New cytotoxic halogenated sesquiterpenes from the Egyptian sea hare, Aplysia oculifera

被引：15

作者：

Hegazy, Mohamed-Elamir F. ^{[1
,2
]}

Moustfa, Alaa Y. ^{[3
]}

Mohamed, Abou El-Hamd H. ^{[4
]}

Alhammady, Montaser A. ^{[5
]}

Elbehairi, Serag Eldin I. ^{[6
]}

Ohta, Shinji ^{[7
]}

Pare, Paul W. ^{[8
]}

机构：

[1] Natl Res Ctr, Chem Med Plants Dept, Giza 12622, Egypt

[2] Natl Res Ctr, Ctr Excellence Adv Sci, Giza 12622, Egypt

[3] Sohag Univ, Fac Sci, Dept Zool, Sohag, Egypt

[4] Aswan Univ, Fac Sci, Dept Chem, Aswan, Egypt

[5] Natl Inst Oceanog & Fisheries, Red Sea Branch, Hurghada, Egypt

[6] Egyptian Org Biol Prod & Vaccines, Giza, Egypt

[7] Hiroshima Univ, Grad Sch Biosphere Sci, Higashihiroshima 7398521, Japan

[8] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 10期

关键词：

Aplysia oculifera; Opisthobranch; Halogenated sesquiterpenes; Cytotoxicity; MARINE NATURAL-PRODUCTS; DACTYLOMELA; LAURENCIA;

D O I：

10.1016/j.tetlet.2014.01.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new sesquiterpenes, oculiferane (1) and epi-obtusane (2) have been isolated and identified from an acetone extract of the digestive gland of the sea hare, Aplysia oculifera. The structures were elucidated by spectroscopic analysis including HREIMS, H-1, C-13, DEPT, H-1-H-1 COSY, HMQC, and HMBC NMR; the relative configuration was confirmed by X-ray analysis. Compounds 1 and 2 exhibited cytotoxic activity in vitro against several human cancer cell lines with IC50 values in the low mu g/ml range. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1711 / 1714

页数：4

共 50 条

[1] SRILANKENYNE, A NEW METABOLITE FROM THE SEA HARE APLYSIA-OCULIFERA
DESILVA, ED
SCHWARTZ, RE
SCHEUER, PJ
SHOOLERY, JN
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03): : 395 - 396
[2] New halogenated sesquiterpenes from South African specimens of the circumtropical sea hare Aplysia dactylomela
McPhail, KL
Davies-Coleman, MT
Copley, RCB
Eggleston, DS
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (12): : 1618 - 1623
[3] Lifetime energy budget in the sea hare Aplysia oculifera
Plaut, I
Borut, A
Spira, ME
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY A-PHYSIOLOGY, 1996, 113 (02): : 205 - 212
[4] New cytotoxic and antibacterial compounds isolated from the sea hare, Aplysia kurodai
Tsukamoto, Sachiko
Yamashita, Yuko
Ohta, Tomihisa
MARINE DRUGS, 2005, 3 (02): : 22 - 28
[5] 2 BICYCLIC C-15 ENYNES FROM THE SEA HARE APLYSIA-OCULIFERA
SCHULTE, GR
CHUNG, MCH
SCHEUER, PJ
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19): : 3870 - 3873
[6] Isolation, characterization, and biological activities of halogenated sesquiterpenes and C15 acetogenins from the Okinawan sea hare, Aplysia argus
Nakamura, Ryunosuke
Matsuyama, Koushi
Arima, Naomichi
Tani, Fumito
Onitsuka, Satoaki
Okamura, Hiroaki
Iwagawa, Tetsuo
Sudoh, Masayuki
Hamada, Toshiyuki
TETRAHEDRON, 2025, 178
[7] New halogenated C15 acetogenins from Okinawan sea hare Aplysia dactylomela
Matsuyama, Koushi
Inoue, Tomoe
Muroga, Tomoki
Arima, Naomichi
Doe, Matsumi
Tani, Fumito
Ookawa, Yuka
Okamoto, Yuuka
Onitsuka, Satoaki
Okamura, Hiroaki
Iwagawa, Tetsuo
Hamada, Toshiyuki
TETRAHEDRON, 2022, 120
[8] Aplydactylonins A-C, three new sesquiterpenes from the Vietnamese sea hare Aplysia dactylomela and their cytotoxicity
Pham Thi Mai Huong
Nguyen Viet Phong
Nguyen Thi Huong
Duong Thu Trang
Do Thi Thao
Nguyen Xuan Cuong
Nguyen Hoai Nam
Nguyen Van Thanh
Journal of Natural Medicines, 2022, 76 : 210 - 219
[9] Aplydactylonins A-C, three new sesquiterpenes from the Vietnamese sea hare Aplysia dactylomela and their cytotoxicity
Pham Thi Mai Huong
Nguyen Viet Phong
Nguyen Thi Huong
Duong Thu Trang
Do Thi Thao
Nguyen Xuan Cuong
Nguyen Hoai Nam
Nguyen Van Thanh
JOURNAL OF NATURAL MEDICINES, 2022, 76 (01) : 210 - 219
[10] Cytotoxic sesquiterpenes from Aplysia dactylomela
Dias, T
Brito, I
Moujir, L
Paiz, N
Darias, J
Cueto, M
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (11): : 1677 - 1679

← 1 2 3 4 5 →