Top

Published in:

01-06-2019 | Alkaloids | Note

New otonecine-type pyrrolizidine alkaloid from Petasites japonicus

Authors: Mariko Kitajima, Kei Okabe, Megumi Yoshida, Ryo Nakabayashi, Kazuki Saito, Noriyuki Kogure, Hiromitsu Takayama

Published in: Journal of Natural Medicines | Issue 3/2019

Abstract

One new otonecine-type pyrrolizidine alkaloid secopetasitenine (1), along with petasitenine (fukinotoxine, 2), neopetasitenine (3), and senkirkine (4), was isolated from the whole plant of Petasites japonicus. The structure of 1 was determined by spectroscopic analyses and chemical conversion from the known alkaloid petasitenine (2).

Hartmann T, Witte L (1995) Chemistry, biology and chemoecology of pyrrolizidine alkaloids. In: Pelletier SW (ed) Alkaloids: chemical and biological perspectives, vol 9. Pergamon, Oxford, pp 155–233 (and references cited therein)

Robins DJ (1995) Pyrrolizidine and quinolizidine alkaloids. In: Cordell GA (ed) The alkaloids: chemistry and pharmacology, vol 46. Academic Press, New York, pp 1–61 (and references cited therein)

Fu PP, Xia Q, Lin G, Chou MW (2004) Pyrrolizidine alkaloids–genotoxicity, metabolism enzymes, metabolic activation, and mechanisms. Drug Metab Rev 36:1–55 (and references cited therein) CrossRef

Xia Q, Zhao Y, Lin G, Beland FA, Cai L, Fu PP (2016) Pyrrolizidine alkaloid-protein adducts: potential non-invasive biomarkers of pyrrolizidine alkaloid-induced liver toxicity and exposure. Chem Res Toxicol 29:1282–1292 (and references cited therein) CrossRef

World Health Organization (1989) World Health Organization, international programme on chemical safety (IPCS), health and safety guide no 26: pyrrolizidine alkaloids health and safety guide. World Health Organization, Geneva, pp 5–17

World Health Organization (1988) World Health Organization, international programme on chemical safety (IPCS), environmental health criteria 80: pyrrolizidine alkaloids. Published under the joint sponsorship of the United Nations Environment Programme and the World Health Organization. World Health Organization, Geneva, pp 12–345

World Health Organization: Joint FAO/WHO Expert Committee On Food Additives (JECFA) (2015) Eightieth report of the joint FAO/WHO Expert Committee On Food Additives: evaluation of certain food additives and contaminants (WHO technical report series 995), pp 65–80

Yamada K, Tatematsu H, Suzuki M, Hirata Y, Haga M, Hirono I (1976) Isolation and the structure of two alkaloids, petasitenine and neopetasitenine from Petasites japonicus Maxim. Chem Lett 5:461–464CrossRef

Yamada K, Tatematsu H, Hirata Y, Haga M, Hirono I (1976) Stereochemistry of petasitenine, the carcinogenic alkaloid from Petasites japonicus Maxim. and transformation of petasitenine to senkirkine. Chem Lett 5:1123–1126CrossRef

10.

Furuta T, Hikichi M, Iitaka Y (1976) Fukinotoxin, a new pyrrolizidine alkaloid from Petasites japonicus. Chem Pharm Bull 24:1120–1122CrossRef

11.

Yamada K, Tatematsu H, Kyotani Y, Hirata Y, Haga M, Hirono I (1978) Senkirkine and a new sesquiterpene glycoside, isopetasoside, from Petasites japonicus. Phytochemistry 17:1667–1668CrossRef

12.

Yamada K, Tatematsu H, Unno R, Hirata Y, Hirano I (1978) Petasinine and petasinoside, two minor alkaloids possessing a new necine isolated from Petasites japonicus Maxim. Tetrahedron Lett 19:4543–4546CrossRef

13.

Kitajima M, Yanagisawa T, Tsukahara M, Yamaguchi Y, Kogure N, Kikura-Hanajiri R, Goda Y, Iida O, Sugimura Y, Kawahara N, Takayama H (2018) Biphenyl ether and biphenyl quinolizidine lactone alkaloids from Heimia salicifolia. Tetrahedron 74:441–452CrossRef

14.

Onozawa T, Kitajima M, Kogure N, Peerakam N, Santiarworn D, Takayama H (2017) A cyclopeptide and a tetrahydroisoquinoline alkaloid from Ophiorrhiza nutans. J Nat Prod 80:2156–2160CrossRef

15.

Tooriyama S, Mimori Y, Wu Y, Kogure N, Kitajima M, Takayama H (2017) Asymmetric total synthesis of pentacyclic indole alkaloid andranginine and absolute configuration of natural product isolated from Kopsia arborea. Org Lett 19:2722–2725CrossRef

16.

Niwa H, Ishiwata H, Yamada K (1983) Separation and determination of macrocyclic pyrrolizidine alkaloids of the otonecine type present in the edible plant Petasites japonicus by reversed-phase high-performance liquid chromatography. J Chromatogr 257:146–150CrossRef

17.

Lin G, Zhou KY, Zhao XG, Wang ZT, But PPH (1998) Determination of hepatotoxic pyrrolizidine alkaloids by on-line high performance liquid chromatography mass spectrometry with an electrospray interface. Rapid Commun Mass Spectrom 12:1445–1456CrossRef

Title: New otonecine-type pyrrolizidine alkaloid from Petasites japonicus
Authors: Mariko Kitajima
Kei Okabe
Megumi Yoshida
Ryo Nakabayashi
Kazuki Saito
Noriyuki Kogure
Hiromitsu Takayama
Publication date: 01-06-2019
Publisher: Springer Singapore
Keywords: Alkaloids
Alkaloids
Published in: Journal of Natural Medicines / Issue 3/2019
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-019-01285-9

At a glance: The STEP trials

Springer Medicine

New otonecine-type pyrrolizidine alkaloid from Petasites japonicus

Abstract

At a glance: The STEP trials

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 3/2019

Analyses of the possible anti-tumor effect of yokukansan

Correction to: Identification of β‑carboline and canthinone alkaloids as anti‑inflammatory agents but with different inhibitory profile on the expression of iNOS and COX‑2 in lipopolysaccharide‑activated RAW 264.7 macrophages

Evaluation of the safety and efficacy of Glycyrrhiza uralensis root extracts produced using artificial hydroponic-field hybrid cultivation systems II: comparison of serum concentration of glycyrrhetinic acid serum concentration in mice

Development of a simple and rapid method for the detection of isomiroestrol in Pueraria candollei by an immunochromatographic strip test

B-ring-homo-tonghaosu, isolated from Chrysanthemum morifolium capitulum, acts as a peroxisome proliferator-activated receptor-γ agonist

Ecological, phylogenetical, and pharmacognostical characteristics of Aconitum kiyomiense endemic to Hida highlands, Takayama city, Gifu Prefecture, Japan