红托竹荪和辣乳菇化学成分及体外抗氧化活性研究
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摘要
本文对两种药食兼用真菌红托竹荪(Dictyophora ruhrovolvata)和辣乳菇(Lactarius piper atus)的化学成分进行了分离纯化、结构鉴定和体外抗氧化活性研究。通过硅胶、Sephadex LH-20凝胶等色谱分离手段,采用1H-NMR、13C-NMR和EI-MS等波谱学测试手段,并且参照SciFinder(科技文献查询)和标准图谱库等有关文献对其进行结构表征,鉴定了12个已知化合物的结构,分属甾醇、倍半萜、脂肪酸、鞘糖脂和生物碱类型。
1.从红托竹荪(D. ruhrovolvata)子实体中共分离鉴定了7个已知化合物,即麦角甾醇(1)、5a,8a-过氧-麦角甾-6,22-二烯-3β-醇(2)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(3)、硬脂酸(9)、CerebrosideB (10)、Cerebroside D (11)和尿嘧啶(12)。
2.从辣乳菇(L. piperatus)子实体中共分离鉴定了8个已知化合物,即麦角甾醇(1)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(3)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β,9α-四醇(4)、3β,5α,9α-三羟基-(22E,24R)-麦角甾-7,22-二烯-6-酮(5)、Isolactarorufin (6)、7α，8β-dihydroxy-5,13-marasmanolide (7)、7α,8α-dihydroxy-5,13-marasmanolide (8)。
3.红托竹荪乙醇提取物(Dre)和辣乳菇乙醇提取物(Lpe)体外抗氧化活性测定结果显示：Dre, Lpe, α-生育酚(α-Tocopherol),奎诺二甲基丙烯酸酯(Trolox),丁基羟基茴香醚(BHA)和2,6-二叔丁基-4-甲基苯酚(BHT)体外抗氧化活性随着其浓度增大而增强,但总体上来说,Dre和Lpe体外抗氧化活性均弱于α-Tocopherol, Trolox, BHA和BHT。
4.红托竹荪和辣乳菇中总酚酸和总黄酮含量测定结果显示：红托竹荪中总酚酸和总黄酮的含量分别为2.74±0.38mg/g和1.305±0.03mg/g,辣乳菇中总酚酸和总黄酮的含量分别为5.20±0.46mg/g和1.430±0.05mg/g。
The chemical constituents and biological actives of the fruiting bodies of D. ruhrovolvata and L. piperatus were investigated. Twelve known compounds were obtained using varied chromatography methods (CC and TLC), and the structures of the compounds were elucidated on the basis of extensive spectroscopic analysis (1D-NMR, MS, etc.). These natural products involve sterols, sesquiterpenoids, fatty acids, sphingolipids, and alkaloids.
1. Seven compounds were isolated from the fruiting bodies of D. ruhrovolvata were elucidated as ergosterol (1),5a,8a-epidioxy-ergosta-6,22-dien-3β-ol (2),(22E,24R)-ergosta-7,22-dien-3β,5a,6β-trilol (3), octadecanoic acid (9), cerebroside B (10), cerebroside D (11) and uracil (12).
2. Eight compounds were isolated from the fruiting bodies of L. piperatus were elucidated as ergosterol (1),(22E,24R)-ergosta-7,22-dien-3β,5a,6β-trilol (3),(22E,24R)-ergosta-7,22-diene-3β,5a,6β,9a-tetrol(4),3β,5a,9a-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (5), Isolactarorufin (6),7a,8β-dihydroxy-5,13-marasmanolide (7), and7a,8a-dihy-droxy-5,13-marasmanolide (8).
3. The antioxidant activities of the ethanolic extracts obtained from the fruiting bodies of D. ruhrovolvata (Dre) and L. piperatus (Lpe) were investigated according to reducing power, metal chelating, DPPH·, O2-and·OH scavenging activity and inhibition of lipid peroxidation, and compared to standard antioxidant compounds such as a-tocopherol, trolox, BHA, and BHT. The antioxidant activities of Dre and Lpe were lower than that of antioxidant compounds, significantly. But the antioxidant activities of Dre and Lpe increased with concentration.
4. Total phenolic and flavonoid compounds in the ethanolic extracts obtained from the fruiting bodies of D. ruhrovolvata and L. piperatus were measured. Total phenolics and flavonoids content of D. ruhrovolvata (2.74±0.38mg/g and1.305±0.03mg/g, respectively) lower than L. piperatus (5.20±0.46mg/g and1.430±0.05mg/g, respectively).
1.从红托竹荪(D. ruhrovolvata)子实体中共分离鉴定了7个已知化合物,即麦角甾醇(1)、5a,8a-过氧-麦角甾-6,22-二烯-3β-醇(2)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(3)、硬脂酸(9)、CerebrosideB (10)、Cerebroside D (11)和尿嘧啶(12)。
2.从辣乳菇(L. piperatus)子实体中共分离鉴定了8个已知化合物,即麦角甾醇(1)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(3)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β,9α-四醇(4)、3β,5α,9α-三羟基-(22E,24R)-麦角甾-7,22-二烯-6-酮(5)、Isolactarorufin (6)、7α，8β-dihydroxy-5,13-marasmanolide (7)、7α,8α-dihydroxy-5,13-marasmanolide (8)。
3.红托竹荪乙醇提取物(Dre)和辣乳菇乙醇提取物(Lpe)体外抗氧化活性测定结果显示：Dre, Lpe, α-生育酚(α-Tocopherol),奎诺二甲基丙烯酸酯(Trolox),丁基羟基茴香醚(BHA)和2,6-二叔丁基-4-甲基苯酚(BHT)体外抗氧化活性随着其浓度增大而增强,但总体上来说,Dre和Lpe体外抗氧化活性均弱于α-Tocopherol, Trolox, BHA和BHT。
4.红托竹荪和辣乳菇中总酚酸和总黄酮含量测定结果显示：红托竹荪中总酚酸和总黄酮的含量分别为2.74±0.38mg/g和1.305±0.03mg/g,辣乳菇中总酚酸和总黄酮的含量分别为5.20±0.46mg/g和1.430±0.05mg/g。
The chemical constituents and biological actives of the fruiting bodies of D. ruhrovolvata and L. piperatus were investigated. Twelve known compounds were obtained using varied chromatography methods (CC and TLC), and the structures of the compounds were elucidated on the basis of extensive spectroscopic analysis (1D-NMR, MS, etc.). These natural products involve sterols, sesquiterpenoids, fatty acids, sphingolipids, and alkaloids.
1. Seven compounds were isolated from the fruiting bodies of D. ruhrovolvata were elucidated as ergosterol (1),5a,8a-epidioxy-ergosta-6,22-dien-3β-ol (2),(22E,24R)-ergosta-7,22-dien-3β,5a,6β-trilol (3), octadecanoic acid (9), cerebroside B (10), cerebroside D (11) and uracil (12).
2. Eight compounds were isolated from the fruiting bodies of L. piperatus were elucidated as ergosterol (1),(22E,24R)-ergosta-7,22-dien-3β,5a,6β-trilol (3),(22E,24R)-ergosta-7,22-diene-3β,5a,6β,9a-tetrol(4),3β,5a,9a-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (5), Isolactarorufin (6),7a,8β-dihydroxy-5,13-marasmanolide (7), and7a,8a-dihy-droxy-5,13-marasmanolide (8).
3. The antioxidant activities of the ethanolic extracts obtained from the fruiting bodies of D. ruhrovolvata (Dre) and L. piperatus (Lpe) were investigated according to reducing power, metal chelating, DPPH·, O2-and·OH scavenging activity and inhibition of lipid peroxidation, and compared to standard antioxidant compounds such as a-tocopherol, trolox, BHA, and BHT. The antioxidant activities of Dre and Lpe were lower than that of antioxidant compounds, significantly. But the antioxidant activities of Dre and Lpe increased with concentration.
4. Total phenolic and flavonoid compounds in the ethanolic extracts obtained from the fruiting bodies of D. ruhrovolvata and L. piperatus were measured. Total phenolics and flavonoids content of D. ruhrovolvata (2.74±0.38mg/g and1.305±0.03mg/g, respectively) lower than L. piperatus (5.20±0.46mg/g and1.430±0.05mg/g, respectively).
引文
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