Lignan Derivatives and a Norditerpene from the Seeds of <i>Vitex negundo</i>

Ono, M.; Nishida, Yoichiro; Masuoka, Chikako; Li, Jian‐Chen; Okawa, Masafumi; Ikeda, Tsuyoshi; Nohara, Toshihiro

doi:10.1021/np040102t

Cited by 87 publications

(65 citation statements)

References 8 publications

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“…To the best of our knowledge, compounds 1 and 2 had never been isolated previously neither from the genus Vitex species nor from any other natural resources. due to the known compounds, 3 and 4 are the main and characteristic constituents in genus Vitex species (Ono et al 2004;Zheng et al 2009), compounds 1 and 2 were assumed to be artefacts resulting from the treatment with EtOAc during the process of fractionation and purification rather than be biogenetic precursors of 3 and 4, respectively. This was also confirmed by HPLC and HPLC-MS analysis, and neither 1 nor 2 was detected in the MeOH extract of the dried fruits of V. negundo var.…”

Section: Resultsmentioning

confidence: 99%

“…According to the literature, compound 3 was previously isolated from the seeds of V. negundo (Chawla et al 1992) and showed antiinflammatory (Chawla et al 1992) and antioxidative (Ono et al 2004) activities. Compounds 4-8 were also reported from the seeds of V. negundo (Ono et al 2004;Zheng et al 2009Zheng et al , 2011. Compounds 9-12 are four polymethoxyflavones and were isolated from V. negundo var.…”

Section: Resultsmentioning

confidence: 99%

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Chemical constituents and their bioactivities from the fruits of Vitex negundo var. cannabifolia

Fang

Kong

Yan

et al. 2016

Natural Product Research

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Chemical constituents and their bioactivities from the fruits of Vitex negundo var. cannabifolia

Fang

Kong

Yan

et al. 2016

Natural Product Research

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“…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 correlation spectroscopy (COSY) spectrum of 1 indicated the presence of the partial structure as shown in Fig. 1 C-NMR signals were assigned with the aid of heteronuclear multiplequantum coherence (HMQC) and heteronuclear multiplebond correlation (HMBC) spectra (Tables 1, 2).…”

Section: )mentioning

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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“…Previous chemical investigations on the leaves and fruits resulted in the isolation of phytoedysteroids 3 . However, the investigation of some other Vitex species have resulted in the isolation of iridoids 4,5,6 , diterpenes 7,8 , steroids 9 , flavonoids 6 and triterpenoids 9 . Several of previous compounds isolated from Vitex genus have shown antioxidants activities 10,11 .…”

Section: Introductionmentioning

confidence: 99%

Antihyperglycemic and Anti-Oxidant Potential of Ethanol Extract of Vitex Thyrsiflora Leaves on Diabetic Rats

Kowa

Nyunaï²,

Tabi

et al. 2018

UJPR

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The antihyperglycemic effect of an ethanol extract of Vitex thyrsiflora leaves was investigated in normal male rats and streptozotocin-induced diabetic male rats and its antioxidant potential was evaluated. After preparation of the extract, it was subjected to a phytochemistry screening, and tested on male rats made hyperglycemic in the Oral Glucose Tolerance Test (OGTT) and in streptozotocin diabetic rats. Glibenclamide (10 mg/kg) was served as a positive control in both experiments. During both experiments, the extract was tested at 200 and 300 mg/kg. The evaluation of the antioxidant potential was done through the determination of the total polyphenols and total flavonoid contents, and by using the ferric reducing antioxidant power assay and the free radical scavenging activity on DPPH method. The results show that the extract contains alkaloids, flavonoids, steroids, saponins and phenolic compounds. The test on hyperglycemic rats in OGTT showed that, the extract was effective (at a dose of 200 mg/kg) to significantly decreased glucose-induced hyperglycemia (**p ˂ 0.01). The extract was ineffective on streptozotocin-induced diabetic rats. The study of the antioxidant potential showed that, polyphenols and flavonoids increase with the concentration of the extracts. IC 50 value was found to be 65.97, based on the log (inhibitor) vs. normalized response-Variable slope. FRAP appears to be significantly highly correlated with total polyphenols content and total flavonoids content. This shows that the ethanol extract of V. thyrsiflora leaves could be served to prevent acute hyperglycema, but not a chronic hyperglycemic state.

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Lignan Derivatives and a Norditerpene from the Seeds of Vitex negundo

Cited by 87 publications

References 8 publications

Chemical constituents and their bioactivities from the fruits of Vitex negundo var. cannabifolia

Chemical constituents and their bioactivities from the fruits of Vitex negundo var. cannabifolia

Three New Monoterpenoids from the Fruit of Genipa americana

Antihyperglycemic and Anti-Oxidant Potential of Ethanol Extract of Vitex Thyrsiflora Leaves on Diabetic Rats

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