Sesquiterpene lactones from two Tithonia species

Schuster, A.; Stokes, Sean; Papastergiou, F.; Castro, Vı́ctor; Poveda, Luis; Jakupovic, Jasmin

doi:10.1016/0031-9422(92)83461-7

Cited by 46 publications

(27 citation statements)

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“…Its molecular formula was determined to be C 19 . The presence of a carbonyl, an ester carbonyl, and a g-lactone carbonyl group in 12 was shown by the 13 C-NMR signals at d 215.0, 176.9, and 170.0, respectively. The molecular formula of 12 was the same of that of 11, and the 13 C-NMR spectral data of 12 showed close similarity to those of 11, except for the signals due to the C-10 and its neighboring carbons.…”

Section: Sesquiterpenoids and Flavonoids From The Aerial Parts Of Titmentioning

confidence: 98%

“…1,10,11) As part of our systematic survey of bioactive compounds from higher plants, we have now conducted a detailed phytochemical screening of the 80% EtOH extract of T. diversifolia using a cytotoxicity-guided fractionation method, which has resulted in the isolation of twelve sesquiterpenoids (1-12), including three new ones (4, 10, 12), and three known flavonoids (13)(14)(15). This paper deals with the structural identification and determination of the sesquiterpenoids and flavonoids, and with their cytotoxic activity.…”

Section: -5)mentioning

confidence: 99%

“…These NMR spectral properties of 4 were similar to those of 2. 13) However, the molecular formula of 4 was higher by one oxygen atom than that of 2 and an oxymethine proton signal could be observed at d 4.06, indicating that 4 has a free hydroxy group. The locus and configuration of the hydroxy group was assigned by the following spectral analysis.…”

mentioning

confidence: 92%

“…tirotundin (1), 12) tirotundin 3-O-methyl ether (2), 13) tagitinin A (3), 14) tagitinin C (5), 12) deacetylviguiestin (6), 15) tagitinin F (7), 12) 1b-methoxydiversifolin (8), 1) 1b-methoxydiversifolin 3-O-methyl ether (9), 1) 4b,10a-dihydroxy-3-oxo-8b-isobutyroyloxyguaia-11(13)-en-6,12-olide (11), 16) luteolin (13), 16) nepetin (14), 16) and hispidulin (15), 16) respectively. (Table 1), signals for an acetalic carbon and a quaternary carbon with an oxygen atom were observed at d 108.8 and 81.3, respectively.…”

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confidence: 99%

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Sesquiterpenoids and Flavonoids from the Aerial Parts of Tithonia diversifolia and Their Cytotoxic Activity

et al. 2007

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Tithonia diversifolia (HEMSL.) A. GRAY (Compositae) is native to Mexico and also grows in parts of Africa, Australia, Asia, and other countries of North America, and is commonly called Mexican sunflower or tree marigold.1) An extract of T. diversifolia has been traditionally used for the treatment of diabetes, diarrhea, menstrual pain, malaria, hematomas, hepatitis, hepatomas, and wound healing. 2-5)Pharmacological studies of Tithonia diversifolia showed that it has anti-diabetic, 6,7) anti-malarial, 8) anti-inflammatory, 9) analgesic, 9) and cancer chemopreventive 10) activity, some of which account for the folkloric claims of this medicinal plant. Several sesquiterpenoids were isolated from T. diversifolia.1,10,11) As part of our systematic survey of bioactive compounds from higher plants, we have now conducted a detailed phytochemical screening of the 80% EtOH extract of T. diversifolia using a cytotoxicity-guided fractionation method, which has resulted in the isolation of twelve sesquiterpenoids (1-12), including three new ones (4, 10, 12), and three known flavonoids (13)(14)(15). This paper deals with the structural identification and determination of the sesquiterpenoids and flavonoids, and with their cytotoxic activity. Results and DiscussionThe dried aerial parts of T. diversifolia were extracted with hot 80% EtOH. The concentrated 80% EtOH extract, which showed cytotoxic activity against HL-60 cells with an IC 50 value of 4.10 mg/ml, was passed through a porous-polymer polystyrene resin (Diaion HP-20) column, and successively eluted with 30% MeOH, EtOH, and EtOAc. The EtOH eluate fraction exhibited cytotoxic activity against HL-60 cells (IC 50 1.03 mg/ml), and was repeatedly subjected to column chromatography on silica gel, octadecylsilanized (ODS) silica gel, Sephadex LH-20, and reversed phase HPLC, giving compounds 1 (8.4 mg), 2 (11.3 mg), 3 (118 mg), 4 (744 mg), 5 (112 mg), 6 (8.7 mg), 7 (67.9 mg), 8 (90.7 mg), 9 (245 mg), 10 (14.0 mg), 11 (24.2 mg), 12 (19.0 mg), 13 (18.8 mg), 14 (60.8 mg), and 15 (6.6 mg).Compounds 1-3, 5-9, 11, and 13-15 were identified as tirotundin (1), 12) tirotundin 3-O-methyl ether (2), 13) tagitinin A (3), 14) tagitinin C (5), 12) deacetylviguiestin (6), 15) tagitinin F (7), 12) 1b-methoxydiversifolin (8), 1) 1b-methoxydiversifolin 3-O-methyl ether (9), 1) 4b,10a-dihydroxy-3-oxo-8b-isobutyroyloxyguaia-11(13)-en-6,12-olide (11), 16) luteolin (13), 16) nepetin (14), 16) and hispidulin (15) Hachioji, Tokyo 192-0392, Japan: b Hiro International Co., Ltd.; 2-16-5 Shibuya, Shibuya-ku, Tokyo 150-0002, Japan: and c Division of Molecular Pharmacology, Cancer Chemotherapy Center, Japanese Foundation for Cancer Research; 3-10-6 Ariake, Koto-ku, Tokyo 135-8550, Japan. Received April 26, 2007; accepted May 15, 2007 Cytotoxicity-guided fractionation of the 80% EtOH extract of Tithonia diversifolia has resulted in the isolation of twelve sesquiterpenoids (1-12), including three new ones (4, 10, 12), and three known flavonoids (13-15). The structures of the new compounds were deter...

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Section: Sesquiterpenoids and Flavonoids From The Aerial Parts Of Titmentioning

confidence: 98%

Section: -5)mentioning

confidence: 99%

mentioning

confidence: 92%

mentioning

confidence: 99%

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Sesquiterpenoids and Flavonoids from the Aerial Parts of Tithonia diversifolia and Their Cytotoxic Activity

et al. 2007

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“…Gray, denominada popularmente por margaridão ou girassol-mexicano, é uma herbácea pertencente a tripo Heliantheae, originária da América Central e que no Brasil se tornou invasora, sugerindo que tenha atividade alelopática sobre outras espécies (SCHUSTER et al, 1992;PEREIRA et al, 1997;TONGMA;KOBAYASHI;USUI, 1998).…”

Section: Tithonia Diversifoliaunclassified

Micro-organismos de interesse farmacêutico e agrícola: estudo químico e biossintético

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Stereochemical assignment of 2,3-epoxy-2-methylbutanoate esters in natural products

1999

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Sesquiterpene lactones from two Tithonia species

Cited by 46 publications

References 11 publications

Sesquiterpenoids and Flavonoids from the Aerial Parts of Tithonia diversifolia and Their Cytotoxic Activity

Sesquiterpenoids and Flavonoids from the Aerial Parts of Tithonia diversifolia and Their Cytotoxic Activity

Micro-organismos de interesse farmacêutico e agrícola: estudo químico e biossintético

Stereochemical assignment of 2,3-epoxy-2-methylbutanoate esters in natural products

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