Oleanane-type triterpene saponins with collagen synthesis-promoting activity from the flowers of Bellis perennis

Toshio Morikawa; Kiyofumi Ninomiya; Yasunobu Takamori; Eriko Nishida; Misato Yasue; Takao Hayakawa; Osamu Muraoka; Xuezheng Li; Seikou Nakamura; Masayuki Yoshikawa; Hisashi Matsuda

doi:10.1016/j.phytochem.2015.05.011

Oleanane-type triterpene saponins with collagen synthesis-promoting activity from the flowers of Bellis perennis

Phytochemistry. 2015 Aug:116:203-212. doi: 10.1016/j.phytochem.2015.05.011. Epub 2015 May 28.

Authors

Affiliations

¹ Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan; Antiaging Centre, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Electronic address: morikawa@kindai.ac.jp.
² Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan; Antiaging Centre, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
³ Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
⁴ Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
⁵ Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan; Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
⁶ Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan. Electronic address: matsuda@mb.kyoto-phu.ac.jp.

PMID: 26028520
DOI: 10.1016/j.phytochem.2015.05.011

Abstract

The methanol extract from Bellis perennis (Asteraceae) flowers was found to promote collagen synthesis in normal human dermal fibroblasts (NHDFs). Seven oleanane-type triterpene saponins, perennisosides XIII-XIX, and two known saponins, bellissaponins BS5 and BS9, were isolated from the methanol extract. The structures were determined based on chemical and physicochemical data, and confirmed using previously isolated related compounds as references. Among the isolates, including 19 previously reported saponins, perennisosides XVIII, I, II, VII, IX, and XI, asterbatanoside D, bernardioside B2, and bellissaponins BS5 and BS9 significantly promoted collagen synthesis at 3-30μM without cytotoxicity.

Keywords: Asteraceae; Bellis perennis; Collagen synthesis promoting activity; Daisy; Oleanane-type triterpene saponin; Perennisoside.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Asteraceae / chemistry*
Collagen / biosynthesis*
Collagen / drug effects
Flowers / chemistry*
Humans
Japan
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oleanolic Acid / analogs & derivatives*
Oleanolic Acid / chemistry
Oleanolic Acid / isolation & purification
Oleanolic Acid / pharmacology
Saponins / chemistry
Saponins / isolation & purification*
Saponins / pharmacology*
Triterpenes / chemistry
Triterpenes / isolation & purification*
Triterpenes / pharmacology*

Substances

Saponins
Triterpenes
asterbatanoside D
oleanane
perennisoside XI
Oleanolic Acid
Collagen