Glancing at the birth of a galaxy of scientists from Rikō Majima

Abstract

Rikō Majima published seven papers in this journal, and seeing these papers and their surrounding contexts allows us to glance at the birth of a galaxy of scientists.

Introduction

“Breathtaking” might be a simple yet perfect word to express how we feel when we see the first series of astonishing images from the James Webb Space Telescope (https://webbtelescope.org/news/first-images/gallery). It might be either the “Cosmic Cliffs” or “First Deep Field” that took your breath away by showing you the moment of star birth or the gathering of thousands of galaxies. Therefore, a picture shown in Fig. 1 should certainly take your breath away. It shows a 1937 alumni meeting of one chemist’s group, and these alumni actually gave birth to many “stars” to form individual galaxies in science and technology sectors of Japan. The mentor, Rikō Majima, indeed named this alumni meeting “the galaxy meeting”.¹⁾ The picture in Fig. 1 appeared in a biography of Majima written by Takashi Kubota who was also an alumnus in the picture. Kubota listed 13 alumni from Tohoku University as “the first generation” in the biography: C. Kuroda (RIKEN/Ochanomizu University), H. Suginome (Hokkaido University), M. Kotake (Osaka University), S. Kawai (RIKEN/Tokyo Bunrika University/University of Tsukuba), T. Ogata (RIKEN), S. Fujise (Tohoku University), T. Hoshino (Tokyo Institute of Technology), S. Akabori (Osaka University), T. Nozoe (Tohoku University), M. Murakami (Osaka University), S. Murahashi (Osaka University), T. Kaneko (Osaka University), and T. Kubota (Osaka City University).^‡ They were the pioneers of new fields including the applied chemistry of dyes, pigments, and polymers, and their leading, inspirational works gave birth to many more stars in various fields. When you glance at a gorgeous list of eminent scientists named as “the second generation” (see Supplementary materials), you would instantly agree in that you have just glanced at galaxies in this picture. Readers should be reminded that many of these “stars” also played important roles in society by serving as deans, presidents, and so on.

Fig. 1.

“Galaxy meeting” of Majima alumni (1937). Reproduced with the publisher’s permission from Ref. 1. From left to right: [front row] Seishi Yamashiro (Yonezawa Higher Technical School/Yamagata University), Hisaya Tani (Osaka University), Teinosuke Kobayashi^% (Gakushuin University), Takashi Kubota^% (Osaka City University), Terutaro Ogata^% (RIKEN), Tetsuo Nozoe^% (Tohoku University), [middle row] Munio Kotake^% (Osaka University), Tsuneharu Tanno (RIKEN), Hitoshi Takaoka (Osaka Research Institute of Industrial Science and Technology), Rikō Majima^%, Chika Kuroda^% (RIKEN/Ochanomizu University), Mizu Wada^% (RIKEN/Tokai University), [back row] Michio Takaoka^% (Hokkaido University), Bunichi Toi (Ajinomoto), Shunseke Murahashi^% (Osaka University), Kunisaburo Tamura^% (Osaka University), Sin-iti Kawai^% (RIKEN/Tokyo Bunrika University/University of Tsukuba), Kunio Okahara (Osaka Institute of Public Health), Shunichi Maruyama (−), Shinichiro Fujise (Tohoku University), Takeji Kashimoto (Kanazawa University), Toshio Hoshino^% (Tokyo Institute of Technology), Masuo Murakami^% (Osaka University), Takeo Kaneko^% (Osaka University), Shiro Akabori^% (Osaka University), Sadao Kitaura (Kyushu University). See the Supplementary materials for “the second generation” of Majima’s family in the academia. Among the 13 first-generation alumni of Tohoku University, Harusada Suginome (Hokkaido University) was missing in this picture. Including Suginome, 17 galaxy members (labeled with ^%) had published papers in this journal.

As an academician, Majima handled and communicated 242 papers at this journal from 1926 to 1955, including seven papers of his own. As it is naturally impossible to cover all the achievements and works of Majima who also initiated an important work of Chemical Abstracts of Japan,²⁾ this commentary should briefly examine Majima’s works that are closely related to those seven papers of Majima in this journal. Together with Majima’s biography by Takashi Kubota,¹⁾ a memorial book dedicated to Majima was an important resource of this commentary.³⁾

Majima was 52 years old when he published his first paper in this journal as a newly appointed academician (1926). By reading this first paper,⁴⁾ the readers should notice his keen interest in fundamental organic reactions and his careful observations that have led him to in-depth investigations. Setting this 1926 paper as the start, this commentary shall mainly cover the late-stage career of this legend. Majima’s career is briefly introduced as a list of his affiliations: 1911 (age 37 years), professor at Tohoku University; 1917 (age 43 years), principal researcher at RIKEN (concurrent position); 1926 (age 52 years), academician at the Japan Academy (concurrent position); 1926 (age 52 years), dean at Tohoku University; 1929 (age 55 years), professor at Tokyo Institute of Technology (concurrent position); 1930 (age 56 years), professor/dean at Hokkaido University (concurrent position); 1932 (age 58 years), professor at Osaka University (concurrent position); 1933 (age 59 years), dean at Osaka University; 1943 (age 69 years), president of Osaka University.

Urushiol

Majima started his most important work, studies on “urushiol”,^5)–7) in 1905 when he was an associate professor at the University of Tokyo. Together with Shunichi Cho who later became a president of a technical college (later integrated as Hiroshima University), Majima collected the saps of lacquer trees and obtained major chemical components.^3),8) He published the first paper on urushiol in 1907 (Fig. 2)^9),10) and “mostly completed the work by 1917” (Majima).^11),§ Recollecting his success in obtaining the first crystalline derivatives of urushiol at Tohoku University,^12)–15) which was critical for structural identification, Majima wrote: “Hydro-urushiol and its ethereal derivatives were the first crystalline derivatives of urushiol, and this was very moment when the study of urushiol was put on track. I would never forget the joy I felt at that time”.¹¹⁾

Fig. 2.

Majima’s representative papers on urushiol. (a) The first paper (reproduced from Ref. 9). See Ref. 10 for a relevant paper in German. (b) The first crystalline ethereal derivative of urushiol via hydrogenation and methylation (reproduced from Ref. 14). See Ref. 15 for a relevant paper in German.

Nonetheless, 16 years after the “completion”, a paper related to urushiol was published by Majima in the 10th issue of this journal in 1933.¹⁶⁾ This paper reported a synthetic study of urushiol derivatives, which also demonstrated Majima’s knowledge and interest in up-to-date organic chemistry. This study was inspired by a few papers published from 1925 to 1933: new synthetic methods for allyl halides by Carothers (1931/1933)^17),18) and a novel synthetic route to urushiol derivatives via the Claisen rearrangement by Sin-iti Kawai, a former student of Majima (1925/1927).^19)–21) However, it also seems that this brief study was mainly designed to train a young, undergraduate student, Kunisaburo Tamura.

Tamura wrote in his recollections²²⁾: “I began to work directly under Professor Majima’s guidance in 1932, when the Faculty of Science at Osaka University was founded. At that time, there were no students in the Faculty of Science. We did not have a building, so we rented a room in the School of Medicine and began experiments. Professor Majima was the Dean of the Faculty and was very busy with administrative work and building constructions. Nonetheless, he took time out of his busy schedule to come and teach me. Professor Majima was truly a research-oriented person and emphasized that research should be given the first priority. The next year, 1933, the building of the Faculty of Science was completed, and I began my research on aconitum alkaloids …”. Thus, Tamura was trained by Majima with the short-term synthetic study of urushiol derivatives and was immediately led to studies on aconitum alkaloids. In 1950, Tamura received the Chemical Society of Japan Award for his studies on aconitum alkaloids jointly with two other alumni of Majima’s group, i.e., Harusada Suginome and Shinichi Morio (see below).²³⁾

Indole

RIKEN started its history in 1917, and Majima was among its first principal researchers. The first patent from RIKEN was obtained in 1918 by Majima for the synthesis of indole.^24),25) From Majima’s synthesis, indole was obtained in 34% yield, the highest record at that time, from direct reactions of acetylene and aniline at 700 °C in their elaborate apparatus (Fig. 3). Most importantly, through this patented study, they accumulated >10 kg of indole that served as a precious precursor for various derivatives.¹⁾

Fig. 3.

Indole synthesis (reproduced from Ref. 24). See Ref. 25 for a relevant paper in German. Reaction scheme (left) and an elaborate apparatus (right).

Among many papers derived from “>10 kg of the RIKEN indole”, one paper appeared in the third issue of this journal in 1927.²⁶⁾ Majima started his synthetic explorations of the Grignard reagent from indole with Munio Kotake in 1920 and published the first paper on the synthesis of tryptophane in 1922.²⁷⁾ Toshio Hoshino joined this exploration in 1923 as an undergraduate student and published β-alkylation reactions of the indole Grignard reagent in 1925.^1),28) In 1926, Putochin reported a follow-up study of this Majima–Hoshino paper with some additional observations such as temperature effects.²⁹⁾ The 1927 paper in this journal was written as a counterargument to Putochin’s paper, which required an intense discussion between Majima and Hoshino.²⁶⁾ Hoshino’s recollection written in 1970 should be most detailed and interesting.³⁰⁾

“A theme of my undergraduate research was the synthesis of indole derivatives using its Grignard reagent, which was pioneered by my senior, Munio Kotake. It was already 40 years ago by now, but I can still feel a vivid passion burning inside me, as I recall those days …. Later on, an important paper on the indole Grignard reaction was published by others. It pointed out our oversight, but there was a serious oversight on their side as well. I thought that the reaction mechanism was poor and full of contradictions. One day, when I was working hard to avenge this paper, Professor Majima invited me for a discussion.

Majima: Experimental facts are facts, if there is no error in the way the experiment is conducted. The reaction mechanism can take any form for reasoning. If we argue back to them, they will come back with more questions and nuisance discussion. If they present a reaction mechanism that is similar to what we are thinking, we can tell them that we have been doing it for a long time and present various data at that time.

Hoshino: Wouldn’t it be like, ‘A defeated general talks a lot about battles?’ ”

As we see in the paper that appeared in this journal,²⁶⁾ they eventually published their counterargument including a mechanistic discussion. Their approach that is based on mechanistic rationales is ahead of their time and even resonates with modern approaches of present organic chemists.

Hoshino’s “burning passion” might have also involved his further synthetic studies with the indole Grignard reagent. On the basis of their β-alkylation reaction,²⁸⁾ Hoshino completed the synthesis of physostigmine (eserine). Under severe competitions with P. K. Julian and R. Robinson,^1),31) Hoshino reported the synthesis in this journal in 1935.³²⁾

Majima also worked on a natural indole derivative, yohimbine, which was started as an undergraduate research of Shunsuke Murahashi in 1930.¹⁾ They reported one paper on the dehydration reactions of yohimbine in this journal in 1934,³³⁾ which also showed their keen interest in alkaloids (see below). However, moving to Osaka University after this publication, they started a different project on matsutakeol.

Aconitine (aconitum alkaloids)

At the “completion” of urushiol studies, Majima started new projects. Among many challenging projects (see above for indole), one of the most challenging subjects was the studies on aconitine and its congeners (aconitum alkaloids) (Fig. 4). Three relevant papers were published by Majima in this journal.^34)–36) A brief summary of aconitine studies can be found in his autography as follows.¹¹⁾

Fig. 4.

Aconitine. (a) Crystal structure of aconitine (CCDC1100898).⁴³⁾ Carbon, gray; hydrogen, white; nitrogen, blue; oxygen, red. The crystal data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. (b) An outline of Majima’s representative works on the aconitum alkaloids (Majima/Morio, 1930; reproduced from Ref. 44).

“Having completed my studies on the structure of lacquer components, I thought about next projects and decided on aconitine, an alkaloid of aconitum. It was because I wanted to examine organic compounds native to Asia and also wished to tackle a tough problem …. Expecting severe difficulties from the beginning, we received sufficient grants from the Ministry of Education and the Keimei-kai to be equipped with various facilities for grinding, extraction, and distillation. We collected about 25 species of aconite plants from China, Manchuria, and Japan and closely examined the alkaloid components. The first papers were published in 1924, which were followed by a series of our publications until around 1940 before World War II. We clarified that what was known as japaconitine was a mixture of impurities, and in addition to aconitine, several new alkaloids such as mesaconitine and hypaconitine were obtained as crystals, and several alkaloids such as luciduscucline were also found. Further studies were carried out to elucidate the molecular structures of these alkaloids, and a part of them were reported. I believe that these studies have taken us a few steps forward to solve the difficult problem of aconitine alkaloids, but we were forced to stop by the war. After the war, I became old and retired, and the continuing research is being conducted by Professor Suginome of Hokkaido University and Professor Ochiai of the University of Tokyo”.

The first results on aconitum alkaloids were published as three consecutive papers in 1924 (German versions)^37)–39) and 1926 (Japanese versions)^40)–42) and were coauthored with Harusada Suginome and Shinichi Morio who joined this project for their undergraduate research in 1918 and 1919, respectively. After starting this project in 1918, it took them at least 6 years to publish the first papers. The easiest way to understand the “toughness” of the project would be seeing the structure of aconitine (see its crystal structure⁴³⁾ in Fig. 4). Moreover, aconitum alkaloids were obtained as a mixture of structurally similar congeners that were extremely difficult to separate. The table shown in Fig. 4 outlines a brief history of Majima’s work.^34),44) Before Majima’s work, three congeners were reported (aconitine, japaconitine, and jesaconitine), and in their first papers in 1924, Majima reported 10 congeners. Further studies clarified that these 10 congeners were indeed composed of four congeners with different mixing ratios. The readers should remember that during these investigations, there are no modern techniques such as chromatography for separation and spectroscopy for identification. The project was finally inherited by Kunisaburo Tamura, when he joined Majima’s group in 1932 (see above). Their studies were first reported as a brief communication in this journal in 1936³⁶⁾ and further elaborated in two long papers (14 and 21 pages).^45)–48) The paper in this journal reported an important finding that was described in italics for emphasis: Demnach ist der Stickstoff des Aconins mit der Äthylgruppe gebunden und nicht wie bisher gedacht wurde, mit der Methylgruppe. (According to this, the nitrogen of aconine is bonded to the ethyl group and not, as previously thought, to the methyl group.)³⁶⁾

Working at RIKEN in 1944, Tamura gave lectures to undergraduate students at a pharmaceutical college that was later integrated in Chiba University. Two senior members of the galaxy meeting, i.e., Shiro Akabori and Masuo Murakami, were also graduates from this school, although they graduated long before this lecture. One student left his recollection on Tamura’s lecture.⁴⁹⁾

“In the last class for his lecture, Dr. Tamura said, ‘Actually, I started my career with structural studies of aconitine, a component of aconite, under the guidance of Professor Majima at Tohoku University, and I am still working on this project’. He further explained his tough experiences on the structural investigations and with some tears in his eyes said, ‘When I found that aconitine had an N-ethyl group, which is rare in natural products, Professor Majima gave me words of his appreciation’. In those days, there were no analytical instruments available for structural studies, and the only way to study aconitine was to elucidate the unknown structure from the results of known chemical reactions. The complicated structure of aconitine was something that could not possibly be handled by any organic chemists then. Nonetheless, at the age of 17, I was strongly attracted to the methods of natural product chemistry. Together with frequent encouragements of professors at my college, saying, ‘Follow in the footsteps of Akabori and Murakami!’, the tears of Dr. Tamura helped me to make up my mind to pursue a career in organic chemistry”.

This student, Shô Itô, later became an eminent professor as the second generation of Majima’s chemistry family (Fig. 5 and Supplementary materials).

Fig. 5.

Majima at his last visit to Sendai (72 years old, 1947). Photograph taken by Shô Itô, then as an undergraduate student. Showing this picture at his lecture (Tohoku University, 2011), Itô said, “I was an undergraduate student working with Professor Nozoe and was at Tohoku University on the occasion of Professor Majima’s last visit. As this was a rare, precious chance, I was waiting for Professor Majima in front of the Department and asked him for a photograph. Well … being asked by an unknown student, Professor Majima surely looks suspicious, doesn’t he?”

Giving birth to stars

The members in the galaxy meeting by themselves were eminent professors/researchers, and they gave birth to many following stars in organic chemistry. The relay still continues to foster next-generation chemists. For us to continue the relay, Majima left us a guide, “Organic Chemistry: A Guide”, which was originally published in 1940.⁵⁰⁾ It contains many useful guides for chemists of any generations, but, here in this commentary, tips for younger generations may be abstracted: 1. Cultivate your observation skills. 2. Perform your analyses both in qualitative and quantitative manners. 3. Be optimistic. 4. Run when you are hit by an idea. 5. Devote yourself wholeheartedly in your research. 6. Always improve your skills/methods. 7. Be thorough. 8. Be efficient to manage your time. 9. Perfect your chemical samples. 10. Do not dump your chemicals. 11. Keep your surroundings neat and tidy. 12. Make full records of your experiments.

Some of the readers might have enjoyed reading researchers’ guidebooks such as “At the Helm” or “At the Bench” by Kathy Barker.^51)–53) One of the authors (H.I.) actually learned much by reading them at a start of his professional career or in struggles with delicate experiments. Reading Majima’s guide, he also felt a similar atmosphere. While preparing the Supplementary materials for this commentary to list the second-generation scientists of Majima’s chemistry family, we were initially surprised yet later found it natural to find a connection between Majima and Barker.** The baton of Majima’s love in science is still handed over, knowingly or unknowingly, to next generations worldwide.

Supplementary materials

Supplementary materials (a list of Majima’s chemistry family) are available at https//doi.org/10.2183/pjab.99.019.

Acknowledgments

We wish to express our gratitude to Dr. Midori Oinuma for her help in literature survey and the Supplementary materials. We also thank the librarians at the Graduate School of Science, the University of Tokyo for helping us in excavating classic papers. H.I. thanks Tokyo Kagakudojin for a generous gift of the last copy of a book, “Professor Rikō Majima—Papers and Reminiscences”. We also acknowledge Mr. M. Takeuchi (Japan Academy) for providing information about Majima’s contributions to the Japan Academy.

Notes

Edited by Keisuke SUZUKI, M.J.A.

Correspondence should be addressed to: H. Isobe, Department of Chemistry, The University of Tokyo, Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033, Japan (e-mail: [e-mail]).

Footnotes

This paper commemorates the 100th anniversary of this journal and introduces the following papers previously published in this journal. Majima, R. and Hoshino, T. (1927) Ueber den Mechanismus der grignardschen Reaktion in der Indolreihe. Proc. Imp. Acad. 3 (6), 339–341 (https://doi.org/10.2183/pjab1912.3.339); Majima, R. and Tamura, K. (1936) Ein Beitrag zur Konstitution der Akonitum-Alkaloide. Proc. Imp. Acad. 12 (8), 235–238 (https://doi.org/10.2183/pjab1912.12.235).

‡ For clarity in this commentary, modern names are adopted to designate universities, institutes, and so on.

§ For representative references of Majima’s studies on urushiol, see Ref. 16 and literatures cited therein.

** There is a column in “At the Helm” entitled, “The Genetics of Full Professors”, and the readers may enjoy it along with this commentary. With the list of Supplementary materials and the preface of the translated Japanese version of “At the Helm”, the readers can track the connection between Majima and Barker.

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Appendices

[From Proc. Imp. Acad., Vol. 3 No. 6, pp. 339–341 (1927)]

[From Proc. Imp. Acad., Vol. 12 No. 8, pp. 235–238 (1936)]

Profile

Hiroyuki Isobe was born in Tokyo in 1970. He received his bachelor and master degrees from Tokyo Institute of Technology in 1994 and 1996 with Professors Eiichi Nakamura and Katsumi Kakinuma as actual and formal supervisors, respectively. He entered the Department of Chemistry of the University of Tokyo in 1996, and in the same year, stayed at Princeton University to work on oligosaccharides with Professor Daniel Kahne for three months. He started his academic career as Assistant Professor at the University of Tokyo in 1998 before receiving his Ph.D. degree (1999) and was promoted to Associate Professor in 2004. His early works on amphiphilic/gene-delivery fullerenes were recognized by several awards, including IUPAC Prize for Young Chemists (2000), Young Scientists Research Award in Natural Product Chemistry (2001), Chemical Society of Japan Award for Young Chemists (2004), Osawa Award (2005), Young Scientists Prize from MEXT (2008) and Nozoe Memorial Award for Young Organic Chemists (2009). In 2007, he was appointed as Professor at Department of Chemistry in Tohoku University where he was concurrently assigned as Principal Investigator of AIMR in 2013. He served as a research director of ERATO Isobe Degenerate π-Integration project from 2013 to 2019. In 2016, he moved back to the University of Tokyo. Since 2007, he renovated his lab space seven times, which involved two award-winning labs (Good Design Award, 2014 and 2017). His scientific works on nanocarbon molecules in these labs were recognized by Honorary International Chair Professorship of Taipei Tech (2015), Chemical Society of Japan Award for Creative Work (2016) and Inoue Prize for Science (2017).

Masahiro Hirama was born in 1948 in Tokyo. He received his Ph.D. at Tohoku University under Prof. Shô Itô in 1977 and completed his postdoctoral studies at the University of Pittsburgh with Prof. S. J. Danishefsky and at MIT with Prof. S. Masamune. In 1980, he returned to Japan and joined the Suntory Institute for Bioorganic Research (Nakanishi’s Institute). In 1983, he transferred to Tohoku University as an assistant professor and was promoted to Professor of Chemistry and Distinguished Professor of Tohoku University in 1989 and 2008, respectively. His research interests are focused on the total syntheses of large, architecturally complicated, and highly strained bioactive natural products, such as ciguatoxins and nine-membered enediyne antibiotics. Related studies with a special emphasis on protein–ligand interactions are also investigated. He retired from Tohoku University in 2012 and joined AcroScale, Inc. as a member of the board of directors and then GlyTech Inc. as an advisor. He received the Incentive Award in Synthetic Organic Chemistry, Japan, and was awarded the Inoue Prize for Science; Synthetic Organic Chemistry Award, Japan; Roche Distinguished Lecturer (USA); Chemical Society of Japan Award; Fujihara Award; National Medal with Purple Ribbon (Medals of Honor, Japan); and Japan Academy Prize.