CN105418725B - Pentacyclic triterpenoid and its application - Google Patents

Pentacyclic triterpenoid and its application Download PDF

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CN105418725B
CN105418725B CN201510834298.0A CN201510834298A CN105418725B CN 105418725 B CN105418725 B CN 105418725B CN 201510834298 A CN201510834298 A CN 201510834298A CN 105418725 B CN105418725 B CN 105418725B
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compound
pentacyclic triterpenoid
pentacyclic
triterpenoid
nmr
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CN105418725A (en
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何祥久
黄洁
王宜海
李船
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Guangdong Pharmaceutical University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/0026—Oxygen-containing hetero ring cyclic ketals

Abstract

The invention discloses pentacyclic triterpenoid and its application, the general structure of pentacyclic triterpenoid is：OrIn formula, R11、R21Stand alone as alkyl, methylol or its ester；R31、R41Stand alone as hydrogen, alkyl.The pentacyclic triterpenoid of the present invention has good antiinflammatory action, and the compound has the advantages of efficient, less toxic, is expected to exploitation as new anti-inflammatory drug and is beneficial to inflammatory patients functional food.

Description

Pentacyclic triterpenoid and its application
Technical field
The present invention relates to a kind of pentacyclic triterpenoid and its application.
Background technology
Inflammation (inflammation) is based on the defence that there is the biological tissue of vascular system pro-inflammatory cytokine to be occurred Reaction.Diseases associated with inflammation is common disease clinically, such as furuncle, carbuncle, pneumonia, gastritis, hepatitis, ephritis, typhoid fever, tuberculosis. Clinical topical manifestations have red, swollen, hot, pain and dysfunction；Whole body often has different degrees of reaction, and such as heating, peripheral blood are thin in vain Born of the same parents increase.NSAIDs (NSAIDs) is a clinical commonly used big antiinflammatory drugs, and its is bad for discovered in recent years Reaction is on the increase, including intestines and stomach, neuropsychiatric, allergic reaction and liver, renal damage etc., wherein bad anti-with intestines and stomach The incidence highest answered, about 30%~50%.Almost all of NSAIDs can cause renal damage, including just be used for clinic in recent years Selective epoxidation enzyme -2- inhibitor.Therefore, the invention good effect and small novel anti-inflammatory drug of toxic side effect has been compeled in eyebrow Eyelash.
Natural drug especially has chemical constitution diversity and diverse biological activities from the medicine of plant, always It is the main source that the mankind prevent and treat disease.The many medicines clinically applied are all directly or indirectly from natural production Thing, natural products act not only as the semi-synthetic precursor of medicine, and the template that can be synthesized as pharmaceutical chemistry, are New drug design provides new approaches.Natural products turns into one of main source for finding novel drugs or lead compound.
Short handle Serrata oaks (Quercus serrata var.brevipetiolata) are Fagaceae (Fagaceae) oak category (Quercus) mutation for plant.According to《Chinese Plants will》Record, about 300 kinds of the Fagaceae oak plant whole world, wherein I State-owned 51 kinds, 14 mutation, 1 modification.Oak category (Quercus L.) plant as it is medicinal first appeared in《Tang materia medica》, later successive dynasties sheet Grass is all on the books, is mainly used in treating the diseases such as rush down dysentery, malignant sore, scrofula.Up to the present, the change of identification is separated from the platymiscium Compound is mainly that compound, the modern pharmacologies such as flavonoids, triterpenes, tanninses, Phenylpropanoid Glycosides class, alkaloids and volatile oil are ground Study carefully and show that these compounds have the effect such as anti-oxidant, antibacterial and antiviral, anti-inflammatory activity.
The main anti-inflammatory active ingredient of short handle Serrata oak seeds is triterpene compound, and existing research is to its chemical constitution study Still not enough thoroughly, thus in short handle Serrata oak seeds triterpenes chemical composition is worth further research and development to utilize.
The content of the invention
It is an object of the invention to a kind of new pentacyclic triterpene class compound and its application.
The technical solution used in the present invention is：
Pentacyclic triterpenoid, its general structure are：
In formula, R11、R21Stand alone as C1~C4 alkyl, methylol or its pharmaceutically acceptable ester；R31、R41Stand alone as The alkyl of hydrogen, C1~C4.
Further, the general structure of pentacyclic triterpenoid is：
In formula, R1=CH3Or OAc；R2=CH3Or CHO；
R3=H or CH3；R4=CH3Or H.
Particularly, the structural formula of pentacyclic triterpenoid is
A kind of composition for treating inflammation, its active component contain above-mentioned pentacyclic triterpenoid.
The beneficial effects of the invention are as follows：
The pentacyclic triterpenoid of the present invention has good security.
The pentacyclic triterpenoid of the present invention, which has, to be suppressed to produce NO by lipopolysaccharide-induced RAW264.7 cells well Effect, illustrate that the compound has good anti-inflammatory activity, be expected to exploitation be new anti-inflammatory drug.
Brief description of the drawings
Fig. 1 is the compounds of this invention 11H-NMR collection of illustrative plates；
Fig. 2 is the compounds of this invention 113C-NMR collection of illustrative plates；
Fig. 3 is the compounds of this invention 21H-NMR collection of illustrative plates；
Fig. 4 is the compounds of this invention 213C-NMR collection of illustrative plates；
Fig. 5 is the compounds of this invention 31H-NMR collection of illustrative plates；
Fig. 6 is the compounds of this invention 313C-NMR collection of illustrative plates；
Fig. 7 is the compounds of this invention 41H-NMR collection of illustrative plates；
Fig. 8 is the compounds of this invention 413C-NMR collection of illustrative plates.
Embodiment
With reference to embodiment, technical scheme is further illustrated.
Short handle Serrata oak seed 34.5Kg are taken, with 70% ethanol heating and refluxing extraction 4 times, 4 hours every time, merges extract solution and subtracts Recycling design is pressed, obtains total concentrate 30L, is respectively extracted 4 times in equal volume with hexamethylene, ethyl acetate and n-butanol successively, wherein Ethyl acetate layer extract 200g.By using silica gel column chromatography, Sephdax LH-20 exclusion chromatographies, ODS mesolow post colors The separation methods such as spectrum, RPLC, the isolated the compounds of this invention 1-4 from ethyl acetate layer extract.It is logical Cross physicochemical constant and Modern spectroscopy learns to do the structure of more than section (HRESIMS, 1D-NMR, 2D-NMR) identification 4 compounds, chemical combination Thing 1 is the α-trihydroxy-24-oxo-olean-12-en-28-oic acid of 2 α, 3 β, 19, and compound 2 is 23-acetoxy, 2 α, 3 β, 19 α-trihydroxyurs-12-en-28-oic acid, compound 3 are 3,23-O-acetyl propyl-2 α, 3 β, 19 α, 23-tetrahydroxy-urs-12-en-28-oic acid β-D-glucopyranosyl ester, compound 4 are 3,23-O-acetyl propyl-2α,3β,19α,23-tetrahydroxy-olean-12-en-28-oic acidβ-D- glucopyranosyl ester.Compound 1~41H-NMR collection of illustrative plates and13C-NMR collection of illustrative plates is respectively as shown in Fig. 1~8.
Compound 1-4 Structural Identification process is as follows：
2 α, 3 β, 19 α-trihydroxy-24-oxo-olean-12-en-28-oic acid (compound 1)：White is without fixed Shape powder；IR(KBr)νmax3454 (OH), 2942,1697 (C=O), 1456,1385,1264,1204,1047cm-1；HR-ESI- MS m/z 503.3349[M+H]+(calcd for C30H46O6, 503.3294), the molecular formula for determining compound 1 is C30H46O6。 1H NMR (500MHz, pyridine-d5) high field region provide six methyl on triterpenoid sapogenin hydrogen signal δ 1.64 (3H, s, H-27), δ 1.58 (3H, s, H-23), δ 1.21 (3H, s, H-29), δ 1.13 (3H, s, H-30), δ 1.01 (3H, s, H-26), δ 0.95(3H,s,H-25)；An olefinic carbon hydrogen signal δ 5.57 (1H, s, H-12) and an active hydrogen signal δ are provided in high field region 10.45(1H,s,H-24)。13C NMR (126MHz, pyridine-d5) in share 30 carbon signals, wherein δ 123.3 (C-12), δ 145.3 (C-13) is the feature carbon signal of oleanane type triterpene, and δ 207.7 (C-24) is aldehyde radical carbon signal, (the C- of δ 181.2 28) it is carboxyl carbon signal, δ 82.7 (C-3), δ 81.2 (C-19), δ 68.8 (C-2) is three company's oxygen carbon signals.The compound13C NMR datas and paradrymoniside are basically identical, only have difference at 28, compound 1 is in 28 ratios Paradrymoniside is connected to a glucose less, i.e., the structure of compound 1 is paradrymoniside aglycon, it is comprehensive with Upper information, the Structural Identification of compound 1 are the α-trihydroxy-24-oxo-olean-12-en-28-oic of 2 α, 3 β, 19 acid. With reference to DEPT,1H-1H COSY, HSQC, HMBC, NOESY spectrums can belong to the signal of the compounds of this invention 1.Compound 1 's1H and13C NMR datas are shown in Table 2,3, and structure is shown in Table 1.
23-acetoxy-2 α-trihydroxyurs-12-en-28-oic the acid of α, 3 β, 19 (compound 2)：White nothing Amorphous powder；IR(KBr)νmax2936,1689 (C=O), 1384,1205,1032cm-1；HR-ESI-MS m/z 547.3647 [M+H]+(calcd for C32H50O7, 547.3557), it is C to determine the molecular formula of compound 232H50O7。1H NMR (500MHz, pyridine-d5) the hydrogen signal δ 1.74 (3H, s, H-27), δ 1.44 of six methyl on triterpenoid sapogenin are provided in high field region (3H, s, H-29), δ 1.11 (3H, s, H-26), δ 1.03 (3H, s, H-25), δ 1.01 (3H, s, H-24), δ 1.12 (3H, d, J= 2.7Hz,H-30)；One acetonyl hydrogen signal δ 1.89 (3H, s, H-2 '), provide a methine hydrogen signal δ in high field region 3.07 (1H, s, H-18), two company Oxymethylene hydrogen signal δ 4.21 (1H, m, H-2), δ 3.87 (1H, d, J=9.3Hz, H-3) With an olefinic carbon hydrogen signal δ 5.60 (1H, s, H-12).13C NMR (126MHz, pyridine-d5) in share 32 carbon signals, Wherein δ 128.2 (C-12), δ 140.3 (C-13), for the feature carbon signal of black bearberry alkane type triterpenoid, δ 181.1 (C-28), δ 171.1 (C-1 ') is two carbonyl carbon signals, and δ 68.8 (C-2), δ 77.6 (C-3), δ 73.1 (C-19), δ 67.0 (C-23) are four companies Oxygen carbon signal.By H-23 α, H-23 β, H-2 ' in HMBC respectively with C-1 ', and H-2 ' is related to C-23's can determine that acetyl Base is connected on 23；With reference to DEPT,1H-1H COSY, HSQC, HMBC, NOESY spectrum can to the signal of the compounds of this invention 2 and Relative configuration is belonged to completely.The Structural Identification of compound 2 is 23-acetoxy-2 α, 3 β, 19 α-trihydroxyurs-12- en-28-oic acid.Compound 21H and13C NMR datas are shown in Table 2,3, and structure is shown in Table 1.
3,23-O-acetoxypropyl-2α,3β,19α,23-tetrahydroxy-urs-12-en-28-oic acid β-D-glucopyranosyl ester (compound 3)：White amorphous powder；IR(KBr)νmax 3454(OH),2926, 1732 (C=O), 1384,1030cm-1；HR-ESI-MS m/z 787.4261[M+Na]+(calcd for C41H64O13Na, 787.4347) molecular formula for, determining compound 3 is C41H64O13。1H NMR (500MHz, pyridine-d5) provided in high field region The hydrogen signal δ 1.66 (3H, s, H-27) of six methyl, δ 1.41 (3H, s, H-29), δ 1.17 (3H, s, H- on triterpenoid sapogenin 24), δ 1.15 (3H, s, H-26), δ 1.00 (3H, s, H-25), δ 1.08 (3H, d, J=6.7Hz, H-30)；Two methylene letters Number δ 2.63 (1H, m, H-2 "), δ 2.17 (1H, m, H-3 ")；Methine hydrogen signal δ 3.59 (1H, s, a H- are provided in high field region 5 "), an olefinic carbon hydrogen signal δ 5.52 (1H, s, H-12), and sugared end group hydrogen signal δ 6.29 (1H, d, J=8.5Hz, a H- 1’)。13C NMR (126MHz, pyridine-d5) in share 41 carbon signals, wherein δ 128.6 (C-12), 139.8 (C-13) are The feature carbon signal of black bearberry alkane type triterpenoid, δ 177.6 (C-28), δ 174.1 (C-4 ") are two carbonyl carbon signals, (the C- of δ 102.2 1 ") it is a hemiacetal group carbon signal, δ 65.3 (C-2), δ 91.2 (C-3), δ 73.2 (C-19), δ 78.8 (C-23) are four companies Oxygen carbon signal.In addition with the carbon signal δ 96.4 (C-1 ') of one group of glucose, δ 74.6 (C-2 '), δ 79.5 (C-3 '), δ 71.8 (C-4’),δ79.8(C-5’),δ62.8(C-6’).The compound13C NMR datas and rubusside A are basically identical, both Only there is difference on the substituent of common connection 3 and 23, the determination composed by HMBC, discovery is commonly connected to compound 3 It is an acetyl propyl group with 23 upper substituents.With reference to DEPT,1H-1H COSY, HSQC, HMBC, NOESY spectrums can be to the present inventionization The signal and relative configuration of compound 3 are belonged to completely.The Structural Identification of compound 3 is 3,23-O-acetoxypropyl-2 α, 3 β,19α,23-tetrahydroxy-urs-12-en-28-oic acidβ-D-glucopyranosyl ester.Compound 3 's1H and13C NMR datas are shown in Table 2,3, and structure is shown in Table 1.
3,23-O-acetoxypropyl-2α,3β,19α,23-tetrahydroxy-olean-12-en-28-oic Acid β-D-glucopyranosyl ester (compound 4)：White amorphous powder；IR(KBr)νmax 3455(OH), 2938,1736 (C=O), 1453,1384,1167,1132,1069,1029cm-1；HR-ESI-MS m/z 787.4305[M+Na ]+(calcd for C41H64O13Na, 787.4347), the molecular formula for determining compound 4 is C41H64O13。1H NMR (500MHz, pyridine-d5) the hydrogen signal δ 1.59 (3H, s, H-27), δ 1.17 of six methyl on triterpenoid sapogenin are provided in high field region (3H, s, H-24), δ 1.14 (3H, s, H-29), δ 1.10 (3H, s, H-26), δ 1.00 (3H, s, H-25), δ 0.97 (3H, s, H- 30)；Two methylene signals δ 2.63 (1H, m, H-2 "), δ 2.19-2.15 (1H, m, H-3 ")；One first is provided in high field region Base hydrogen signal δ 3.59 (1H, s, H-5 "), an olefinic carbon hydrogen signal δ 5.47 (1H, s, H-12), and a sugared end group hydrogen signal δ 6.35 (1H, d, J=8.1Hz, H-1 ').13C NMR (126MHz, pyridine-d5) in share 41 carbon signals, wherein δ 177.6 (C-28), δ 174.1 (C-4 ") are two carbonyl carbon signals, and δ 102.0 (C-1 ") is a hemiacetal group carbon signal, δ 65.0 (C-2), δ 90.9 (C-3), δ 81.3 (C-19), δ 78.6 (C-23) are four company's oxygen carbon signals.In addition with one group of grape The carbon signal δ 96.2 (C-1 '), δ 74.4 (C-2 '), δ 79.2 (C-3 '), δ 71.3 (C-4 '), δ 79.6 (C-5 '), δ 62.4 of sugar (C-6’).The compound13C NMR datas and compound 3 are basically identical, and two olefinic carbon signals of only 12 and 13 are not Together, the olefinic carbon signal δ 124.1 (C-12) of compound 4,144.6 (C-13) are the feature carbon signal of oleanane type triterpene.With reference to DEPT,1H-1H COSY, HSQC, HMBC, NOESY spectrums can be returned completely to the signal and relative configuration of the compounds of this invention 4 Category.The Structural Identification of compound 4 is 3,23-O-acetoxypropyl-2 α, 3 β, 19 α, 23-tetrahydroxy-olean-12- en-28-oic acidβ-D-glucopyranosyl ester.Compound 41H and13C NMR datas are shown in Table 2,3, and structure is shown in Table 1.
Table 1：The structure of 4 compounds of the invention
Table 2：The compounds of this invention 1-4's1H-NMR modal datas (pyridine-d5,500MHz)
Table 3：The compounds of this invention 1-4's13C-NMR modal datas (pyridine-d5,126MHz)
With reference to experiment, the activity of the compounds of this invention is further illustrated.
Anti-inflammatory activity is tested：
The RAW264.7 cells that the compounds of this invention is induced LPS produce NO inhibitory action.
Suppress NO generation (Greiss methods)
By RAW264.7 cell seedings among 96 orifice plates, treat that it grows into concentration as 2 × 105Add during individual cell number/mL Enter 1 μ g/mL LPS and sample to be tested, 24h is cultivated at 37 DEG C, take 50 μ L of supernatant liquid to add 50 μ L Griess The μ L Griess Reagent II of Reagent I and 50, then measure OD values in 546nm, and NO generation inhibiting rates press following formula Calculate, and the half-inhibition concentration (IC of tested sample is calculated with CalcuSyn softwares50)
Experimental result is shown in Table 4.
The half-inhibition concentration of table 4, different compounds
Sample ID Half-inhibition concentration IC50(μM)
Compound 1 5.4±1.2
Compound 2 19.1±6.1
Compound 3 8.2±0.6
Compound 4 12.8±0.8
Positive drug (Indomethacin) 47.4±4.5
It was found from the experimental data of table 4, compound 1-4 is respectively provided with good anti-inflammatory activity, available for anti-inflammatory drug or guarantor Health food.

Claims (5)

1. pentacyclic triterpenoid, its structural formula are：
Or。
2. pentacyclic triterpenoid is preparing the application in treating anti-inflammatory drugs, wherein, pentacyclic triterpenoid is
Or。
3. pentacyclic triterpenoid is beneficial to the application in inflammation functional food in preparation, wherein, pentacyclic triterpene chemical combination Thing is
Or。
A kind of 4. composition for treating inflammation, it is characterised in that：Its active component is
Or。
5. the preparation method of pentacyclic triterpenoid described in claim 1, comprises the following steps：
1) short handle Serrata oak seeds are taken, with ethanol heating and refluxing extraction, recovery ethanol obtains concentrate；
2) hexamethylene, ethyl acetate and extracting n-butyl alcohol are used successively, collect ethyl acetate layer extract；
3) by chromatographic isolation ethyl acetate layer extract, pentacyclic triterpenoid is obtained.
CN201510834298.0A 2015-11-25 2015-11-25 Pentacyclic triterpenoid and its application Active CN105418725B (en)

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Publication number Priority date Publication date Assignee Title
CN108659092B (en) * 2018-06-25 2021-05-25 广东药科大学 Anti-inflammatory triterpenoid saponin compound and extraction method and application thereof

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