Syntheses of All Stereoisomers of Goniodiol from Yeast-Reduction Products and Their Antimicrobiological Activity

Yoshida, Takahiro; Yamauchi, Satoshi; Tago, Ryosuke; Maruyama, Masafumi; Akiyama, Koichi; Sugahara, Takuya; Kishida, Taro; Koba, Yojiro

doi:10.1271/bbb.80262

Cited by 17 publications

(5 citation statements)

References 12 publications

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“…The presence of one free‐OH group was confirmed by the IR spectrum with hydroxy stretching at 3397 cm −1 . The overall data suggest that compound 6 has a phenyl pyrano‐pyrone type skeleton [22,28–31] . Compound 6 has 1 H, 13 C‐NMR and 2D NMR parameters similar to (+)‐8‐epi‐9‐deoxygoniopypyrone ( 6 ), which have been reported earlier from the leaves of Goniothalamus tamirensis [31] .…”

Section: Resultssupporting

confidence: 65%

“…The overall data suggest that compound 6 has a phenyl pyrano-pyrone type skeleton. [22,[28][29][30][31] Compound 6 has 1 H, 13 C-NMR and 2D NMR parameters similar to (+)-8-epi-9-deoxygoniopypyrone (6), which have been reported earlier from the leaves of Goniothalamus tamirensis. [31] This structure was confirmed to have chairboat conformation for fused pyrano pyrone skeleton, between the possible conformations of chair-boat, boat-boat and chairchair conformation, which was confirmed by 1 H-1 H nuclear Overhauser effect spectroscopy (NOESY).…”

Section: Isolation and Characterisationsupporting

confidence: 61%

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Isolation, Structure Elucidation and in Vitro Anticancer Activity of Phytochemical Constituents of Goniothalamus wynaadensis Bedd. and Identification of α‐Tubulin as a Putative Molecular Target by in Silico Study

Sharma,

Talimarada,

Dhuri

et al. 2023

Chemistry & Biodiversity

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The phytochemical analysis of ethyl acetate and methanol extract of Goniothalamus wynaadensis Bedd. leaves led to an isolation of eight (1–8) known molecules, among them seven (2–8) isolated for the first time from this species, which includes (+)‐goniothalamin oxide (2), goniodiol‐7‐monoacetate (3), goniodiol‐8‐monoacetate (4), goniodiol (5), (+)‐8‐epi‐9‐deoxygoniopypyrone (6) etc. The phytochemical modification by acetylation of 3 and 4 gave goniodiol diacetate (9) with absolute configuration (6R, 7R, 8R) confirmed by single crystal X‐ray diffraction. Compounds 3–9 were cytotoxic against breast, ovarian, prostate and colon cancer cell lines with IC50<10 μM. Cell cycle analysis and Annexin‐V assay on MDA‐MB‐231 cell using goniodiol‐7‐monoacetate (3) exhibited apoptotic response as well as necrotic response and showed cell proliferation arrest at G2/M phase. An in silico target identification for these molecules was carried out with an α‐tubulin protein target by covalent docking. To gain an in‐depth understanding and identify the stability of these protein‐ligand complexes on thermodynamic energy levels, further assessment of the isolated molecules binding to the Cys‐316 of α‐tubulin was performed based on reaction energetic analysis via DFT studies which hinted the isolated molecules may be α‐tubulin inhibitors similar to Pironetin. Molecular dynamics reiterated the observations.

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Section: Resultssupporting

confidence: 65%

Section: Isolation and Characterisationsupporting

confidence: 61%

Isolation, Structure Elucidation and in Vitro Anticancer Activity of Phytochemical Constituents of Goniothalamus wynaadensis Bedd. and Identification of α‐Tubulin as a Putative Molecular Target by in Silico Study

Sharma,

Talimarada,

Dhuri

et al. 2023

Chemistry & Biodiversity

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“…The spectroscopic data of compounds 8 ([α] D 20 −51), 9 ([α] D 20 −241), 11 ([α] D 20 −63), and 12 ([α] D 20 −132) (Table S1, Supporting Information), with a 6 S configuration, were similar to the reported data of ( S )-goniothalamin, (−)- ent -goniothalamin oxide, (6 S ,7 S ,8 S )-goniodiol, and (−)-7- epi -goniodiol [(6 S ,7 R ,8 S )-goniodiol], respectively. These have been synthesized previously and have been isolated from Nature for the first time in the present study.…”

Section: Resultsmentioning

confidence: 99%

Bioactive 6S-Styryllactone Constituents of Polyalthia parviflora

Liou

Thăng

et al. 2014

J. Nat. Prod.

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Parvistones A-E (1-5), five new styryllactones possessing a rare α,β-lactone moiety and a 6S configuration, were isolated from a methanolic extract of Polyalthia parviflora leaves. The structures and the absolute configuration of the isolates were elucidated using NMR spectroscopy, specific rotation, circular dichroism, and X-ray single-crystal analysis. Compounds 8, 9, 11, and 12 were isolated for the first time. The results were supported by comparing the data measured to those of 6R-styryllactones. Moreover, a plausible biogenetic pathway of the isolated compounds was proposed. The structure-activity relationship of the compounds in an in vitro anti-inflammatory assay revealed the 6S-styryllactones to be more potent than the 6R derivatives. However, the effect was opposite regarding their cytotoxic activity. In addition, 6S-styrylpyrones isolated showed more potent anti-inflammatory and cytotoxic activity when compared to the 1S-phenylpyranopyrones obtained.

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“…The air-dried twigs and leaves of G. pentaphylla were extracted with 95% ethanol. After partition and column chromatography, three new compounds named glyfuran (1), glyphyllamide (2), and glyphyllazole (3), along with 25 known compounds, (+)isoaltholactone (4) [17], (+)-altholactone (5) [18], 6R-goniothalamin (6) [19], (6R,7R,8S)-8-chlorogoniodiol (7) [20], (6R,7S,8R)-8-chlorogoniodiol (8) [21], 7-epi-(+)-gonidiol (9) [22], 8-epi-(+)-goniodiol (10) [23], (6S,7S,8S)-goniodiol (11) [24], (+)-9-deoxygoniopypyrone (12) [25], (−)-8-epi-9-deoxygoniopyrone (13) [25], leiocarpin C (14) [26], dictamine (15) [27], 2-hydroxy-6,8-dimethoxy-3-methyl-9H-carbazole (16) [28], glycoborinine (17) [29], N-(4hydroxyphenethyl)cinnamamide (18) [30], uvariadiamide (19) [31], alpinetin (20) [32], tsugafolin (21) [33], naringenin trimethyl ether (22) [33], 4 ,6 -dihyroxy-2 ,4-dimethoxydihydro chalcone (23) [34], 2 ,4 -dihyroxy-4,6 -dimethoxychalcone (24) [35], flavokawain A (25) [36], glycothiomin-A (26) [37], penangin (27) [38], and ellipeiopsol B (28) [39], were obtained (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Components with Anti-Diabetic Activity Isolated from the Leaves and Twigs of Glycosmis pentaphylla Collected in Vietnam

et al. 2022

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A phytochemical investigation of the leaves and twigs of Glycosmis pentaphylla (Rutaceae), collected in Vietnam, yielded three new compounds named glyfuran (1), glyphyllamide (2), and glyphyllazole (3), along with twenty-five known compounds (4–28). The structures of isolates were determined by IR, MS, NMR, and UV data analyses. In the anti-diabetic activity screening, (+)-isoaltholacton (4), glycoborinine (17), 2′,4′-dihydroxy-4,6′-dimethoxychalcone (24), and flavokawain A (25) simultaneously exhibited inhibition of dipeptidyl peptidase-4 (DPP4) and stimulation of the glucagon-like peptide-1 (GLP-1) secretion on the murine intestinal secretin tumor cell line (STC-1).

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Syntheses of All Stereoisomers of Goniodiol from Yeast-Reduction Products and Their Antimicrobiological Activity

Cited by 17 publications

References 12 publications

Isolation, Structure Elucidation and in Vitro Anticancer Activity of Phytochemical Constituents of Goniothalamus wynaadensis Bedd. and Identification of α‐Tubulin as a Putative Molecular Target by in Silico Study

Isolation, Structure Elucidation and in Vitro Anticancer Activity of Phytochemical Constituents of Goniothalamus wynaadensis Bedd. and Identification of α‐Tubulin as a Putative Molecular Target by in Silico Study

Bioactive 6S-Styryllactone Constituents of Polyalthia parviflora

Components with Anti-Diabetic Activity Isolated from the Leaves and Twigs of Glycosmis pentaphylla Collected in Vietnam

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