalsamum and C.myrrha,and the dominant constituents were curzerene(38.91%) and furanoeudesma-1,3-diene(30.24%),respectively.The two kinds of essential oil showed inhibitory effects against plant pathogenic fungi Fusarium oxysporum with IC_(50) of 11.7 and 9.16μg/mL,respectively.
The biotransformation of cycloartane-type triterpenoid was evaluated using fourteen microorganism,and Penicillium janthinellum was adopted to biotransform cycloartan-24-ene-1α,2α,3β-triol.Incubation of P.janthinellum afforded two products, cycloartane-1α,2α,3β,24α,25-pentaol(45) and cycloartane-1α,2α,3β,24β,25-pentaol (46).
本文首次对爱伦堡没药石油醚提取物进行系统的化学成分研究,共分离鉴定27个化合物,包括9个环阿尔廷烷型三萜(1-9),1个长链脂肪醇苷(10),15个倍半萜(11-25),1个长链脂肪酸(26),1个甾体化合物(27)。其中新化合物15个,包括:环阿尔廷-24-烯-1α,2α,3β-三醇(1),环阿尔廷-24-烯-1α,2α,3α-三醇(2),3β-乙酰氧基-环阿尔廷-24-烯-1α,2α-二醇(3),1α-乙酰氧基-环阿尔廷-24-烯-2α,3β-二醇(4),3β-异戊酰氧基-环阿尔廷-24-烯-1α,2α-二醇(5),环阿尔廷-24-烯-1α,3β-二醇(6),环阿尔廷-23E-烯-1α,2α,3β,25-四醇(7),24,25-环氧-环阿尔廷-1α,2α,3β-三醇(8-9),十八烷-1,2S,3S,4R-四醇1-O-α-L-鼠李糖苷(10),桉烷-1β,5α,11-三醇(11),愈创木烷-6α,7α-环氧-4α,10α-二醇(12),吉玛烷-2α-甲氧基-1(10),7(11)-二烯-6-羰基-8,12-内酯(13),愈创木烷-2α-甲氧基-7(11),8(9)-二烯-10α-羟基-6-羰基-8,12-内酯(14)和呋喃杜松烷-1(10),6,8-三烯-4-醇(15)。化合物1-10对前列腺癌细胞株PC3和DU145表现出中等的生长抑制作用,其半数抑制浓度(IC_(50)值)为7.1至34.7μM。此外,化合物1和10能够明显抑制前列腺癌LNCaP细胞中雄激素受体的表达。
本文对正品没药的石油醚提取物进行系统的化学成分研究,共分离鉴定17个化合物,包括1个重排达玛烷型三萜(28),4个环阿尔廷烷型三萜(1,7-9),12个倍半萜类化合物(16-20,22,32-34)。Myrrhasin(28)和myrrhanolides A-C(29-31)4个为新化合物。Myrrhasin(28)为新30(14→13)-重排-达玛烷型三萜;myrrhanolideA为新14(10→1)-重排-桉烷型倍半萜。化合物29和30/31的混合物对人前列腺癌PC3细胞株显示较弱的细胞毒活性,其IC_(50)值分别为38.3和46.0μM。
本文对来源于穆库尔没药胶状分泌物的乙酸乙酯提取物进行系统的化学成分研究,共分离获得14个化合物,采用波谱法对其进行结构鉴定,包括3个甾体(35-37),10个倍半萜(24,33-34,38-44),1个三萜类化合物(1)。其中化合物豆甾烷-5,22E-二烯-3β,11α-二醇(35),豆甾烷-5,22E-二烯-3β,7α,11α-三醇(36),穆库尔内酯A-B(38-39)和穆库尔素A-B(40-41)等6个为新化合物。穆库尔内酯A-B(38-39)为新的倍半萜骨架。
采用GC-MS方法分别从爱伦堡没药和正品没药挥发油中鉴定出25和20种化学成分,主要成分分别为莪术烯(38.91%)和呋喃桉烷-1,3-二烯(30.24%)。两种没药挥发油对植物致病性真菌尖镰孢表现出很好的生长抑制作用,IC_(50)值分别为11.7和9.16μg/mL。
本文评价了刺囊毛霉等14种微生物菌种对环阿尔廷烷型三萜的转化能力,并选定微紫青霉(Penicillium janthinellum)进行环阿尔廷-24-烯-1α,2α,3β-三醇生物转化制备型实验,并获得2个转化产物,分别为环阿尔廷-1α,2α,3β,24α,25-五醇(45)和环阿尔廷-1α,2α,3β,24β,25-五醇(46)。
The resinous exudates of three Commiphora species,C.opobalsamum,C.myrrha, and C.mukul,have been phytochemically investigated,and their cytotoxicities against human prostate cancer cells have also been evaluated.A total of twenty-five new secondary metabolites,including nine cycloartane-type triterpenoids,one rearranged dammarane-type triterpenoid,one aliphatic alcohol glycoside,two steroids,and twelve sesquiterpenoids,were isolated from above three Commiphora species.The essential oil of C.opobalsamum and C.myrrha was extracted hydrodistillation using a Clevenger-type apparatus,separated by gas chromatography(GC),and identified by GC-MS.The antifungal activity was also tested.In addition,microbial transformation of cycloartane-type triterpenoid was carded out,and two new compounds were obtained.
Twenty-seven compounds,including cycloartane-type nine tfiterpenoids(1-9),an aliphatic alcohol glycoside(10),fifteen sesquiterpenoids(11-25),one long chain aliphatic alcohol(26),and one steroid(27) were isolated from the PE extract of C. opobalsamum,of which fifteen were new compounds.The new isolates were identified to be cycloartan-24-ene-1α,2α,3β-triol(1),cycloartan-24-ene-1α,2α,3α-triol(2),3β-acetoxy cycloartan-24-ene-1α,2α-diol(3),1α-acetoxycycloartan-24-ene-2α,3β-diol(4), 3β-isovaleroyloxycycloartan-24-ene-1α,2α-diol(5),cycloartan-24-ene-1α,3β-diol(6), cycloartan-23E-ene-1α,2α,3β,25-tetrol(7),24,25-epoxy cycloartane-1α,2α,3β-triol(8 and 9),octadeeane-1,2S,3S,4R-tetrol 1-O-α-L-rhamnopyranoside(10),eudesmane-1β, 5α,11-triol(11),guaia-6α,7α-epoxy-4α,10α-diol(12),germacr-2α-methoxy-1(10), 7(11)-dien-6-oxo-8,12-olide(13),guaia-2α-methoxy-7(11),8(9)-dien-10α-hydroxy-6-oxo-8,12-olide(14),and furanocadina-1(10),6,8-triene-4-ol(15).The new cycloartane- type triterpenoids 1-9 and aliphatic alcohol glycoside 10 exhibited moderate inhibitory effect against human prostate cancer cells PC3 and DU145 with IC_(50) values ranging from 7.1 to 34.7μM.Furthermore,1 and 10 were able to inhibit the expression of androgen receptor(AR) in LNCaP cells.
Seventeen compounds were obtained from the PE extract of C.myrrha,including five triterpenoids(28,1,7-9),and twelve sesquiterpenoids(16-20,22,32-34). Myrrhasin(28),a 30(14→13)abeo-dammarane triterpenoid,myrrhanolide A(29),a 14(10→1)abeo-eudesmane sesquiterpenoid,and myrrhanolides B-C(30-31),were four new compounds.Compound 29 and the mixture of 30 and 31 exhibited weak cytoxicity against the PC3 cell line with IC_(50) values of 38.3 to 46.0μM,respectively.
Fourteen compounds,including three steroids(35-37),ten sesquiterpenoids(24, 33-34,38-44),and one triterpenoids(1),were isolated from the EtOAc extract of C. mukul.The two steroids,stigmasta-5,22E-diene-3β,11α-diol(35),stigmasta-5,22Ediene -3β,7α,11α-triol(36),and four sesquiterpenoids,mukulolides A-B(38-39) and mukulsins A-B(40-41),were new compounds.Mukulolides A-B(38-39) were novel sesquterpenoid skeleton.
Twenty-five and twenty components were identified from the essential oil of C. opobalsamum and C.myrrha,and the dominant constituents were curzerene(38.91%) and furanoeudesma-1,3-diene(30.24%),respectively.The two kinds of essential oil showed inhibitory effects against plant pathogenic fungi Fusarium oxysporum with IC_(50) of 11.7 and 9.16μg/mL,respectively.
The biotransformation of cycloartane-type triterpenoid was evaluated using fourteen microorganism,and Penicillium janthinellum was adopted to biotransform cycloartan-24-ene-1α,2α,3β-triol.Incubation of P.janthinellum afforded two products, cycloartane-1α,2α,3β,24α,25-pentaol(45) and cycloartane-1α,2α,3β,24β,25-pentaol (46).
引文
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