A new diarylhexane and two new diarylpropanols from the roots of <i>Knema globularia</i>

Sriphana, Uraiwan; Yenjai, Chavi; Suthiwong, Jittra; Poopasit, Kitisak

doi:10.1080/14786419.2020.1815736

Cited by 12 publications

(11 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The known compounds were identified by comparison of their NMR spectroscopic data with those previously reported. The known compounds were characterized as lophirone C (9), 24 6‴-hydroxylophirone B (10), 25 embelin (11), 26 rapanone (12), 27 5,4′-dimethoxy-6,7-methylenedioxyisoflavone (iriso-lone methyl ether) (13), 28 5,3′,4′-trimethoxy-6,7-methylenedioxyisoflavone (iriskumaonin methyl ether) (14), 28 calodenins A (15) and B ( 16), 29 and calodenone (17) along with a high-intensity signal in the range 1.20−1.30 ppm]. In the lower field region, a singlet proton at δ H 6.28 and an ABX spin system of a 1,2,4-trisubstituted benzene ring [δ H 6.97 (1H, s), 6.84 (1H, d, J = 8.4 Hz), 6.82 (1H, d, J = 8.4 Hz)] were observed (Table 1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The n -hexane and EtOAc extracts of its roots showed significant cytotoxicity against NCI-H187 lung cancer cells . Phytochemical analyses of this plant have revealed the presence of 42 compounds mostly isolated from the fruits and roots: flavonoids, polyketides, steroids, and lignans. − However, there is a lack of phytochemical and pharmacological data on the stems of this plant. In addition, no report regarding the α-glucosidase inhibition of K. globularia extracts and isolated compounds has appeared.…”

mentioning

confidence: 99%

See 1 more Smart Citation

α-Glucosidase Inhibitors from the Stems of Knema globularia

Danova

Aree

et al. 2022

J. Nat. Prod.

View full text Add to dashboard Cite

Six new compounds, globunones A−F (1−6), and two new flavonoids (7 and 8) together with nine known compounds (9−17) were isolated from the stems of Knema globularia. The chemical structures of 1−8 were elucidated by an analysis of their NMR and high-resolution electrospray ionization mass spectrometry data as well as by comparison with literature values. The absolute configurations were determined using time-dependent density functional theory electronic circular dichroism (TD-DFT-ECD). Globunones A−E (1−5) represent the initial combined structures of a flavan-3-ol core and a 1,4-benzoquinone core. Globunone F (6) is the first flavanone-type compound bearing a 2-(2,4-dihydroxyphenyl)-2-oxoethyl group found to date in Nature. Compounds 1−3 and 6−17 were tested for their yeast α-glucosidase inhibitory activity. All compounds tested (except for 13 and 14) showed potent inhibition toward α-glucosidase with IC 50 values in the range 0.4−26.6 μM. Calodenin A (15) was the most active compound with an IC 50 value of 0.4 μM (the positive control, acarbose, IC 50 93.6 μM). A kinetic analysis of 15 revealed that it is a noncompetitive inhibitor with a K i value of 3.4 μM.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

α-Glucosidase Inhibitors from the Stems of Knema globularia

Danova

Aree

et al. 2022

J. Nat. Prod.

View full text Add to dashboard Cite

show abstract

“…Giffithane, a compound isolated and characterized from the roots of Knema globularia (Lamk.) Warb, showed strong cytotoxicity against the NCI-H187 and MCF-7 cell lines with IC 50 values of 3.08 and 6.68 mg/mL, respectively [ 48 ]. Six compounds, knecorticosanones C–H were isolated from the fruits of Knema globularia (Lamk.)…”

Section: Resultsmentioning

confidence: 99%

Ethnomedicinal Plants in Herbal Remedies Used for Treatment of Skin Diseases by Traditional Healers in Songkhla Province, Thailand

Saising

Maneenoon

Sakulkeo

et al. 2022

Plants

View full text Add to dashboard Cite

Skin disorders are a worldwide health problem that normally affect human life. A traditional healer is an important expert in researching notable medicinal plants for skin disease treatment. This study aimed to determine the traditional knowledge and the use of medicinal plants for the treatment of skin diseases among traditional healers in the Songkhla province, Thailand. The ethnobotanical information was collected from experienced traditional healers by semi-structured interviews and participant observations. Plant specimens were also collected and identified using the standard taxonomic method. The data were analyzed by interpretation and descriptive statistics. Twenty-five polyherbal formulations for the treatment of skin diseases were obtained from traditional healers with at least 10 years of experience. A total of 66 plant species in 38 families were documented. Leaves and trees were the most commonly employed plant parts and plant habits included in the herbal remedies, respectively. Fabaceae, Rubiaceae, and Zingiberaceae were the majority of the cited families. Oryza sativa L. and Zingiber montanum (J. Koenig) Link ex A.Dietr. were the most preferred plants combined in the prescriptions, which had the highest use value (UV = 0.83). The highest relative frequency of citation was represented by Curcuma longa L., Eurycoma longifolia Jack, Knema globularia (Lamk.) Warb, and Senna siamea (Lam.) Irwin & Barneby. (0.55 each). This research suggests the importance of traditional healers in the healing of skin diseases with herbal remedies. A variety of medicinal plants are used in the prescriptions for the treatment of skin disorders in the Songkhla province, in the south of Thailand. Pharmacological and toxicological activities as well as phytochemical constituents of polyherbal remedies should be further investigated to scientifically verify further applications of widely practiced herbal medicines.

show abstract

“…These chiral alcohols are bioactive natural products also isolated from plants that produce flavans, suggesting a biosynthetic relationship. 8 Furthermore, 1,3diarylpropan-1-ols bearing a 2-OH group at ring B are known as key synthetic intermediates for the synthesis of flavans through Mitsunobu cyclization. 4,9 Thus, we hypothesized that the one-pot C�C/C�O reduction of chalcones through a Ru-catalyzed ATH could stand out as a convenient alternative for the preparation of these intermediates, allowing the enantioselective synthesis of flavans in two steps from readily accessible substrates (Scheme 1c).…”

Section: ■ Introductionmentioning

confidence: 99%

Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of Chalcones in Water: Application to the Enantioselective Synthesis of Flavans BW683C and Tephrowatsin E

et al. 2022

View full text Add to dashboard Cite

The oxo-tethered-Ru(II) precatalyst promoted the one-pot C�C/C�O reduction of chalcones using sodium formate as the hydrogen source in water through asymmetric transfer hydrogenation. Twenty-seven 1,3-diarylpropan-1-ols were obtained in good to excellent yields (up to 96%) and enantiomeric purities (up to 98:2). Our data suggested that the enones are first reduced to the corresponding dihydrochalcones (1,4-selectivity) and then into 1,3-diarylpropan-1-ols (C�O reduction). The stereoelectronic effects of electron-donating and electron-withdrawing groups at the ortho, meta and para positions of both aromatic rings were evaluated. The 2-OH group at the B ring was well tolerated, allowing a straightforward enantioselective synthesis of two flavans through the Mitsunobu cyclization, the antiviral (S)-BW683C and the natural flavan (S)-tephrowatsin E.

show abstract

A new diarylhexane and two new diarylpropanols from the roots of Knema globularia

Cited by 12 publications

References 25 publications

α-Glucosidase Inhibitors from the Stems of Knema globularia

α-Glucosidase Inhibitors from the Stems of Knema globularia

Ethnomedicinal Plants in Herbal Remedies Used for Treatment of Skin Diseases by Traditional Healers in Songkhla Province, Thailand

Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of Chalcones in Water: Application to the Enantioselective Synthesis of Flavans BW683C and Tephrowatsin E

Contact Info

Product

Resources

About