In the previous work⁽¹⁾ the author succeeded in the production of a new, physiologically active ergot alkaloid, “agroclavine”, C₁₆H₁₈N₂, m. p. 203, 5° (dec. ), [α]_D-153°, [α]₅₄₆₁-180° (C 0.98 in CHCl₃), by the culture on an industrial scale. The alkaloid was obtained from the mycelium and the culture medium at the rate of 0.2-0.6% and 0.02-0.03%, respectively, when the fungus was grown at 26° for a month in a 3 L. Bernhauer flask containing 1.2 L. of the culture medium consisting of: mannitol 50g., ammonium succinate 7g., KH₂PO₄ 1g., MgSO₄. 7H₂O 0.3g., and water 1000cc. (pH 5.2).
It has further been found that the fungus productive of agroclavine on the culture medium produces no other alkaloid than this agroclavine both on the culture medium and on the host plants - the Agropyrum, Trisetum, Festuca, etc. grown in Japan or Manchuria, while those productive of such alkaloids as hitherto known to us produce agroclavine neither in nature nor on the culture medium. These findings have fairly enabled the author to clarify various situations under which the alkaloids are produced by an ergot fungus.
The resume of the present work will appear in the next number.

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In the papers (XVII-i, -ii, , and-iii) the author has studied the observation that the ergot alkaloid accumlated in and out of the mycelium in the culturing process decreases sharply when the culture gets into the hungry state. As a result of the study, the following facts have been observed: (1) The ergot alkaloid produced in and out of the mycelium in the culturing process is gradually consumed by the fungus in the whole course of its development. (2) The consumption of the ergot alkaloid by the fungus in its course of development is attributable to the decomposition in cells in the process of self-digestion. (3) The ergot alkaloid added to the culture medium, not to mention that excreted by the fungus into the culture medium, permeates into cells during the whole course of its development and is stored therein. (4) The ergot alkaloid added to culture medium permeates not only into the cells of ergot fungus but also into those of various kinds of fungi and bacteria during the whole course of their development and is stored therein. (5) The quantity of the ergot alkaloid which can be found in cells at a certain period of the culturing process is considered to be the balance between the total alkaloid permeated into cells and that decomposed therein by that time. (6) The ergot alkaloid in culture medium exhibits a certain growth inhibitory action upon various kinds of fungi and bacteria including ergot fungus. (7) The permeation of an ergot alkaloid into cells has a close relation to its growth inhibitory action, and the former follows the latter. (8) The state of permeation of the ergot alkaloid into cells is analogous to that of the vital staining with methylene blue.

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(1),曩に分離し得たのうち寄主別の26株並にClaviceps purpurea Tul.及びClaviceps microce phala Tul.の28株を各種の人工培養基に培養して,各菌株の形成する分生胞子の數を酵母計算器を以て計算し,或はその發育速度を比較して逆に接腫菌苔中の分生胞子數の多寡を比較した.(2),は分生胞子形成上菌株に依り固有の能力を有する.(3),の分生胞子形成能力は培養温度24～28°,培養基の最初の水素イオン濃度4.8～6.8,寒天量3～6%なる範圍内に於て發育を完了せしむる時之等の培養條件との間に一定の關係がない.(4),の分生胞子形成能力は培養基の適否或はその量に依り左右され,之等の榮養條件の改善に從つて愈々數の分生胞子を形成する.(5),從つては寄主植物の種類に依り分生胞子形成の上に影響を受くべき可能性がある.(6),供試菌株28株を分生胞子形成能力の強弱に應じて7種の階級に分屬せしめ得た.(7),各階級と之に屬する菌株を寄主別に示せば次の如くになる.註 カモジグサ(1) は本邦産の2品種,カモジグサ(2) は満洲國産の1品種,ツルヨシ(2)はヨシの群落に隣接して居たもの.(8),各階級間の分生胞子形成能力の差異は榮養條件の改善に伴つて小となる.(9), Sphacelia-Mützchenに於ては該の分生胞子形成能力に應じた數の分生胞子を留めて居る.(10),分生胞子の大さに於て同一種と見做し得た菌株は分生胞子形成能力に於ても同一の階級に屬す.
終りに臨み本研究に際し終始御指導御鞭撻を賜りたる武田二郎博士並に本報告の發表を許可されたる當研究所長桑田智博士に對し深謝する。又御懇篤なる御指導を仰げる朝比奈泰彦,中澤亮治の兩先生及び本報告の御校閲を賜りたる坂口謹一郎先生に深甚の謝意を表する.尚ほ本實驗の御助力を願ひたる山野藤吾氏に對し厚く感謝する.

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(1) 各種麦角アルカロイドの相互識別法を検討してこれを設定した.またこの研究の過程で新たに未知の麦角アルカロイド4種を発見した.
(2) 代表的な10種のの菌核と培養とにおける個個の麦角アルカロイドを検索してこれを明らかにした.
(3) どの種のも天然と培養との別なくすべての麦角アルカロイドを共通に生産し得るものである.

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(1) はその種類により,あるいは菌株によってそれぞれtriseclavineとisosetoclavineとを異なる割合で生産する.
(2) この事実は天然,培養両者に存在するtriseclavineとisosetoclavineとがいずれも菌によって生産されたものであることを示している.
(3) Triseclavineとisosetoclavineとは互にC⁸における置換基の配位を異にする異性体であり,したがってisosetoclavineという名はisotriseclavineと改名さるべきものと思われる.
終りに臨み終始御鞭撻を賜わった当所長佐藤喜吉博士に謝意を表する.また終始御懇篤な御指導を仰いだ朝比奈泰彦,中沢亮治の両先生および坂口謹一郎先生に深甚の謝意を表する.なお,本研究に御助力願った山田三郎氏,理化学的諸測定と元素分析とに御協力下さった菅 正巳,仲町秀雄の両氏に厚く感謝する.

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菌体からクラビン型麦角アルカロイドagroclavineおよびelymoclavineに対して変換作用を示すセルフリー系を調製することに成功し,かつそのような活性セルフリー系によって両アルカロイドを他のアルカロイドに変換させる際の反応条件を設定した.

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The conversions of clavine-type alkaloids have been studied by the use of non-labeled alkaloids and the acetone-treated mycelia of the strains of the Claviceps as well as those of the Aspergillus, Penicillium and others which were productive of clavine-type ergot alkaloids. It was found that agroclavine could be converted to elymoclavine not only by ergot fungi but also by the fungus other than ergot fungi. This finding indicates that the theory presented by authors that elymoclavine is the primary product of the ergot alkaloids has become untenable to some extent. While, it was found that, besides the previous cyclic route, elymoclavine→lysergolI→lysergene→agroclavine→elymoclavine, another biosynthetic route from agroclavine to elymoclavine through lysergene, lysergol and an unestablished alkaloid PS might exist in various fungi on the one hand. This finding indicates that agroclavine rather than elymoclavine will be the primary product of the alkaloids, and that chanoclavine (secaclavine) will be a biosynthetic precursor of agroclavine, and therefore, of the remaining alkaloids. Judging from the data of Stauffacher et al., it was presumed that the reversible reaction, chanoclavine_??_agroclavine, which was found in all of the tested strains would be effected through a certain intermediary compound, possibly iso-chanoclavine-(I), and indeed this intermediary compound would be an obligatory precursor of agroclavine.
The present finding indicates that the conversion reaction, elymoclavine→peptide-type alkaloids, cannot be effected through lysergol, but possibly through 6-methyl-Δ^{8, 9}-ergolene-8-carboxylic acid which was discovered by Kobel et al. The outline of this study was given at the 3 rd International Symposium on “Biochemistry and Physiology of Alkaloids” held in Halle (Saale), June 24_??_27, 1965.

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