Rotenoids and isoflavones from the leaf and pod extracts of Millettia brandisiana Kurz

Meesakul, Pornphimon; Suthiphasilp, Virayu; Teerapongpisan, Passakorn; Rujanapun, Narawadee; Chaiyosang, Boonyanoot; Tontapha, Sarawut; Phukhatmuen, Piyaporn; Maneerat, Tharakorn; Charoensup, Rawiwan; Duangyod, Thidarat; Patrick, Brian O.; Andersen, Raymond J.; Laphookhieo, Surat

doi:10.1016/j.phytochem.2022.113440

Cited by 2 publications

(7 citation statements)

References 34 publications

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“…This configuration was corroborated by the IR band pattern between 1350 and 1000 cm −1 (Figure S136, Supporting Information), which indicated a cis configuration. 37,38 Based on the spectroscopic data, the new compound 2 was identified as (6aR,12aR)-9,10-dimethoxy-2,3methylenedioxy-12a-hydroxyrotenoid and was given the trivial name oblarotenoid F. It is structurally closely related to the previously reported oblarotenoid A, 18 39 The ECD and the specific rotation data of rotenoids may not be complementary, which has been previously pointed out. 18,39 Compound 3 was isolated as a light yellow solid.…”

Section: ■ Results and Discussionmentioning

confidence: 84%

“… 37 , 38 Based on the spectroscopic data, the new compound 2 was identified as (6a R ,12a R )-9,10-dimethoxy-2,3-methylenedioxy-12a-hydroxyrotenoid and was given the trivial name oblarotenoid F. It is structurally closely related to the previously reported oblarotenoid A, 18 differing in the substitution of its ring D. It should be emphasized that despite structural similarities, the specific rotation of oblarotenoid F, [α] 20 D +42, has an opposite sign as compared to those of oblarotenoid A, [α] 20 D −38.3, and of (−)-(6a R ,12a R )-12a-hydroxy-α-toxicarol, [α] 20 D −108, recently reported from Millettia brandisiana . 39 The ECD and the specific rotation data of rotenoids may not be complementary, which has been previously pointed out. 18 , 39 …”

Section: Resultsmentioning

confidence: 93%

“… 39 The ECD and the specific rotation data of rotenoids may not be complementary, which has been previously pointed out. 18 , 39 …”

Section: Resultsmentioning

confidence: 93%

“…37,38 Based on the spectroscopic data, the new compound 2 was identified as (6aR,12aR)-9,10-dimethoxy-2,3methylenedioxy-12a-hydroxyrotenoid and was given the trivial name oblarotenoid F. It is structurally closely related to the previously reported oblarotenoid A, 18 39 The ECD and the specific rotation data of rotenoids may not be complementary, which has been previously pointed out. 18,39 Compound 3 was isolated as a light yellow solid. Its molecular formula, C 18 H 12 O 6 , was established based on HRESIMS ([M + H] + m/z 325.0714, calcd 325.0712) and NMR data (Table 1, Figures S18−S24 Supporting Information).…”

Section: Journal Of Naturalmentioning

confidence: 84%

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Antiviral Rotenoids and Isoflavones Isolated fromMillettiaoblatassp.teitensis

Kiganda,

Bogaerts,

Wieske

et al. 2024

J. Nat. Prod.

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Three new (1−3) and six known rotenoids (5−10), along with three known isoflavones (11−13), were isolated from the leaves of Millettia oblata ssp. teitensis. A new glycosylated isoflavone (4), four known isoflavones (14−18), and one known chalcone (19) were isolated from the root wood extract of the same plant. The structures were elucidated by NMR and mass spectrometric analyses. The absolute configuration of the chiral compounds was established by a comparison of experimental ECD and VCD data with those calculated for the possible stereoisomers. This is the first report on the use of VCD to assign the absolute configuration of rotenoids. The crude leaves and root wood extracts displayed anti-RSV (human respiratory syncytial virus) activity with IC 50 values of 0.7 and 3.4 μg/mL, respectively. Compounds 6, 8, 10, 11, and 14 showed anti-RSV activity with IC 50 values of 0.4−10 μM, while compound 3 exhibited anti-HRV-2 (human rhinovirus 2) activity with an IC 50 of 4.2 μM. Most of the compounds showed low cytotoxicity for laryngeal carcinoma (HEp-2) cells; however compounds 3, 11, and 14 exhibited low cytotoxicity also in primary lung fibroblasts. This is the first report on rotenoids showing antiviral activity against RSV and HRV viruses.

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Section: ■ Results and Discussionmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 93%

“… 39 The ECD and the specific rotation data of rotenoids may not be complementary, which has been previously pointed out. 18 , 39 …”

Section: Resultsmentioning

confidence: 93%

Section: Journal Of Naturalmentioning

confidence: 84%

See 2 more Smart Citations

Antiviral Rotenoids and Isoflavones Isolated fromMillettiaoblatassp.teitensis

Kiganda,

Bogaerts,

Wieske

et al. 2024

J. Nat. Prod.

View full text Add to dashboard Cite

show abstract

“…In addition, recent studies discovered structurally distinct isoflavonoids in the various tissues of known Millettia species. [8][9][10][11][12][13][14][15][16] Prenylated isoflavonoids and rotenoids are the most frequently identified isoflavonoid subclasses. Other subclasses of isoflavonoids that have been found include, among others, isoflavans, aglycone isoflavones, glycosylated isoflavones, geranylated isoflavonoids, phenylcoumarins, pterocarpans and coumaronochromenes.…”

Section: Introductionmentioning

confidence: 99%