Startseite Naturwissenschaften (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
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(6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6

  • Chen-Yu Lu , Jiang-Hai Ye , Yu-Ling Luo , Ren-Song Chen ORCID logo , Chen-Liang Zhao und Jing-Jie Zhang EMAIL logo
Veröffentlicht/Copyright: 23. November 2023

Abstract

C22H26O6, orthorhombic, P212121 (no. 19), a = 7.6648(5) Å, b = 11.2663(6) Å, c = 22.7321(7) Å, V = 1963.0(2) Å3, Z = 4, Rgt (F) = 0.0652, wRref (F 2) = 0.1399, T = 273(2) K.

CCDC no.: 2307526

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.21 × 0.19 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 33.7°, >99 %
N(hkl)measured, N(hkl)unique, R int: 35,325, 7783, 0.092
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3580
N(param)refined: 259
Programs: Olex2 [1], Bruker [2], SHELX [3], Diamond [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
C1 0.4047 (4) 0.4586 (2) 0.44400 (13) 0.0336 (7)
C2 0.3225 (4) 0.3503 (2) 0.45150 (12) 0.0337 (7)
C3 0.2930 (4) 0.2791 (2) 0.40290 (13) 0.0345 (7)
C4 0.3537 (4) 0.3135 (2) 0.34835 (13) 0.0367 (7)
C5 0.4404 (4) 0.4216 (2) 0.34069 (13) 0.0334 (6)
C6 0.5027 (4) 0.4544 (2) 0.27973 (13) 0.0378 (7)
C7 0.6896 (4) 0.4183 (3) 0.26219 (13) 0.0418 (8)
C8 0.8326 (4) 0.5048 (2) 0.28439 (13) 0.0386 (7)
C9 0.8332 (4) 0.5285 (2) 0.35109 (13) 0.0392 (7)
C10 0.7196 (4) 0.6319 (2) 0.36874 (13) 0.0349 (7)
C11 0.7935 (4) 0.7455 (2) 0.36757 (13) 0.0401 (7)
C12 0.6880 (4) 0.8395 (2) 0.38108 (14) 0.0400 (7)
C13 0.5158 (4) 0.8266 (2) 0.39381 (14) 0.0401 (7)
C14 0.4378 (4) 0.7166 (2) 0.39621 (13) 0.0359 (7)
C15 0.5433 (4) 0.6173 (2) 0.38354 (12) 0.0333 (7)
C16 0.4633 (4) 0.4971 (2) 0.38862 (12) 0.0315 (6)
C17 0.7258 (5) 0.2881 (3) 0.27694 (16) 0.0573 (10)
C18 1.0139 (5) 0.4675 (3) 0.26351 (17) 0.0579 (10)
C19 0.5723 (5) 1.0186 (3) 0.39071 (19) 0.0647 (11)
C20 0.3162 (5) 0.2161 (3) 0.53307 (15) 0.0520 (9)
C21 0.1255 (5) 0.1163 (3) 0.36574 (16) 0.0523 (9)
C22 0.1920 (5) 0.7603 (3) 0.45637 (16) 0.0649 (11)
H1A 0.380035 0.503031 0.520284 0.074*
H2 0.216526 0.080274 0.342883 0.078*
H3 0.061660 0.171128 0.341612 0.078*
H4 0.047938 0.055934 0.380018 0.078*
H5 0.693227 0.423330 0.219163 0.050*
H6 0.634738 0.239378 0.260880 0.086*
H7 0.729467 0.278302 0.318876 0.086*
H8 0.835776 0.264943 0.260334 0.086*
H9 0.808498 0.581293 0.265573 0.046*
H10 0.951926 0.543973 0.363672 0.047*
H11 0.793062 0.457820 0.371362 0.047*
H12 0.910326 0.756657 0.357935 0.048*
H13 0.264071 0.746754 0.490241 0.097*
H14 0.187388 0.843801 0.448123 0.097*
H15 0.076301 0.731433 0.463979 0.097*
H17 1.096012 0.529407 0.272168 0.087*
H18 1.011402 0.453642 0.221849 0.087*
H19 1.048152 0.396030 0.283388 0.087*
H19A 0.580572 1.078027 0.421483 0.078*
H20 0.493240 0.539896 0.275649 0.045*
H21 0.422994 0.419264 0.251538 0.045*
H22 0.336724 0.263929 0.316142 0.044*
H23 0.285660 0.215581 0.574031 0.078*
H24 0.259655 0.150968 0.513586 0.078*
H25 0.440312 0.208260 0.529048 0.078*
H196 0.544316 1.058553 0.354102 0.078*
O1 0.4318 (3) 0.53025 (17) 0.49175 (9) 0.0492 (6)
O2 0.2605 (3) 0.32603 (16) 0.50692 (9) 0.0454 (6)
O3 0.1995 (3) 0.17743 (17) 0.41377 (9) 0.0480 (6)
O4 0.7335 (3) 0.95823 (17) 0.38514 (11) 0.0582 (7)
O5 0.4406 (3) 0.93643 (17) 0.40461 (12) 0.0575 (7)
O6 0.2639 (3) 0.69888 (18) 0.40673 (10) 0.0469 (6)

1 Source of material

The rhizome of Schisandra sphenanthera produced in Guizhou was dried and crushed to obtain 7.5 kg of coarse powder, which was extracted three times (7 days/time) with 100 %, 90 % and 70 % methanol (MeOH) respectively at room temperature. The combined extract was then concentrated under reduced pressure to obtain a total extract of 1.02 kg. After suspending the total extract in warm water, petroleum ether, ethyl acetate and n-butanol were used for further extraction to afford three fractions: the petroleum ether (PE) extract (209 g), ethyl acetate (EtOAc) extract (423 g) and n-butanol extraction extract (201 g). Further, the EtOAc extract was applied to a MCI column (MeOH/H2O 30:70 to 100:0) to obtain 6 fractions (H1–H6). Fr. H4 was subjected to a silica gel column, eluting with the a gradient solvent system (PE:EtOAc 50:1 to 0:1) to give 4 subfractions (H4-1–H4-4). Fr. H4-2 was recrystallized with methanol to obtain the title compound which was suitable for X-ray single crystal diffraction. The compound name was determined as: (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo [3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol.

2 Experimental details

The carbon-bound hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms with d(C–H) = 0.93–1.43 Å, U iso(H) = 1.5 times U eq(C) and 1.2 times U eq(O).

3 Comment

S. sphenanthera belongs to the Schisandra genus in the Schisandracea family, commonly known as “South Schisandra” [5]. This species is widely distributed in Asia and North America, especially in the southwest and southeast areas of China [6]. S. sphenanthera was used as a Chinese medicine, which was found to possess astringing effect that could nourish kidney yin and relieve mental stress, supplement qi and promote the production of body fluid. It is reported that people in Guizhou traditionally used S. sphenanthera as a medicinal herb and called the stem of S. sphenanthera purple gold bark, wind vine, etc., which was used to dispel wind, dehumidify system, and promote blood circulation to arrest pain. Previous studies have shown that the chemical components of S. sphenanthera are rich, mainly including lignans, triterpenes, sesquiterpenes, volatile oils, polysaccharides, flavonoids, organic acids, and amino acids [7]. The main chemical components are lignans, which are also the main active ingredients. Lignans have significant effects in anti-tumor [8], anti-inflammatory [9], liver protective, sedative, and hypnotic aspects [10], and can effectively improve the learning and memory abilities of model animals, as well as elderly dementia [11]. Our research group has conducted a phytochemical study on S. sphenanthera produced in Guizhou and isolated a variety of new compounds with novel structures and interesting bioactivities. This finding has encouraged us to further conduct an in-depth study on this species. As a result, a lignan was isolated from this plant. The compound, as shown in Figure, consists of an octacillar, 2 benzene rings, 2 ether bonds, 2 methyl groups, 3 methoxy groups and one hydroxyl group. The ether bonds were confirmed by the distances of 1.387(3) Å (C13–O5) and 1.385(3) Å (C12–O4). And the methoxyl groups were confirmed by the distance of 1.374(3) Å (C2–O2), 1.374(3) Å (C3–O3) and 1.369(4) Å (C14–O6), respectively. The hydroxyl was confirmed by the distance of 1.369(3) Å (C1–O1) [1214].


Corresponding author: Jing-Jie Zhang, Guizhou University of Traditional Chinese Medicine, The Dongqing South Road#, Guiyang City, Guizhou Province, Guiyang 550025, P.R. China, E-mail:

Funding source: General Projects Guizhou Science and Technology Department

Award Identifier / Grant number: Qiankehejichu [2021] general 0017

  1. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

  2. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  3. Research funding: General Projects Guizhou Science and Technology Department [grant number Qiankehejichu [2021] general 0017].

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Received: 2023-10-23
Accepted: 2023-11-13
Published Online: 2023-11-23
Published in Print: 2024-02-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
  10. Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
  17. Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
  26. Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
  32. The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
  33. Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
  34. Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
  35. (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
  36. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
  37. Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
  38. Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
  39. Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
  40. Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
  41. Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
  42. The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
  43. Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
  44. The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
  45. The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
  46. Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
  47. Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
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