Home Physical Sciences Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
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Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5

  • Lu Zhang , Hang Yuan , Jiang-Hai Ye , Kang He , Chun-Hua Lai and Juan Zou ORCID logo EMAIL logo
Published/Copyright: March 23, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 3

Abstract

C20H26O5, monoclinic, P212121 (no. 19), a = 7.5455(15) Å, b = 12.735(3) Å, c = 18.333(4) Å, V = 1761.6(6) Å3, Z = 4, R g t (F) = 0.0529, w R r e f (F 2) = 0.1407, T = 273(2) K.

CCDC no.: 2231786

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 needle
Size: 0.24 × 0.21 × 0.19 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 28.3°, >99%
N(hkl) measured, N(hkl) unique, R int: 27,421, 4336, 0.061
Criterion for I obs, N(hkl) gt: I obs > 2 σ(I obs), 2967
N(param) refined: 232
Programs: Bruker [1], SHELX [2, 3], Olex2 [4]
Table 2:

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

Atom x y z U iso*/U eq
C1 0.8471 (5) 0.2771 (3) 0.4121 (2) 0.0518 (9)
C2 0.8452 (5) 0.1959 (3) 0.3505 (2) 0.0569 (10)
C3 0.6592 (5) 0.1614 (3) 0.3310 (2) 0.0527 (9)
C4 0.5187 (5) 0.2482 (2) 0.32738 (17) 0.0414 (7)
C5 0.5469 (4) 0.3384 (2) 0.38096 (15) 0.0321 (6)
C6 0.4294 (4) 0.4240 (2) 0.34983 (16) 0.0368 (7)
C7 0.4855 (4) 0.5357 (2) 0.36708 (16) 0.0354 (7)
C8 0.5843 (4) 0.5440 (2) 0.44028 (18) 0.0371 (7)
C9 0.7307 (4) 0.4558 (2) 0.45429 (17) 0.0373 (7)
C10 0.7414 (4) 0.3755 (2) 0.39092 (17) 0.0374 (7)
C11 0.9037 (5) 0.5030 (3) 0.4829 (3) 0.0613 (11)
C12 0.8702 (6) 0.5773 (3) 0.5468 (3) 0.0694 (12)
C13 0.7071 (6) 0.6488 (3) 0.5343 (2) 0.0668 (12)
C14 0.6623 (5) 0.6541 (3) 0.4531 (2) 0.0545 (9)
C15 0.4622 (5) 0.5354 (3) 0.50565 (17) 0.0431 (8)
C16 0.5398 (6) 0.6022 (3) 0.5643 (2) 0.0602 (10)
C17 0.4570 (9) 0.6200 (5) 0.6270 (2) 0.1008 (19)
C18 0.3348 (5) 0.1973 (3) 0.3375 (2) 0.0611 (10)
C19 0.5020 (5) 0.3094 (3) 0.25723 (18) 0.0495 (8)
C20 0.8288 (5) 0.4218 (3) 0.3219 (2) 0.0524 (9)
H3 0.663376 0.126622 0.283979 0.063*
H5 0.499969 0.317523 0.428649 0.039*
H5A 0.852105 0.536358 0.590738 0.083*
H6 0.767329 0.665714 0.423659 0.065*
H7 0.576090 0.708646 0.442898 0.065*
H8 0.727567 0.719160 0.554172 0.080*
H9 0.974162 0.620896 0.554102 0.083*
H10 0.980744 0.445854 0.499507 0.074*
H11 0.796315 0.246362 0.455747 0.062*
H12 0.913651 0.135097 0.365330 0.068*
H14 0.244240 0.248492 0.328137 0.092*
H16 0.322155 0.139721 0.304160 0.092*
H17 0.564196 0.560466 0.328185 0.043*
H17A 0.346407 0.590269 0.635595 0.121*
H17B 0.509614 0.662205 0.662257 0.121*
H18A 0.307287 0.413062 0.366314 0.044*
H18 0.323600 0.172052 0.386668 0.092*
H20 0.901358 0.225795 0.307694 0.068*
H21 0.968583 0.296653 0.422828 0.062*
H22 0.955360 0.420081 0.327170 0.079*
H23 0.794863 0.381076 0.280111 0.079*
H24 0.790580 0.493137 0.315459 0.079*
H25 0.684333 0.415208 0.495478 0.045*
H33 0.621109 0.109786 0.366628 0.063*
O1 0.3321 (3) 0.6009 (2) 0.36854 (13) 0.0456 (6)
H1A 0.358 (2) 0.666 (3) 0.345 (2) 0.068*
O2 0.9913 (5) 0.5581 (4) 0.4242 (2) 0.1079 (13)
H2A 1.119 (12) 0.555 (5) 0.431 (2) 0.162*
O3 0.3277 (3) 0.4826 (2) 0.50977 (13) 0.0564 (7)
O4 0.5312 (5) 0.2806 (2) 0.19502 (13) 0.0695 (9)
O5 0.4395 (4) 0.40646 (18) 0.27029 (12) 0.0506 (6)

1 Source of material

The acrial part of Pteris dispar Kunze collected from Liping County, Guizhou Province were extracted with methanol for three times (once every five days) at room temperature. The combined filtrate was concentrated and extracted with ethyl acetate. The crude product (348 g) was treated by MCI column with methanol/water (volume radio 50–95%) to obtain five fractions of A–F. The title compound was further purified and isolated from D fraction by silica gel column chromatography. The white needle crystal of the title compound (28 mg) suitable for X-ray diffraction was obtained after recrystallization with ethyl acetate for three days.

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) = 0.82–0.98 Å, U iso (H) = 1.5times U eq(C) and 1.2times U eq(O).

3 Comment

Ent-kauranediterpene is the main active ingredient of Pteris. In recent years, many scholars have reported that there were a certain amount of ent-kauranediterpenes found in Pteris dispar Kunze. Such as geopyxin B, geopyxin E, neolaxiflorin L and so on [5, 6]. Combined with the literature review, ent-kauranediterpene showed good inhibitory activity against breast cancer (MCF-7,MDA–MB-231 and SK–BR-3), colorectal cancer, nasopharyngeal cancer(CNE-2Z), liver cancer, lung cancer (A549), laryngeal cancer and other tumors [7], [8], [9], [10], [11], [12]. The title compound is a member of ent-kauranediterpene, and we hypothesize that it also has antitumor effects. Therefore, it is significant to investigate further examples of ent-kauranediterpene along with their unambiguous structures.

The title molecular structure consists of three six-membered rings, one five-membered ring and one lactone ring, it contains one keto, one alkenyl, two hydroxyl and two methyl groups (see the figure). The bond lengths and angles derived from the compound are within the normal range. The keto bonds were confirmed by the distance of 1.220(4) Å(C15–O3). The olefinic bond was identified by the distance of 1.327(7) Å(C16–C17). And the hydroxyl groups were confirmed by the distance of 0.95(4) Å(O1–H1A) and 0.97(9) Å(O2–H2A), respectively.

Corresponding authors: Chun-Hua Lai and Juan Zou, The Third Hospital of Nanchang, Nanchang 330008, P. R. China, E-mail:

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 81660723

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

  2. Research funding: National Natural Science Foundation of China [No. 81660723], the Youth Science and Technology Talent Project of Guizhou Province [No. (2017) 5618], the Science and Technology Tip-top Talent Foundation of Universities in Guizhou Province [No. KY (2021) 034], the Key Projects of Guizhou Basic Research Program [No. Qiankehejichu–ZK (2022) key 046] and the Sinopharm Grou Tongjitang (Guizhou) Pharmaceutical co., Ltd. [Project Contract No. JS-YF-KY-201912014].

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

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Received: 2023-02-09
Accepted: 2023-03-09
Published Online: 2023-03-23
Published in Print: 2023-06-27

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

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

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https://doi.org/10.1515/ncrs-2023-0061
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,Nʹ,Nʺ]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N′1,N′3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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