Halichonic Acid B, a Rearranged Nitrogenous Bisabolene-Type Sesquiterpene from a Marine Sponge Axinyssa sp.

被引：3

作者：

Hitora, Yuki ^{[1
]}

Ogura, Kenta ^{[1
]}

El-Desoky, Ahmed H. H. ^{[1
,2
]}

Ise, Yuji ^{[3
]}

Angkouw, Esther D. ^{[4
]}

Mangindaan, Remy E. P. ^{[4
]}

Tsukamoto, Sachiko ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, 5-1 Oe Honmachi, Kumamoto 8620973, Japan

[2] Natl Res Ctr, Pharmaceut Ind Res Div, Pharmacognosy Dept, 33 Bohouth El St,PO 12622, Giza, Egypt

[3] Univ Ryukyus, Sesoko Stn, Trop Biosphere Res Ctr, 3422 Sesoko, Motobu, Okinawa 9050227, Japan

[4] Sam Ratulangi Univ, Fac Fisheries & Marine Sci, Kampus Bahu, Manado 95115, Indonesia

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2021年 / 69卷 / 08期

关键词：

marine sponge; Axinyssa species; nitrogenous bisabolone-type sesquiterpene;

D O I：

10.1248/cpb.c21-00392

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new rearranged nitrogenous bisabolone-type sesquiterpene, halichonic acid B (1), was isolated from a marine sponge Axinyssa sp. together with halichonic acid (2) and (6R,7S)-7-amino-7,8-dihydro-alpha-bisabolene (3). The structure of 1 was determined by extensive NMR and MS analyses, revealing an unprecedented carbon framework, and its absolute configuration was elucidated by time-dependent density-functional theory (TDDFT)-based electronic circular dichroism (ECD) spectrum calculation. We propose that 1 and 2 may be biosynthesized in the same pathway, involving the reaction between farnesyl pyrophosphate and glycine, followed by cyclization.

引用

页码：802 / 805

页数：4

共 9 条

[1] A dimeric urea of the bisabolene sesquiterpene from the Okinawan marine sponge Axinyssa sp inhibits protein tyrosine phosphatase 1B activity in Huh-7 human hepatoma cells [J].

Abdjul, Delfly B. ;

Kanno, Syu-ichi ;

Yamazaki, Hiroyuki ;

Ukai, Kazuyo ;

Namikoshi, Michio .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (02) :315-317

[2] Formamidobisabolene-based derivatives from a sponge Axinyssa sp. [J].

Cheng, Wei ;

Liu, Dong ;

Zhang, Fengying ;

Zhang, Qingying ;

Pedpradab, Patchara ;

Proksch, Peter ;

Liang, Hong ;

Lin, Wenhan .

TETRAHEDRON, 2014, 70 (22) :3576-3583

[3] NITROGENOUS BISABOLENE SESQUITERPENES FROM MARINE-INVERTEBRATES [J].

GULAVITA, NK ;

DESILVA, ED ;

HAGADONE, MR ;

KARUSO, P ;

SCHEUER, PJ ;

VANDUYNE, GD ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5136-5139

[4] New nitrogenous bisabolene-type sesquiterpenes from a Micronesian marine sponge, Axinyssa species [J].

Li, CJ ;

Schmitz, FJ ;

Kelly, M .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (09) :1330-1332

[5] New Nitrogenous Bisabolene-Type Sesquiterpenes from a Formosan Sponge Axinyssa sp. [J].

Liu, Wangta ;

Liang, Kai-Ju ;

Chiang, Ching-Ying ;

Lu, Mei-Chin ;

Su, Jui-Hsin .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2014, 62 (04) :392-394

[6] New nitrogenous bisabolene-type Sesquiterpenes from a Hainan sponge Axinyssa aff. variabilis [J].

Mao, Shui-Chun ;

Guo, Yue-Wei ;

van Soest, Rob ;

Cimino, Guido .

HELVETICA CHIMICA ACTA, 2007, 90 (03) :588-593

[7] Halichonic acid, a new rearranged bisabolene-type sesquiterpene from a marine sponge Halichondria sp. [J].

Raiju, Kenta ;

Hitora, Yuki ;

Kato, Hikaru ;

Ise, Yuji ;

Angkouw, Esther D. ;

Mangindaan, Remy E. P. ;

Tsukamoto, Sachiko .

TETRAHEDRON LETTERS, 2019, 60 (15) :1079-1081

[8] (6R,7S)-7-AMINO-7,8-DIHYDRO-ALPHA-BISABOLENE, AN ANTIMICROBIAL METABOLITE FROM THE MARINE SPONGE HALICHONDRIA SP [J].

SULLIVAN, BW ;

FAULKNER, DJ ;

OKAMOTO, KT ;

CHEN, MHM ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5134-5136

[9] Lamellodysidines A and B, Sesquiterpenes Isolated from the Marine Sponge Lamellodysidea herbacea [J].

Torii, Masumi ;

Kato, Hikaru ;

Hitora, Yuki ;

Angkouw, Esther D. ;

Mangindaan, Remy E. P. ;

de Voogd, Nicole J. ;

Tsukamoto, Sachiko .

JOURNAL OF NATURAL PRODUCTS, 2017, 80 (09) :2536-2541

← 1 →