| Pinus kesiya var.Langbianensis is a plant of the genus Pinaceae that is used as a traditional Chinese medicine to treat diseases such as humid heat diarrhea,bruises,joint inflammation and skin ulcers.According to literature reports,diterpenoids,triterpenoids and flavonoids are the main secondary metabolites of Pinus kesiya var.Langbianensis,with antitumor,anti-inflammatory and antibacterial biological activities.Since Pinus kesiya var.Langbianensis is a geographical variant of Pinus cassiasa,natural medicinal chemists have limited research on it,so its active ingredients need to be further explored.In order to explore more natural organic small molecule compounds with good biological activity and novel structure,the pine joints and needles of the pine plant Pinus spp.were systematically studied using silica gel column chromatography,Sephadex LH-20 gel column chromatography,octadecyl bonded silica gel column chromatography,MCI column chromatography and other chromatographic separation technologies,as well as nuclear magnetic resonance spectroscopy,mass spectrometry,circular dichromatography,infrared spectroscopy and other structural identification technologies,and finally 49 compounds were separated,including two new compounds.Among them,the new compounds were identified as two diterpenoids:4R,5S,10R-10,15-dihydroxy-10-methyl-9,10-secoabieta-8,11,13-trien-18-oic acid(1)and 4R,10R-pinuskvlsone A(2).In addition,47 known compounds were isolated from Pinus kesiya var.Langbianensis,and compound 3-29 were identified as diterpenoids:8(14)podocarpen-13-oxo-18-oic acid(3),7-oxo-13β-hydroxyabiet-8(14)-en-18-oic acid(4),7α-hydroxypodocarpen-8(14)-en-13-oxo-18-oic acid(5),7-oxo-15-hydroxydehydroabietic acid(6),12β-hydroxy-13-oxo-8(14)-podocarpen-18-oic acid(7),12α-hydroxy-13-oxo-8(14)-podocarpen-18-oic acid(8),15-hydroxy dehydroabietic acid(9),12-oxo-abietic acid(10),12α-hydroxyabiet acid(11),7-oxo-dehydroabietic acid(12),17-nor-7,15-dion-8,11,13-abietatrien-18-oic acid(13),8,11,13-abietatriene-15methoxy-18-oic acid(14),13-hydroxy-8,11,13-podocarptrien-18-oic acid(15),methyl 7-oxo-15-hydroxy-dehydroabietate(16),7α-hydroxydehydroabietic acid(17),methyl 7α-hydroxydehydroabietate(18),17-nor-15-oxo-8,11,13-abietatrien-18-oic acid(19),13-propenyl-7-oxo-abieta-8,11,13-trien-18-oic acid(20),7,13-dioxo-8(14)-podocarpen18-oic acid(21),abieta-8,1 1,13,1 5-tetraen-18-oic acid(22),abieta-6,8,11,13-tetraen-18oic acid(23),oxo-13-epi-pimara-14,15-dien-18-oic acid(24),dehydroabietic acid(25),14-hydroxy-abieta-8,11,13-trien-18-oic acid(26),11-oxo-8-en-podocarpen18-oic acid(27),picealactone(28)and 12-hydroxy-7-oxoabieta-8,11,13-trien-18-oic acid(29);compound 30 and 31 were identified as lignans:(-)-nortrachelogenin(30)and(-)-matairesinol(31);compounds 33-35 were identified as stilbene compounds:(E)-3-hydroxyl-5-methoxy stilbene(32),(Z)-3-methoxy-5-hydroxy stilbene(33),(E)-3,5-dihydroxy stilbene(34)and(Z)-3,5-dihydroxy stilbene(35);compounds 36 and 49 were identified as sesquiterpenes:epitodomatuic acid(36)and caryophylenol-Ⅱ(49);compound 37 was identified as a flavonoid:pinocembrin(37);compounds 38-42 was identified as triterpenoids:3β-methoxyserrat-14-en-21-one(38),3β,21α-dimethoxyserrat-14-ene(39),3α-hydroxyserrat-14-ene-21-one(40)and 3β,21β-dihydroxystictane(42);compound 41 was identified as steroid:β-sitosterol(41);compounds 43-48 were identified as simple aromatic compounds:4-hydroxy-3-methoxy-benzaldehyde(43),4-hydroxybenzaldehyde(44),apocynin(45),3-hydroxy-5-methoxybenzylbenzoate(46),frambinone(47)and p-hydroxyacetophenone(48).The effect of new compounds 1 and 2 and known compounds 3-7,12-14,17,21,26 and 38 on NO production of lipopolysaccharide(RAW 264.7 cells)induced by mouse macrophages(LPS)was determined,the experimental results showed that compounds 13,26,6,7,12 and 4 had moderate levels of inhibitory activity in NO generation(IC50:26.4 μM,39.7 μM,43.3μM,45.2 μM,45.6 μM and 48.7 μM,respectively);compounds 14,21,17 and 2 had a weak degree of NO inhibitory activity(IC50:59.3 μM,64.4 μM,72.8 μM and 74.μM,respectively);compounds 1,3,5 and 38 showed no inhibitory activity of NO generation(IC50:141.6 μM,83.5 μM,82.1 μM and 103.3 μM,respectively).Penicillium oxalicum ΔlaeA belongs to Penicillium fungi,and the ethyl acetate extr act of Penicillium oxalicum Δ laeA was separated and identified by silica gel column chromatography,Sephadex LH-20 gel column chromatography,octadecyl bonded silica gel column chromatography,and spectroscopy,finally a total of 8 compounds were obtained,including four steroids:stigmast-4-en-3-one(50),ergosterol(51),(22E,24R)3β-hydroxy-ergosta-5,8(14),22-trien-7-one(52)and ergosterol peroxide(53);one terpene-ester compound:4-methyl-7-(9,9,13-trimethylcyclohexyl)heptanyl-3’,7’,7’trimethylcyclohexa-2’,4’-dien-1’-oate(54);two lactone compounds:1,2,4,8-tetramethyl dec-3,5,7-trien enolide(55)and 3-methyl-2-penten-5-olide(57);one class of vitamin A derivative:9-cis-retinoic acid(56). |
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