著者

桑野 晴光 田村 千尋

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.81, no.5, pp.764-767, 1961-05-25 (Released:2010-02-19)

参考文献数

5

被引用文献数

2 2

---

Polymorphism of chloramphenicol was examined by the X-ray diffraction method and quantitative relationship between the two crystal forms was examined. In general, proportionation of concentration to diffraction intensity can be quantitated in polymorphs but the method was inconvenient for use with organic compounds due to strict packing conditions. In the binary system (α- and β-forms) of chloramphenicol palmitate, specific intensity and specific concentration of the component were in proportion and quantitative straight line independent of packing codition was obtained. This was found to be effective in the range of over 3% of the β-form and precision is within 1%. As the quantitative linear equation: the following was obtained: xβ/xα=(0.347±0.005)⋅Iβ/Iα, where x is the concentration of the component and I is the intensity of reflection.

著者

田村 千尋 桑野 晴光

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.81, no.5, pp.759-764, 1961-05-25 (Released:2010-02-19)

参考文献数

6

被引用文献数

1 1

---

From the consideration of X-ray diffraction, infrared absorption spectra, and various transition conditions of long-chain esters of chloramphenicol, and some assumptions were made on their crystal structure.1) According to X-ray diffraction, all-trans configuration for the long-chain portion of the β-form molecule results in good agreement between the molecular models and the long axis by X-ray measurement. In the case of α-form, the long axis of the crystal cannot be explained unless the molecule is assumed to have some cis linkages or the long chain part is a trans structure but deeply twined with each other.2) Infrared absorption spectra suggest that the α-form is closely resembled to a solution state and crystals with a cis configuration, having distorted molecule, may be assumed. The β-form is considered to have a higher order molecular arrangement as a crystal and it is convenient to assume an all-trans configuration by X-ray measurement.3) Stability of the β-form can be assumed form the measurement of melting point and specific gravity. On the other hand, similarity to the α-form and solution state (or amorphous state) as found from transition conditions and these agree well with the above two measurements.

著者

田村 千尋 桑野 晴光

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.81, no.5, pp.755-759, 1961-05-25 (Released:2010-02-19)

参考文献数

6

被引用文献数

13 19

---

It was found that chloramphenicol palmitate, myristate, and caprylate come in two kinds of crystalline form and one amorphous form. These compounds were prepared and their transition conditions were examined.1) When the crystals is dissolved in a solvent and crystallized out, optional form of crystals can be obtained by controlling crystallization rate and this form is not affected by polarity or pH of the solvent. Crystals of α-form is obtained by rapid crystallization while the β-form is obtained by gradual crystallization. When a small amount is fused and cooled rapidly in a refrigerator, a vitrious substance is obtained.2) Transition between the solids occur only in the direction of amorphous to α-form to β-form, and there is no reverse progress. The transition rate is faster, the nearer the melting point. The mechanism of such a transition is thought to be the transition to a stable form by the heat motion of the molecule itself. The transition rate becomes suddenly rapid after formation of β-form crystal and this is considered to be due to added effect of catalytic transition.

著者

桑野 晴光

出版者

星薬科大学

巻号頁・発行日

1996

---

博士論文

著者

室伏 良信 木村 美佐子 桑野 晴光 飯島 康輝 山崎 光郎 金子 正勝

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.10, pp.3760-3769, 1988-10-25

---

Addition reactions of the C^<4′>-C^<5′> double bond of griseolic acid were investigated. C^<4′>-C^<5′>Dihydrogrisiolic acid was obtained by reduction of the adduct having halogen at the 4′-position.The ring juncture of the two five-membered rings of the C^<4′>-C^<5′> dihydro derivaticves was of all-"cis"configuration. Acetolysis of the protected dihydrogriseolic acid gave the corresponding 1′-acetoxy sugar derivative. Reaction of this sugar derivative with silylated bases gave guanine and uracil derivatives of the dihydrogriseolic acid. The cyclic nucleotide phosphodiesterase (PDE)-inhibitory activity of the C^<4′>-C^<5′> cis dihydrogriseolic acid derivative was weaker than that of griseolic acid.The uracil derivative of C^<4′>-C^<5′> cis dihydrogriseolic acid completely lost the inhibitory activity against both adenosine 3′, 5′-cyclic monophosphate (cAMP) and guanosine 3′, 5′-cyclic monophosphate (cGMP) PDE, whereas the guanine derivative showed reduced inhibitory activity against cAMP PDE, but retained its activity against cGMP PDE. It was also apparent that the C^<4′>-C^<5′>trans dihydro derivative which was obtained as a minor product from the same culture broth of griseolic acid had almost the same inhibitory activity as griseolic acid.

著者

寺原 昭 羽石 達生 新井 守 桑野 晴光

出版者

天然有機化合物討論会実行委員会

雑誌

天然有機化合物討論会講演要旨集

巻号頁・発行日

vol.18, pp.286-293, 1974

---

The antifungal metabolite, herbicidin A (C_<23>H_<29>O_<11>N_5) and herbicidin B (C_<18>H_<23>O_9N_5) obtained from Streptmyces saganonensis (Strain No 4075) have a plant growth inhibiting effects against to baryard glass, green panicum, tomato and radish ect., in a concentration 37-300ppm without effect to rice. Basic hydrolysis of herbicidin A affords an unsaturated acid 3 which has been confirmed to be 2-hydroxymethyl-2-butenoic acid, and herbicidin B acid 4. Methanolysis of herbicidin A and B with Amberlyst 15 in methanol affords adenine, and C_<19>H_<28>O_<12> 8 and C_<15>H_<24>O_<10> 5 respectively. On the bases of chemical and physico-chemical evidences of these derivatives, structures of herbicidin A and B have been determined to be nucleosides which consist of adenine and an unusual sugar moiety.