Maoecrystal V is a pentacyclic norditerpene isolated from the Chinese herb Isodon eriocalyx. It is expected to be a new drug lead, and many total and partial synthesis studies have been reported.
-Construction of the CDE-ring core was performed by oxidative deprotection of the thiane-triol precursor.
-The A ring was stereoselectively constructed by Diels-Alder reaction of the DE bicyclo ring with Kitahara-Danishefsky diene, leading to the ABDE ring compound.
261. "Synthesis of the A/D/E-ring core compound of maoecrystal V"
　　H. Asao, Y. Shimasaki, A. Sasaki, S. Katayama, K. Ida, M. kotake, E. Sato, Y. Sato, T. Ishimoto, C. J. Vavricka, M. Izumi, S. Kuwahara and H. Kiyota, Biosci. Biotechnol. Biochem., 88, 733-741 (2024) DOI: 10.1093/bbb/zbae049.

262. "Synthesis of the C/D/E-ring core compound of maoecrystal V"
　　S. Katayama, M. Nishimoto, T. Ura, T. Ishimoto, K. Ida, Y. Sato, C. J. Vavricka, M. Izumi, and H. Kiyota, Synth. Commun., 53(10), 708-712 (2023) DOI: 10.1080/00397911.2023.2191853.

We have isolated echinopines A (1) and B (2), novel sesquiterpenoids with an unprecedented rearranged skeleton named echinopane, from the roots of Echinops spinosus. The structures were elucidated by extensive spectroscopic analysis. The relative configuration of 1 was assigned by combination of NOESY correlations and a simulation analysis.
(Prof. Qing-Wen Shi (Hebei Med. Univ., China), Yuta Nagashima, Koji Tanaka)
118. "Echinopines A and B: Sesquiterpenoids Possessing an Unprecedented Skeleton from Echinps spinosus"
M. Dong, B. Cong, S.-H. Yu, F. Sauriol, C.-H. Huo, Q.-W. Shi,Y.-C. Gu, L. O. Zamir, H. Kiyota, Org. Lett., 10, 701-704 (2008).

Achillinine A 2011.9 (Prof. Q.-W. Shi, Hebei Med. Univ.)

Achillinin A, a new guaianolide isolated from the flower of Achillea millefolium, exhibited potential antiproliferative activity to A549, RERF-LC-kj and QG-90 cells with 50% inhibitory concentration (IC50) values of 5.8, 10 and 0.31 microM, respectively.

162. "Achillinin A, a Cytotoxic Guaianolide from the Flower of Yarrow, Achillea millefolium"
Y. Li, M.-L. Zhang, B. Cong, S.-M. Wang, M. Dong, F. Sauriol, C.-H. Huo, Q.-W. Shi, Y.-C. Gu, H. Kiyota, Biosci. Biotechnol. Biochem., 75, 1554-1556.

Methylated Catechins (Anti-Inflammation) 2009.5

Methylated catechins contained in green tea "Beni-Fuuki" (Camellia sinensis) showed anti-inflammatory activity. The synthetic ECG3''Me and CG3''Me suppressed the TPA (phrbol ester)-induced inflammation of mouse ears by 50 and 43%, respectively. Thier activities are stronger than those of indomethacin and glycyrrhetinic acid.
(Prof. Hidefumi Makabe (Shinshu Univ.), Momoko Takai)
136. "Synthesis and Anti-inflammatory Activity of (-)-Epicatechin-3-(3-O-methylgallate) and (+)-Catechin-3-(3-O-methylgallate)"
T. Iijima, Y. Mohri, Hattori, A. Kashima, T. Kamo, M. Hirota, H. Kiyota, H. Makabe, Chem. Biodivers., 6, 520-526 (2009).

Ancistrocladinium A 2009.1

This is the first N,C-coupled naphtyldihydroisoquinoline alkaloid isolated from a Congolese Ancistrocladus sp. showed promising antileishmanial activities.

(Akihito Saito, Momoko Takai)
"Synthetic Studies of Ancistrocladinium A"

Sulforaphane Derivatives2010.1

Sulforaphane present in cruciferous vegetables such as broccoli and cabbage showed potent anti-inflammatory and chemopreventive activities. Its congener, 6-MITC (6-(methylsulfiniyl)hexyl isothiocyanate) isolated from the pungent spice (Japanese "WASABI", Wasabia japonica) and the synthetic derivatives showed anti-NO production activity.
(Prof. Toshiro Noshita (Hiroshima Pref. Univ.), Prof. Kazuo Ryoyama (Aomori Univ.))
142. "Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lopophilicity"
T. Noshita, Y. Kidachi, S. Funayama, H. Kiyota, H. Yamaguchi, K. Ryoyama, Eur. J. Med. Chem., 44, 4931-4936 (2009).

Denudalide from a Magnolia Plant Magnolia denudata2009.7

Magnolia plants are widely cultivated in Japan as garden plants, and has been found to contain various compounds, terpenoids, lignans, and neolignans. We investigated the constituents of matured fruits of M. denudata, and two new phenolic derivatives named denudalide and were isolated and characterized, and one known neolignan (denudatin A) was isolated. Denudalide and denudaquinol are new natural products.
(Prof. Toshiro Noshita (Hiroshima Pref. Univ.), Prof. Tetsuya Murayama (Yamagata Univ.), Prof. Kazuo Ryoyama (Aomori Univ.))
133. "New Cytotxic Phenolic Derivatives from Matured Fruits of Magnolia denudata"
T. Noshita, H. Kiyota, Y. Kidachi, K. Ryoyama, S. Funayama, K. Hanada, T. Murayama, Biosci. Biotechnol. Biochem., 73, 726-728 (2009).

Shikimic Acid

Synthesis of methyl (-)-shikimate (-)-1 was achieved via lipase-catalyzed optical resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one.
42. "Synthesis of Methyl (-)-Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one"
T. Oritani, R. Ueda, H. Kiyota, Bioscience, Biotechnology, and Biochemistry, 65 (9), 2106-2109 (2001).

Altholactones

(by the late Dr T. Sugiyama and Mr A. Hiratate) 47 "Synthesis of (-)-ent-Altholactone, (+)-7a-epi-Altholactone, (-)-ent-Isoaltholactone and (-)-7a-epi-Isoaltholactone from 2,3-O-Cyclohexylidene-D-glyceraldehyde"
A. Hiratate, H. Kiyota, T. Oritani, Journal of Pesticide Science, 26(4), 361-365 (2001).

46. "Synthesis of Both Enantiomers of Altholactone, Isoaltholactone and 5-Hydroxygoniothalamin, and Their Biological Activities"
A. Hiratate, H. Kiyota, T. Noshita, R. Takeuchi, T. Oritani, Journal of Pesticide Science, 26(4), 366-370 (2001).