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Two New Halogenated Compounds from the Marine Red Alga Laurencia nipponica Yamada from the Kunashiri and Etorofu Islands
Author(s) -
Sato Kosuke,
Kaneko Kensuke,
Kamekawa Tsuyoshi,
Taba Kanako,
Ishigami Shinnosuke,
Wada Masahiro,
Ishii Takahiro,
Abe Tsuyoshi,
Kamada Takashi,
Suzuki Minoru
Publication year - 2021
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202100397
Subject(s) - chemistry , race (biology) , algae , laurencia , botany , stereochemistry , biology
The red alga Laurencia nipponica comprises various chemical races distributed relative to the ocean current in Japanese coastal areas. We investigated the chemical compositions and chemical races of L. nipponica distributed from the Kunashiri and Etorofu Islands, the confluence of the Soya warm current and Oya‐shio cold current. Two new halogenated secondary metabolites, deacetylneonipponallene ( 1 ) and neopacifenol ( 2 ), along with four known compounds, deoxyprepacifenol ( 3 ), pacifenol ( 4 ), halo‐chamigrene diether ( 5 ), and isolaurallene ( 6 ) were isolated from L. nipponica collected at Chikappunai, Kunashiri Island, while Zaimokuiwa (Kunashiri Island) and Sana (Etorofu Island) populations contained 3 , 7‐hydroxylaurene ( 7 ), 2,10‐dibromo‐3‐chloro‐9‐hydroxy‐α‐chamigrene ( 8 ), and (3 Z )‐laurefucin ( 9 ). The structures of 1 and 2 were established using spectroscopic methods. The chemical races of L. nipponica distributed in this area were divided into 6 ‐ and 9 ‐producing races. Interestingly, both races contained 4 as an additional race‐index, as well as its derivatives, 2 and 5 . To the best of our knowledge, this is the first example of a race comprising a mixture of two race‐index compounds, suggesting that the convergence of two currents causes the production of new and diverse chemical races in this species.