Biofunctional Effects of Thiohemiaminal-Type Dimeric Sesquiterpene Alkaloids from Nuphar Plants.

Abstract

Dimeric sesquiterpene thioalkaloids from the rhizomes of Nuphar pumilum exhibited immunosuppressive effects using a sheep erythrocyte plaque forming cell (PFC) assay, as well as an anti-metastasis effect, and rapid apoptosis-inducing effects in tumor cell lines. In particular, dimeric sesquiterpene thioalkaloids with a hydroxy group (6-hydroxythiobinupharidine, 6,6'-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B) showed substantial effects, whereas dimeric sesquiterpene thioalkaloids lacking the hydroxy group (thiobinupharidine, thionuphlutine B, 6'-hydroxythionuphlutine B, neothiobinupharidine, thionuphlutine B β-sulfoxide, neothiobinupharidine β-sulfoxide) and monomeric sesquiterpene alkaloids (nupharidine, 7-epideoxynupharidine, nupharolutine) showed weak activity. In this review, we summarize our studies of the biofunctional effects of these alkaloids.

• Authors: Hisashi Matsuda, Seikou Nakamura, Souichi Nakashima, Masashi Fukaya, Masayuki Yoshikawa
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 67 Issue 7 Pg. 666-674 ( 2019) ISSN: 1347-5223 [Electronic] Japan
• PMID: 31257322 (Publication Type: Journal Article, Review)

Chemical References

• Alkaloids
• Antineoplastic Agents
• Immunosuppressive Agents
• Sesquiterpenes

Topics

• Alkaloids (chemistry, isolation & purification, pharmacology)
• Animals
• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Apoptosis (drug effects)
• Cell Movement (drug effects)
• Erythrocytes (cytology, drug effects, metabolism)
• Humans
• Immunosuppressive Agents (chemistry, isolation & purification, pharmacology)
• Nuphar (chemistry, metabolism)
• Sesquiterpenes (chemistry)