Home 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
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6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5

  • Yin-Ju Zhang , Qi-ji Li ORCID logo , Fa-ju Chen , Xiong Pan , Lang Zhou ORCID logo EMAIL logo and Xiao-Sheng Yang EMAIL logo
Published/Copyright: October 16, 2024

Abstract

C20H26O5, orthorhombic, P212121 (no. 19), a = 5.2825(10) Å, b = 13.0652(2) Å, c = 26.4176(4) Å, V = 1823.26(5) Å3, Z = 4, R gt (F) = 0.0338, wR ref (F 2) = 0.0821, T = 150 K. CCDC No.: 2377464.

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 plate
Size 0.10 × 0.09 × 0.07 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.73 mm−1
Diffractometer, scan mode: XtaLAB AFC12 (RINC), ω
θ max, completeness: 73.9°, >99 %
N(hkl)measured , N(hkl)unique, R int: 17,041, 3,653, 0.046
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3,364
N(param)refined: 233
Programs: Olex2, 1 SHELX 2 , 3
Table 2:

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

Atom x y z U iso*/U eq
C1′ 0.2310 (4) 0.27497 (15) 0.36932 (7) 0.0361 (4)
H1′A 0.129627 0.234968 0.344785 0.043*
H1′B 0.113050 0.318512 0.388927 0.043*
C1″ 0.5611 (4) 0.62884 (15) 0.32281 (7) 0.0390 (5)
H1″A 0.625850 0.660446 0.291301 0.047*
H1″B 0.382839 0.650401 0.327229 0.047*
C2′ 0.3644 (3) 0.20121 (14) 0.40547 (7) 0.0280 (4)
H2′A 0.482511 0.157884 0.385065 0.034*
C2 1.1047 (4) 0.49086 (16) 0.23038 (7) 0.0382 (5)
C2″ 0.7152 (4) 0.66586 (14) 0.36701 (8) 0.0370 (4)
H2″ 0.866809 0.629289 0.373890 0.044*
C3′ 0.1810 (3) 0.12958 (14) 0.43342 (7) 0.0301 (4)
C3″ 0.6636 (4) 0.74378 (16) 0.39750 (7) 0.0384 (4)
C3 1.1042 (4) 0.38152 (16) 0.22168 (7) 0.0394 (5)
H3 1.221991 0.353033 0.198446 0.047*
C4 0.9412 (4) 0.31937 (15) 0.24569 (7) 0.0361 (5)
H4 0.947316 0.247732 0.239649 0.043*
C4′ 0.3214 (4) 0.06704 (15) 0.47310 (8) 0.0363 (4)
H4′A 0.205009 0.017505 0.488420 0.054*
H4′B 0.387279 0.112804 0.499375 0.054*
H4′C 0.462208 0.030542 0.457065 0.054*
C4″ 0.4483 (6) 0.8158 (2) 0.38997 (12) 0.0685 (8)
H4″A 0.332936 0.788024 0.364376 0.103*
H4″B 0.513166 0.882187 0.378596 0.103*
H4″C 0.357217 0.824518 0.421999 0.103*
C5 0.5869 (4) 0.29991 (15) 0.30770 (7) 0.0326 (4)
H5 0.590302 0.227703 0.303537 0.039*
C5′ 0.0477 (4) 0.05945 (16) 0.39589 (8) 0.0419 (5)
H5′A −0.064601 0.100107 0.374272 0.063*
H5′B −0.052000 0.008435 0.414371 0.063*
H5′C 0.174085 0.024683 0.374856 0.063*
C5″ 0.8246 (6) 0.7657 (2) 0.44297 (9) 0.0576 (7)
H5″A 0.973951 0.721209 0.442509 0.086*
H5″B 0.726621 0.752800 0.473809 0.086*
H5″C 0.878578 0.837468 0.442296 0.086*
C6 0.4125 (4) 0.34266 (15) 0.34071 (7) 0.0336 (4)
C7 0.4091 (4) 0.44986 (15) 0.34505 (7) 0.0346 (4)
C8 0.5728 (4) 0.51340 (14) 0.31806 (7) 0.0344 (4)
C9 0.7493 (4) 0.46614 (14) 0.28684 (7) 0.0331 (4)
C10 0.7577 (4) 0.35997 (14) 0.28039 (6) 0.0320 (4)
C11 0.2921 (5) 0.50260 (17) 0.42739 (8) 0.0453 (5)
H11A 0.149495 0.531230 0.446417 0.068*
H11B 0.440317 0.547013 0.431351 0.068*
H11C 0.331613 0.434126 0.440312 0.068*
O1′ 0.5132 (2) 0.25973 (10) 0.44047 (5) 0.0309 (3)
H1′ 0.661104 0.236204 0.441405 0.046*
O1 0.9186 (3) 0.52903 (10) 0.26183 (5) 0.0378 (3)
O2′ −0.0158 (3) 0.18863 (12) 0.45742 (5) 0.0375 (3)
H2′ 0.020309 0.197435 0.488078 0.056*
O2 1.2502 (3) 0.55211 (12) 0.21228 (5) 0.0474 (4)
O3 0.2264 (3) 0.49593 (11) 0.37495 (5) 0.0439 (4)

1 Source of material

The fruits of Rosa roxburghii Tratt were extracted with 95 % ethanol under reflux. The crude extract (914.5 g) was loaded onto a silica gel column and eluted with a solvent system of dichloromethane/methanol (1:0 to 1:1, v/v) to afford eight fractions (Fr. A–H). The colourless block crystals were isolated from fraction B and recrystallized with ethyl acetate/methanol (1:5, v/v). The title compound (23 mg) was obtained after 3 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) = 0.95–0.99 Å, U iso (H) = 1.5 times U eq (C) and 1.2 times U eq (O).

3 Comment

Recent studies have shown that a series of coumarins with various structures have been found in R. roxburghii fruit, and exhibit multifarious biological activities, including antioxidant, 4 antibacterial, 5 anti-inflammatory, 6 anticancer, 7 neuroprotective 8 effects. The title compound contains two hydroxyl groups, one double bond, a methoxy and four methyl groups. The hydroxyl was confirmed by the distances d(C2′–O4) = 1.434(2) Å and d(C3′–O5) = 1.442(2) Å, the olefinic bond was identified by the distance d(C2″–C3″) = 1.326(3) Å, the methoxy was confirmed by the distances d(C7–O3) = 1.385(2) Å, respectively. And the structural characteristics of the title compound are similar to those of 7-methoxy-8-(3-methyl-2-butenyl)coumarin 9 and Buntansin C. 10 and related compounds. 11


Corresponding authors: Lang Zhou, State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guizhou, 550014, P.R. China; and Natural Products Research Center of Guizhou Province, Guizhou, 550014, P.R. China, E-mail: ; and Xiao-Sheng Yang, Natural Products Research Center of Guizhou Province, Guizhou, 550014, P.R. China; and Guizhou University of Traditional Chinese Medicine, 550025, P.R. China, E-mail:

Acknowledgements

The authors gratefully acknowledge support from: National Natural Science Foundation of China [No. 32160104], The construction of innovation capacity of scientific research institutions in Guizhou province [No. QJHFQ[2024]005], Guizhou Provincial Basic Research Program (No. 2023-239), Science and Technology Program of Guizhou Province (No. [2023]077).

  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. 32160104], The construction of innovation capacity of scientific research institutions in Guizhou province [No. QJHFQ[2024]005], Guizhou Provincial Basic Research Program (No. 2023-239), Science and Technology Program of Guizhou Province (No. [2023]077).

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

References

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Received: 2024-08-16
Accepted: 2024-10-04
Published Online: 2024-10-16
Published in Print: 2024-12-17

© 2024 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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