CN102250181B - Polyhydroxy steroid compounds and purpose thereof - Google Patents
Polyhydroxy steroid compounds and purpose thereof Download PDFInfo
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- CN102250181B CN102250181B CN 201110119322 CN201110119322A CN102250181B CN 102250181 B CN102250181 B CN 102250181B CN 201110119322 CN201110119322 CN 201110119322 CN 201110119322 A CN201110119322 A CN 201110119322A CN 102250181 B CN102250181 B CN 102250181B
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- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 229930187017 sarcsteroid Natural products 0.000 claims abstract description 34
- 239000000126 substance Substances 0.000 claims abstract description 10
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims description 16
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- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 11
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- 238000002474 experimental method Methods 0.000 description 3
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 3
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Landscapes
- Steroid Compounds (AREA)
Abstract
The invention relates to the technical field of medicine. The invention provides a class of polyhydroxy steroid compounds which are separated from three corals (Muriceopsis flavida, Sarcophyton sp., and Anthogorgia sp.) collected from Hainan and have antibacterial and anti-microalgae activity, and the chemical structure formula of the polyhydroxy steroid compounds is as shown in the following picture. In vitro antibacterial tests show that the compounds, which contains Muristeroids A-G, Sarcsteroids A-F, Anthsteroids A-B, cholesteric-5alpha, 6beta-diol-3beta-acetic acid ester, cholesteric-5alpha-methoxy-3beta, 6beta-diol, (22E)-22-alkene-cholesteric-3beta, 5alpha, 6beta-triol, 24(28)-alkene-ergosta-3beta, 5alpha, 6beta-triol, cholesteric-3beta, 5alpha, 6beta-triol, cholesteric-1beta, 3beta, 5alpha and 6beta-tetrol, have an obvious effect of inhibiting fungi, bacteria and algae, and can be used for preparing antibacterial and anti-microalgae medicaments. The polyhydroxy steroid compounds provided by the invention are of great significance for developing and utilizing China's marine medicinal biological resources.
Description
Technical field
The present invention relates to medical technical field, be specifically related to from marine invertebrate-coral (Muriceopsis flavida, Sarcophyton sp., Anthogorgia sp.) in, separate 15 of obtaining new have antibiotic, the polyhydroxysteroids compounds Muristeroids A～G of anti-activity of microalgae, Sarcsteroids A～F, AnthsteroidsA～B and 6 known have antibiotic, the polyhydroxysteroids compounds of anti-activity of microalgae: courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-1 β, 3 β, 5 α, the new purposes of 6 β-tetrol.
Background technology
South China Sea located in subtropical zone zone, the coral resource is particularly abundant, is coral one of the marine site of concentrated distribution in the world, and in more than the 6100 kind of coral that the whole world is found at present, China Seas just has 719 kinds.Coral is without the vertebra lower animal, for numerous biologies provides habitat, and as crinosity section, bivalve section, abdominal foot section, fish etc.Although coral self lacks effective physics defence capability, can secrete some chemical defensive substances, resists the invasion of protozoon and other biological, this phenomenon is to study in the world the theoretical basis of secondary metabolite in corallum.Coral can be divided into alcyon and two subclasses of zoantharian according to the number of branches of gastrovascular cavity, and the soft coral in Alcyonaria and gorgonian become the focus of marine natural product research because containing novel structure, the good secondary metabolite of biological activity.
Purple willow coral (Muriceopsis flavida) belongs to Coelenterata (Coelenterata) Anthozoa (Anthoaoa) Alcyonaria (Octocorallia) Gorgonacea (Gorgonacea) the clump Muriceopsis of gorgonian section (Pexuridae) and belongs to animal.The purple willow coral mainly is distributed in east, the Pacific Ocean, California seashore and Caribbean Division.At present, the report of relevant this genus coral chemical constitution study only has one piece both at home and abroad, 5 four sterol that methylates [Kokke WCMC have therefrom been obtained, Bihlin L, Fenical W, Djerassi C.Novel dinoflagaellate 4 α-methylated sterols from four Caribbean gorgonians[J] .Phytochemistry, 1982,21 (4): 881-887], and have no the pertinent literature of its active report.
Meat sesame soft coral (Sarcophyton sp.) belongs to soft coral order (Alcyonacea) Alcyoniidae (Alcyonacea) meat sesame soft coral and belongs to (Sarcophyton) animal.It is various that this belongs to the soft coral kind, distributes wide.Highly oxidized lax alkane diterpene and sterol are the main metabolites of this genus soft coral, except lax alkane diterpene and sterol, have also therefrom found the tetraterpene of the lax alkane type of dimerization that structure is very peculiar.More than 180 new compounds from this genus coral, have been found so far.India scholar Anjaneyulu had once done detailed summary [Anjaneuyulu A.S.R., Rao G.V.J.Ind.Chem.Soc., 1997,74,272.] to the chemical constitution study situation of meat sesame soft coral.
Piece flower gorgonian (Anthogorgia sp.) belongs to Gorgonacea (Gorginacea) sour jujube gorgonian section (Acanthogorgiidae) animal.Literature search finds no the relevant report of closing piece flower gorgonian chemical constitution study.
Summary of the invention
The invention provides from three kinds of South Sea coral (Muriceopsis flavida, Sarcophyton sp., Anthogorgia sp.) extract in and separate 21 polyhydroxysteroids compounds that obtain, difference called after Muristeroids A～G, Sarcsteroid A～F, Anthsteroids A～B, courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-1 β, 3 β, 5 α, 6 β-tetrol.Wherein compound Muristeroids A～G and courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-1 β, 3 β, 5 α, 6 β-tetrol separates and obtains from the purple willow coral, compound S arcsteroids A～F separates and obtains from meat sesame soft coral, compd A nthsteroids A～B separates and obtains from piece flower gorgonian, their chemical structure of general formula is as follows:
Wherein Muristeroids A～G, Sarcsteroids A～F, Anthsteroids A～B are new compound.
Muristeroid A is white powder, and systematic naming method falls courage steroid-5 α for (22E)-22-alkene-24-, 6 beta-diols-3 β-acetic ester.The accurate molecular weight m/z 469.3294[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of carbon spectrum hydrogen spectrum, the molecular formula that provides this compound is C
28h
46o
4, molecular weight is 446;
iR (film) v
max: 3454,2953,2941,2867,1716,1599,1496,1452,1382,1367,1281,1161,1037,968,699; UV (CHCl
3) λ
maxnm (Abs): 257 (0.3642);
1h and
13the C nuclear magnetic resonance data is in Table 1.
Muristeroid B is white powder, and systematic naming method is (22E)-22-alkene-courage steroid-5 α, 6 beta-diols-3 β-acetic ester.The accurate molecular weight m/z483.2188[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, reach carbon spectrum hydrogen spectrum and resolve, provide the molecular formula C of this compound
29h
48o
4, molecular weight 460;
infrared spectra IR (film) v
max: 3369,2956,2927,1736,1664,1599,1458,1378,1260,1043,968,699; UV (CHCl
3) λ
maxnm (Abs): 240 (0.8793);
1h and
13the C nuclear magnetic resonance data is in Table 2.
Muristeroid C is white powder, and systematic naming method is (22E)-22-alkene-5 α-methoxyl group-courage steroid-3 β, 6 beta-diols.The accurate molecular weight m/z455.3498[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
28h
48o
3, molecular weight 432;
infrared spectra IR (film) v
max: 3374,3026,2929,2867,1600,1496,1454,1379,1262,1078,1032,754,699; UV (CHCl
3) λ
maxnm (Abs): 337 (0.4653);
1h and
13the C nuclear magnetic resonance data is in Table 3.
Muristeroid D is white powder, and systematic naming method falls courage steroid-3 β for (22E)-22-alkene-24-, 5 α, 6 beta-diols.The accurate molecular weight m/z427.6338[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
26h
44o
3, molecular weight 404;
infrared spectra IR (film) v
max: 3373,3026,2959,2928,2854,1600,1496,1453,1379,1302,1260,1040,966,749,699; UV (CHCl
3) λ
maxnm (Abs): 278 (0.4411);
1h and
13the C nuclear magnetic resonance data is in Table 4.
Muristeroid E is white powder, and systematic naming method is 24 (25)-alkene-courage steroid-3 β, 5 α, 6 beta-triols.The accurate molecular weight m/z 441.6371[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, in conjunction with hydrogen spectrum carbon spectrum, to resolve, the molecular formula that provides this compound is C
27h
46o
3, molecular weight 418; ,
1h-NMR,
13c-NMR, DEPT,
1h-
1hCOSY, NOESY, HMBC, HMQC deterministic laminate structures,
1h and
13the C nuclear magnetic resonance data is in Table 5.
Muristeroid F is white powder, and systematic naming method falls courage steroid 1 β for (22E)-22-alkene-24-, 3 β, 5 α, 6 β-tetrol.The accurate molecular weight m/z443.2857[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
26h
44o
4, molecular weight 420;
infrared spectra IR (film) v
max: 3316,2953,2926,2851,1600,1496,1455,1379,1212,1098,1040,1009,960; UV (CHCl
3) λ
maxnm (Abs): 278 (0.1204);
1h and
13the C nuclear magnetic resonance data is in Table 6.
Muristeroid G is white powder, and systematic naming method is (22E)-22-alkene-courage steroid 1 β, 3 β, 5 α, 6 β-tetrol.The accurate molecular weight m/z 457.3291[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
26h
44o
4, molecular weight 434;
infrared spectra IR (film) v
max: 3337,2951,2927,2867,1604,1459,1371,1042,1007,964;
1h and
13the C nuclear magnetic resonance data is in Table 7.
Courage steroid-5 α, 6 beta-diols-3 β-acetic ester: be white powder, by ESI-MS,
1h-NMR,
13c-NMR, DEPT and in conjunction with document deterministic laminate structures [Joao FS Carvalho, M Manuel Cruz Silva, MLuisa Sa Emelo.Efficient trans-diaxial hydroxylation of △
5steroids[J] .Tetrahedron, 2010,66; 2455-2462].
Courage steroid-5 α-methoxyl group-3 β, 6 beta-diols: be white powder.By ESI-MS,
1h-NMR,
13c-NMR, DEPT and in conjunction with document deterministic laminate structures [Blunt J W, Fischer A, Hartshorn M P, Jones FW, Kirk D N, Yoong S W.Acid catalyzed reactions of 5 α-hydroxy steroids.III.Westphalen rearrangement[J] .Tetrahedron, 1965,21 (6); 1567-1580].
(22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols: white powder, by ESIMS,
1h-NMR,
13c-NMR in conjunction with document deterministic laminate structures [Giacino Notaro, Bincenzo Piccialli, Donato Sica.3 β, 5 α, 6 β-trihydrolylated sterols with a saturated mucleus from two populations of the marine sponge Cliona copiosa[J] .Journal of natural products, 1991,54 (6); 1570-1575].
24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols: white powder, by ESIMS,
1h-NMR,
13c-NMR in conjunction with document deterministic laminate structures [Kobasyashi; Masaru; Madala M Krishna; et al.Isolation of 23-Demethylgorgost-7-ene-3 β, 5 α, 6 β-triol and (24)-Ergostane-3 β; 5 α; 6 β, 7 β, 15 β-pentol from soft corals of the Andaman and Micobar coasts[J] .Chemical & Phamaceutical Bulletin, 1993,41 (1); 87-89].
Courage steroid-3 β, 5c, 6 beta-triols: white powder, by ESIMS,
1h-NMR,
13c-NMR in conjunction with document deterministic laminate structures [Giacomo Notaro, Vincenzo Piccialli, Donato Sica.3 β, 5 α, 6 β-trihydrolylated sterols with a saturated nucleus from two populations of the marine sponge Cliona copiosa[J] .Journal of natural products.1991,54 (6); 1570-1575].
Courage steroid-1 β, 3 β, 5 α, 6 β-tetrol; White powder, by ESIMS,
1h-NMR,
13c-NMR in conjunction with document deterministic laminate structures [Kobayashi Masaru, Hayashi Takaaki, Nakajima Fumie, Mitsuhashi Hiroshi.Marine steroids.IX.Occurrence of 24 ε-methylcholastane-1 β, 3 β, 5 α, 6 β, 25-pentol-25-monoacetate in the soft coral Sarcophyton glaucum[J] .Steroids, 1979,34 (3); 285-293].
Sarcsteroid A is white powder, and systematic naming method is 11 α-acetoxyl group-24-methyl-22 (23), 25 (27)-diene-courage steroid-3 β, 5 α, 6 beta-triols.The accurate molecular weight m/z 511.2634[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
30h
48o
5, molecular weight 488; By
1h-NMR,
13c-NMR, DEPT, and a complete set of two dimensional NMR deterministic laminate structures;
1h and
13the C nuclear magnetic resonance data is in Table 8.
Sarcsteroid B is white amorphous powder, and systematic naming method is 11 α-acetoxyl group-24 (25)-alkene-courage steroid-3 β, 5 α, 6 beta-triols.The accurate molecular weight m/z 499.4274[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
29h
48o
5, molecular weight 476; By
1h-NMR,
13c-NMR, DEPT, and a complete set of two dimensional NMR deterministic laminate structures;
1h and
13the C nuclear magnetic resonance data is in Table 9.
Sarcsteroid C is the white powder solid, and systematic naming method is 23,24-dimethyl-22 (23)-diene-courage steroid-3 β, 5 α, 6 beta-triols.The accurate molecular weight m/z 485.3532[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
29h
50o
5, molecular weight 478; By
1h-NMR,
13c-NMR, DEPT, and a complete set of two dimensional NMR deterministic laminate structures;
1h and
13the C nuclear magnetic resonance data is in Table 10.
Sarcsteroid D is the white powder solid, and systematic naming method is 23,24-dimethyl-22 (23)-diene-courage steroid-3 β, 5 α, 6 beta-triols.The accurate molecular weight m/z 485.3532[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
29h
50o
5, molecular weight 478; By
1h-NMR,
13c-NMR, DEPT, and a complete set of two dimensional NMR deterministic laminate structures;
1h and
13the C nuclear magnetic resonance data is in Table 11.
Sarcsteroid E is the white powder solid, and systematic naming method is 11 α-acetoxyl group-gorgostane-3 β, 5 α, 6 β, 12 α-tetrol.The accurate molecular weight m/z 557.5432[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
32h
54o
6, molecular weight 534; By
1h-NMR,
13c-NMR, DEPT, and a complete set of two dimensional NMR deterministic laminate structures;
1h and
13the C nuclear magnetic resonance data is in Table 12.
Sarcsteroid F is the white powder solid, and systematic naming method is (24S)-24-methyl-courage steroid-1 α, 3 β, 5 α, 6 β, 11 α-pentol.The accurate molecular weight m/z 489.4582[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
28h
50o
5, molecular weight 466; By
1h-NMR,
13c-NMR, DEPT, and a complete set of two dimensional NMR deterministic laminate structures;
1h and
13the C nuclear magnetic resonance data is in Table 13.
AnthsteroidA is the white powder solid, and systematic naming method is courage steroid-3 β, 5 α, 6 β, 11 α-tetrol.The accurate molecular weight m/z 435.3476[M-H that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
-, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
27h
48o
4, molecular weight 436; By
1h-NMR,
13c-NMR, DEPT, and a complete set of two dimensional NMR deterministic laminate structures;
1h and
13the C nuclear magnetic resonance data is in Table 14.
Anthsteroid B is the white powder solid, and systematic naming method is 22 (23)-alkene-courage steroid-3 β, 5 α, 6 β, 11 α-tetrol.The accurate molecular weight m/z 457.3295[M+Na that quasi-molecular ion peak provides in high resolution mass spectrum (HR-ESI-MS)]
+, and the parsing of hydrogen spectrum carbon spectrum, the molecular formula that provides this compound is C
27h
46o
4, molecular weight 434; By
1h-NMR,
13c-NMR, DEPT, and a complete set of two dimensional NMR deterministic laminate structures;
1h and
13the C nuclear magnetic resonance data is in Table 15.
Table 1.Muristeroid A's
1h and
13c nuclear magnetic resonance data (CDCl
3, 400MHz/100MHz)
J value: coupling constant
Table 2.Muristeroid B's
1h and
13c nuclear magnetic resonance data (CDCl
3, 400MHz/100MHz)
J value: coupling constant
Table 3.Muristeroid C's
1h and
13c nuclear magnetic resonance data (CDCl
3, 400MHz/100MHz)
J value: coupling constant
Table 4.Muristeroid D's
1h and
13c nuclear magnetic resonance data (CD
30D, 400MHz/100MHz)
J value: coupling constant
Table 5.Muristeroid E's
1h and
13c nuclear magnetic resonance data (CDCl
3, 500MHz/100MHz)
J value: coupling constant
Table 6.Muristeroid F's
1h and
13c nuclear magnetic resonance data (CD
3oD, 400MHz/100MHz)
J value: coupling constant
Table 7.Muristeroid G's
1h and
13c nuclear magnetic resonance data (CD
3oD, 400MHz/100MHz)
J value: coupling constant
Table 8.Sarcsteroid A's
1h and
13c nuclear magnetic resonance data (CDCl
3, 400MHz/100MHz)
J value: coupling constant
Table 9.Sarcsteroid B's
1h and
13c nuclear magnetic resonance data (CDCl
3, 400MHz/100MHz)
J value: coupling constant
Table 10.Sarcsteroid C's
1h and
13c nuclear magnetic resonance data (CDCl
3, 400MHz/100MHz)
J value: coupling constant
Table 11.Sarcsteroid D's
1h and
13c nuclear magnetic resonance data (CDCl
3, 400MHz/100MHz)
J value: coupling constant
Table 12.Sarcsteroid E's
1h and
13c nuclear magnetic resonance data (CDCl
3, 400MHz/100MHz)
J value: coupling constant
Table 13.Sarcsteroid F's
1h and
13c nuclear magnetic resonance data (CDCl
3, 500MHz/100MHz)
J value: coupling constant
Table 14.Anthsteroid A's
1h and
13c nuclear magnetic resonance data (CD
3oD, 400MHz/100MHz)
J value: coupling constant
Table 15.Anthsteroid B's
1h and
13c nuclear magnetic resonance data (CD
3oD, 400MHz/100MHz)
J value: coupling constant
Muristeroids A～G of the present invention, courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-1 β, 3 β, 5 α, 6 β-tetrol, Sarcsteroids A～F, the preparation method of AnthsteroidsA～B is as follows:
1.Muristeroids the preparation of A～G and 6 known compounds
Get fresh purple willow coral and clean and to shred, the acetone that is 5～10 times with weight ratio (adding a small amount of water in acetone) supersound extraction is to extracting liquid colourless, and reclaim under reduced pressure acetone is extremely distinguished the flavor of without acetone, use the equal-volume water-dispersion, extracted with diethyl ether several, combining extraction liquid, the reclaim under reduced pressure ether, to dry, obtains total medicinal extract.By total normal phase silica gel chromatography (200～300 order) separation for medicinal extract, with sherwood oil/acetone system gradient elution, by thin layer plate, monitor, according to cut polarity size, collect, total medicinal extract is merged into to 16 parts.
Fr.6 partly passes through Sephandex LH-20 gel column chromatography, and (moving phase: sherwood oil: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.6-1～Fr.6-6.The Fr.6-5 part is passed through normal phase silica gel chromatography (400-600 order) separation again, sherwood oil: 4: 1 wash-outs of acetone, the thin layer plate monitoring, be divided into 4 parts (Fr.6-5-1～Fr.6-5-4) by component.Fr.6-5-2 is by semi-preparative RP-HPLC purifying, take methyl alcohol: the mixed solvent that the volume ratio of water is 90: 10 carries out wash-out, the differential detector monitors, collect containing Muristeroid C and courage steroid-5 α-methoxyl group-3 β, stream part of 6 beta-diols, reclaim under reduced pressure, to dry, obtains compound Muristeroid C and courage steroid-5 α-methoxyl group-3 β, 6 beta-diols.Fr.6-5-3 is by semi-preparative RP-HPLC purifying, take methyl alcohol: the mixed solvent that the volume ratio of water is 95: 5 carries out wash-out, the differential detector monitors, collect containing Muristeroid A, B and courage steroid-5 α, stream part of 6 beta-diols-3 β-acetic ester, reclaim under reduced pressure, to dry, obtains compound MuristeroidA, Muristeroid B and courage steroid-5 α, 6 beta-diols-3 β-acetic ester.
Add the addition of C HCl in the Fr.12 part
3, filter, obtain filter residue, by filter residue CH
3oH: CHCl
3the mixed solvent of 1: 1 dissolves, and through Sephadex LH-20 gel column chromatography, separates (moving phase CH
3oH: CHCl
3=1: 1), thin layer plate detects, collection merges to obtain Fr.12-1～Fr.12-4, Fr.12-3 is purified (moving phase with semi-preparative RP-HPLC, 85% methanol-water), the parallax detector detects, collect containing MuristeroidsD, Muristeroids E, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, stream part of 6 beta-triols, reclaim under reduced pressure is to dry, obtain compound Muristeroids D, Muristeroids E, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α t, 6 beta-triols.
The Fr.13 part is separated through normal phase silica gel column chromatography, by the chloroform/methanol gradient elution, according to thin layer plate, detects monitoring, collects and merges to obtain Fr.13-1～Fr.13-4.Add appropriate chloroform in Fr.13-3, filter, obtain filter residue.Filter residue is dissolved by the chloroform/methanol of 1: 1, through Sephadex LH-20 gel column chromatography, separate (moving phase, CH
3oH: CHCl
3=1: 1).Thin layer plate detects, and collects and merges to obtain Fr.13-3-1～Fr.13-3-3.Fr.13-3-2 is purified (moving phase with semi-preparative RP-HPLC, 85% methanol-water), the parallax detector detects, and collects containing Muristeroids F～G, courage steroid-1 β, 3 β, 5 α, stream part of 6 β-tetrol, reclaim under reduced pressure is to dry, obtain compound Muristeroid F, Muristeroid G and courage steroid-1 β, 3 β, 5 α, 6 β-tetrol.
2.Sarcsteroids the preparation of A～F
Getting green meat sesame soft coral cleans and to shred, the acetone that is 5～10 times by weight ratio (adding a small amount of water in acetone) supersound extraction is to extracting liquid colourless, reclaim under reduced pressure acetone is to distinguishing the flavor of without acetone, use the equal-volume water-dispersion, extracted with diethyl ether for several times, combining extraction liquid, the reclaim under reduced pressure ether, to dry, obtains total medicinal extract.By total normal phase silica gel chromatography (200～300 order) separation for medicinal extract, with n-hexane/acetone system gradient elution, by thin layer plate, monitor, according to cut polarity size, collect, total medicinal extract is merged into to 23 parts.
Fr.20 partly passes through Sephandex LH-20 gel column chromatography, and (moving phase: normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.20-1～Fr.20-7.The Fr.20-3 part is passed through Sephandex LH-20 gel column chromatography again, and (moving phase: normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.20-3-1～Fr.20-3-4.Fr.20-3-3 is by semi-preparative RP-HPLC purifying, take methyl alcohol: the mixed solvent that the volume ratio of water is 96: 4 carries out wash-out, the differential detector monitors, collect the stream part containing Sarcsteroid A, Sarcsteroid B, Sarcsteroid D, reclaim under reduced pressure, to dry, obtains compound S acrsteroid A, Sacrsteroid B, Sacrsteroid D.
Fr.21 partly passes through Sephandex LH-20 gel column chromatography, and (moving phase: normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.21-1～Fr.21-7.The Fr.21-5 part is passed through normal phase silica gel column chromatography again, and (moving phase: methyl alcohol: chloroform=1: 50) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.21-5-1～Fr.21-5-5.Fr.21-5-5 is by semi-preparative RP-HPLC purifying, take methyl alcohol: the mixed solvent that the volume ratio of water is 95: 5 carries out wash-out, the differential detector monitors, collect the stream part containing Sarcsteroid E, Sarcsteroid F, reclaim under reduced pressure, to dry, obtains compound S arcsteroidE, Sarcsteroid F.
Fr.22 partly passes through Sephandex LH-20 gel column chromatography, and (moving phase: normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.22-1～Fr.22-6.The Fr.22-3 part is passed through Sephandex LH-20 gel column chromatography again, and (moving phase: normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.22-3-1～Fr.22-3-6.Fr.22-3-5 is by normal phase silica gel column chromatography (moving phase: chloroform/methanol=40: 1) wash-out, pass through again semi-preparative RP-HPLC purifying, take methyl alcohol: the mixed solvent that the volume ratio of water is 94: 6 carries out wash-out, the differential detector monitors, collect the stream part containing Sarcsteroid C, reclaim under reduced pressure, to dry, obtains compound S arcsteroid C.
3.Anthsteroids the preparation of A～B
Getting fresh block of colored gorgonian cleans and to shred, the acetone that is 5～10 times by weight ratio (adding a small amount of water in acetone) supersound extraction is to extracting liquid colourless, reclaim under reduced pressure acetone is to distinguishing the flavor of without acetone, use the equal-volume water-dispersion, extracted with diethyl ether for several times, combining extraction liquid, the reclaim under reduced pressure ether, to dry, obtains total medicinal extract.By total normal phase silica gel chromatography (200～300 order) separation for medicinal extract, with sherwood oil/acetone system gradient elution, by thin layer plate, monitor, according to cut polarity size, collect, total medicinal extract is merged into to 32 parts.
Fr.21 partly passes through reversed-phase silica gel column chromatography (moving phase: methyl alcohol: water=50%, 70%, 80%, 90%) wash-out, according to thin layer plate, detects monitoring, collects and merges to obtain Fr.21-1～Fr.21-6.Fr.21-5 is by semi-preparative RP-HPLC purifying, take methyl alcohol: the mixed solvent that the volume ratio of water is 75: 25 carries out wash-out, the differential detector monitors, collect the stream part containing Anthsteroid A and Anthsteroid B, reclaim under reduced pressure, to dry, obtains compd A nthsteroid A and Anthsteroid B.
Literature search shows, compound Muristeroids A～G, courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-1 β, 3 β, 5 α, 6 β-tetrol, Sarcsteroids A～F, Anthsteroids A～B does not all have the research report of antibiotic and activity of microalgae.
The in-vitro antibacterial that the present invention carries out above-mentioned 21 compounds and anti-micro-algae test show, they have obvious inhibition for test with fungi, bacterium and algae, therefore, the invention provides the application in antibiotic in preparation, the anti-micro-algae medicine of above-mentioned polyhydroxysteroids compounds.
Embodiment
Now the present invention is described in detail in conjunction with the embodiments.
Embodiment 1. preparation Muristeroids A～G and 6 known compounds.
Get purple willow coral (Muriceopsis flavida) 1500g of Chinese Sanya, Hainan surrounding waters, clean, shred, by the acetone supersound extraction of 5 times of weight, reclaim under reduced pressure acetone is to distinguishing the flavor of without acetone, use the equal-volume water-dispersion, extracted with diethyl ether 6 times, each 1000ml, combining extraction liquid, reclaim ether and be concentrated into dryly, obtain total medicinal extract 12.5g.Total medicinal extract is separated through normal phase silica gel chromatography (200～300 order), the petrol ether/ethyl acetate gradient elution that the volume ratio of take is 80: 1,40: 1,20: 1,10: 1,5: 1,3: 1,2: 1,1: 1,1: 5,1: 15, according to thin layer plate, monitor, each flow point is collected by the polarity size, collects altogether to obtain 16 part Fr.1～Fr.16.
Fr.6 partly uses Sephandex LH-20 gel column chromatography (mobility sherwood oil: methyl alcohol: chloroform=2: 1: 1) separate, according to the thin layer plate monitoring, collect and merge stream part, obtain six part Fr.6-1～Fr.6-6.The Fr.6-5 part is passed through normal phase silica gel chromatography (400-600 order) separation and purification (4: 1 wash-outs of sherwood oil/acetone) again, and the thin layer plate monitoring, be divided into 4 parts (Fr.6-5-1～Fr.6-5-4) by component.Fr.6-5-2 is by partly preparing the RP-HPLC purifying, take methyl alcohol: the mixed solvent that the volume ratio of water is 90: 10 is moving phase, differential detector monitors, coutroi velocity 1.5ml/min, 30 ℃ of constant column temperature temperature, stream part when the collection retention time is 30min, reclaim under reduced pressure, to dry, obtains compound Muristeroid C (1.3mg), stream part when the collection retention time is 45min, reclaim under reduced pressure, to dry, obtains compound courage steroid-5 α-methoxyl group-3 β, 6 beta-diols (1.6mg).Fr.6-5-3 is by semi-preparative RP-HPLC purifying, take methyl alcohol: the mixed solvent that the volume ratio of water is 95: 5 is moving phase, the differential detector monitors, coutroi velocity 1.5ml/min, 30 ℃ of constant column temperature temperature, stream part when the collection retention time is 30min, reclaim under reduced pressure is to dry, obtain compound MuristeroidA (8mg), stream part when the collection retention time is 42min, reclaim under reduced pressure is to dry, obtain compound Muristeroid B (5mg), stream part when the collection retention time is 55min, reclaim under reduced pressure is to dry, obtain compound courage steroid-5 α, 6 beta-diols-3 β-acetic ester (3mg).
Add appropriate chloroform in the Fr.12 part, filter, get filter residue, use chloroform: the methyl alcohol mixed solvent of 1: 1 dissolves, with Sephandex LH-20 gel column chromatography (mobility methyl alcohol: chloroform=1: 1) separate, according to the thin layer plate monitoring, collect and merge stream part, obtain four part Fr.12-1～Fr.12-4.The Fr.12-3 part is again through more than half preparation RP-HPLC purifying (methanol-waters of moving phase 85%; Flow velocity: 1.5ml/min; Column temperature: 30 ℃), differential detector monitors, the stream part when collection retention time is 52min, reclaim under reduced pressure, to dry, obtains compound Muristeroid D (2mg), the stream part when collection retention time is 68min, reclaim under reduced pressure, to dry, obtains compound Muristeroid E (2mg); Stream part when the collection retention time is 75min, reclaim under reduced pressure, to dry, obtains compound (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols (5.5mg); Stream part when the collection retention time is 90min, reclaim under reduced pressure, to dry, obtains compound 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols (3.5mg); Stream part when the collection retention time is 119min, reclaim under reduced pressure, to dry, obtains compound courage steroid-3 β, 5 α, 6 beta-triols (11.0mg).
Fr.13 part is separated through normal phase silica gel column chromatography, by chloroform: methyl alcohol 40: 1,30: 1,20: 1,15: 1, for eluent do gradient elution at 10: 1, detect monitoring according to thin layer plate, collect and merge stream part, obtain four part Fr.13-1～Fr.13-4.Add appropriate chloroform in Fr.13-3, filter, get filter residue, the chloroform by filter residue with 1: 1: dissolve with methanol, separate (moving phase CH through Sephadex LH-20 gel column chromatography
3oH: CHCl
3=1: 1).Thin layer plate detects monitoring, collects and merges stream part, obtains three part Fr.13-3-1～Fr.13-3-3.Fr.13-3-2 is purified the (methanol-water of moving phase 85% with semi-preparative RP-HPLC; Flow velocity: 1.5ml/min; Column temperature: 30 ℃), the parallax detector monitors, the stream part while collecting containing retention time 66min, reclaim under reduced pressure, to dry, obtains compound Muristeroid F (2.5mg); Stream part while collecting retention time 78min, reclaim under reduced pressure, to dry, obtains compound Muristeroid G (5.0mg); Stream part while collecting retention time 85min, reclaim under reduced pressure, to dry, obtains compound courage steroid-1 β, 3 β, 5 α, 6 β-tetrol (8.0mg).
Embodiment 2. preparation Sarcsteroids A～F
Get meat sesame soft coral (Sarcophytum sp) 1642g of surrounding waters, the Guangxi China North Sea, clean, shred, by the acetone supersound extraction of 5 times of weight, reclaim under reduced pressure acetone is to distinguishing the flavor of without acetone, use the equal-volume water-dispersion, extracted with diethyl ether 6 times, each 1000ml, combining extraction liquid, reclaim ether and be concentrated into dryly, obtain total medicinal extract 21.6g.Total medicinal extract is separated through normal phase silica gel chromatography (200～300 order), the volume ratio of take is done gradient elution as 99: 1,79: 1,69: 1,59: 1,49: 1,39: 1,29: 1,25: 1,22: 1,17: 1,15: 1,12: 1,9: 1,8: 1,7: 1,6: 1,5: 1,4: 1,3: 1,2: 1,1: 1,1: 2,1: 5,1: 10, the petrol ether/ethyl acetate of 100% ethyl acetate, according to the thin layer plate monitoring, each flow point is collected and is merged into 23 part Fr.1～Fr.23 altogether from small to large by the polarity size.
Through Sephandex LH-20 gel column chromatography, (moving phase: normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.20-1～Fr.20-7 to Fr.20 (210mg) part.Fr.20-3 (72mg) part is passed through Sephandex LH-20 gel column chromatography again, and (moving phase normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.20-3-1～Fr.20-3-4.Fr.20-3-3 is by the semi-preparative RP-HPLC purifying (methanol-water of moving phase 96%; Flow velocity 1.5ml/min; 30 ℃ of column temperatures), the differential detector monitors, collect the stream part while containing retention time, being 19min, reclaim under reduced pressure is to dry, Sarcsteroid A (2.3mg), collect retention time stream part while being 26min, reclaim under reduced pressure is to dry, obtains Sarcsteroid B (3.3mg), collects retention time stream part while being 54min, reclaim under reduced pressure, to dry, obtains Sarcsteroid D (5.4mg).
Fr.21 partly passes through Sephandex LH-20 gel column chromatography, and (moving phase normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.21-1～Fr.21-7.The Fr.21-5 part is passed through normal phase silica gel column chromatography again, and (mobile phase methanol: chloroform=1: 50) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.21～5-1～Fr.21-5-5.Fr.21-5-5 is by semi-preparative RP-HPLC purifying (moving phase 95% methanol-water; Flow velocity 1.5ml/min; 30 ℃ of column temperatures), the differential detector monitors, collect the stream part while containing retention time, being 30min, reclaim under reduced pressure is to dry, Sarcsteroid E (3.4mg), collect retention time stream part while being 38min, reclaim under reduced pressure, to dry, obtains Sarcsteroid F (3.4mg).
Fr.22 partly passes through Sephandex LH-20 gel column chromatography, and (moving phase normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.22-1～Fr.22-6.The Fr.22-3 part is passed through Sephandex LH-20 gel column chromatography again, and (moving phase normal hexane: methyl alcohol: chloroform=2: 1: 1) wash-out, according to thin layer plate detection monitoring, collection merges to obtain Fr.22-3-1～Fr.22-3-6.Fr.22-3-5 is by normal phase silica gel column chromatography (moving phase chloroform: methyl alcohol=40: 1) wash-out, then pass through semi-preparative RP-HPLC purifying (moving phase 94% methanol-water; Flow velocity 1.5ml/min; 30 ℃ of column temperatures), the differential detector monitors, collect the stream part while containing retention time, being 23min, and reclaim under reduced pressure, to dry, obtains SarcsteroidC (1.4mg).
Embodiment 3. preparation Anthsteroids A～B
Get piece flower gorgonian (Anthogorgia sp) 2167g of surrounding waters, the Guangxi China North Sea, clean, shred, by the acetone supersound extraction of 5 times of weight, reclaim under reduced pressure acetone, to without the acetone flavor, is used the equal-volume water-dispersion, extracted with diethyl ether 6 times, each 2000ml, combining extraction liquid, reclaim ether and be concentrated into dry.Water suspendible by total medicinal extract with 2000ml, extract respectively 6 times with ether and propyl carbinol successively, merges and the reclaim under reduced pressure ether, obtains ether layer medicinal extract 28g, merges propyl carbinol reclaim under reduced pressure propyl carbinol and obtain n-butanol layer medicinal extract 5g.Ether layer medicinal extract (28g) separates through normal phase silica gel column chromatography (200～300 order), take volume ratio as 99: 1,49: 1,34: 1,29: 1,24: 1,19: 1,14: 1,11: 1,9: 1,8: 1,7: 1,6: 1,5: 1,4: 1,3: 1,2: 1,1: 1, the sherwood oil of 100% acetone/acetone gradient elution, according to the thin layer plate monitoring, each flow point is collected as 32 part Fr.1～Fr.32 from small to large altogether by the polarity size.
Fr.21 partly passes through reversed-phase silica gel column chromatography (mobile phase methanol: water=50%, 70%, 80%, 90%) and does gradient elution, according to thin layer plate, detects monitoring, collects and merges to obtain Fr.21-1～Fr.21-6.Fr.21-5 is by semi-preparative RP-HPLC purifying (moving phase 75% methanol-water; 30 ℃ of column temperatures; Flow velocity 1.5ml/min), differential detector monitors, the stream part when collection retention time is 165min, reclaim under reduced pressure is to dry, Anthsteroid A (1.2mg), collect retention time stream part while being 86min, reclaim under reduced pressure, to dry, obtains Anthsteroid B (2.1mg).
Embodiment 4: In vitro Bactericidal Experiments
One, fungi, bacterium and algae are used in test
1. fungi is used in test: anther smut (Microbotryum violaceum) and septoria musiva leaf spoting bacteria (Septoria tritici).
2. bacterium is used in test: intestinal bacteria (Escherichia coli), bacillus megaterium (Bacillus megaterium).
3. algae is used in test: chlorella (Chlorella fusca).
Two, experimental drug
1. positive control drug: penicillin (Penicillin), Streptomycin sulphate (Streptomycin), KETOKONAZOL.
2. negative control product: acetone (Acetone).
3.Muristeroids A～G, courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-1 β, 3 β, 5 α, 6 β-tetrol, Sarcsteroids A～F, Anthsteroids A～B, by embodiment 1 preparation
Three, experimental technique
1. compounding pharmaceutical solution: by penicillin, Streptomycin sulphate, KETOKONAZOL, Muristeroids A～G, courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-1 β, 3 β, 5 α, 6 β-tetrol, Sarcsteroids A～F, Anthsteroids A～B is mixed with acetone the solution that concentration is 2mg/ml respectively, single test consumption 25 μ l.
2. above-mentioned 2 kinds of fungies, 2 kinds of bacteriums and a kind of algae are mixed with to bacterium liquid with the 7ml aqua sterilisa respectively by the requirement of aseptic technique, each gets 4ml bacterium liquid with atomizer, evenly be sprayed on respectively the media surface of culture dish separately, place respectively again two of diameter 1cm sterilizing filter paper in each culture dish, be covered in media surface, then the liquid 50 μ l that get respectively above-mentioned preparation drip on filter paper, cover the substratum lid and are cultivated.All indicate corresponding kinds of culture medium, bacterial classification, compound title, inoculation time on each culture dish lid.20 ℃ of cultivations of anther smut 4 days, 20 ℃ of cultivations of septoria musiva leaf spoting bacteria 4 days, 37 ℃ of cultivations of intestinal bacteria 24 hours, 37 ℃ of cultivations of bacillus megaterium 24 hours, 20 ℃ of cultivations of chlorella 5 days.Observations on time, measure the size (radius) of inhibition zone, and parallel test 3 times, average, and the results are shown in Table 16.
Table 16. agar diffusion experiment screening active ingredients (mm)
From table 16, Muristeroids A～G of the present invention, Sarcsteroids A～F, AnthsteroidsA～B, courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, 24 (28)-alkene-ergot steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-1 β, 3 β, 5 α, 6 β-tetrol is to anther smut, the septoria musiva leaf spoting bacteria, Gram-negative bacteria-intestinal bacteria, gram-positive microorganism-bacillus megaterium and chlorella all have significant restraining effect, therefore can be used for preparing antibacterials.
The present invention provides new lead compound for developing new antibacterials, significant to developing Chinese marine pharmaceutical organism resource.
Claims (2)
1. polyhydroxyl steroid compounds Muristeroids A ~ C, F, G, Anthsteroids A ~ B is characterized in that their chemical structure of general formula is as follows:
The R of each compound wherein
1, R
2, R
3, R
4, R
5and R
6group collocation as follows:
2. the application of polyhydroxyl steroid compounds in preparation antibacterials or anti-micro-algae medicine, is characterized in that this compound is polyhydroxysteroids compounds Muristeroids A ~ G, Sarcsteroids A ~ F, Anthsteroids A ~ B; And courage steroid-5 α, 6 beta-diols-3 β-acetic ester, courage steroid-5 α-methoxyl group-3 β, 6 beta-diols, (22E)-22-alkene-courage steroid-3 β, 5 α, 6 beta-triols, courage steroid-3 β, 5 α, 6 beta-triols, or courage steroid-1 β, 3 β, 5 α, 6 β-tetrol;
Polyhydroxysteroids compounds Muristeroids A ~ G wherein, Sarcsteroids A ~ F, Anthsteroids A ~ B, chemical structure of general formula is as follows:
The R of each compound wherein
1, R
2, R
3, R
4, R
5and R
6group collocation as follows:
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