Terpenoids and a Diarylheptanoid from <i>Zingiber </i><i>ottensii</i>

Akiyama, Kayo; Kikuzaki, Hiroe; Aoki, Takako; Okuda, Atsushi; Lajis, Nordin H.; Nakatani, Nobuji

doi:10.1021/np0603119

Cited by 55 publications

(37 citation statements)

References 22 publications

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“…These HMBC and COSY correlations are in agreement with the side chain [-CH 2 -CH=C (CHO)-CH 2 -COO-] being attached to C-9′. The geometry between the C-12′ and C-13′ double bond was confirmed to be E on the basis of the ROESY correlation between H-12′ and H-16′ [10]. The relative stereochemistry about the chiral centers of the partial structure 1b was confirmed based on the similar reasoning used for determining that of partial structure 1a and upon comparison with that of zerumin A (11) (l " Table 1, Fig.…”

supporting

confidence: 75%

“…Since H-12 for 1a was observed at δ H 7.07, the E-isomer of the α,β-unsaturated γ-lactone ring was confirmed. The geometry between C-12 and C-13 was further verified to have an E-configuration as indicated by the absence of a ROESY correlation between H-12 and H-14 [10]. Biogenetically, for known labdane diterpenes bearing the same skeleton, the orientation of Me-18, being equatorial while that of Me-19 is axial, in the partial structure 1a, was confirmed based on comparison of the chemical shifts of C-18 and C-19 with literature values which indicate that the equatorial methyl group is usually located further downfield compared to the axial methyl group at C-4 [11,12].…”

mentioning

confidence: 94%

“…Therefore, 1 was named pahangensin C, a new bis-labdanic diterpene. The structure of the remaining known compounds were identified as ottensinin (2) [6,7,10,[15][16][17][18][19]. This is the first occurrence of compounds 2 and 12 in the genus Alpinia and the second in the Zingiberaceae family.…”

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confidence: 99%

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A New Bis-Labdanic Diterpene from the Rhizomes of Alpinia pahangensis

et al. 2013

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!The rhizomes of Alpinia pahangensis yielded a new bis-labdanic diterpene for which the name pahangensin C (1) was proposed along with twelve known analogues (2-13). The structure of 1 was elucidated via spectroscopic methods including 1D and 2D NMR techniques and LCMS-IT-TOF analysis. Compounds 2 and 12 were isolated for the first time from the genus Alpinia. This is the second occurrence of compounds 2 and 12 in the Zingiberaceae family. Selected analogues exhibited moderate to strong inhibitory activity against Staphylococcus aureus and Bacillus cereus.

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confidence: 75%

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confidence: 94%

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A New Bis-Labdanic Diterpene from the Rhizomes of Alpinia pahangensis

et al. 2013

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“…22) Furthermore, the planer structure of 3 was characterized by means of DQF COSY and HMBC experiments (Fig. 1).…”

Section: Kaempferol 3-o-(2љ-a-l-rhamnopyranosyl)-b-d-glucuronopyranosidementioning

confidence: 99%

Medicinal Flowers. XXIV. Chemical Structures and Hepatoprotective Effects of Constituents from Flowers of Hedychium coronarium

Nakamura

Okazaki

Ninomiya

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Hedychium coronarium KOEN. (Zingiberaceae) is widely cultivated in Japan, India, South China, and Southeast Asian countries. The rhizomes of H. coronarium have been used for the treatment of headache, contusion inflammation, and sharp pain due to rheumatism in Chinese traditional medicine. Previously, we reported that the extract from the rhizomes of H. coronarium showed inhibitory effects on increase in vascular permeability and nitric oxide production and on the release of b-hexosaminidase from RBL-2H3 cells and the structures of various farnesane-type sesquiterpenes and labdane-type diterpene were characterized.2,3) However, the chemical constituents as well as the pharmacological properties of the flowers of H. coronarium have not been characterized. In the course of our serial studies on the bioactive constituents of medicinal flowers, 1,[4][5][6][7][8][9][10][11][12][13][14][15] the 80% aqueous acetone extract from the flowers of H. coronarium was found to show a protective effect on D-galactosamine (D-GalN)-induced cytotoxicity in primary cultured mouse hepatocytes. In addition, we have isolated two new labdane-type diterpene glycosides, coronalactosides I (1) and II (2), and a new labdane-type trinorditerpene, coronadiene (3), together with 8 known compounds including labdane-type diterpene derivatives from the extracts, which were obtained with chloroform and 80% aqueous acetone from the flowers of H. coronarium. Furthermore, we examined the protective effects of principal constituents on D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. In this paper, we describe the isolation and structure elucidation of the new constituents (1-3) and the hepatoprotective effects of principal constituents from the flowers of H. coronarium.The fresh flowers of H. coronarium were extracted with chloroform under room temperature [the yield (0.46%) was obtained from the fresh flowers]. Subsequently, the residue was extracted with 80% aqueous acetone under room temperature, followed by 80% aqueous acetone under reflux (0.75% and 0.43% were obtained, respectively). The 80% aqueous acetone extract obtained under room temperature was partitioned into an EtOAc-H 2 O mixture to furnish an EtOAc-soluble fraction (0.074%) and aqueous layer. The aqueous layer was further extracted with n-BuOH to give n-BuOH-and H 2 O-soluble fractions (0.10% and 0.56%, respectively). In the same procedure, the EtOAc-, n-BuOHand H 2 O-soluble fractions were given from the 80% aqueous acetone extract obtained under reflux (0.18%, 0.044%, and 0.21%, respectively). The chloroform extract (0.46%), EtOAcsoluble fraction given from the 80% aqueous acetone extract obtained under room temperature, and n-BuOH-soluble fraction given from the 80% aqueous acetone extract obtained under reflux were subjected to normal-phase and reversedphase column chromatographies, and finally HPLC to give coronalactosides I (1, 0.00029% from the flowers) and II (2, 0.00014%) and coronadiene (3, 0.00008%) together with 8 known compounds, (E)-labda-8(17),12-die...

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“…In addition, local traditional knowledge also attributes ginger to have antiemetic, anti-flatulence, anti-diarrhea, cardiotonic and expectorant as well as to cure swollen body and snake bite [4,5]. Generally, ginger has been reported to contain diverse bioactive secondary metabolites from terpenoids to aromatic compounds [6][7][8][9][10][11]. The secondary metabolites isolated from ginger have been reported to exhibit antifungal potentials [10,11].…”

Section: Introductionmentioning

confidence: 99%