Production of Anti-Tumor-Promoting Iridoid Glucosides in Genipa americana and Its Cell Cultures

Ueda, Shinichi; Iwahashi, Yasuhiro; Tokuda, Harukuni

doi:10.1021/np50078a032

Cited by 61 publications

(36 citation statements)

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“…On acidic hydrolysis, 2 afforded D-glucose, and the b-glycosidic linkage was determined based on the coupling constant of the anomeric proton. In comparing the chemical shifts of 1 H-NMR signals in CD 3 OD between 1 and 2, the signals due to Ha-6 of Ag, Hb-6 of Ag and H-9 of Ag in 2 were shifted by ϩ0.45, Ϫ0.62 and ϩ0.25 ppm, respectively. Therefore, 2 was recognized as an isomer at C-7 and/or C-8 of Ag in 1.…”

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“…As far as we know, 1-4 are new iridoid glucosides, and 7 and 8 are the first examples of the isolation from the fruit of Genipa americana, although 7 was isolated form the callus and cell suspension cultures of G. americana, 1) and the hexaacetate of 2 was previously synthesized from pentaacetate of 6. 7) Although the absolute configurations of Ag moieties of 1-4 have not been confirmed because of the lability of Ag of 1-4 on the acidic hydrolysis, they are probably the same as that 10) of 6 from a biogenetic point of view.…”

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Iridoid Glucosides from the Fruit of Genipa americana

Ono

Ueno

Masuoka

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Iridoid Glucosides from the Fruit of Genipa americana

Ono

Ueno

Masuoka

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…2) As part of the continuing study of the constituents of this fruit, we now describe the isolation and structural elucidation of three new monoterpenoids (1)(2)(3), along with four known iridoids (4-7) from this fruit.…”

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confidence: 99%

“…Compounds 4-7 were identified as genipin (4), 3) gardendiol (5), 4) deacetyl asperulosidic acid methyl ester (6), 5) and shanzhiside (7) 6) based on their physical and spectral data, although detailed 1 H-and 13 C-NMR spectral data of 6 and 7 have not been reported in the literature.…”

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confidence: 99%

Three New Monoterpenoids from the Fruit of Genipa americana

Ono

Ishimatsu

Masuoka

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Genipa americana L. (Rubiaceae) is widely distributed in tropical Central and South America. The fruit of this plant is edible and popular as source of beverages. The white flesh turns yellow to bluish-purple and finally to jet-black on exposure to the air. 1)We earlier reported the isolation and structural elucidation of eight iridoid glucosides from the fruit of G. americana. 2)As part of the continuing study of the constituents of this fruit, we now describe the isolation and structural elucidation of three new monoterpenoids (1-3), along with four known iridoids (4-7) from this fruit.Compounds 4-7 were identified as genipin (4), 3) gardendiol (5), 4) deacetyl asperulosidic acid methyl ester (6), 5) and shanzhiside (7) 6) based on their physical and spectral data, although detailed 1 H-and 13 C-NMR spectral data of 6 and 7 have not been reported in the literature.Compound 1, called genipacetal, was obtained as a colorless syrup and exhibited an [MϩNa] ϩ ion peak at m/z 249 in the positive FAB-MS; the high-resolution (HR) FAB-MS indicated the molecular formula of 1 to be C 11 H 14 O 5 . The C-NMR signals were assigned with the aid of heteronuclear multiplequantum coherence (HMQC) and heteronuclear multiplebond correlation (HMBC) spectra (Tables 1, 2). From the cross-peaks observed in the HMBC spectrum (H-1/C-5, C-8, C-9, and C-10; H-3/C-10 and C-11; H-4/C-3, C-5, C-6, C-9, and C-11; H-5/C-3; H-6/C-3, C-7, C-8, and C-9; H-7/C-5; H-10/C-1 and C-3; and H 3 CO/C-11) the planar structure of 1, which is a monoterpenoid possessing a new skeleton with one methoxycarbonyl group, one five-membered cyclic acetal group, and one five-membered cyclic hemiacetal group, could be suggested (Fig. 1). Ordinary acetylation of 1 with acetic anhydride and pyridine afforded the corresponding monoacetate (1a) rather than triacetate. Comparing the chemical shifts of the signals between 1 and 1a, the signal due to H-1 in 1 was shifted downfield by 0.85 ppm. Thus the presence of a hemiacetal group at C-1 and an epoxy bridge between C-3 and C-10 was established. The relative configurations at the C-5, C-7, C-8, C-9, and C-10 chiral centers were automatically established by forming the epoxy bridge. In the nuclear Overhauser and exchange spectroscopy (NOESY) spectrum of 1, a key NOE was observed between H-1 and H-4; this indicated that the relative configurations at C-1 and C-4 were as shown in Fig. 2. Furthermore, the coupling constant values for the signals in the 1 H-NMR spectrum were analogous to those calculated for the dihedral angles, which was simulated using CAChe CONFLEX, 6) and the Karplus equation 7) (Table 3). Consequently, the structure of 1 was concluded to be as shown in Fig. 3. Three new monoterpenoids, called genipacetal, genipamide, and genipaol, were isolated from the fruit of Genipa americana L. (Rubiaceae), along with the four known iridoids genipin, gardendiol, deacetyl asperulosidic acid methyl ester, and shanzhiside. Their chemical structures were determined on the basis of spectroscopic data.

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“…They have shown various biological activities such as antimicrobial, antitumoral, hemodynamic, choleretic, hepatoprotective and anti-inflammatory properties [23]. There are promising reports of chemoprevention of skin and lung cancer by genipin, an iridoid obtained on hydrolysis of geniposide, a glycoside isolated from the fruits of Genipa americana and Gardenia jasmoindes [24] , [25]. Since colon cancer is prevalent worldwide and chemical anticancer drugs often have more side effects compared to medicinal plant extract, we examined the antimetastasis effect of Scrophularia striata on colon cancer cells in cell culture to find its probable anticancer properties.…”

Section: Introductionmentioning

confidence: 99%

Antimetastasis Effects of Scrophularia striata Extract on Colon Cancer Cells

2016

2016 International Conference on Biological and Environmental Science (BIOES-16) June 8-9, 2016 New Jersey (USA)

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Production of Anti-Tumor-Promoting Iridoid Glucosides in Genipa americana and Its Cell Cultures

Cited by 61 publications

References 10 publications

Iridoid Glucosides from the Fruit of Genipa americana

Iridoid Glucosides from the Fruit of Genipa americana

Three New Monoterpenoids from the Fruit of Genipa americana

Antimetastasis Effects of Scrophularia striata Extract on Colon Cancer Cells

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