Alkaloidal constituents of Crinum latifolium and Crinum bulbispermum (amaryllidaceae).

Kobayashi, Shigeru; Tokumoto, T.; Kihara, Masaru; Imakura, Yasuhiro; Shingu, Tetsuro; Taira, Zenei

doi:10.1248/cpb.32.3015

Cited by 58 publications

(29 citation statements)

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“…The presence of two s at d(H) 6.57 and 6.80 in the 1 H-NMR spectrum, assigned to the two aromatic signals for HÀC (7) and HÀC(10), respectively, indicated disubstitution at C(8) and C(9) [17], and the appearance of two olefinic signals at d(H) 6.63 (d, HÀC(1)) and 5.96 (dd, HÀC(2)) indicated the presence of a D 1 C¼C bond and a substituent at C(3). The presence of an a-ethano bridge in addition to the quasi-axial b-orientated 3-OH function was deduced from the coupling constants J(1,3) ¼ 0 Hz, J(2,3) ¼ 4.8 Hz, and J(3,4a) ¼ 4.4 Hz, and from the absence of allylic coupling between HÀC(1) and HÀC(3) [18].…”

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confidence: 99%

Phytochemical and Biological Investigation of Hymenocallis littoralisSalisb.

Abou‐Donia

Toaima

Hammoda

et al. 2008

Chemistry & Biodiversity

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A phytochemical investigation of the bulbs and flowers of Hymenocallis littoralis SALISB., cultivated in Egypt, was carried out, which resulted in the isolation of four alkaloids, lycorine (1), hippeastrine (2), 11-hydroxyvittatine (3), and (+)-8-O-demethylmaritidine (4), and of two flavonoids, quercetin 3'-O-glucoside (5), and rutin (6). The volatile constituents of the plant flowers were analyzed for the first time by GC/MS, which led to the identification of 26 known compounds (Table 1). Finally, the antimicrobial activity of the petroleum ether extract of the flowers of H. littoralis was investigated.

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confidence: 99%

Phytochemical and Biological Investigation of Hymenocallis littoralisSalisb.

Abou‐Donia

Toaima

Hammoda

et al. 2008

Chemistry & Biodiversity

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“…(Amaryllidaceae) together with eleven known bases, vittatine (6), alkaloid-13 (7), 3-epimacronine (8), ismine (9), pretazettine (10), lycoramine (11), lycorine (12), tazettine (13), haemanthamine (14), galanthamine (15), and N-demethylgalanthamine (16). Keywords (6), alkaloid-13 (7 ) , 3-epimacronine (8), ismine (9), pretazettine (10), lycoramine (11), lycorine (12), tazettine (13), haemanthamine (14), galanthamine (15), and N-demethylgalanthamine (16) All melting points are given as uncorrected values. The spectrophotometers used were a Hitachi IR-215 for IR spectra, a JEOL JMS-D 300 for MS, a Shimadzu UV-200 for UV spectra, a Union PM-201 for optical rotation, a JASCO ORD/UV-5 spectrometer for ORD, and a JEOL JNM-PS-100 or a Hitachi R-22 for 1H-NMR spectra with tetramethylsilane (TMS) as an internal standard.…”

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confidence: 99%

Alkaloidal constituents of Hymenocallis rotata Herb. (Amaryllidaceae).

Kihara

Koike

Imakura

et al. 1987

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…18) Over 100 alkaloids have been isolated from members of the Amaryllidaceae family, and most of these compounds can be classified into eight skeletally homogeneous groups. Crinine-type alkaloids such as crinamine, 19) haemanthidine 20,21) and pretazettine 21,22) have a perhydroindole skeleton connected to an aromatic ring at the ring junction (Fig. 3).…”

Section: Total Syntheses Of (؉)-Crinamine (؊)-Haemanthidine and (؉)mentioning

confidence: 99%

“…Detosylation of 29b followed by methylenation and then deacetylation gave alcohol, of which the [a] D value and spectral data agreed with those of (ϩ)-crinamine reported in the literature. 19) Thus, we succeeded in the first asymmetric total synthesis of (ϩ)-crinamine from the cyclohexenol derivative 21c using the palladium-catalyzed asymmetric allylic amination and the carbonyl-ene reaction as the key steps. The overall yield was 19% via 10 steps from cyclohexenol derivative.…”

Section: Total Syntheses Of (؉)-Crinamine (؊)-Haemanthidine and (؉)mentioning

confidence: 99%

Development of a Novel Synthetic Method for Ring Construction Using Organometallic Complexes and Its Application to the Total Syntheses of Natural Products

Mori

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Organometallic complexes are useful tools in synthetic organic chemistry. In particular, they play an important role in carbon-carbon bond formation. A metalacycle, i.e., a ring compound containing a transition metal, is a useful intermediate in synthetic organic chemistry. Oxidative cyclization of unsaturated hydrocarbons, such as alkene, alkyne, carbonyl compounds, or nitrile, using a low-valent transition metal is a useful reaction for synthesis of metalacycles. It is known that a metalacycle formed from a late transition metal and unsaturated hydrocarbons is not stable and is easily converted into the reductive elimination product or b-hydrogen elimination product (Eq. 1). Since the low-valent metal complex is regenerated in this reaction, the reaction proceeds with a catalytic amount of the transition metal. On the other hand, the metalacycle formed from an early transition metal and unsaturated hydrocarbons is fairly stable and can be converted into various compounds with functional groups by treatment with various agents (Eq. 2). Therefore a stoichiometric amount of the metal complex is required in this reaction.(1) (2) Negishi et al.2) and Nugent and Calabrese 3) reported the syntheses of zirconacycles 2 from diene, enyne, and diyne 1 using zirconocene (Cp 2 Zr). Hydrolysis of zirconacycle afforded the cyclized compound 3 (Chart 1).Negishi et al. also found a synthetic method of dibutylzirconocene (Cp 2 ZrBu 2 ) from zirconocenedichloride (Cp 2 ZrCl 2 ) and butyl lithium, and dibutylzirconocene is easily converted into zirconocene coordinated by a butene ligand in situ at room temperature 4) (Eq. 3).This was a great discovery in zirconium chemistry because it is difficult to isolate zirconocene with no ligand. We were interested in those results and attempted to form carbon-carbon bonds between the unsaturated hydrocarbons, such as enyne and diene, using zirconocene. Synthesis of Heterocycles Using Zirconium-Mediated Cyclization and Total Synthesis of (؊)-DendrobineThe zirconacycles 2 were easily synthesized in situ from Cp 2 ZrCl 2 and diene, enyne, or diyne 1. To a THF solution of Cp 2 ZrCl 2 and unsaturated hydrocarbon 1 was added BuLi at Ϫ78°C under argon gas, and the solution was stirred at room Organometallic complexes are useful tools in synthetic organic chemistry. We investigated a novel synthetic method for ring construction using organometallic complexes and synthesized natural products and biologically active substances using these methods. Metalacycles formed from an early transition metal and diene, enyne, and diyne are stable under the reaction conditions and they are easily converted into compounds with functional groups by the addition of various agents. We have developed a novel synthetic method of heterocycles from enyne and diene using Cp 2 ZrBu 2 . The total syntheses of (؊)-dendrobine, (؎)-mecembrane, and (؎)-mecembrine were achieved using this procedure. To synthesize these natural products as a chiral form, a novel palladium-catalyzed asymmetric allylic amination was developed, an...

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Alkaloidal constituents of Crinum latifolium and Crinum bulbispermum (amaryllidaceae).

Cited by 58 publications

References 1 publication

Phytochemical and Biological Investigation of Hymenocallis littoralisSalisb.

Phytochemical and Biological Investigation of Hymenocallis littoralisSalisb.

Alkaloidal constituents of Hymenocallis rotata Herb. (Amaryllidaceae).

Development of a Novel Synthetic Method for Ring Construction Using Organometallic Complexes and Its Application to the Total Syntheses of Natural Products

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