Literature DB >> 21589528

9α-Acet-oxy-1β,10α-ep-oxy-parthenolide.

Mohamed Moumou, Mohamed Akssira, Ahmed El Hakmaoui, Lahcen Elammari, Ahmed Benharref, Moha Berraho.

Abstract

The title compound, C(17)H(22)O(6), was semi-synthesized from 9-hy-droxy-arthenolide, which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule contains fused five- and ten-membered rings: the five-membered lactone ring has a twisted conformation, whereas the ten-membered ring displays an approximate chair-chair conformation. The dihedral angle between the rings is 24.76 (9)°.

Entities: Chemical Disease Species

Year: 2010 PMID： 21589528 PMCID： PMC3011600 DOI： 10.1107/S1600536810047471

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the isolation of 9-hydroxyarthenolide, see: El Hassany et al. (2004 ▶); Abdel Sattar et al. (1996 ▶). For the reactivity of this sesquiterpene, see: Castaneda-Acosta et al. (1993 ▶); Neukirch et al. (2003 ▶). For its biological activity, see: Abdel Sattar et al. (1996 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For conformations of ten-membered rings, see: Castaneda-Acosta et al. (1997 ▶); Watson & Zabel (1982 ▶); Moumou et al. (2010 ▶).

Experimental

Crystal data

C17H22O6 M = 322.35 Monoclinic, a = 8.2390 (3) Å b = 10.6482 (4) Å c = 9.4633 (3) Å β = 102.039 (2)° V = 811.96 (5) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 298 K 0.38 × 0.27 × 0.12 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer 12911 measured reflections 2718 independent reflections 2480 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.115 S = 1.05 2718 reflections 211 parameters 1 restraint H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.17 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047471/fj2367sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047471/fj2367Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₂₂O₆	F(000) = 344
M_r = 322.35	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 12911 reflections
a = 8.2390 (3) Å	θ = 2.2–31.0°
b = 10.6482 (4) Å	µ = 0.10 mm⁻¹
c = 9.4633 (3) Å	T = 298 K
β = 102.039 (2)°	PRISM, colourless
V = 811.96 (5) Å³	0.38 × 0.27 × 0.12 mm
Z = 2

Bruker X8 APEX CCD area-detector diffractometer	2480 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
graphite	θ_max = 31.1°, θ_min = 2.2°
φ and ω scans	h = −11→11
12911 measured reflections	k = −15→15
2718 independent reflections	l = −13→13

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0742P)² + 0.0491P] where P = (F_o² + 2F_c²)/3
2718 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	U_iso*/U_eq
C14	0.6599 (2)	−0.1768 (2)	1.05001 (19)	0.0485 (4)
H14A	0.5629	−0.2265	1.0509	0.073*
H14B	0.7023	−0.1440	1.1450	0.073*
H14C	0.7431	−0.2282	1.0210	0.073*
C15	0.6072 (3)	−0.3610 (2)	0.7190 (3)	0.0648 (5)
H15A	0.7103	−0.3776	0.6906	0.097*
H15B	0.5426	−0.4367	0.7113	0.097*
H15C	0.6289	−0.3319	0.8172	0.097*
C1	0.46449 (18)	−0.06799 (17)	0.82978 (17)	0.0403 (3)
H1	0.4716	−0.0145	0.7470	0.048*
C2	0.3450 (2)	−0.1765 (2)	0.7955 (2)	0.0521 (4)
H2A	0.2344	−0.1481	0.8005	0.063*
H2B	0.3768	−0.2417	0.8675	0.063*
C3	0.3418 (3)	−0.2314 (3)	0.6452 (3)	0.0644 (6)
H3A	0.2744	−0.3068	0.6327	0.077*
H3B	0.2905	−0.1712	0.5724	0.077*
C4	0.5134 (3)	−0.2628 (2)	0.6226 (2)	0.0537 (4)
C5	0.5937 (2)	−0.1649 (2)	0.55053 (18)	0.0501 (4)
H5	0.5264	−0.0892	0.5253	0.060*
C6	0.7768 (2)	−0.14210 (17)	0.57840 (17)	0.0447 (4)
H6	0.8377	−0.2171	0.6195	0.054*
C7	0.82874 (19)	−0.02749 (15)	0.67649 (15)	0.0366 (3)
H7	0.7357	0.0318	0.6601	0.044*
C8	0.87578 (18)	−0.05478 (18)	0.83958 (15)	0.0393 (3)
H8A	0.8723	−0.1449	0.8535	0.047*
H8B	0.9894	−0.0279	0.8751	0.047*
C9	0.76603 (17)	0.00787 (16)	0.93218 (15)	0.0352 (3)
H9	0.8333	0.0204	1.0295	0.042*
C10	0.61532 (17)	−0.06993 (15)	0.94522 (15)	0.0356 (3)
C11	0.9645 (2)	0.02787 (18)	0.61024 (19)	0.0464 (4)
C12	0.9353 (3)	−0.0178 (2)	0.4586 (2)	0.0559 (5)
C13	1.0911 (3)	0.1006 (3)	0.6654 (3)	0.0665 (6)
H13A	1.1656	0.1250	0.6091	0.080*
H13B	1.1060	0.1276	0.7607	0.080*
C16	0.8244 (2)	0.22159 (18)	0.9006 (2)	0.0460 (4)
C17	0.7628 (3)	0.3407 (2)	0.8271 (2)	0.0597 (5)
H17A	0.7451	0.4011	0.8976	0.090*
H17B	0.6600	0.3254	0.7600	0.090*
H17C	0.8432	0.3726	0.7760	0.090*
O1	0.5260 (3)	−0.2753 (2)	0.47208 (17)	0.0731 (5)
O2	0.47027 (14)	−0.00130 (14)	0.96360 (14)	0.0473 (3)
O3	0.8194 (2)	−0.10899 (18)	0.44012 (14)	0.0622 (4)
O4	0.9965 (3)	0.0176 (3)	0.36135 (19)	0.0840 (6)
O5	0.71087 (14)	0.12924 (11)	0.87370 (13)	0.0387 (2)
O6	0.96035 (19)	0.20593 (19)	0.9760 (2)	0.0711 (5)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C14	0.0535 (9)	0.0498 (10)	0.0430 (8)	0.0018 (8)	0.0119 (7)	0.0129 (7)
C15	0.0920 (16)	0.0371 (9)	0.0689 (13)	0.0029 (10)	0.0251 (12)	0.0000 (9)
C1	0.0353 (6)	0.0393 (7)	0.0477 (7)	0.0015 (6)	0.0119 (5)	0.0030 (6)
C2	0.0378 (7)	0.0526 (10)	0.0660 (11)	−0.0065 (7)	0.0109 (7)	0.0037 (9)
C3	0.0513 (10)	0.0673 (14)	0.0683 (12)	−0.0167 (10)	−0.0022 (9)	−0.0061 (11)
C4	0.0654 (11)	0.0462 (10)	0.0474 (9)	−0.0088 (8)	0.0072 (8)	−0.0093 (7)
C5	0.0593 (9)	0.0500 (10)	0.0377 (7)	−0.0004 (8)	0.0028 (7)	0.0003 (7)
C6	0.0588 (9)	0.0410 (8)	0.0367 (7)	0.0087 (7)	0.0156 (6)	0.0014 (6)
C7	0.0414 (6)	0.0376 (7)	0.0331 (6)	0.0092 (5)	0.0134 (5)	0.0039 (5)
C8	0.0379 (6)	0.0472 (8)	0.0340 (6)	0.0098 (6)	0.0105 (5)	0.0069 (6)
C9	0.0367 (6)	0.0383 (7)	0.0307 (5)	−0.0009 (5)	0.0077 (4)	−0.0002 (5)
C10	0.0374 (6)	0.0353 (7)	0.0366 (6)	0.0030 (5)	0.0135 (5)	0.0008 (5)
C11	0.0546 (8)	0.0436 (8)	0.0470 (8)	0.0113 (7)	0.0244 (7)	0.0111 (7)
C12	0.0688 (11)	0.0586 (12)	0.0482 (9)	0.0182 (10)	0.0303 (8)	0.0098 (8)
C13	0.0757 (14)	0.0592 (13)	0.0730 (13)	−0.0089 (11)	0.0347 (11)	0.0052 (11)
C16	0.0531 (9)	0.0411 (8)	0.0491 (8)	−0.0111 (7)	0.0231 (7)	−0.0132 (7)
C17	0.0799 (13)	0.0397 (9)	0.0674 (12)	−0.0121 (10)	0.0336 (10)	−0.0033 (9)
O1	0.0935 (12)	0.0769 (12)	0.0452 (8)	−0.0166 (11)	0.0059 (7)	−0.0190 (8)
O2	0.0473 (6)	0.0429 (6)	0.0586 (7)	0.0051 (5)	0.0267 (5)	−0.0034 (6)
O3	0.0873 (10)	0.0679 (10)	0.0372 (6)	0.0057 (9)	0.0268 (6)	−0.0042 (6)
O4	0.1043 (14)	0.1021 (15)	0.0613 (9)	0.0130 (13)	0.0531 (10)	0.0150 (11)
O5	0.0410 (5)	0.0329 (5)	0.0432 (5)	−0.0035 (4)	0.0110 (4)	−0.0027 (4)
O6	0.0544 (8)	0.0626 (10)	0.0909 (13)	−0.0184 (8)	0.0025 (8)	−0.0182 (9)

C14—C10	1.504 (2)	C6—C7	1.539 (2)
C14—H14A	0.9600	C6—H6	0.9800
C14—H14B	0.9600	C7—C11	1.511 (2)
C14—H14C	0.9600	C7—C8	1.5386 (19)
C15—C4	1.493 (3)	C7—H7	0.9800
C15—H15A	0.9600	C8—C9	1.537 (2)
C15—H15B	0.9600	C8—H8A	0.9700
C15—H15C	0.9600	C8—H8B	0.9700
C1—O2	1.444 (2)	C9—O5	1.442 (2)
C1—C10	1.474 (2)	C9—C10	1.519 (2)
C1—C2	1.508 (3)	C9—H9	0.9800
C1—H1	0.9800	C10—O2	1.4419 (18)
C2—C3	1.534 (3)	C11—C13	1.316 (3)
C2—H2A	0.9700	C11—C12	1.486 (3)
C2—H2B	0.9700	C12—O4	1.199 (2)
C3—C4	1.511 (3)	C12—O3	1.348 (3)
C3—H3A	0.9700	C13—H13A	0.9300
C3—H3B	0.9700	C13—H13B	0.9300
C4—O1	1.456 (3)	C16—O6	1.207 (3)
C4—C5	1.476 (3)	C16—O5	1.345 (2)
C5—O1	1.439 (3)	C16—C17	1.484 (3)
C5—C6	1.496 (3)	C17—H17A	0.9600
C5—H5	0.9800	C17—H17B	0.9600
C6—O3	1.467 (2)	C17—H17C	0.9600

C10—C14—H14A	109.5	C7—C6—H6	110.6
C10—C14—H14B	109.5	C11—C7—C8	115.88 (14)
H14A—C14—H14B	109.5	C11—C7—C6	101.30 (13)
C10—C14—H14C	109.5	C8—C7—C6	115.81 (14)
H14A—C14—H14C	109.5	C11—C7—H7	107.8
H14B—C14—H14C	109.5	C8—C7—H7	107.8
C4—C15—H15A	109.5	C6—C7—H7	107.8
C4—C15—H15B	109.5	C9—C8—C7	115.78 (12)
H15A—C15—H15B	109.5	C9—C8—H8A	108.3
C4—C15—H15C	109.5	C7—C8—H8A	108.3
H15A—C15—H15C	109.5	C9—C8—H8B	108.3
H15B—C15—H15C	109.5	C7—C8—H8B	108.3
O2—C1—C10	59.23 (10)	H8A—C8—H8B	107.4
O2—C1—C2	117.75 (14)	O5—C9—C10	108.82 (11)
C10—C1—C2	124.07 (16)	O5—C9—C8	110.26 (12)
O2—C1—H1	114.7	C10—C9—C8	113.44 (13)
C10—C1—H1	114.7	O5—C9—H9	108.1
C2—C1—H1	114.7	C10—C9—H9	108.1
C1—C2—C3	112.05 (17)	C8—C9—H9	108.1
C1—C2—H2A	109.2	O2—C10—C1	59.36 (10)
C3—C2—H2A	109.2	O2—C10—C14	113.50 (13)
C1—C2—H2B	109.2	C1—C10—C14	123.48 (15)
C3—C2—H2B	109.2	O2—C10—C9	116.46 (13)
H2A—C2—H2B	107.9	C1—C10—C9	120.62 (13)
C4—C3—C2	112.34 (16)	C14—C10—C9	112.01 (13)
C4—C3—H3A	109.1	C13—C11—C12	122.04 (18)
C2—C3—H3A	109.1	C13—C11—C7	131.20 (19)
C4—C3—H3B	109.1	C12—C11—C7	106.75 (17)
C2—C3—H3B	109.1	O4—C12—O3	121.8 (2)
H3A—C3—H3B	107.9	O4—C12—C11	129.0 (3)
O1—C4—C5	58.81 (14)	O3—C12—C11	109.18 (15)
O1—C4—C15	113.58 (19)	C11—C13—H13A	120.0
C5—C4—C15	123.53 (19)	C11—C13—H13B	120.0
O1—C4—C3	114.76 (18)	H13A—C13—H13B	120.0
C5—C4—C3	115.6 (2)	O6—C16—O5	122.27 (19)
C15—C4—C3	116.7 (2)	O6—C16—C17	125.43 (18)
O1—C5—C4	59.90 (14)	O5—C16—C17	112.30 (16)
O1—C5—C6	119.44 (19)	C16—C17—H17A	109.5
C4—C5—C6	124.49 (17)	C16—C17—H17B	109.5
O1—C5—H5	114.1	H17A—C17—H17B	109.5
C4—C5—H5	114.1	C16—C17—H17C	109.5
C6—C5—H5	114.1	H17A—C17—H17C	109.5
O3—C6—C5	107.57 (14)	H17B—C17—H17C	109.5
O3—C6—C7	105.02 (14)	C5—O1—C4	61.28 (13)
C5—C6—C7	112.25 (14)	C10—O2—C1	61.41 (10)
O3—C6—H6	110.6	C12—O3—C6	110.63 (14)
C5—C6—H6	110.6	C16—O5—C9	115.58 (13)

6 in total

1. Antitumor germacranolides from Anvillea garcinii.

Authors: E Abdel Sattar; A M Galal; G S Mossa
Journal: J Nat Prod Date: 1996-04 Impact factor: 4.050

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

3. Parthenolide and its photochemically synthesized 1(10)Z isomer: chemical reactivity and structure-activity relationship studies in human leucocyte chemotaxis.

Authors: Hannes Neukirch; Nicole C Kaneider; Christian J Wiedermann; Antonio Guerriero; Michele D'Ambrosio
Journal: Bioorg Med Chem Date: 2003-04-03 Impact factor: 3.641

1 in total

1. Comparison of the effects of alcoholic extract of aerial parts of Anvillea garcinii and atorvastatin on the lipid profile and thyroid hormones in hypercholesterolemic rats.

Authors: Fatemeh Rasekh; Zohre Atashi-Nodoshan; Ali Zarei; Amir Abbas Minaeifar; Saeed Changizi-Ashtiyani; Zahra Afrasyabi
Journal: Avicenna J Phytomed Date: 2022 Mar-Apr